Gladly
How do you contact companies you do business with? Voice, chat, email, SMS, social media? Gladly was built to help rethink how the world’s top brands communicate with their customers.
We're currently hiring software engineers to join our growing team in San Francisco.
What’s life at Gladly like?
We’d like to give you a good idea of what it's like to work at Gladly. We value the strength of our team above everything else. We believe in open communication and in sharing opinions, not in micromanagement. We openly discuss all aspects of our business, and avoid internal politics. We learn from each other, and we help each other learn. We focus on a common goal, which is the success of our customers, and through it the success of our business and our people. We have a collaborative culture of mutual respect - many of us are working together for a second and even a third time. We have a strong work ethic, but value life outside of work, so we don't spend our entire lives in the office. Come join us!
About the Role
We're in search of a software engineer with experience in machine learning to use Gladly's unique dataset and to develop high-impact products. You will collaborate with a cross-functional team of engineers, product managers and designers to identify product opportunities, validate and tune machine learning models, and integrate them directly into our platform. This is a greenfield opportunity where you’ll be involved in making critical decisions that will have a far reaching impact on our product and data pipeline from the ground up.
What You'll Do
- Analyze and derive insights from large, complex data sets, including real-world conversational data.
- Iteratively develop, test and integrate state-of-the-art machine learning and neural network models to improve our customer service platform.
- Build and prototype analysis pipelines to ensure quality and scalability from ingestion to transformation and storage.
- Apply coding skills to integrate your models directly into the product, collaborating with other engineers and designers.
Some example projects include:
- Apply deep learning techniques to automatically respond to customer inquiries.
- Design a speech recognition system for high quality multi-speaker call transcriptions.
- Develop optimal routing algorithms to prioritize and match customers with agents best suited to handle their questions.
This position offers multiple degrees of freedom. Whatever your role is here, you'll able to branch out and work on different projects as needed.
We are looking for a candidate who:
- Is highly inquisitive and can derive patterns and insights from large structured and unstructured datasets.
- Has a keen desire to solve business problems through tailored data science and machine learning techniques. Can see the big picture and understand requirements from other points of view, beyond just the spec.
- Excels at making complex concepts simple and easy to understand by those around you. Able to communicate both high level principles and nuances of machine learning methods to product managers and engineers.
- Has a deep understanding of statistical and predictive modeling, feature selection and dimensionality reduction, and classification, ranking and recommendation techniques.
- Has solid coding ability in a high level language and fluency with machine learning libraries. We mainly use Go, JavaScript and Python.
Desired Experience:
- Production experience with NLP, ASR and search.
- Experience working with large-scale data frameworks.
The ideal candidate is a software engineer currently practicing machine learning techniques in a production environment. However we are also open to candidates with deep expertise in machine learning who are transitioning from academia.
Just to highlight why you'll love working here at Gladly:
- We're still a small and bureaucracy-free company, so you'll be able to see projects from concept to production, ship and iterate quickly.
- We have a collaborative culture of mutual respect - many of us are working together for a second and even a third time.
- We believe in open communication and in sharing opinions, not in micromanagement.
- We have a strong work ethic, but value life outside of work, so we don't spend our entire lives in the office.
Gladly offers competitive salaries, stock options, and generous paid time off as well as:
- Medical, Dental, Vision and Life insurance
- Paid Parental Leave
- 401K
- Flexible Spending Accounts
- Fitness Stipend
- Equipment of your choice
- Commuter Benefits
Gladly is based in San Francisco and funded by Greylock Partners, NEA and GGV Capital. Learn more about the company and our team here.
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About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world’s most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
The Team
The Finance team at Gladly is small, high-performing, and operates well above its weight class. The culture here is defined by high autonomy, direct visibility with leadership, and a bias toward action over process. Your work directly impacts how deals close and how leadership makes decisions. There are no layers, no committees, and no waiting around for approval. The team values over-communication, intellectual curiosity, and a willingness to context-switch quickly across priorities.
You will report to the Director of FP&A and work closely with RevOps, Sales, Systems Design, and GTM leadership as a collaborative partner and reliable operational resource across the commercial side of the business.
The Opportunity
This role sits at the center of deal desk operations and commercial finance, giving you a front-row seat to how deals get structured, priced, and closed. You will be deeply embedded in the quote-to-cash workflow from day one, owning deal reviews, pricing analysis, and the operational rigor that keeps the commercial motion running cleanly.
You are the kind of person who thrives on precision and process. You catch what others miss, you follow through without cutting corners, and you are comfortable owning the final review on deals before they close. You bring a natural attention to detail and a strong bias toward execution.
Gladly’s commercial motion is accelerating, and the Finance team is scaling to match. You will play a central role in that, helping build the operational rigor that supports a growing deal volume while also supporting pricing analysis and margin modeling that inform deal structure decisions.
What You’ll Do
Deal Desk & Commercial Finance Operations
- Conduct deal reviews for completeness, accuracy, and compliance before close, ensuring all required approvals are in place and deals are structured correctly across pricing, discounting, and contract terms
- Review deals for compliance with pricing guidelines, discount thresholds, and revenue recognition requirements (ASC 606); escalate edge cases to Finance leadership as needed
- Manage the day-to-day quote-to-cash workflow in Salesforce: deal progression tracking, certification process management, renewals tracking, and pipeline reporting
- Maintain a clean approval audit trail and deal log to support accurate pipeline reporting and downstream revenue recognition
- Support and over time own the margin calculator used to evaluate different pricing structures when working with the sales team on custom-priced enterprise deals, including analysis of AI vs. Team margin dynamics
- Partner with Sales Operations and Systems Design on Deal Desk process alignment, consulting on workflow design and driving consistent execution once processes are defined and deployed
- Bring a continuous improvement mindset: flag friction points in the Deal Desk process and collaborate with SalesOps and Systems Design on solutions, with a longer-term eye toward automating manual steps
Systems Administration & Process Design
- Support deal desk systems including DealHub (CPQ), Salesforce, and related commercial tools, ensuring data integrity and process consistency
- Partner with the Systems Design team on configuring and optimizing deal desk tooling, including approval workflows, pricing rules, and quote templates
- Help identify opportunities to automate recurring processes and reduce manual effort across the deal desk function over time
AI and Automation
- Show genuine curiosity about AI tools (Claude, ChatGPT, Copilot, or similar) and a willingness to learn how they can help you move faster and reduce the lift on repetitive tasks
- Apply an automation-first lens to your own work: if you are doing something manually more than twice, start thinking about how to streamline it
- Partner with the Finance team on identifying and implementing AI-assisted workflows across Deal Desk processes
What We’re Looking For
- 3-5 years of experience in deal desk, commercial finance, or a related operational finance role. B2B SaaS experience is a strong plus but not required
- English proficiency at C1-C2 level (business fluent). This role requires daily written and verbal communication with US-based teams
- Based in Colombia or Mexico with the ability to work US business hours
- Deal desk or quote-to-cash experience: you understand deal review, pricing compliance, approval workflows, and what it takes to close a deal cleanly
- Salesforce proficiency: comfortable navigating opportunity records, pipeline reports, and deal data independently. You work in the system, not just look at it
- Solid grasp of SaaS business model fundamentals: ARR, ACV, NRR, and SaaS revenue recognition (ASC 606)
- Comfortable with pricing analysis and margin modeling: you can work within existing models and help evaluate the financial impact of different deal structures
- Advanced Google Sheets or Excel skills: complex formulas, pivot tables, scenario modeling, and data visualization
- High attention to detail and a strong sense of accountability. You follow through, you notice when something is off, and you say something
- Collaborative by nature: you partner well with Sales, RevOps, and Finance teammates and bring people along rather than going it alone
- DealHub, CPQ, or deal desk systems admin experience is a strong plus
Salary for this role: $60,000 - $90,000 USD annually DOE (can be paid in MX pesos; COR only option available)
The cash compensation above includes base salary, and is not reflective of potential commission for employees in eligible roles, or annual bonus targets under Gladly's bonus plan for eligible roles. In addition to cash compensation, all Gladly employees are eligible to participate in Gladly's equity incentive plan to receive stock options per the terms of the agreement. Individual compensation packages are based on a few different factors unique to each candidate, including their career level, skills, experience, specific geographic location qualifications and other job-related reasons.
Why Join Gladly?
Gladly is redefining customer experience AI — designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy:
- Competitive salaries, stock options, and comprehensive benefits
- Generous paid time off, parental leave, and home office stipends
- A fully remote work environment with opportunities for in-person team gatherings
- A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive
- A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily
We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.
Ready to apply?
Apply to Gladly
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
The Team
The Finance team at Gladly is small, high-performing, and operates well above its weight class. The culture here is defined by high autonomy, direct visibility with leadership, and a bias toward action over process. Your work directly impacts how deals close and how leadership makes decisions. There are no layers, no committees, and no waiting around for approval. The team values over-communication, intellectual curiosity, and a willingness to context-switch quickly across priorities.
You will report to the Director of FP&A and work alongside experienced deal desk and systems teammates. You will have direct exposure to how deals move through the commercial pipeline and how the systems that support that process are built and maintained.
The Opportunity
This role puts you at the center of deal desk operations and commercial finance at a company redefining customer experience through agentic AI. You will start by working alongside experienced Finance and Systems teammates to build fluency in how deals get structured, priced, and closed, and you will move quickly toward ownership of the quote-to-cash workflow. This is not a back-seat role. We are looking for someone who learns fast, takes initiative, and is ready to own outcomes within their first six months.
You are detail-oriented, execution-focused, and energized by operational work that has real business impact. You do not wait to be told what to do next. You see a gap, you close it. You are not intimidated by ambiguity or new systems, and you bring the kind of follow-through and accountability that earns trust fast. You may be earlier in your career, but you operate like someone who has been doing this for years.
Gladly is at the forefront of AI-powered customer experience, and our commercial motion is accelerating to match. This role gives you direct responsibility across deal review, pricing analysis, systems configuration, and cross-functional partnership with sales. The technology is evolving fast, the deal structures are evolving with it, and the right person in this seat will grow into a core operator on the Finance team, not stay in a support role.
What You'll Do
Deal Desk Operations
- Support deal reviews for completeness, accuracy, and compliance before close, working alongside senior Finance teammates to ensure deals are structured correctly across pricing, discounting, and contract terms
- Help manage the day-to-day quote-to-cash workflow in Salesforce: deal progression tracking, certification process management, renewals tracking, and pipeline reporting
- Maintain a clean approval audit trail and deal log to support accurate pipeline reporting and downstream revenue recognition
- Learn and apply pricing compliance guidelines, discount thresholds, and revenue recognition requirements (ASC 606) with increasing independence over time
- Support the margin calculator used to evaluate pricing structures on enterprise deals, building comfort with how AI vs. Team margin dynamics affect deal economics
- Flag friction points in the Deal Desk process and bring ideas for improvement to the team
Systems Support & Process Design
- Help support deal desk systems including DealHub (CPQ) and Salesforce, contributing to data integrity and process consistency under the guidance of the Systems Design team
- Assist with configuring and optimizing deal desk tooling, including approval workflows, pricing rules, and quote templates
- Help identify opportunities to automate recurring processes and reduce manual effort across the deal desk function
AI and Automation
- Show genuine curiosity about AI tools (Claude, ChatGPT, Copilot, or similar) and a willingness to learn how they can help you move faster and reduce the lift on repetitive tasks
- Apply an automation-first lens to your own work: if you are doing something manually more than twice, start thinking about how to streamline it
- Partner with the Finance team on identifying and implementing AI-assisted workflows across Deal Desk processes
What We're Looking For
- 2-4 years of experience in deal desk, commercial finance, revenue operations, sales operations, or a related operational finance role. B2B SaaS experience is a plus but not required
- Based in the US with the ability to work standard US business hours
- Exposure to deal desk or quote-to-cash processes: you have some familiarity with deal review, pricing compliance, approval workflows, or commercial operations even if you have not owned the full function
- Salesforce experience: comfortable navigating the platform and working with deal data. Admin-level experience is a plus
- Familiarity with SaaS business model fundamentals: ARR, ACV, and how subscription revenue works. You do not need to be an expert, but you should understand the basics
- Comfortable with spreadsheets: Google Sheets or Excel at an intermediate-to-advanced level (formulas, pivot tables, data analysis)
- Strong attention to detail and follow-through. You notice when something is off and you do not let it slide
- A bias toward action and execution. You do not need to be told what to do next, you figure it out
- Collaborative and communicative: you over-communicate, you ask good questions, and you are comfortable working across teams
- DealHub, CPQ, or deal desk systems experience is a strong differentiator
Compensation
The expected OTE for this role is $85,000-$100,000, inclusive of base salary plus equity. Final offer amounts are determined by multiple factors including candidate experience, expertise, and geographic location.
For cash compensation, we set standard ranges based on function, level, and geographic location, benchmarked against similar-stage growth companies.
Research has shown that individuals from underrepresented groups are less likely to apply to jobs where they don't meet 100% of the criteria. Gladly values diversity of experience. If you believe you have the right skill set, we welcome you to apply even if you don't check every box. We are committed to an inclusive workplace and would love to see if you could be the next great addition to our team.
Why Join Gladly?
Gladly is redefining customer experience AI — designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy:
- Competitive salaries, stock options, and comprehensive benefits
- Generous paid time off, parental leave, and home office stipends
- A fully remote work environment with opportunities for in-person team gatherings
- A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive
- A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily
We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.
Ready to apply?
Apply to Gladly
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world’s most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
The Team
The Finance team at Gladly is small, high-performing, and operates well above its weight class. The culture here is defined by high autonomy, direct visibility with leadership, and a bias toward action over process. Your work directly impacts how deals close and how leadership makes decisions. There are no layers, no committees, and no waiting around for approval. The team values over-communication, intellectual curiosity, and a willingness to context-switch quickly across priorities.
You will report to the Director of FP&A and work closely with RevOps, Sales, Systems Design, and GTM leadership as a collaborative partner and reliable operational resource across the commercial side of the business.
The Opportunity
This role sits at the center of deal desk operations and commercial finance, giving you a front-row seat to how deals get structured, priced, and closed. You will be deeply embedded in the quote-to-cash workflow from day one, owning deal reviews, pricing analysis, and the operational rigor that keeps the commercial motion running cleanly.
You are the kind of person who thrives on precision and process. You catch what others miss, you follow through without cutting corners, and you are comfortable owning the final review on deals before they close. You bring a natural attention to detail and a strong bias toward execution.
Gladly’s commercial motion is accelerating, and the Finance team is scaling to match. You will play a central role in that, helping build the operational rigor that supports a growing deal volume while also supporting pricing analysis and margin modeling that inform deal structure decisions.
What You’ll Do
Deal Desk & Commercial Finance Operations
- Conduct deal reviews for completeness, accuracy, and compliance before close, ensuring all required approvals are in place and deals are structured correctly across pricing, discounting, and contract terms
- Review deals for compliance with pricing guidelines, discount thresholds, and revenue recognition requirements (ASC 606); escalate edge cases to Finance leadership as needed
- Manage the day-to-day quote-to-cash workflow in Salesforce: deal progression tracking, certification process management, renewals tracking, and pipeline reporting
- Maintain a clean approval audit trail and deal log to support accurate pipeline reporting and downstream revenue recognition
- Support and over time own the margin calculator used to evaluate different pricing structures when working with the sales team on custom-priced enterprise deals, including analysis of AI vs. Team margin dynamics
- Partner with Sales Operations and Systems Design on Deal Desk process alignment, consulting on workflow design and driving consistent execution once processes are defined and deployed
- Bring a continuous improvement mindset: flag friction points in the Deal Desk process and collaborate with SalesOps and Systems Design on solutions, with a longer-term eye toward automating manual steps
Systems Administration & Process Design
- Support deal desk systems including DealHub (CPQ), Salesforce, and related commercial tools, ensuring data integrity and process consistency
- Partner with the Systems Design team on configuring and optimizing deal desk tooling, including approval workflows, pricing rules, and quote templates
- Help identify opportunities to automate recurring processes and reduce manual effort across the deal desk function over time
AI and Automation
- Show genuine curiosity about AI tools (Claude, ChatGPT, Copilot, or similar) and a willingness to learn how they can help you move faster and reduce the lift on repetitive tasks
- Apply an automation-first lens to your own work: if you are doing something manually more than twice, start thinking about how to streamline it
- Partner with the Finance team on identifying and implementing AI-assisted workflows across Deal Desk processes
What We’re Looking For
- 3-5 years of experience in deal desk, commercial finance, or a related operational finance role. B2B SaaS experience is a strong plus but not required
- English proficiency at C1-C2 level (business fluent). This role requires daily written and verbal communication with US-based teams
- Based in Colombia or Mexico with the ability to work US business hours
- Deal desk or quote-to-cash experience: you understand deal review, pricing compliance, approval workflows, and what it takes to close a deal cleanly
- Salesforce proficiency: comfortable navigating opportunity records, pipeline reports, and deal data independently. You work in the system, not just look at it
- Solid grasp of SaaS business model fundamentals: ARR, ACV, NRR, and SaaS revenue recognition (ASC 606)
- Comfortable with pricing analysis and margin modeling: you can work within existing models and help evaluate the financial impact of different deal structures
- Advanced Google Sheets or Excel skills: complex formulas, pivot tables, scenario modeling, and data visualization
- High attention to detail and a strong sense of accountability. You follow through, you notice when something is off, and you say something
- Collaborative by nature: you partner well with Sales, RevOps, and Finance teammates and bring people along rather than going it alone
- DealHub, CPQ, or deal desk systems admin experience is a strong plus
Salary for this role: $60,000 - $90,000 USD annually DOE (may be paid in COL pesos depending on EOR/COR contract selection)
The cash compensation above includes base salary, and is not reflective of potential commission for employees in eligible roles, or annual bonus targets under Gladly's bonus plan for eligible roles. In addition to cash compensation, all Gladly employees are eligible to participate in Gladly's equity incentive plan to receive stock options per the terms of the agreement. Individual compensation packages are based on a few different factors unique to each candidate, including their career level, skills, experience, specific geographic location qualifications and other job-related reasons.
Why Join Gladly?
Gladly is redefining customer experience AI — designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy:
- Competitive salaries, stock options, and comprehensive benefits
- Generous paid time off, parental leave, and home office stipends
- A fully remote work environment with opportunities for in-person team gatherings
- A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive
- A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily
We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.
Ready to apply?
Apply to Gladly
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
The Team
The AI Knowledge team owns the surface that makes Gladly's AI actually useful. Our AI is only as good as what it can see and what it can do, and we control both. We build the integrations that give the AI real-world context (customer data, product catalogs, external systems) and the integrations that let it take action on a customer's behalf. If the AI can look up an order, check inventory, or trigger a return, our team built the path.
We provide all the Knowledge and Connectors that our AI needs to be effective. We are a small, senior team that ships fast, debates openly, and goes deep on root causes. We over-communicate, we care about the craft, and we expect a lot of each other. If you want a front-row seat to how AI gets applied in a real product at real scale, this is the team.
The Opportunity
We are looking for a Staff Software Engineer, ideally bordering on Principal, to be the most senior individual contributor on the AI Knowledge team. This is a deeply technical, high-autonomy seat, not a management role. You will own the full connector and knowledge surface that feeds Gladly's AI, and you will set the direction for how that surface evolves over time.
Your first six months will likely center on two things: making the actions our AI can take easier for customers to configure and extend, and building tooling that lets customers stand up new integrations without writing custom code. You will work shoulder to shoulder with product, design, and customer-facing teams, and you will have real customers on the other end of your decisions.
You are the kind of engineer who owns problems end to end, keeps digging when everyone else has accepted an answer, and raises the bar of the team around you without being asked. You are comfortable moving between domains, you enjoy mentoring, and you use AI coding tools every day because they make you faster, not because it is trendy.
What You'll Do
- Own the integration architecture. Set the technical direction for how external systems connect to Gladly's AI. Evolve what exists, design what doesn't, and know when to do which.
- Build the connective tissue for AI. The LLM needs context to be useful and pathways to take action. You will build both, expanding what the AI can see and what it can do across the customer's full tech stack.
- Solve product-level problems, not just technical ones. Partner with product and design on how integrations should feel for customers, not just how they work under the hood. Your work does not stop at the API boundary.
- Ship at a high bar, fast. Features go from idea to production with direct input from customers like Crate & Barrel and REI. You will build, iterate, and ship, not design in a vacuum.
- Mentor and raise the bar. Demo your work, share what you learn, and help Senior engineers grow into Staff. You will be the senior technical IC the rest of the team looks to.
- Collaborate across the company. Work closely with product managers, designers, and customer-facing teams to solve problems that matter to the business.
What We're Looking For
- 8+ years of full-stack engineering experience with a track record of shipping large-scale product. Comfortable across the stack.
- Proven Staff or Principal-level ownership. You have owned domains end to end, made architectural decisions independently, and driven projects to completion with minimal oversight.
- Daily, hands-on use of AI coding tools (Copilot, Cursor, Claude, or similar) as part of how you build. You have opinions on where they help, where they get in the way, and when to override them.
- A strong track record of turning ambiguous ideas into shipped product, especially in 0-to-1 settings.
- Deep experience with, or real willingness to learn, TypeScript, React, Go, and PostgreSQL.
- The ability to go deep on root cause rather than stopping at the first plausible answer. You are the person others bring the hardest bugs to.
- Strong communication skills. You can zoom out and explain a system at a high level of abstraction, and zoom in and debug a specific behavior in the code.
- A customer-centric mindset. You care about what you are building and who you are building it for.
Bonus Points For
- Experience building integration platforms, API ecosystems, or developer-facing tools
- Familiarity with protocols like MCP (Model Context Protocol) or similar LLM integration patterns
- Hands-on experience with LLMs (OpenAI, Claude, etc.), embeddings, or vector search in production
- Familiarity with operational tools like DataDog, SumoLogic, and LangSmith
- Open source work, public talks, or thought leadership in AI or engineering
Compensation
$183,000 to $246,000 annual salary + equity + benefits
For cash compensation, we set standard ranges for all U.S.-based roles based on function, level, and geographic location, benchmarked against similar-stage growth companies. In order to be compliant with local legislation, as well as to provide greater transparency to candidates, we share salary ranges on all job postings regardless of desired hiring location. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise, and may vary from the amounts listed above.
Why Join Gladly?
Gladly is redefining customer experience AI — designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy:
- Competitive salaries, stock options, and comprehensive benefits
- Generous paid time off, parental leave, and home office stipends
- A fully remote work environment with opportunities for in-person team gatherings
- A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive
- A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily
We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.
Ready to apply?
Apply to Gladly
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 300M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT scores, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
The Team
You will join a high-impact team of strategic account managers who own revenue outcomes across our Enterprise accounts. We are a group of commercially-driven experts fueled by underdog grit and a commitment to mutual accountability. We don’t just manage accounts; we operate as the CEO of our book of business—driving net dollar retention, identifying expansion opportunities, and delivering measurable ROI for B2C leaders.
The Opportunity
We are looking for a Strategic Account Manager to own a portfolio of Enterprise accounts across the install base. This is a quota-carrying, revenue-accountable role where you will drive renewals, expansion, and net dollar retention across a higher-volume book of business.
The ideal candidate is a commercially-minded operator who thrives in a fast-paced environment, can manage multiple accounts simultaneously, and knows how to turn customer relationships into revenue growth. You are proactive, organized, and relentless in identifying opportunities to expand Gladly’s footprint within your accounts.
What You’ll Do
- Revenue Ownership: Carry a net dollar retention quota. Own the full renewal cycle, proactively identify and close expansion and cross-sell opportunities, and drive adoption of Gladly’s AI products across your portfolio.
- Account Planning & Prioritization: Build efficient account plans that balance high-impact strategic engagement with portfolio-wide coverage. Identify key accounts for deeper investment and develop playbooks for scalable growth.
- Customer Engagement: Lead QBRs, renewal discussions, and strategic conversations with VP and Director-level stakeholders. Translate platform value into business outcomes that support retention and growth.
- Commercial Negotiation: Manage renewal and expansion negotiations with confidence. Navigate procurement and approval processes efficiently across a larger book of business.
- Product & Solutions Expertise: Leverage knowledge of Gladly’s platform and Customer AI capabilities to recommend solutions that drive efficiency and customer value. Position AI adoption as a strategic expansion lever.
- Cross-functional Collaboration: Partner with Sales, Product, and CX teams to advocate for the Voice of the Customer and ensure alignment on account priorities and timelines.
What We’re Looking For
- Experience: 5+ years in a quota-carrying, client-facing role (Account Management, Customer Success with commercial ownership, or Install Base Sales) within a SaaS environment.
- Revenue Track Record: Proven success owning renewal and expansion targets. Experience managing five-to-six figure commercial cycles.
- Portfolio Management: Strong ability to manage a higher-volume book of business without sacrificing quality of engagement or commercial rigor.
- Commercial Mindset: You see customer success and revenue growth as inseparable. Every interaction is an opportunity to deepen value and expand the relationship.
- Operational Discipline: Excellent organizational skills and the ability to prioritize effectively across competing demands in a fast-paced environment.
- Ownership & Initiative: A proactive, “CEO of your book” mindset. You identify risk early, surface opportunities independently, and drive action without waiting for direction.
- Underdog Grit: A willingness to learn, adapt, and strive for excellence in an environment that values transparency and winning as one team.
Why Join Gladly?
Gladly is redefining customer experience AI — designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy:
- Competitive salaries, stock options, and comprehensive benefits
- Generous paid time off, parental leave, and home office stipends
- A fully remote work environment with opportunities for in-person team gatherings
- A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive
- A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily
We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.
Ready to apply?
Apply to Gladly