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

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 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).