About the team & opportunity 

*This is a hybrid position located in the Bay Area; the expectation is to go into the San Francisco office 2 times per week.

What’s so great about working on Calendly’s Product team?

We design seamless product experiences that delight our customers. Calendly takes the work out of scheduling so our customers have more time to focus on what matters most. Millions of people worldwide use our software every day—with thousands more signing up daily.

As a Staff Product Manager on the Scheduling team, you’ll be working on an incredible opportunity to evolve and scale a category-defining product while ushering it into the AI era. You’ll help ensure Calendly stays the most intuitive, powerful scheduling platform in the world, while leveraging AI to make it smarter, more proactive, and even more effortless for customers.

A day in the life of a Staff Product Manager at Calendly

This position will report to our Senior Director of Product. You will be working in an environment where collaboration is key to the best ideas, and you will be encouraged to use your creativity and drive to bring new features and ideas to market! You will work closely with engineering, design, sales, product marketing, customer experience and product leadership to ensure our defined growth, product/business outcomes, and customer satisfaction goals are met.

On a typical day, you will be working on: 

• Understanding customer needs, crafting a strategic product roadmap, and leading execution for one of our newest product initiatives
• Prioritizing feature requirements and partnering cross-functionally with R&D stakeholders (Design, Research, Engineering) to build a new 0-to-1 product
• Partnering closely with our go-to-market teams (marketing, customer success, sales, finance) to ensure successful product launches across multiple customer segments
• Driving up awareness, adoption, continual engagement and retention of new use cases that unlock more product capabilities within Calendly
• Defining and measuring the relevant objectives and key results (OKRs) and key performance measures to support strategy and roadmap decisions

What do we need from you?

• A minimum of 8-10 years of varied PM experiences across both startups and scaled companies; bonus points if you have been a founder in a SaaS company
• Keen product sense, UX design experience with a deep empathy for customers; highly motivated to build delightful and frictionless experiences for customers; bonus if you have used AI/ML to bring these experiences to life
• Experience in building 0-to-1 SaaS products and scaling from 1-to-100 in a product-led-growth environment
• Deep understanding and demonstrated experience building and monetizing teams-based productivity solutions in either a B2C or B2B
• The ability to work in our San Francisco office 2 days per week
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

About the team & opportunity 

What’s so great about working on Calendly’s Engineering team? 

We make things possible for our customers through innovation.

Why do we need you? Well, we are looking for a Full Stack Engineer who will bring technical know-how and enthusiasm to our team. You will report to one of our Engineering Managers and will be responsible for supporting features and architecture designed to maintain our users’ confidence in Calendly. 

A day in the life of a Full Stack Engineer at Calendly

The Calendly platform is a monolith that is being decomposed into various services in order for us to scale our platform and team. We need ambitious, experienced engineers who can help us drive this stage of growth. As an engineer at Calendly, you will both build new features and work to scale our platform and architecture. You will build tooling and automation to fine tune our delivery process as you grow into a service oriented specialist. You will also learn to work with multiple technologies such as Google Cloud Platform, Go, Typescript, NodeJS, React, PostgreSQL, Redis, Kubernetes, Rails, to name a few.

When you join Calendly, you get the opportunity to deliver on a product used by millions and known for its best-in-class quality. Help us continue to deliver critical features to our users with excellence.

On a typical day, you will be working on: 

• Collaborating within your team to build new features that are targeted at our highest impact enterprise customers
• Contributing to platform scaling initiatives
• Meeting regularly with Product and Design to fine tune requirements
• Attending agile ceremonies to help your team plan out their work and get it done
• Working across squads to improve Engineering practices at Calendly
• Reviewing implementation plans and pull requests from your peers
• Mentoring and coaching other team members

What do we need from you?

• 4-6 years of professional software development experience in a SaaS or technology-driven environment.
• Strong, hands-on full-stack engineering skills, with the ability to independently design, build, and ship production changes across frontend and backend systems
• Experience building and maintaining Node.js services that interface with distributed APIs, LLMs, or similar mixed-stack environments.
• Hands-on experience with Service-Oriented Architectures (SOA), microservices, and involvement in monolith-to-services modernization or large-scale refactoring initiatives.
• Proven ability to own features end-to-end, including technical discovery, design, implementation, testing, release, and ongoing maintenance.
• Strong analytical and problem-solving skills, with the ability to dissect complex systems, identify root causes of issues, and deliver scalable, maintainable solutions.
• A commitment to writing clean, reliable, and maintainable code, with an emphasis on readability, simplicity, and performance.
• Adaptability to new technologies, evolving architectural patterns, and changing organizational priorities.
• Experience using AI coding assistants (Copilot, Cursor, etc.) as productivity tools, with a clear understanding of generated code and the ability to defend implementation choices.
• Availability for participation in an on-call rotation, ensuring timely and effective responses to critical production issues outside of regular working hours.
• Authorized to work lawfully in the United States, as Calendly does not offer immigration sponsorship at this time.

A day in the life of a Senior Director, Growth Marketing at Calendly

What's so great about working on Calendly's Growth Marketing team?

Growth marketing is a key strategic bet for Calendly. We have a highly viral product by nature and therefore a funnel that has huge potential if optimized and leveraged correctly. At the same time we are sprinting to launching multiple new products this year. The Growth marketing team is key to both optimizing our scheduling funnel while building new funnels for our new products. We move fast, think boldly, and are deeply committed to telling stories that matter — and we're looking for a leader to help us do it at scale.

Why do we need you?

We are seeking an experienced and strategic Senior Director of Growth Marketing to lead our customer acquisition, retention, and revenue growth initiatives across digital and lifecycle channels. This leader will be responsible for building and scaling data-driven marketing strategies that accelerate growth, optimize funnel performance, and maximize customer lifetime value. They will own web, lifecycle marketing and upper funnel acquisition.

The ideal candidate combines strategic vision, analytical rigor, and team leadership, with a proven track record of driving measurable business results in high-growth environments. This role will partner cross-functionally with Product, Sales, Brand, Analytics, and Finance teams to deliver integrated growth programs aligned with company goals.

On a typical day, you will focus on:

Growth Strategy & Leadership

• Partner closely with the Growth Product leader to jointly define and drive unified company wide growth strategy, aligning product led and marketing led initiatives across the full customer lifecycle.
• Develop and execute the company’s comprehensive growth marketing strategy across acquisition, activation, retention, and re-engagement.
• Own growth KPIs including customer acquisition cost (CAC), conversion rates, customer lifetime value (LTV), retention, and revenue contribution.
• Identify and prioritize new growth opportunities through testing, experimentation, and channel expansion.
• Lead annual and quarterly growth planning, forecasting, and budget allocation.

Lifecycle & Retention Marketing

• Build lifecycle marketing strategies that improve onboarding, engagement, retention, and customer advocacy.
• Partner with CRM and product teams to develop personalized customer journeys across email, SMS, in-app, and push channels.
• Improve customer lifetime value through segmentation, automation, and upsell/cross-sell initiatives.

Web

• Own the website end to end
• Define goals and a roadmap to achieve them
• Partner with product marketing to ensure we tell compelling stories about our products that drive adoption
• Experiment to improve conversion rates
• Ensure the website is a highly optimized revenue driver but also an incredible experience as the front door to our brand

Demand Generation & Acquisition

• Oversee paid acquisition channels including paid search, paid social, affiliate, display, SEO, and partnerships.
• Optimize multi-channel campaigns to improve lead generation, customer acquisition, and ROI.
• Drive full-funnel demand generation strategies that align with sales and revenue targets.
• Evaluate and scale emerging acquisition channels.

Analytics & Experimentation

• Establish a culture of experimentation through A/B testing and performance optimization.
• Analyze funnel performance, attribution, and cohort behavior to identify growth opportunities.
• Build dashboards and reporting frameworks to track campaign effectiveness and business impact.
• Leverage data insights to inform strategic decisions and improve marketing efficiency.

Team Leadership & Cross-Functional Collaboration

• Build, mentor, and lead a high-performing growth marketing team.
• Collaborate closely with Product, Brand, Analytics, Finance, and Sales to align growth initiatives with business objectives.
• Foster a performance-driven culture focused on accountability, innovation, and continuous improvement.
• Manage external agencies, vendors, and marketing technology partners.

What do we need from you?

Basic Qualifications:

• 10+ years of progressive experience in growth marketing, demand generation, or performance marketing.
• 5+ years of leadership experience managing high-performing marketing teams.
• Proven success scaling customer acquisition and retention programs in fast-paced, high-growth environments.
• Deep expertise in paid media, lifecycle marketing, funnel optimization, and attribution.
• Strong analytical skills with experience using tools such as Google Analytics, Tableau, HubSpot, Marketo, or similar platforms.
• Experience managing significant marketing budgets and delivering measurable ROI.
• Excellent leadership, communication, and stakeholder management skills.

Preferred Qualifications:

• Strategic thinker with strong execution capabilities.
• Highly data-driven with a bias toward action and experimentation.
• Collaborative leader who thrives in cross-functional environments.
• Adaptable and comfortable navigating ambiguity in evolving business environments.
• Have an analytical and experimental mindset
• Understand customer journeys and how to design experiences that resonate with customers to take action

About the team & opportunity 

We’re looking for a hands-on Engineering Manager who blends strong people leadership with technical execution and a product-driven mindset. In this role, you’ll partner closely with the Director of Engineering in our Growth group to build a best-in-class scheduling experience—empowering users to host exceptional meetings while delivering the smoothest booking experience in the industry.

A day in the life of an Engineering Manager, Growth and Monetization

As an Engineering Manager at Calendly, you have the chance to mentor and grow some of the best and brightest engineers in the world. This role will work alongside our engineering, product, and design teams to make Calendly even simpler and more powerful for our user base. We are seeking a versatile technical leader who relishes the chance to work on impactful technology and can help accelerate and empower our development teams while helping us create the future of scheduling.

Top candidates bring clarity where there is ambiguity and can work autonomously to research and uncover solutions. If chosen for this role, you’ll be responsible for mentoring, coaching, and planning for the future of your team. At Calendly, you’ll have the opportunity to make a huge impact on the quality and development of a product impacting millions.

• Hiring engineers to build out both new and existing squads for the company, with oversight on all team members that get hired onto the squad
• Solving problems for millions of users, from local businesses to our largest enterprise customers
• Driving initiatives that reimagine how the world meets
• Coach, mentor, and onboard new engineering team members
• Ensure the career development, satisfaction, and productivity of the engineers on your team
• Identify future technical needs and create plans to meet them
• Provide feedback and guidance to help us continuously grow and scale 

What do we need from you?

• 5+ years experience managing a team of Software Engineers 
• 10+ years of overall development experience (Ruby on Rails is preferred, however other languages such as Python, Go, and PHP are accepted)
• Prior experience leading software development teams focused on Product Growth (including Activation, Retention, Onboarding and Monetization)
• Deep proficiency with web application development and SaaS
• Experience planning and leading development efforts on large projects
• Previous experience leading and mentoring teams and driving them toward big goals with consistent execution
• Previous experience in a service-oriented architecture. Bonus if you have experience migrating a monolith application into services
• You are an excellent communicator who can succinctly explain deep technical concepts
• Experience leading Agile/Scrum ceremonies
• Previous experience working within a balanced engineering and product team
• Experience with MVC frameworks for backend development 
• Availability for participation in on-call rotation, ensuring prompt and effective responses to business-critical alerts outside of regular working hours
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

About the team & opportunity
What’s so great about working on Calendly’s Engineering team? 

Calendly is the scheduling automation and meeting lifecycle platform used by millions of users for eliminating the back-and-forth emails to find the perfect time — and so much more. We are looking for an experienced and hands-on leader in the product development space. 

This is an exciting opportunity to create, drive, and evangelize a vision for Calendly’s shared services platform. In this role, you will lead a group of engineers that build critical core services depended upon by the wider product development organization. 

Why do we need you? Well, we are looking for an experienced Engineering leader who will bring operational maturity, technical subject-matter expertise, and the ability to empower the wider product development organization. 

A day in the life of a Senior Director, Engineering at Calendly 

On a typical day, you will be working on: 

• Defining and executing the vision and strategy for a key product area aligning with the Calendly’s goals and priorities 
• Supporting and mentoring a team of managers and engineers, providing technical guidance and coaching on their career development 
• Driving innovation and adoption of new technologies and methodologies that enhance Calendly’s services 
• Ensuring the quality, performance, security, and scalability of a product line of business following best practices and standards 
• Collaborating with other engineering teams, product managers, and stakeholders to understand the business requirements and deliver solutions that meet or exceed expectations
• Driving innovation and adoption of new technologies and methodologies that core capabilities and user experience

What do we need from you? 

• 15+ years of software engineering experience, with at least 10+ years in a leadership role
• Experience helping to build and scale an AI-first engineering organization, including integrating AI/ML capabilities into core services, developer workflows, and product strategy
• Experience leading high-performance engineering teams 
• Experience building highly-available distributed back-end systems 
• Comfortable working as a change-agent, and drive adoption of modern engineering methodologies 
• Knowledge of cloud platforms, such as GCP and their services and tools 
• Experience operating in both high-growth startup technology companies and larger, more established organizations, with the ability to adapt leadership style and processes to each
• Strong communication, collaboration, and problem-solving skills 
• Passion for delivering high-quality products and services that delight customers 
• Ability to iterate and ship fast 
• The ability to work in our San Francisco office 2 days per week
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

About the team & opportunity

*This is a hybrid role with an expectation of working in our San Francisco office two (2) times per week. 

We're looking for a Staff Product Designer for our Growth team, with an opportunity to drive the strategy on increasing overall customer engagement across a growing suite of interconnected Calendly products. You'll be identifying and executing on high impact experiments for solopreneurs and small teams engaging with key experiences, including our AI product suite, contact management experience, and commerce offerings, in a meaningful way.  As a key team member, you’ll be shaping the user experience for millions of users, designing simple and intuitive experiences that improve our users' day-to-day work.

We believe that great design starts with talking with our users and that the best solutions come from interdisciplinary collaboration. You’ll be part of Calendly’s incredible Design team, collaborating with Product Designers, Content Designers, UX Researchers, Product Managers, and Engineers. 

A day in the life of a Staff Product Designer on the Growth team at Calendly

On a typical day, you will:

• Lead design strategy and execution on high-impact experiments and experiences focused on improving growth funnels across the product
• Leverage quantitative and qualitative inputs to understand user habits and inform consecutive, iterative experiment loops
• Drive experimentation with a focus on curiosity, innovation, and a balance of users understanding and business impact
• Make high-quality decisions with incomplete data, iterating through shipping, learning, and updating
• Expertly communicating your design approach with strong storytelling, to inspire and align the cross-functional team to move in new directions
• Partner with designers, product managers, engineers, content designers, design systems, and researchers to improve and refine the Calendly experience
• Be an additive design team member by mentoring and collaborating with other designers, participating in critique, sharing expertise, and helping elevate design quality and culture

What do we need from you?

• 8+ years building and delivering experiences for digital products in product-led B2B or B2C companies
• 4+ years as a user oriented growth leader with experience partnering tightly with Product partners to build experiences that drive growth while remaining user focused
• Strong instincts around driving discovery, activation, and adoption of new products
• An expert understanding of the levers that balance business goals, team processes, and user needs
• A strong portfolio demonstrating strategic thinking, experiments of varying complexity and their impact on system-level solutions, and measurable impact on both customer experience and business outcomes
• Exceptional design storytelling and communication skills, with the ability to influence product direction and tradeoff decisions with senior leaders and cross-functional partners
• A track record of acting as a trusted design leader, mentoring designers, improving processes, and elevating design quality across teams
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

About the team & opportunity 

What’s so great about working on Calendly’s Data Science & Machine Learning team? 

We make things possible for our customers through innovation in data, analytics and AI.

Why do we need you? Well, we are looking for a Machine Learning Engineer who will deliver business value by executing the full machine learning lifecycle hands-on, from problem discovery through model deployment and monitoring. You will report to the head of Data Science & Machine Learning and will be responsible for building and operating ML-powered features that create magical experiences for our customers.

Our team:

• Drives business insights, strategic decision making, executive level and cross organizational business growth, and magical customer experiences for our end customers through impactful innovation.
• Works closely with product, design, marketing, customer success, and engineering teams to implement ML models that improve the customer journey in service to growth and efficiency (for example, understanding the relationships among customers’ behavior and business performance).
• Has a strong product focus and passion for using machine learning to solve real world problems, and understands that being an effective MLE is about collaborating with people as much as it is about writing code.

You will join a high performing AI team and be an integral part of building new, machine learning based experiences for internal and external customers alike.

What you’ll do

On a typical day, you’ll own features end to end within our ML ecosystem, with growing independence and impact.

• Own ML powered features from design through deployment, partnering with product, design, and engineering to scope work and define success metrics.
• Understand and share domain knowledge, answering domain specific questions for your product area and documenting what you learn for the team.
• Prioritize your work independently, balancing feature development, quality, and maintenance, and communicating tradeoffs clearly.
• Proactively seek and offer support to teammates pairing, reviewing, and collaborating to move projects forward.
• Understand and troubleshoot our deployment pipelines, including build, test, and release steps for ML services and data pipelines.
• Use our monitoring and observability tools to effectively triage alerts and incidents, collaborating with partners to restore service and prevent recurrence, and participate in the team’s on-call rotation and incident response. 
• Serve as a subject matter expert for the features and services you own, including their data contracts, SLAs, and dependencies.
• Be a frequent user of AI Tools and champion of adoption to the rest of the company.  

What do we need from you?

• 4+ years of industry experience in applied Machine Learning or closely related fields (or equivalent combination of education and experience) with a demonstrated track record of shipping and operating ML models in production.
• Deep and demonstrated ability to traverse the full spectrum of ML life cycle: exploratory data analysis, feature engineering, data visualization, feature and algorithm selection, model experimentation, model training and validation, model serving, monitoring and retraining
• Experience developing and implementing statistical and ML models to uncover patterns, trends, and predictions in areas such as revenue forecasting, churn analysis, personalization and recommendation, anomaly detection, or natural language processing.
• Hands-on experience implementing ML models using a managed service (for example, Vertex AI or SageMaker) for high-traffic, low-latency, large-data applications that produced tangible impact for end users.
• Understanding of foundation models and the open-source ecosystem, including model fine-tuning and prompt engineering for real product use cases.
• Strong programming (Python / Scala / Java / SQL etc) and data engineering skills
• Proficiency in ML frameworks such as: Keras, Tensorflow and PyTorch and ETL and ML workflow frameworks like Apache Spark, Beam, Airflow and VertexAI
• Experience working with time series data and related machine learning problems. Working knowledge of semantic search and embeddings 
• Recognize when to seek assistance and willing to learn whatever is needed to get the job done; curiosity and growth mindset are essential. 
• You have strong verbal and written communication skills. Ability to communicate complex technical concepts to both technical and business stakeholders. You are comfortable working remotely and with enabling tools like Slack, Confluence, etc.
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time 
  
  

What’s in it for you? 

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey. 

Our Hiring Process:

We aim to provide an inclusive and equitable candidate experience to everyone who expresses interest in working at Calendly. To learn more about our hiring process, please visit our careers page at www.careers.calendly.com.

Once selected for an opportunity, the recruiter assigned to the role will keep you informed every step of the way. Have questions? Let your recruiter know! Want to share your experience? We are passionately committed to improving and building on our process, and we consider feedback a gift. 

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please contact us at recruiting@calendly.com . 

Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Alabama, Delaware, Hawaii, Idaho, Montana, North Dakota, South Dakota, Nebraska, Iowa, West Virginia, and Rhode Island, you will not be eligible for employment. Note that all individual roles will specify location eligibility.

All candidates can find our Candidate Privacy Statement here

Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection

About the team & opportunity 

Calendly’s Foundational Product Capabilities organization is the backbone of how we build secure, reliable, and intelligent products at scale. We’re looking for an Engineering Manager to lead our Trust & Safety (T&S) And Identity & Access Management (IAM) engineering teams — the groups responsible for keeping our platform safe, secure, & compliant.

You’ll play a crucial role in shaping our platform’s security and integrity by leading both Identity & Access Management (IAM) and Trust & Safety initiatives. You'll design, develop, and maintain Identity, AuthN and AuthZ services that empower our engineering teams while ensuring scalability, resiliency, and performance. Simultaneously, you'll oversee our Trust & Safety efforts, and build capabilities for fraud prevention, abuse mitigation, and compliance through automated, real-time threat detection and response. You’ll partner closely with Product, Security, and Platform teams to shape how Calendly manages identity, authorization, and abuse prevention across current and future products. We value leaders who are excited to incorporate AI into engineering practices as well as into the products and platforms their teams own. Your technical expertise and leadership will directly influence platform architecture and engineering best practices, driving the success of our products.

Why do we need you? Well, we are looking for an Engineering Manager who has a strong background in people leadership; brings strong domain experience in these domains, technical competency and distributed systems experience; enjoys solving complex problems with a results driven mindset; and fosters a strong sense of ownership and operational excellence. You will report to the Head of Foundational Product Capabilities in this role.

A day in the life of an Engineering Manager, Identity & Trust at Calendly

As an Engineering Manager at Calendly, you have the chance to mentor and grow some of the best and brightest engineers in the world. You will provide hands-on mentorship, guidance, and decision-making to help engineering teams deliver effective, high-quality solutions — including when and how to apply AI/ML, automation, and data products to Identity, Auth and Trust & Safety problems. You will define and evolve our Identity capabilities to meet future demands while shaping the Trust & Safety roadmap in alignment with company priorities, emerging threats, and new opportunities created by AI. 

Top candidates bring clarity where there is ambiguity and can work autonomously to research and uncover solutions. If chosen for this role, you’ll be responsible for mentoring, coaching, and planning for the future of your teams. 

On a typical day, you will be working on:

• People Leadership: Recruit, manage, and mentor a diverse team of Identity and Trust & Safety engineers, fostering a culture of collaboration, accountability, and continuous improvement
• Technical Leadership: Provide hands-on mentorship, guidance, and decision-making to help engineering teams deliver effective, high-quality solutions
• Planning & Execution: Own and drive execution on critical initiatives, ensuring timely, high-quality outcomes while promoting incremental delivery and impact
• Vision & Strategy: Define and evolve our Identity and Access management capabilities to meet future demands while shaping the Trust & Safety roadmap in alignment with company priorities and emerging threats
• Operational Excellence: Design and implement scalable systems to detect, prevent, and respond to fraud and abuse, leveraging key metrics to measure effectiveness
• Cross-Functional Collaboration: Partner with Product, Security, Design, Engineering, Legal, and Compliance teams to embed security and safety considerations throughout the development lifecycle
• Architectural Design: Shape technical strategy and North Star Architecture while guiding the design and implementation of key services and components

What do we need from you?

• 5+ years experience as a people leader within a platform engineering organization
• Domain expertise with customer-facing Identity & Access Management (IAM)  And/Or Trust & Safety 
• Strong technical acumen with a deep understanding of design of detection and prevention systems, and a practical understanding of how to apply machine learning and AI to Trust & Safety and/or security problems
• Deep understanding of distributed systems and cloud computing
• Experience building, operating, and maintaining high-traffic, high-availability platforms and systems
• Excellent problem-solving skills and the ability to analyze complex systems to identify root causes and implement effective mitigations and resolutions
• Demonstrated ability to drive innovation and propose new solutions or improvements that align with organizational goals
• Strong communication and interpersonal skills, with the ability to convey complex technical concepts to non-technical stakeholders
• Proven leadership capabilities with experience mentoring and guiding engineering teams
• Ability to adapt to new technologies, changing requirements, and evolving organizational needs
• Availability for participation in on-call rotation, ensuring prompt and effective responses to business-critical alerts outside of regular working hours
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

What’s in it for you?

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a phenomenal time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional career.

About the team & opportunity 

What’s so great about working on Calendly’s Security team? 

Calendly is growing rapidly and is scaling its security team to ensure the security of its users. You will have the chance to work with a small team of exceptional security engineers to build Calendly’s security practice from the ground up. 

Why do we need you? Well, we are looking for a Security Automation Engineer who will help scale Calendly’s security impact through thoughtful automation and engineering. You will report to the Head of Product Security and operate as a shared service across the broader Security organization, partnering with Product Security, Security Operations, and GRC to design and build automation that reduces risk, improves efficiency, and enables teams to move faster. You’ll bring strong software engineering skills, a systems mindset, and curiosity about security domains along with a passion for leveraging modern tools (including AI) to accelerate development and problem solving.

A day in the life of a Security Automation Engineer at Calendly

On a typical day, you will be working on: 

• Identifying opportunities to eliminate manual security workflows and replace them with scalable, automated solutions
• Building internal tools and integrations that automate processes such as vulnerability triage and prioritization, alert enrichment and routing, and GRC evidence collection
• Partnering with security and engineering stakeholders to understand pain points and translate them into practical technical solutions
• Designing and building reusable “paved road” solutions that standardize how security workflows are executed across teams
• Using AI-assisted development tools and LLM APIs to accelerate implementation
• Continuously improving, maintaining, and scaling solutions to handle increasing volume, complexity, and organizational needs
• Supporting Product Security workflows as needed, such as security reviews, vulnerability triage, or tooling
• Supporting the secure usage and development of AI/LLM-powered features across Calendly as needed

What do we need from you?

• 3+ years of professional software engineering experience, with the ability to build and maintain production-quality systems, services, or automation
• Proficiency in at least one modern programming language (Python, Go, Ruby, or TypeScript preferred)
• Experience building integrations with APIs and cloud-native architectures. GCP experience is a plus.
• Strong system design skills, with the ability to build scalable, maintainable automation solutions and improve complex workflows
• Experience working across multiple domains and partnering with diverse stakeholders
• Strong communication skills, with the ability to translate ambiguous problems into clear technical solutions and explain tradeoffs to diverse stakeholders
• Foundational knowledge of common security concepts, tools, and domains such as application or cloud security.
• Experience using modern AI tools (Claude, Copilot, ChatGPT, or similar) to accelerate development workflows
• Curiosity and willingness to learn new security domains quickly
• Understanding of Kubernetes and cloud-native systems
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

What’s in it for you? 

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey. 

Our Hiring Process:

We aim to provide an inclusive and equitable candidate experience to everyone who expresses interest in working at Calendly. To learn more about our hiring process, please visit our careers page at www.careers.calendly.com.

Once selected for an opportunity, the recruiter assigned to the role will keep you informed every step of the way. Have questions? Let your recruiter know! Want to share your experience? We are passionately committed to improving and building on our process, and we consider feedback a gift. 

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please contact us at recruiting@calendly.com . 

Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Alabama, Delaware, Hawaii, Idaho, Montana, North Dakota, South Dakota, Nebraska, Iowa, West Virginia, and Rhode Island, you will not be eligible for employment. Note that all individual roles will specify location eligibility.

All candidates can find our Candidate Privacy Statement here

Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection

About the team & opportunity

As a Senior Software Engineer on the Support Engineering team, you’ll have the opportunity to shape and scale the internal tools, integrations, and in product capabilities that power our go to market teams. You’ll work closely with Sales, Marketing, and Customer Success to uncover operational gaps and turn them into thoughtful, high impact solutions. This role offers end to end ownership including defining problems and architecting systems to building, launching and continuously improving them. It’s a chance to blend deep technical expertise with cross functional collaboration in a highly visible, business critical area. Your work will directly enable teams to move faster, operate more effectively, and deliver a better experience to our customers. Experience with Go, Ruby and React is a plus.

A day in the life of a Senior Full Stack Engineer at Calendly

• Design, build, and operate services and APIs for contacts, companies, syncing third party data sources, deduplication, enrichment, and search - prioritizing reliability, performance, and maintainability.
• Partner with Product and Design to shape requirements, sequence milestones, and deliver incremental value that supports our customers..
• Contribute to our data model and storage strategies for people and related objects, ensuring consistency, privacy, and scalability.
• Improve platform resilience with robust observability, fault-tolerant patterns, and production readiness; participate in on-call to support business critical services.
• Collaborate with adjacent squads to evolve architecture and shared components; participate in code reviews and provide mentorship to peers.
• If you have React/TypeScript experience, contribute to end to end delivery by partnering on UI contracts and occasionally implementing UI that integrates with your services.

On a typical day, you will be working on: 

• Design, build and maintain internal tools, integrations and in product features that enable Sales, Marketing and Customer Success teams to operate efficiently and scale.
• Partner closely with cross functional stakeholders to identify pain points, define requirements, and deliver high impact, user centric solutions.
• Own projects end to end, from discovery and system design through implementation, testing, deployment and ongoing iteration.
• Ensure reliability, performance and scalability of systems while continuously improving developer workflows and internal user experience.

What do we need from you?

• 7-10+ years of professional software development experience, including owning production services at scale in a SaaS environment.
• Strong proficiency in backend development, building services, APIs, and data-intensive backend workflows. Must-have.
• Experience designing for scalability, reliability and observability in cloud environments (GCP preferred) with container orchestration (Kubernetes).
• Experience with service oriented architectures and modernizing or decomposing legacy systems to services where appropriate.
• Proficient with relational databases (PostgreSQL preferred) and data modeling for complex domains.
• Bias for clean, maintainable code, thoughtful testing and incremental delivery; strong collaboration and communication skills.

Nice to have:

• Frontend experience with React and TypeScript or a strong interest in partnering closely on UI contracts and end-to-end delivery.
• Experience with microfrontends, Node services, Rails ecosystems, and event-driven architectures.

Other requirements:

• Availability to participate in an on-call rotation for critical services.
• Authorized to work lawfully in the United States of America, as Calendly does not engage in immigration sponsorship at this time.

A day in the life of a Director, Brand and Advocacy at Calendly

What's so great about working on Calendly's Marketing team?

We are the team behind how millions of people discover, understand, and fall in love with Calendly. From shaping our brand narrative to mobilizing customers and employees as authentic advocates, our Marketing team drives the awareness and affinity that fuels Calendly's growth. We move fast, think boldly, and are deeply committed to telling stories that matter — and we're looking for a leader to help us do it at scale.

Why do we need you?

We are looking for a Director of Brand and Advocacy who will bring strategic vision, operational excellence, and a genuine passion for brand storytelling to one of our most critical functions. You will report to the Vice President, Brand and Product Marketing and be responsible for owning Calendly's brand amplification strategy across social media, PR and communications, and customer advocacy channels. You will lead a talented team — a Social Media Lead, a Customer Advocacy Lead, and a PR Contractor — and be accountable for both the channel programs that maximize distribution and the compelling content and campaigns that feed them. You will also serve as a key cross-functional partner to our Internal Communications and Employee Experience teams, helping to activate employees as authentic brand voices.

On a typical day, you will:

• Define and evolve Calendly's integrated brand amplification strategy, setting a 1–3 year vision for how we show up across social, PR, and advocacy channels to grow awareness, share of voice, and brand affinity. Translate company and product priorities into coordinated programs that make Calendly's story impossible to ignore.
• Lead and develop your team — a Social Media Lead, Customer Advocacy Lead, and PR Contractor — by setting clear goals, providing coaching, and creating an environment where each person can do their best work. Hold the team accountable to outcomes while removing blockers and advocating for resources needed to execute.
• Oversee Calendly's social media strategy and execution, partnering with the Social Media Lead to develop platform strategies, content pillars, editorial calendars, and channel-specific playbooks that grow reach and drive meaningful engagement. Ensure social content is on-brand, audience-first, and connected to the broader marketing narrative.
• Guide and provide strategic direction to our PR contractor, helping shape Calendly's narrative, prioritize media opportunities, and ensure PR efforts are tightly connected to broader brand and business goals. Serve as the internal voice of the brand in all communications decisions, translating company priorities into clear story angles and messaging frameworks the PR contractor can execute against.
• Build and scale customer advocacy programs that identify, activate, and nurture brand champions — turning customer success into reviews, testimonials, case studies, speaking opportunities, and community engagement that amplify Calendly's story at scale. Design the systems and incentive structures that make participation easy and sustainable.
• Partner with Internal Communications, Employee Experience, and the Social Media Lead to activate employees as authentic brand voices on social and professional networks. Provide strategic direction, content toolkits, and brand guidance that makes it easy for employees to share Calendly's story in ways that feel genuine and impactful.
• Partner cross-functionally with creative, product marketing, demand gen, and executive communications teams to develop compelling content and campaigns that feed all brand and advocacy channels. Ensure creative quality, message consistency, and strong alignment between brand moments and business objectives.
• Establish KPIs and a reporting cadence to measure the impact of brand, PR, and advocacy programs — tracking reach, share of voice, engagement, and pipeline influence. Use data and insights to continuously optimize strategy and communicate program effectiveness to senior leadership.

What do we need from you?

Basic Qualifications

• 15+ years of progressive experience in brand, communications, or marketing roles, with at least 3 years in a director-level or equivalent senior leadership position managing cross-functional teams.
• Demonstrated track record of developing and scaling integrated brand amplification strategies across social media and customer advocacy channels, with the ability to set strategic direction for PR and communications efforts executed by agency or contractor partners.
• Proven experience leading and developing direct reports and contractor/agency relationships, with a strong track record of building high-performing, accountable teams.
• Deep expertise in B2B social media strategy and content development, including platform best practices across LinkedIn, X (Twitter), and other key channels relevant to a SaaS audience.
• Comfort working with and providing strategic guidance to PR contractors or agency partners — able to set messaging direction, prioritize story opportunities, and evaluate PR output without needing to be a hands-on media relations practitioner.
• Experience building or scaling customer advocacy, reference, or community programs — including reviews, testimonials, brand ambassadors, and customer marketing initiatives.
• Data-driven mindset with the ability to establish KPIs, measure program effectiveness across channels, and translate insights into strategic decisions.
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time.

Preferred Qualifications

• Experience in B2B SaaS or technology companies, ideally in a product-led growth environment where brand and advocacy play a key role in the growth flywheel.
• Familiarity with customer advocacy platforms (e.g., Influitive, Khoros, or similar) and community management tools used to manage and scale advocate programs.
• Experience partnering with internal communications or people teams to shape employee-facing brand initiatives, or familiarity with employee advocacy platforms (e.g., EveryoneSocial, Bambu) as a collaborator or sponsor of the program rather than a primary operator.
• Strong existing relationships with B2B technology, productivity, or SaaS media contacts that can be activated for Calendly's benefit.
• Experience launching integrated brand campaigns from concept through execution, including partnering with creative and design resources to develop compelling content.
• Background spanning both in-house and agency environments, with a strong understanding of how to set clear scopes of work and get the most from contracted relationships.

A day in the life of a Director, Customer Education at Calendly

What’s so great about working on Calendly’s Marketing team?

We are the team behind how millions of people discover, understand, and get value from Calendly. Our Marketing team spans brand, product marketing, and customer education — working in close partnership with Product, Sales, and Customer Success to shape the story we tell and ensure customers have what they need to succeed. We move fast, think ambitiously, and care deeply about the quality of what we put into the world. As Calendly expands its product portfolio, education has never been more central to how we grow.

Why do we need you?

We are looking for a Director, Customer Education who will define and lead a full-funnel educational content strategy for Calendly — one that spans product demos, feature education, the Calendly Learning Hub, and Help Center content. This is a high-impact leadership role for someone who thinks beyond content production and sees education as a strategic lever for customer activation, adoption, and long-term retention.

You will report to the Vice President, Brand & Product Marketing and lead a team of content specialists. You will be responsible for both the strategy and the execution — setting the vision for how Calendly educates its customers across the full lifecycle, and building the systems, content, and team capabilities to deliver it at scale. You will serve as a key cross-functional partner to Product Marketing, Product, and Customer Success, ensuring that education content is a core part of every product launch and customer journey.

On a typical day, you will:

• Define and evolve Calendly’s Customer Education strategy, setting a clear vision for how educational content — video demos, self-serve tutorials, Help Center articles, Learning Hub courses, and live programming — maps to customer segments, product surfaces, and lifecycle stages from onboarding through deep feature adoption.
• Lead and develop your team of education specialists and multimedia content producers, setting clear goals, providing coaching, and building an environment where each person can do their best work. Hold the team accountable to outcomes while advocating for the resources needed to execute.
• Partner closely with Product Marketing to ensure education content is embedded in every product launch — developing Help Center articles, demo videos, feature walkthroughs, and in-product guidance that help customers understand and adopt new capabilities quickly.
• Partner with Customer Success and Support to identify where customers are getting stuck, surface education content gaps that are contributing to support volume or churn risk, and build content that proactively answers the questions customers have before they need to ask.
• Build and scale the Calendly Learning Hub as a best-in-class self-serve education destination — developing a curriculum strategy, overseeing course development, and creating a content roadmap that keeps pace with Calendly’s product evolution.
• Raise the bar on multimedia content quality across the education function, partnering with your multimedia producer and the broader creative team to develop demo videos, feature tutorials, and educational experiences that are compelling, on-brand, and built for how customers actually learn.
• Establish KPIs and a reporting cadence to measure the impact of education content — tracking metrics like feature activation rates, Help Center deflection, Learning Hub engagement, and time-to-value for new users. Use data and insights to continuously improve strategy and communicate program effectiveness to senior leadership.
• Build the operational systems and workflows that allow your team to produce high-quality content at the speed of Calendly’s product cadence, including processes for content planning, review, localization, and maintenance.

What do we need from you?

Basic Qualifications

• 15+ years of progressive experience in customer education, content strategy, instructional design, or a related field, with at least 3 years in a director-level or equivalent senior leadership role managing teams.
• Demonstrated track record of building and scaling a full-funnel customer education function in a B2B SaaS or technology environment — not just managing an existing content operation.
• Experience developing education content strategy across multiple formats, including video and multimedia, written documentation, and structured learning programs.
• Proven ability to partner cross-functionally with Product, Product Marketing, and Customer Success to align education content with product launches and customer lifecycle milestones.
• Strong track record of leading and developing direct reports, with experience building high-performing, accountable teams.
• Excellent editorial judgment across written and multimedia formats, with a high bar for content quality, clarity, and brand consistency.
• Data-driven mindset with the ability to establish KPIs, measure the business impact of education content, and translate insights into strategic decisions.
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time.

Preferred Qualifications

• Experience at a multi-product SaaS company managing education content across more than one product line or customer segment.
• Familiarity with Learning Management Systems (LMS), knowledge base platforms (e.g., Zendesk Guide, Guru), and video production workflows for educational content.
• Background in instructional design or curriculum development, with experience creating structured learning experiences for adult learners.
• Experience building or overseeing a multimedia or video content production function, including partnering with producers and creative teams to develop high-quality educational video at scale.
• Experience working within a brand and marketing organization, with an understanding of how education content fits into a broader go-to-market and brand strategy.
• Familiarity with Calendly’s product and the scheduling, calendar management, or meeting intelligence category.

About the team & opportunity

What’s so great about working on Calendly’s Engineering team?

We make things possible for our customers through innovation.

We are looking for a Full Stack Engineer for the Commerce Squad who brings strong user empathy, clear product intuition, and solid engineering skills to a team that powers how customers discover, buy, and get value from Calendly. You will report to one of our Engineering Managers and will be responsible for shipping high‑impact features quickly and safely to support revenue growth and a best‑in‑class commerce experience. We are a pragmatic, high‑trust group with a professional casual style, low ego, and a bias for action. This role is a good fit for an engineer who is entrepreneurial, scrappy, and motivated by delivering user value fast.

We also expect engineers to leverage AI in their daily workflow to increase velocity and quality, exercising sound judgment, performing rigorous human review, and following company AI usage guidelines.

What we especially value on Commerce

We value an entrepreneurial approach and scrappy execution. You make pragmatic trade offs and prefer MVPs and iterative experimentation that deliver user value fast.

A day in the life of a Full Stack Engineer at Calendly

The Calendly platform is a monolith that is being decomposed into various services so we can scale our platform and our team. We need ambitious experienced engineers who can help us drive this stage of growth. As an engineer at Calendly, you will both build new features and work to scale our platform and architecture. You will build tooling and automation to improve our delivery process as you grow into a service oriented specialist. You will also learn to work with multiple technologies such as Google Cloud Platform, Kubernetes, Argo Workflows, TypeScript, Rails, Node.js, React, PostgreSQL, Redis, and GraphQL.

When you join Calendly, you get the opportunity to deliver on a product used by millions and known for its best‑in‑class quality. Help us continue to deliver critical commerce features to our users with excellence.

On a typical day, you will be working on:

• Collaborating within your squad to build and iterate on commerce features that drive measurable business impact across self‑serve and enterprise customers.
• Contributing to platform scaling initiatives while improving reliability and performance in user critical flows.
• Meeting regularly with Product and Design to fine tune requirements, define MVPs, and instrument experiments that validate value quickly.
• Attending agile ceremonies to help your team plan out their work and get it done with predictable delivery.
• Working across squads to improve engineering practices and evolve shared monorepo tooling and service boundaries.
• Reviewing implementation plans and pull requests from your peers with a focus on simplicity, maintainability, and incremental delivery.
• Contributing to a high trust, professional casual culture grounded in respect and ownership.
• Using AI assistants thoughtfully to scaffold code, generate tests, draft documentation, analyze logs, and accelerate experiments. Choosing when not to use AI based on risk, privacy, and correctness considerations.

What do we need from you?

• 3+ years of professional software development experience in a SaaS or technology driven environment.
• Strong proficiency in React and TypeScript for modern front end web development, supporting end to end feature delivery.
• Professional experience in backend engineering with Node.js, including building and maintaining scalable services and APIs that are observable, reliable, and secure.
• Experience with PostgreSQL, including schema design, query optimization, and data modeling for transactional systems.
• Experience designing and consuming GraphQL APIs in production environments.
• Background in mixed stack environments, such as Node.js services interfacing with a Ruby on Rails monolithic API, or similar mixed stack environments.
• Hands-on experience with Service Oriented Architecture (SOA), microservices, and involvement in monolith to services modernization or large scale refactoring initiatives.
• Proven ability to own features end to end, including technical discovery, design, implementation, testing, release, and ongoing maintenance, with a bias toward small, incremental, high quality releases.
• Strong analytical and problem solving skills, with the ability to dissect complex systems, identify root causes, and deliver scalable, maintainable solutions.
• A commitment to writing clean, reliable, and maintainable code, with an emphasis on readability, simplicity, and performance.
• Adaptability to new technologies, evolving architectural patterns, and changing organizational priorities.
• Availability for participation in an on call rotation, ensuring timely and effective responses to critical production issues outside of regular working hours.
• Comfort and proficiency using AI tools in engineering workflows to increase velocity and quality, including effective prompt craft, critical review of outputs, and responsible data handling in line with privacy and security expectations.
• Authorized to work lawfully in the United States, as Calendly does not offer immigration sponsorship at this time.

What’s in it for you? 

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey. 

About the team & opportunity 

We are looking for a hands-on Engineering Manager who combines people leadership with a strong background in technical execution and a product mindset. You will work directly with our Senior Director of Engineering, partnering closely with product, design, data, security, and go‑to‑market stakeholders to define and deliver the roadmap for new Scheduling products. 

What you'll bring:

• A track record of leading teams that build and operate highly-available products at scale.
• A coaching mindset that grows engineers through clear expectations, actionable feedback, and regular performance and career conversations.
• Strong technical judgment in distributed, service-oriented architectures and API design, with the ability to navigate trade-offs and guide engineers through complex decisions.
• Comfort operating in ambiguous, cross-functional environments — partnering with Product, Design, Security, CX, and GTM to align on priorities and outcomes.
• A bias for action, measurable outcomes, and continuously improving how your team executes, ships, and operates its services.
• Ability to balance technical execution with team development and stakeholder management.

A day in the life of an Engineering Manager at Calendly

As a Manager at Calendly, you have the chance to mentor and grow some of the best and brightest engineers in the world. This role will work alongside our other Engineering teams to make Calendly even simpler and more powerful for our user base. 

We are seeking a versatile technical leader who relishes the chance to work on impactful technology and can help accelerate and empower our development teams while helping us create the future of scheduling. At Calendly, you’ll have the opportunity to make a huge impact on a product used by millions.

On a typical day, you will be: 

• Working on products and services aimed at simplifying scheduling for millions of users
• Leading agile ceremonies to help your team plan out their work and get it done
• Coaching, mentoring, and onboarding new engineering team members
• Identifying future technical needs and creating plans to meet them
• Providing feedback and guidance to help us continuously grow and scale 
• Hiring engineers to build out both new and existing squads for the company, with oversight on all team members that get hired onto the squad

What do we need from you?

• 2+ years experience managing a team of Software Engineers 
• 5+ years of overall development experience, ideally using TypeScript, Node.js, and React
• Deep proficiency with distributed / data-oriented application development and SaaS
• Experience planning and leading development efforts on large projects
• Previous experience leading and mentoring teams and driving them toward big goals with consistent execution
• Excellent communication skills, with the ability to succinctly explain deep technical concepts
• Experience leading Agile / Scrum ceremonies
• Availability for participation in on-call rotation, ensuring prompt and effective responses to business-critical alerts outside of regular working hours
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

What’s in it for you? 

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey. 

About the Team & Opportunity? 

The GTM Operations team at Calendly is the engine behind how we go to market, building the systems, programs, and capabilities that help our Sales, Customer Success, and Support teams perform at their best. As Senior Manager, GTM Enablement, you’ll lead a small team of two enablement professionals and own the full enablement lifecycle across our Sales, Customer Success, and 24/7 Support organizations. You’ll report directly to the Senior Director, GTM Operations.

This is a role for a builder: someone energized by designing programs that actually move the needle, not just delivering training for training’s sake. You’ll partner closely with GTM leadership, Product Marketing, and Product to ensure our teams are equipped to sell, support, and succeed.

A day in the life of a Senior Manager, GTM Enablement at Calendly

What’s so great about working on Calendly’s GTM Operations Team team? 

We are a lean, high-impact team that moves fast and takes pride in building things that actually work. You’ll have the autonomy to shape how enablement runs at Calendly, with the support of a team and leadership who value your expertise.

Why do we need you? We’re looking for someone who brings a builder’s instinct, a systems mindset, and genuine passion for developing people to own end-to-end enablement across Sales, Customer Success, and our 24/7 Support organization.

On a typical day, you will: 

• Design and deliver full-lifecycle enablement programs (onboarding, product training, skill-building, and ongoing process training) across our Sales & Customer Success and 24/7 Support organizations
• Lead and develop your team of two as a player-coach, building and delivering programs yourself while delegating, mentoring, and raising the bar for the team
• Define repeatable operating playbooks and program cadences for GTM initiatives (launches, operational changes, vertical programs), partnering cross-functionally with Sales, Support, Product Marketing, GTM Ops, and Product 
• Own release and launch readiness for all customer-facing teams, defining the activities, workflows, and deliverables (trainings, documentation, etc.) tied to each release tier and playbook, in partnership with Product and Product Marketing
• Own and build out Calendly's GTM coaching and quality programs — including a Sales coaching program leveraging tools like Gong and a Support QA program with a focus on auto-QA 
• Build and own a Support QA program (with a focus on auto-QA) and a Sales coaching program leveraging tools like Gong
• Build and maintain a mix of live and asynchronous training experiences, including hands-on, demo-based formats that reflect how our teams actually work
• Build AI-native enablement experiences that help our teams learn and apply skills faster
• Define and track measurable impact metrics for all enablement programs, connecting training to business outcomes
• Partner with GTM managers and senior leaders to identify skill gaps and design targeted 1:1 training support for individuals who need additional development

What do we need from you?

Basic Qualifications

• 10+ years of experience in GTM enablement, learning & development, or a closely related function, with at least 4 years managing a team
• Experience in a SaaS environment with a strong understanding of Sales and Customer Success motions
• Proven track record building full-lifecycle enablement programs with measurable, data-driven outcomes
• Strong command of enablement technology (e.g., Gong, Seismic, Lessonly, LMS platforms, QA tools) and instructional design best practices
• Excellent written and verbal communication skills; comfortable presenting to and influencing senior leadership
• A builder’s mindset: you prototype, iterate, and define the path forward without waiting for permission

Preferred Qualifications

• Experience enabling 24/7 support teams, including designing QA programs with auto-QA tooling
• Hands-on experience building AI-native or AI-assisted training experiences; you’ve prototyped with tools yourself, not just managed a team that did
• Demonstrated ability to operate credibly with senior GTM leaders and in executive forums
• Experience setting annual enablement strategy and translating it into a clear operating plan across multiple teams and stakeholders

About the team & opportunity 

*This is a hybrid position located in the Bay Area; the expectation is to go into the San Francisco office 2 times per week.

Calendly is expanding from a scheduling tool into a multi-product platform powered by AI. We are hiring a Staff Product Manager, New Products to lead 0→1 innovation, focusing on creating new product experiences that transform how solopreneurs and small businesses run and grow their business.

This is a highly entrepreneurial, high-visibility, high-autonomy role for a PM who thrives in ambiguous spaces, partners well with leadership, and loves building new product lines from scratch.

What's Great About Working on Calendly's Product Team

We design seamless product experiences that delight our customers. Calendly takes the work out of scheduling so our customers have more time to focus on what matters most. Millions of people worldwide use our software every day — with thousands more signing up daily.

As a Staff Product Manager, New Products, you'll have the rare opportunity to shape the future of Calendly's multi-product strategy. This role is focused on incubating and validating new 0-to-1 product ideas, with many of these ideas leveraging the power of AI. You'll explore bold concepts, test hypotheses quickly, and partner closely with engineering and design to bring new solutions to life.

Your Mission

Build the next generation of Calendly products. Your charter is to identify, incubate, and scale new product experiences that:

• Extend Calendly's value beyond scheduling into new product lines powered by AI
• Drive retention, and new revenue
• Deliver net-new value that delights solopreneurs and small businesses
• Leverage AI to create experiences that feel intelligent, proactive, and effortless

You will own discovery, strategy, launch, and lifecycle ownership — including defining and delivering the success metrics for activation, adoption, revenue expansion, and customer satisfaction.

A Day in the Life

This position reports to our Chief Product Officer. You'll thrive in an environment where creativity and experimentation are encouraged, and where speed matters as much as precision.

On a typical day, you will:

• Lead discovery and validation of new product ideas, including rapid prototyping and customer testing
• Explore how AI can power new experiences across scheduling, meetings and beyond
• Collaborate with R&D (Engineering, Design, Research) to build MVPs and experiments that unlock high-potential opportunities
• Partner with leadership to align new initiatives with Calendly's long-term multi-product vision
• Define success metrics and run experiments to quickly evaluate product-market fit

What Makes This a True 0→1 Role

You will:

• Define entirely new product experiences
• Build rapid prototypes and Minimum Delightful Products
• Validate problems, define user segments, and drive upgrades
• Create the product narrative, roadmap, and long-term strategy
• Own the execution path from concept → beta → GA → scale
• Influence the future of Calendly’s evolution 

This is not optimization work — this is category creation.

AI + LLM Technologies You'll Leverage

You will have access to Calendly's rapidly evolving AI Platform and modern LLM capabilities, including:

• LLM-powered contextual reasoning (OpenAI + future models)
• Evaluation frameworks to measure AI quality, accuracy, and reliability across features
• AI tools for prototyping to rapidly iterate on UI designs 
• Agentic tasks and workflows
• AI-assisted generation, summarization, and relationship insights

Cross-Functional Partnership

You will collaborate closely with:

• CPO — product vision and multi-product strategy
• Director of AI Products — AI platform, vision, and product alignment
• XFN: Engineering, ML/AI, Design, Data Science, GTM, Support

You are expected to lead through clarity, influence, and crisp decision-making.

What We Need From You

• 8–10 years of PM experience across startups and scaled companies; bonus points if you've been a founder or early employee at a SaaS company
• Track record of building 0-to-1 products and validating new ideas in ambiguous environments
• Strong product sense and customer empathy; able to translate insights into bold, differentiated solutions
• Experience, curiosity, and eagerness to explore what's possible with AI is a must
• Ability to work in our San Francisco office 2–3 times per week
• Authorized to work lawfully in the United States (Calendly does not engage in immigration sponsorship at this time)

Why You'll Love This Role

• Build one of Calendly's next-generation product lines
• Launch capabilities that reach millions of users
• Define new revenue lines for the company
• Operate like an entrepreneur with access to Calendly's massive distribution, brand, and customer base
• Create products at the intersection of AI, productivity, and relationships

About the team & opportunity 

What’s so great about working on Calendly’s Engineering team? 

We make things possible for our customers through innovation, and we have fun while doing it.

Why do we need you?

Well, we are looking for a Full Stack Engineer who will bring technical know-how and enthusiasm to our team. You will report to one of our Engineering Managers and will be responsible for supporting features and architecture designed to maintain our users’ confidence in Calendly.

A day in the life of a Full Stack Engineer at Calendly

The Calendly platform is a monolith that is being decomposed into various services in order for us to scale our platform and team. We need ambitious, experienced engineers who can help us drive this stage of growth. As an engineer at Calendly, you will both build new features and work to scale our platform and architecture. You will build tooling and automation to fine tune our delivery process as you grow into a service oriented specialist. You will also learn to work with multiple technologies such as Google Cloud Platform, Go, Typescript, NodeJS, React, PostgreSQL, Redis, Kubernetes, Rails, to name a few.

When you join Calendly, you get the opportunity to deliver on a product used by millions and known for its best-in-class quality. Help us continue to deliver critical features to our users with excellence.

On a typical day, you will be working on: 

• Collaborating within your team to build new features that are targeted at our highest impact enterprise customers
• Contributing to platform scaling initiatives
• Meeting regularly with Product and Design to fine tune requirements
• Attending agile ceremonies to help your team plan out their work and get it done
• Working across squads to improve Engineering practices at Calendly
• Reviewing implementation plans and pull requests from your peers
• Mentoring and coaching other team members

What do we need from you?

• 3-5 years of professional software development experience in a SaaS or technology-driven environment.
• Strong proficiency in front-end web development using React and TypeScript, with an understanding of backend engineering principles and practices.
• Experience building and maintaining Node.js services that interface with distributed APIs, or similar mixed-stack environments.
• Hands-on experience with Service-Oriented Architectures (SOA), microservices, and involvement in monolith-to-services modernization or large-scale refactoring initiatives.
• Proven ability to own features end-to-end, including technical discovery, design, implementation, testing, release, and ongoing maintenance.
• Strong analytical and problem-solving skills, with the ability to dissect complex systems, identify root causes of issues, and deliver scalable, maintainable solutions.
• A commitment to writing clean, reliable, and maintainable code, with an emphasis on readability, simplicity, and performance.
• Adaptability to new technologies, evolving architectural patterns, and changing organizational priorities.
• Experience using AI coding assistants (Copilot, Cursor, etc.) as productivity tools, with a clear understanding of generated code and the ability to defend implementation choices.
• Availability for participation in an on-call rotation, ensuring timely and effective responses to critical production issues outside of regular working hours.
• Authorized to work lawfully in the United States, as Calendly does not offer immigration sponsorship at this time.

About the team & opportunity 

*This is a hybrid position located in the Bay Area; the expectation is to go into the office 1-3 times a week.*

What’s so great about working on Calendly’s Product team?

We strive to design a seamless product experience that delights our customers.

Calendly takes the work out of scheduling so our customers have more time to work on what’s really important. Our software is used by millions of people worldwide—with thousands more signing up every day. We’re continually looking for top talent to join our team as we help shape the future of our product. 

We strive to design a seamless product experience that delights our customers.

Why do we need you? Well, we are looking for a Senior Director of Product Growth who will play a pivotal role in leading and executing our product growth strategy by overseeing the development and optimization of our product portfolio.

A day in the life of the Senior Director of Product  Growth at Calendly

This position will report to our Chief Product Officer. You will be responsible for driving key initiatives for the entire business. You will collaborate closely with cross-functional teams, including Marketing, Sales, Engineering, and Customer Success, to align our product roadmap with market demand and customer needs. This position requires a strong blend of business insight, product management expertise, and strategic thinking. 

On a typical day, you will be working on:

• Developing and executing on the company's product growth strategy, aligning it with overall business goals and market dynamics
• Identifying growth opportunities, market trends, and customer insights to inform product development and expansion plan
• Overseeing the entire customer & user lifecycle, from acquisition and activation all the way through monetization and expansion
• Using data-driven insights to guide decision-making and validate product development initiatives
• Collaborating closely with the Sales and Marketing teams to define go-to-market strategies, product positioning, and messaging
• Collaborating with Engineering and Design teams to ensure timely and successful product delivery, meeting quality standards and customer expectations
• Growing, managing, and mentoring a team of product managers and other relevant partners
• Establishing key performance indicators (KPIs) and metrics to track product performance, adoption, and revenue growth

What do we need from you?

• Experience: 10+ years of demonstrated ability in product management, growth strategy, or an equivalent field, preferably in a B2B company
• Proven track record of driving growth and successfully launching new products
• Product Expertise: Proven understanding of product management methodologies, product development lifecycles, and go-to-market strategies; familiarity with B2B product dynamics, SaaS (Software-as-a-Service) solutions, or technology-enabled products is highly desirable
• Strategic Thinking: Ability to think strategically and translate market trends and customer insights into practical growth strategies; skilled in identifying new business opportunities, setting product priorities, and making informed decisions based on data and market analysis
• Leadership and Collaboration: Demonstrated experience in leading and developing impactful teams; proven ability to collaborate effectively with cross-functional stakeholders, including Engineering, Marketing, Sales, and Customer Success, to achieve common goals
• Analytical and Data-Driven: Strong analytical skills with the ability to derive insights from complex data sets and translate them into practical recommendations; proficiency in applying analytical tools, market research techniques, and customer feedback mechanisms
• Communication Skills: Excellent verbal and written communication skills, with the ability to articulate complex concepts in a clear and concise manner; experience in presenting to executive-level partners and influencing decision-making
• Adaptability: Comfortable working in a fast-paced, agile environment
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

About the team & opportunity

What’s so great about working on Calendly’s Engineering team?

We make things possible for our customers through impactful innovation.

Why do we need you? Well, we are looking for a Site Reliability Engineer who will bring creative problem solving and a keen eye for detail. You will report to a Senior Manager of Engineering and be responsible for designing, building, maintaining, and operating our next-generation infrastructure platform. With a growing team and a mindset for scalability, SREs build their own tools, deploy open-source solutions, and consume cloud services as needed to extend the platform.

A day in the life of a Site Reliability Engineer at Calendly

As a Senior Site Reliability Engineer at Calendly, you'll use your expertise of the infrastructure to empower application engineering teams. This includes enabling and evangelizing monitoring best practices, and advising on optimal infrastructure use. An ideal candidate demonstrates exceptional skills in communicating patterns and improvements that automate tasks, support stability, and improve performance.

On a typical day, you will be working on:

• Building tools and applications to extends Calendly’s infrastructure platform
• Evaluating and deploying cloud native open source tools
• Exercising expertise in cloud infrastructure concepts and patterns
• Instituting resilient infrastructure through Infrastructure as code
• Maintaining and improving observability of our infrastructure platform, and offers patterns for application teams to consume for application observability
• Participating in an on-call rotation to support the infrastructure platform
• Fostering a collaborative environment of learning and knowledge dissemination
• Defining standard practices and tooling around new services, changes, incidents, postmortems, and capacity management, and work with application engineering teams to adopt those practices

What do we need from you?

• An eagerness and drive to learn, and the skills for sharing your knowledge with and mentor others
• Creative problem-solving, a keen eye for detail, and can think your way through complex issues
• Comfortable working directly with internal facing customers to understand needs/requirements and collaborate on solutions
• A strong understanding of the Linux operating system
• Strong technical knowledge of cloud infrastructure (especially GCP), distributed systems, and reliability practices
• Deep experience designing, building, and running highly-available production infrastructure
• Strong Golang or Python development experience; especially writing APIs to build, orchestrate and manage cloud infrastructure
• Solid working knowledge of patterns and principles for designing and implementing cloud native applications on Kubernetes, such as Controllers and Operators
• Robust knowledge of computer networking principles and extensive experience with cloud networking technologies to create scalable and secure environments.
• Extensive working experience with software and infrastructure monitoring tools (especially Datadog)
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Our Hiring Process:

We aim to provide an inclusive and equitable candidate experience to everyone who expresses interest in working at Calendly. To learn more about our hiring process, please visit our careers page at www.careers.calendly.com.

Once selected for an opportunity, the recruiter assigned to the role will keep you informed every step of the way. Have questions? Let your recruiter know! Want to share your experience? We are passionately committed to improving and building on our process, and we consider feedback a gift. 

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please contact us at recruiting@calendly.com. 

Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Alabama, Delaware, Hawaii, Idaho, Montana, North Dakota, South Dakota, Nebraska, Iowa, West Virginia, and Rhode Island, you will not be eligible for employment. Note that all individual roles will specify location eligibility.

All candidates can find our Candidate Privacy Statement here

Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection

About the team & opportunity

Our Mission

We empower product engineering teams to build consistent, high-quality features efficiently through shared tooling, standards, and infrastructure that accelerate development while maintaining coherence across our platform.

How you will contribute

As a Senior Engineer on Calendly’s App Platform team, you will be instrumental in building the foundational capabilities that power our product ecosystem. Your work will directly impact how our engineering teams ship features and how millions of users experience Calendly.

You will focus on critical platform services including:

• Analytics and Experimentation to enable data-driven decision making across product teams
• Feature Flagging infrastructure to provide controlled and predictable releases at scale
• Real-time UX Infrastructure to enable server-to-client data delivery to support dynamic and responsive experiences
• Future Platform Services as our platform continues to grow and evolve

Why this role matters

We’re at an inflection point. As Calendly continues to scale, our product teams need increasingly sophisticated platform capabilities to move quickly without sacrificing quality. In this role you will help define how we approach distributed platform services, contribute to engineering standards, and build resilient infrastructure that our growing platform demands. Your technical expertise and collaboration will shape not only what we build, but how we build across our engineering organization.

A day in the life of a Senior Full Stack Engineer at Calendly

Building Platform Infrastructure
Design, develop, and maintain the services and frameworks that product teams depend on. You will work hands-on with technologies like Ruby / Rails and Go to build highly resilient, scalable systems; from real-time server-to-client data infrastructure to analytics and experimentation services.

Technical Leadership and Collaboration
Contribute to architectural decision and technical strategy for platform services. Provide guidance to engineers across the organization, share your expertise in distributed systems, and help establish patterns and practices that raise the bar for engineering excellence.

Contribute To Critical Initiatives
Own and contribute to significant projects from concept to production. Whether it’s building and launching real-time server-to-client infrastructure, optimizing service performance, or designing new platform capabilities, you will deliver high impact solutions with quality and reliability at the forefront.

Cross-Functional Partnership
Partner with product managers, designers, and engineering teams across Calendly to understand their needs and translate them into robust platform solutions that serve the entire organization.

Operational Excellence
Ensure reliability and performance of platform services through thoughtful monitoring, testing, and incident response. Participate in on-call rotation to support business-critical systems and drive continuous improvement based on operational learnings.

What do we need from you?

• 7+ years of software engineering experience at a SaaS or technology company with a strong focus on backend and distributed systems
• Deep experience in service-oriented architecture, microservice patterns, and building highly resilient / scalable systems
• Proven experience building and operating high traffic, high availability platforms in production environments
• Strong proficiency in building internal tools, frameworks, and SDKs that other engineers use
• Experience with API design and real-time data systems (Server Side Events, Websockets, etc)
• Excellent problem solving skills with the ability to diagnose complex system issues and implement effective solutions
• Strong communication skills, you can explain complex technical concepts clearly to both technical and non-technical stakeholders
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Bonus

• Experience with Golang, Ruby / Rails, NodeJS / Typescript (our primary backend languages)
• Background in platform engineering roles
• Experience performing major architectural refactors, particularly decomposing monolithic applications into microservices
• Familiarity with our cloud ecosystem: Google Cloud Platform, Kubernetes, PostgreSQL, Redis

What will make you successful here

• You take deep ownership and drive initiatives with a results-oriented mindset
• You thrive in collaborative environments, working effectively with remote and distributed teams
• You’re adaptable, comfortable with evolving requirements and new technologies
• You’re passionate about enabling others and see platform engineering as a force multiplier
• You’re available to participate in our on-call rotation to ensure the reliability of business-critical services

About the team & opportunity 

This is an exciting opportunity to take on a high visibility role in delivering against Calendly’s most important business outcomes, and will also be an opportunity to set the standard for operational excellence at Calendly. We are looking for a dynamic and strategic contributor who can influence stakeholders across the organization, drive cross-functional alignment, and lead through influence to deliver on a portfolio of high-impact, high-complexity programs and projects. 

This role reports to the Senior Director of Product Operations. 

A day in the life of a Staff Product Operations Manager at Calendly

As a Staff Product Operations Manager,  you will manage a portfolio of R&D programs and projects, ensuring that all aspects of the program are well defined and aligned – from setting program-level objectives and success metrics to driving alignment around scope, timelines, and dependencies; and actively managing and triaging ongoing risks and decisions to remove obstacles and impediments along the way. You may also launch and oversee core PDLC initiatives that span the R&D organization.

On a typical day, you will be working on: 

• Leading end-to-end delivery of a portfolio of strategic programs and projects from problem space definition to customer impact – including defining program-level OKRs, scope, resourcing requirements, milestone timelines, dependency management, risk mitigation, decision making, progress/impact tracking, health metrics, etc.
• Partnering with leadership and cross-functional stakeholders across the organization to surface underlying needs and desired outcomes, anticipate and remove obstacles, and drive progress through clear problem framing and decision-making facilitation.
• Establishing (and modeling) the standard for the Product Operations craft at Calendly – including establishing best practices for planning, prioritization, execution, governance, data-driven decision making, etc.
• Improving cross-functional collaboration and communication by creating shared understanding and alignment, and serving as a leader to the team as we navigate uncertainty and change.
• Identifying organizational problems and opportunities, then defining and leading the programs, processes, and tools needed to help the organization operate effectively and achieve its goals.

What do we need from you?

• 10+ years of product operations or direct program management experience managing high-complexity, high-visibility, high-impact enterprise-wide programs

Candidates located in San Francisco are highly preferred; this role requires frequent travel to San Francisco for the first 6-12 months (up to 2-3 times a month for several days at a time)

• Demonstrated ability in leading programs across a wide range of business and technology-related topics from problem space definition to customer impact (bonus: strong understanding of SaaS technologies, Product Development Lifecycles or demonstrated ability to collaborate with engineering teams on complex technology programs)
• The ability to assimilate different points of view to create shared understanding across a broad spectrum of stakeholders
• Exceptional leadership and communications skills; proven ability to influence without authority, build trust, manage complexity and drive business results
• Demonstrated experience managing programs in a remote-first environment, with familiarity applying change management practices to drive adoption; strong command of collaboration tooling administration and enablement (e.g., Jira, Confluence, automation workflows)
• B.A. in a business or technical field; M.B.A., P.M.P, or comparable certification a plus
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

What’s in it for you? 

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

About the team & opportunity

*This is a remote role. However, if you reside within commuting distance of our San Francisco office, there is an expectation of working in the office two (2) days per week.

We're looking for a Senior Product Designer for our Growth team. You'll be helping solopreneurs and small teams increase their discovery and engagement with key new products, like our AI Notetaker and contact management experience, in a meaningful way.  As a key team member, you’ll be shaping the user experience for millions of users, designing simple and intuitive experiences that improve our users' day-to-day work.

We believe that great design starts with talking with our users and that the best solutions come from interdisciplinary collaboration. You’ll be part of Calendly’s incredible Design team, collaborating with Product Designers, Content Designers, UX Researchers, Product Managers, and Engineers. 

A day in the life of a Senior Product Designer on the Growth team at Calendly

On a typical day, you will:

• Design hypothesis-driven experiences focused on understanding and improving activation funnels across the product
• Leverage quantitative and qualitative data to understand user habits and needs
• Drive discovery work to uncover hidden insights on user behavior
• Partner with designers, product managers, engineers, content designers, design systems, and researchers to improve and refine the Calendly experience
• Effectively communicating your design approach with strong storytelling, to inspire and align the cross-functional team to move in new directions

What do we need from you?

• 5+ years building and delivering experiences for digital products in product-led B2B or B2C companies
• 2+ years defining and designing growth experiments focused on different parts of the user funnel 
• A strong portfolio of design work that delivers customer and business value
• Expert design storytelling with an ability to communicate design solutions to leaders and peers
• Values being an active member of our design team, collaborating with a team of designers, including partnering on design work, providing feedback, sharing expertise, and mentoring
• A demonstrated understanding of the levers that balance business goals, team processes, and user needs
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

About the team & opportunity

Our Mission

We power Calendly's products with reliable, high-performance calendar data infrastructure. Our services provide the foundation for how users interact with their scheduling data, serving as the single source of truth across our platform.

How you will contribute

As a Senior Engineer on Calendly's Calendar Platform team, you will build and evolve the core infrastructure our products depend on. Your work will directly shape how millions of users access and interact with their calendar data.

You will focus on critical platform services including:

• Core calendar data API development, building and scaling a new unified interface and underlying data infrastructure for calendar data across all Calendly products
• Synchronization services to maintain data integrity across internal systems and external providers like Google and Microsoft
• Search infrastructure using ElasticSearch to surface relevant calendar data for users
• Novel platform services as new product needs emerge

Why this role matters

Calendar data is central to the Calendly platform. As we grow, our products need fast, reliable access to this data through modern, resilient infrastructure. You will help us move beyond legacy patterns and build services designed for scale. The technical decisions you make will ripple across our entire product ecosystem.

A day in the life of a Senior Full Stack Engineer at Calendly

Building Calendar Infrastructure

Design, develop, and maintain services our product teams depend on. You will work hands-on with Golang, Ruby/Rails, and PostgreSQL to build resilient systems handling high data volumes and complex synchronization requirements.

Technical Leadership and Collaboration

Contribute to architectural decisions for calendar platform services. Share your distributed systems expertise with engineers across the organization and help establish patterns for engineering excellence.

Contribute To Critical Initiatives

Own and contribute to significant projects from concept to production. Whether you're evolving the core calendar API, improving sync reliability, or optimizing search performance, you will deliver high-impact solutions with quality and reliability at the forefront.

Cross-Functional Partnership

Partner with product engineering teams, Data Platform, and Infrastructure to understand their needs and translate them into robust solutions. This is a highly collaborative team where your input shapes how we serve internal customers.

Operational Excellence

Ensure reliability and performance through thoughtful monitoring, testing, and incident response. Participate in on-call rotation for business-critical systems and drive continuous improvement based on operational learnings.

What do we need from you?

• 7+ years of software engineering experience at a SaaS or technology company with strong backend and distributed systems focus
• Deep experience in service-oriented architecture, microservice patterns, and building resilient, scalable systems
• Proven experience building and operating high-traffic, high-availability platforms in production
• Strong proficiency building internal tools, frameworks, and SDKs other engineers use
• Experience with API design and data synchronization across multiple external providers
• Excellent problem-solving skills with the ability to diagnose complex system issues
• Strong communication skills, able to explain technical concepts clearly to technical and non-technical stakeholders
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Bonus

• Experience with Golang, Ruby/Rails, NodeJS/Typescript
• Background in platform engineering roles
• Experience decomposing monolithic applications into microservices
• Familiarity with Google Cloud Platform, Kubernetes, PostgreSQL, Redis, Pub/Sub
• Experience with ElasticSearch or similar search infrastructure

What will make you successful here

• You take deep ownership and drive initiatives with a results-oriented mindset
• You thrive in collaborative environments, working effectively with remote and distributed teams
• You’re adaptable, comfortable with evolving requirements and new technologies
• You’re passionate about enabling others and see platform engineering as a force multiplier
• You’re available to participate in our on-call rotation to ensure the reliability of business-critical services

About the Role

Calendly is looking for a Principal Product Marketing Manager to help define what we build, why it matters, and how we bring it to market. This is a highly strategic, highly influential role for a seasoned product marketer who can develop a clear point of view, pressure-test it with leaders with confidence (and take feedback), and take ownership driving alignment.

This is an individual contributor role with high ownership, visibility, and strategic impact. You’ll lead through influence and partnership, working closely with Product and Marketing Leadership as well as Research and Product teams to shape the product narrative early, influence prioritization, and ensure what we ship is positioned to win.

You’ll partner closely with Product and Marketing Leadership as well as Research teams to shape product narrative early, influence prioritization, and ensure what we ship is positioned to win. 

You’ll also own end-to-end go-to-market for new products and initiatives, translating strategy into strong execution that measurably impacts new product discovery: increasing awareness, intent, and early engagement with new products through clear narrative, smart packaging, and effective in-product and lifecycle motions.

This role is ideal for someone who can move comfortably between up front strategy (insight → POV → decision) and downstream GTM execution (positioning → launch → adoption).

What You’ll Do:

Lead product strategy influence (front-end impact)

• Shape product direction with Product Leadership by clarifying the market problem, target audience, differentiated value, and why it matters now.
• Define positioning and narrative early for new products, including AI capabilities, translating technical concepts into customer value with appropriate expectations and trust.
• Create alignment through strategy artifacts such as PR FAQs, narrative briefs, and executive decision memos.
• Bring structure to ambiguity by reframing big picture positioning and roadmap conversations into the real decisions that need to be made, and guiding stakeholders to clarity.
• Take ownership of the unique position Product Marketing is in to frame these conversations and bring these ideas up in a product meeting context

Own high-impact GTM (senior-level execution)

• Lead go-to-market for major product bets, from planning to launch, adoption, and iteration.
• Own the strategy for new product discovery across in-product surfaces, lifecycle, web, and enablement, and track impact through agreed metrics.
• Partner with Growth and Product to improve discovery and adoption through testing, iteration, and performance reviews.
• Work with research and product metrics dashboards to inform strategy, performance, and course corrections.
• Adopt a “researcher mindset” to establish hypotheses, run learning loops with Growth/CS/Research (as relevant), and refine messaging based on market signal and customer feedback, especially for emerging AI-driven capabilities.
• Craft clear and compelling messaging and positioning that scales across the customer journey.
• Build the core toolkit (messaging, one-pagers, internal FAQs, enablement) with a high bar for clarity and narrative craft.
• Own the “GTM stack”: recommend channel mix (in-app, email, web, video strategy, lifecycle marketing updates, etc.), build the plan, drive readiness, and ensure follow-through.
• Build and maintain core PMM assets (one-page briefs, messaging houses, high level roadmaps, internal FAQs, etc., with an exec-level bar for clarity and consistency in storytelling.

Drive cross-functional and executive alignment

• Serve as a senior cross-functional leader across Product, Brand, Support, Research, Customer Success, and Growth, and take ownership of shared success metrics.
• Facilitate executive reviews: present recommendations, incorporate feedback without losing the thread (or your confidence), and drive fast decisions that unlock momentum via rapid iterations and feedback cycles.
• Act as an internal evangelist for your product area: championing customer value, representing PMM leadership, and raising the bar for narrative craft.
• Continuously test, learn, and iterate by bringing a data-informed mindset and adapting based on customer feedback and behavior.

Improve product marketing excellence

• Revisit and iterate on reusable frameworks and templates as needed (positioning, narrative, PRFAQ, launch readiness) that improve how Product Marketing operates.
• Mentor other PMMs and help level up strategic thinking, storytelling, and executive communication across the team.
• Ensure a high bar for storytelling and work with creative brand teams to execute compelling, polished campaigns

Who You Are

• 12+ years of product marketing experience in SaaS (PLG or hybrid GTM preferred), with a track record of leading major launches and driving discovery and adoption
• Proven ability to operate as a strategic partner to Product Leadership and C-Suite, influencing roadmaps, prioritization, positioning, and narrative direction (not just executing downstream GTM).
• Strong critical thinking and judgment: can zoom out from day-to-day product decisions to identify the bigger strategic questions, tradeoffs, and second-order impacts that need leadership discussion.
• An AI-native PMM comfortable using AI tools to scale your impact: speeding up analysis and content creation, improving consistency across messaging, and building repeatable GTM workflows.
• Deeply customer-obsessed and insight-driven (research, interviews, win/loss, competitive intel), with the ability to translate inputs into strategy.
• Brings structure to ambiguity: you separate signal from noise, pressure-test assumptions, and make clear, and develop well-reasoned recommendations.
• Exceptional storyteller who can simplify complex concepts into clear, compelling narratives with a high bar for craft and simplicity.
• Confident, resilient product marketer who stays steady under pressure: able to navigate ambiguity, competing opinions, and fast-changing priorities without losing momentum, conviction or confidence.
• Brings a growth mindset: seeks feedback early, learns fast, iterates quickly, and treats feedback as fuel for better work— without getting derailed or losing confidence.
• Executive-ready communicator: can hold the room, simplify complexity into crisp narratives, and advocate effectively up and across the org. You also know when to back off and listen, go back to the drawing board. You are comfortable engaging in healthy debate (you can disagree, commit, and move on); you don’t freeze when decisions are imperfect or your POV is questioned.
• Strong operator with high standards: can run multiple high-stakes workstreams, align cross-functional partners, and deliver launches with quality and speed without feeling overwhelmed.

Bonus Points 

• Experience marketing to both self-serve and enterprise customers. 

• Experience with Miro, Asana, G-Suite, User Interviews, and product analytics tools

• Experience with PLG tactics and lifecycle marketing.

• Experience positioning AI-powered products and features

• Experience shaping early product narrative through PR FAQs (or equivalent).