As the Enterprise Solutions Engineering Manager at Ashby, you’ll lead and grow a high-performing team of Solutions Engineers who own our most strategic, complex deals. Your team partners closely with Enterprise Account Executives to secure both the technical and commercial win—guiding large organizations through deep technical evaluations and showing them how Ashby can fundamentally transform the way they hire.

You’ll be responsible for shaping and scaling the enterprise SE motion at Ashby: hiring exceptional talent, coaching them toward mastery, operationalizing excellence, and refining the processes that help the team—and the business—win more often and more efficiently.

This is a highly strategic role with direct impact on revenue, product direction, and customer value.

Why Lead Enterprise SE at Ashby?

Product-Market Fit That Makes Your Team’s Job Easier

Your team will support a product that prospects genuinely love—and often ask to buy before the demo ends. This creates a coaching environment focused on technical excellence and deal strategy, not convincing skeptics.

Product Depth That Rewards Real Solutioning

Ashby is a deeply configurable product, and enterprise prospects come with highly specific, nuanced hiring processes. Your team won’t be running generic demos—they’ll be diagnosing how each organization hires and architecting solutions that map Ashby’s capabilities to those workflows. The coaching opportunity here is rich: breadth across the full product, depth in custom solutioning, and the creativity to show prospects something they didn’t know was possible.

A Leadership Role Designed for Builders

You’ll inherit an enterprise SE motion that works and level it up. The initiatives you lead—from POC frameworks to RFP libraries to competitive playbooks—will define how the enterprise SE team operates for years to come.

A Seat at the Product Table

You’ll work in tight collaboration with Product and Engineering, translating enterprise field insights directly into roadmap input. The problems your team uncovers shape what Ashby builds next.

What You’ll Do

Lead & Grow a High-Performing Enterprise SE Team

• Hire, onboard, and develop world-class Solutions Engineers who become trusted technical advisors to enterprise prospects.

• Coach SEs on enterprise-specific skills: discovery with complex buying committees, POC design and execution, security and compliance conversations, API-level technical fluency, and executive-level storytelling.

• Create a culture of ownership, rigor, and continuous improvement.

Drive Excellence in Enterprise Deal Execution

• Partner with Enterprise sales leadership to align on pipeline and priorities, with SEs leading the technical track alongside AEs on the commercial.

• Oversee the team’s involvement in demos, POCs, trials, security reviews, and RFPs across 3–5 stakeholder buying groups—including IT, Legal, HR, Finance, and executive sponsors.

• Review and elevate team execution, stepping in as a technical expert when the deal demands it.

Build Scalable Systems, Processes & Enablement

• Refine and evolve the existing enterprise SE motion—improving demo workflows, POC frameworks, trial structures, RFP processes, and internal knowledge bases.

• Build enablement for complex, long-horizon deals: competitive positioning, security questionnaire libraries, integration playbooks, and value frameworks.

• Identify patterns from the field and translate them into product feedback, roadmap insights, and internal process improvements in close partnership with Product and Engineering.

• Partner cross-functionally with CS, Product, Marketing, and Implementation to ensure seamless handoffs and consistent enterprise messaging.

Drive Strategic Initiatives from Diagnosis to Impact

• Identify high-leverage problems across the enterprise SE motion—through data, field observation, and stakeholder input—and develop a clear point of view on what to solve and why.

• Validate your hypotheses with the right stakeholders, write crisp proposals, and earn executive buy-in by connecting your recommendations to business outcomes.

• Own implementation end-to-end—managing change, aligning stakeholders, and driving adoption—with little oversight and a high bar for follow-through.

• Operate as a strategic contributor beyond your team—your projects will shape how Ashby scales, not just how the SE org runs.

You could be a great fit if:

🎯 You have experience managing or mentoring Solutions Engineers in complex, multi-stakeholder enterprise SaaS sales motions.

👥 You thrive in hiring, growing, and developing people—your success comes from your team’s success.

🧭 You think strategically about process, enablement, and operational excellence—not just individual deal execution.

🤝 You partner naturally with Sales Leadership and cross-functional stakeholders (CS, Product, Implementation) and can influence with clarity and conviction.

🧠 You have strong business and technical acumen and can guide your team on connecting Ashby’s capabilities to measurable enterprise outcomes.

📣 You’re a clear communicator who can simplify complex concepts—and coach others to do the same, whether in a security review or an exec boardroom.

⚙️ You love building—POC frameworks, RFP libraries, competitive playbooks, demo environments—and you do it with intentionality.

💙 You have empathy for enterprise Talent teams and are energized by solving their real, nuanced challenges.

Bonus Points For

🤝 Experience with Applicant Tracking Systems or deep familiarity with enterprise TA workflows.

🧩 Experience building POC frameworks, value engineering models, or technical trial structures for enterprise deals.

📈 Experience leading cross-functional projects in rapidly scaling organizations.

🔧 A background as a technical IC (SE, Solutions Architect, or similar) before moving into management.

Reasons You Shouldn’t Apply

• You’d rather execute deals yourself than enable a team around you to excel.

• You’re uncomfortable refining a motion that’s already partially built—you want either a blank slate or a fully finished playbook.

• Multi-stakeholder enterprise complexity—security reviews, procurement, legal, executive sponsors—feels like friction rather than the core of the job.

• You’re uncomfortable coaching people through feedback, growth, and evolving expectations.

• Fast-paced, high-change environments feel overwhelming rather than exciting.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.

As the Mid-Market Solutions Engineering Manager at Ashby, you’ll lead and grow a high-performing team of Solutions Engineers who sit at the center of our sales motion. Your team partners closely with Account Executives to secure both the technical and commercial win—showing prospects how Ashby can fundamentally transform the way they hire.

You’ll be responsible for shaping the next generation of SEs at Ashby: hiring exceptional talent, coaching them toward mastery, operationalizing excellence, and building scalable processes that help the team—and the business—win more often and more efficiently.

This is a highly strategic role with direct impact on revenue, product innovation, and customer value.

Why Lead SE at Ashby?

Product-Market Fit That Makes Your Team’s Job Easier

Your team will support a product that prospects genuinely love—and often ask to buy before the demo ends. This creates a coaching environment focused on excellence, not convincing.

Impact on a Market That’s Ripe for Transformation

Talent teams have been historically underserved. Your team will help prospects reimagine what a modern hiring platform can do—and you’ll have a front-row seat to shaping the next wave of innovation in TA tech.

A Leadership Role Designed for Builders

You’ll shape not just how Ashby sells, but how Ashby scales. The initiatives you lead will define how the SE team operates for years to come.

What You’ll Do

Lead & Grow a High-Performing SE Team

• Hire, onboard, and develop world-class Solutions Engineers who become trusted advisors to mid-market prospects.

• Coach SEs on discovery, storytelling, demo excellence, product knowledge, competitive positioning, and commercial partnership with AEs.

• Create a culture of ownership, collaboration, and continuous improvement.

Drive Excellence in Mid-Market Deal Execution

• Partner with Mid-Market sales leadership to align on pipeline and priorities, ensuring SE coverage accelerates deal momentum.

• Oversee the team's involvement in demos, trials, technical evaluations, and RFPs—ensuring every touchpoint is crisp, consultative, and actionable.

• Review and elevate team execution, stepping in as a technical expert when needed.

Support Building Scalable Systems, Processes & Enablement

• Standardize and evolve demo workflows, trial frameworks, RFP processes, and internal product knowledge.

• Identify patterns from the field and translate them into product feedback, roadmap insights, and internal process improvements.

• Ensure the team is equipped with the right tools, enablement, and infrastructure to support complex multi-stakeholder sales cycles.

You could be a great fit if:

• 🎯 You have experience managing or mentoring Solutions Engineers in complex, multi-stakeholder SaaS sales motions.

• 👥 You thrive in hiring, growing, and developing people—your success comes from your team’s success.

• 🧭 You think strategically about process, enablement, and operational excellence, not just individual deal execution.

• 🤝 You partner naturally with Sales Leadership and can influence cross-functional leaders with clarity and conviction.

• 🧠 You have strong business acumen and can guide your team on how to connect Ashby’s capabilities to measurable customer outcomes.

• 📣 You’re a clear communicator who can simplify complex concepts and coach others to do the same.

• ⚙️ You love building—systems, playbooks, processes, knowledge bases, demo environments—and you do it with intentionality.

• 💙 You have empathy for Talent teams and are energized by solving their real, nuanced challenges.

Bonus Points For

• 🤝 Experience with Applicant Tracking Systems or deep familiarity with TA workflows

• 🧩 Experience building demo infrastructure, value frameworks, or trial structures

• 📈 Experience leading cross-functional projects in rapidly scaling organizations

Reasons You Shouldn’t Apply

• You prefer maintaining the status quo rather than building new systems and iterating quickly.

• You’re uncomfortable coaching people through feedback, growth, and evolving expectations.

• You would rather execute deals yourself than enable a team around you to excel.

• You’re not energized by both the business side and the technical side of solutioning.

• Fast-paced, high-change environments feel overwhelming rather than exciting.

• You have never owned a strategic project from inception through execution.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.

Engagement Manager - Americas

Hi, I’m John and I’m the Head of Professional Services at Ashby. One of my favorite aspects of Ashby is our operating principle of . Coupled with our principle of caring deeply about our customers, we often find ourselves wondering ‘what is a better way to accomplish this’. That’s why I am thrilled to be hiring our first Enterprise Engagement Manager! As a highly cross-functional member on our growing Professional Services team (within Ashby’s Customer Success organization), you’ll have the opportunity to start shaping our customers’ journeys before they kick off, ultimately upleveling the overall customer experience.

About the Role

As an Engagement Manager, you will have responsibility for implementation and services scoping and design, as well as Statement of Work creation to capture recommendations. The SA is a member of the Professional Services (PS) organization and a close partner to the Enterprise Sales team. Broadly, the goal of this role is to ensure the success of Enterprise customers through professional services.

You will work directly with prospective customers and our Solutions Engineering team during the sales cycle to understand the current state, define a clear path to success, and shape both the deal and implementation approach accordingly. You will provide continuity between what was sold and what is delivered by ensuring a comprehensive handoff from Sales to PS.

This is a high-impact, highly cross-functional role focused on aligning pre-sales motions with implementation work to improve Enterprise sales win rates, accelerate time-to-value, and drive long-term customer outcomes. You will play a critical role in matching prospective customers with the approaches that best meet their needs, while helping Sales win complex deals by increasing buyer confidence and reducing perceived implementation risk.

What You’ll Do

Design and Close Successful Professional Services Opportunities (Pre-Sales)

• Act as a trusted advisor to help prospective customers understand how to successfully implement Ashby

• Partner with Account Executives and Solutions Engineers to scope and design implementation approaches for complex enterprise opportunities

• Translate prospective customer needs and constraints into a tailored path to go-live, including an implementation strategy, success milestones, and services offerings required to support the customer

• Align customer stakeholders (including executives) on desired outcomes, timelines, and responsibilities

• Create, negotiate, and execute Statements of Work (SOWs) aligned with Professional Services best practices and offerings that accurately the required scope, effort, and sequencing

Create Continuity into Delivery (Post-Sales / Early Lifecycle)

• Participate in the Sales handoff to ensure effective transition of recommendations and expectations to the post-sales team

• Ensure alignment between pre-sales commitments and post-sales execution by participating in kickoff calls for customers with complex or highly custom recommended approaches

Improve Professional Services GTM Motions

• Identify patterns across opportunities (what works, what breaks) and use these to refine our Enterprise Sales motion in partnership with Leadership.

• Refine how and when services are introduced and scoped within the sales cycle

• Contribute to playbooks, frameworks, and assets that improve how we sell and deliver services

What We’re Looking For

• 5+ years of experience in Enterprise SaaS across one or more of: Solutions Consulting, Professional Services, or Management Consulting

• Strong ability to diagnose business processes and translate them into scalable technical solutions

• Experience with complex, multi-stakeholder deals with meaningful implementation components

• Comfort navigating collaboration with both pre-sales and post-sales teams

• Excellent communication skills, with the ability to influence executives and align cross-functional teams

• Strong judgment and ability to balance customer needs, business outcomes, and operational feasibility

What Success Looks Like

• Increasing win rates, especially in the Enterprise

• Clear alignment between scope, expectations, and customer outcomes

• Reduced implementation friction and faster time-to-value

• Improved customer confidence and sentiment at kickoff and early lifecycle

• Stronger partnership between Sales, Professional Services, and Customer Success

• Increased retention and expansion driven by successful customer outcomes

Why This Role Matters

As we move upmarket, the complexity of our customers—and the importance of getting implementations just right—continues to increase. This role ensures we are not just closing quickly, but closing them in a way that sets customers up for long-term success.

The Interview

At Ashby, our team and interview process want to help you show your best self. Our interview process is structured to get to know you and your career as well as empower you with insight into our key focus areas. Here is the process in its entirety:

• 30 min - Recruiter Screen with Talent Team

• 45 min - Interview with Head of Professional Services (Hiring Manager)

• 45 min - Change Management Challenge

• Final Round Part 1:

  • 30 min - Interview with VP of Customer Success

  • 30 min - Interview with our Global Head of Solutions Engineering

• Final Round Part 2:

  • 30 min - Interview with CEO

  • 10 min - Closing Questions with Hiring Manager

Benefits

• You’ll get the time to do things the right way; we put a lot of emphasis on high quality work and avoid quick hacks as much as possible.

• You get to sell a product that our prospects & customers are truly excited about.

• Competitive compensation is offered.

• 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable.

• Unlimited PTO with four weeks recommended per year. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅

• Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise.

• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!

• $100/month education budget with more expensive items (like conferences) covered with manager approval

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.

Hi 👋🏾 I’m , Ashby's Co-Founder and VP of Engineering. This role is close to my heart because, as someone who can both design and code, it’s where I’ve always done my best work, but also where I was seen as a rebel and an outsider. I want folks like me to feel at home at Ashby, and so I made Design Engineering a formal role and department that works closely with me. Our first hire was over five years ago, and we’re doubling the team from five to over ten in the next year.

This role truly expects you to design and code. Design Engineer at Ashby isn’t just a Frontend Engineer with new branding, nor is it a Designer vibe coding prototypes. Combining excellence in both is where magic happens. I found that when I put my best effort into both the design and technical implementation of a feature, I had a nimbleness and creativity that was hard to achieve when I did only one or the other. For instance, the UX and UI I envisioned often influenced the data model's design and flexibility, while the understanding of technology's capabilities often simplified or improved the design. This role embraces that.

The Design Engineer role is more common today than five years ago, but I believe Ashby offers a unique opportunity that few can match:

• First, this role has always had the commitment of both Benji (CEO & Co-Founder) and me: I’ve held the role, steadfastly championed it since we started hiring in 2020, and haven’t diluted its responsibilities as we’ve grown (in fact, we’ve doubled down).

• Second, you work on a product at scale, not at an early-stage startup struggling to find users and get feedback on what you’ve designed and built. At Ashby, your work will touch over 100,000 weekly active users, millions of candidates per week, and notable customers like Notion, Linear, Shopify, and Snowflake. You’ll get to test out ideas with our own recruiting team and hiring managers who use Ashby every day (like me), and often hear customer feedback as early as the day you release.

In this role, you’ll work on our most challenging design problems, help others improve their designs by expanding and enhancing our in-house design system, and consult on bespoke design work needed by Product Engineers. To ground it with examples, Design Engineers at Ashby have:

• Redesigned our mobile web app by talking with customers who use it often, wireframing new flows, implementing its design system, and using it to make the wireframes a reality.

• Built a set of flexible, composable components in our design system that allow other engineers to easily build beautiful, consistent setup wizards across our product.

• Helped a Product Engineer improve the information hierarchy and scannability of their design for viewing a candidate’s assessments. Recruiters can quickly parse information and pick out anomalies.

Why You Shouldn’t Apply

Design Engineers come in many flavors, not all of which fit our model. Here are some reasons you might not enjoy the role:

• You only want to work on design systems. While improving our design system is one of many responsibilities, you won’t be able to work on it exclusively.

• You like to do extensive research and user testing before implementation. The beauty of being part-Engineer is that you can build conviction by shipping to a subset of users (including our own team) and gathering feedback!

• You want everything to be perfect before it gets into a user’s hands. One of the drivers of our success is that we ship fast. That often means we don’t agonize over every detail and instead iterate over time, often letting user feedback and business needs drive prioritization.

• You don’t have excellent taste and execution in visual design. Design Engineers set the bar for visual design in our app and continually improve it, pushing its boundaries with each new feature or redesign.

• You need company-driven process and structure to get your projects across the finish line. Sprint planning and well-defined project management processes are things you need or look to others to lead. You’d rather focus on the design and technical details.

• You only want to do exciting work. We’re building a team of kind, collaborative folks. Customer issues and investigations are distributed across the team, including our high-level ICs.

What Seniority/Level To Apply For

We’ve posted levels from Junior to Staff. The higher the level, the more experience and alignment with the role we expect when reviewing your application and while interviewing. Please apply to the one that sets the right expectations.

• Junior Design Engineer - You should have no more than 2 years of industry experience as a designer or engineer. We want to see projects (personal or professional) with at least a couple of users that showcase great visual taste and burgeoning talent in both UI/UX and Engineering.

• Design Engineer (This Posting) - This posting covers both Mid and Senior levels. You have 2+ years of continuous experience (e.g., internships don’t count) as an Engineer or a Designer. You have good proficiency in both Design and Engineering, with exceptional proficiency in the discipline you practice full-time. Regardless of which discipline you’re coming from, we expect experience designing products and shipping code to hundreds of users (even if through side projects).

• Staff Design Engineer - We’re looking for folks who’ve practiced our flavor of Design Engineering professionally. It may not be through a formal title, but you’ve made major contributions to a design system and designed and implemented features for hundreds of users and iterated on them through user feedback.

Internally, we do not use these titles, but Engineers are leveled based on proficiency (which you can read about ).

What We’re Building

As engineers, we are used to tooling that makes us better at what we do. When we started Ashby, we saw the opposite with Talent Acquisition software. Recruiting teams were leveling up how they did their work, but instead of software meeting this new standard, it held them back.

Scheduling a final round is an excellent example. Recruiting teams wanted to schedule candidates faster, track interviewer preparation and quality, and do it with half the headcount. A recruiter needed to manually collect availability from the candidate, identify qualified interviewers, perform “Calendar Tetris” to find who is available to interview the candidate, schedule on the earliest date possible, and make any last-minute adjustments as availability changed. They must do this while considering the interview load on each individual and whether interviewers need to be trained and shadowing others. 🥵 TA software didn’t help.

As hiring managers, we know TA is a critical function, and as engineers, we know software can do better. So, we built and continue to build Ashby to give TA teams the highest standard of tooling. Software that’s intelligent and powerful. Software that provides insights into where they’re failing and automates or simplifies many of the tasks they’re underwater with. We want other functions and departments to be jealous of what TA teams can do with Ashby, and today they often are!

Engineering Culture

Our engineering culture is motivated by Benji’s (my Co-founder and CEO) and my belief that a small, talented team, given the right environment, can build high-quality software fast (and work regular hours!). We do it through:

• Minimal process with ownership over decisions normally made by product and design

• Natural collaboration and deliberate communication

• Investing in tools and abstractions that give us leverage

• Putting effort into building a diverse team

Minimal Process & Lots of Ownership

The best engineers we’ve worked with delivered reliably magical outcomes. They took customer problems and relentlessly drove them to solutions that were not only successful but often brilliant and creative. While they did this with minimal oversight, stakeholders were never in the dark as to what was going on, and no setback was a surprise.

Traditional product-development processes aren’t meant for the best engineers. Their purpose is to create consistent outcomes regardless of the engineer’s skill. But, consistency comes at the expense of an engineer’s time and freedom—both ingredients necessary to generate those magical outcomes. As a result, process stifles the best engineers and doesn’t give others the opportunity to practice the behaviors that made the best engineers the “best.”

At Ashby, we want to build an environment that encourages every engineer to be their best. So, at Ashby, every Engineer runs their project. Product Managers (and Designers) build strategy, do customer research, and hand off problem briefs to Engineers. Engineers take on the rest: they research the problem, write product specs, build wireframes, and implement their solution end-to-end. We rely on engineers, not process, to push information outward to the relevant folks (e.g., Product Managers) and pull folks in to help (e.g., Designers, Infra). It’s a new level of ownership for many engineers, but we’d rather an engineer fail a bit and coach up their skills than use process as a crutch. Not everyone succeeds in our culture, but those who do thrive.

Collaboration is Natural & Communication is Deliberate

Our engineering team consists of lifelong learners who are talented but also humble and kind (meet them !). These attributes create an environment where collaboration happens naturally. We combine this with research, prototyping, and written proposals to see around corners and get feedback from the team across time zones. Focus time is something that we hold sacred, and, with thoughtful and deliberate communication, engineers are in <2h meetings per week (I wrote about it ).

Today, 25% of engineers and 50% of our engineering leaders at Ashby are from underrepresented groups. We are taking conscious steps to improve, like sourcing diverse candidates, providing generous paid family leave, no leetcode interviews, and more.

We also meet in person at least twice a year, once as a department and once as a company. You also have a small budget to meet up with folks in your city/region.

Increase Leverage, not Team Size

We built Ashby with the quality, breadth, and depth that many customers would expect from much larger teams over larger time scales. We’ve done this through investment in:

• Great developer tooling. Our CI/CD takes ~10m, and we deploy at least 15x a day. A debugger that works out of the box. Everyone on the team has contributed to our developer experience 💪🏾.

• Building blocks to create powerful and customizable products fast. At the core of Ashby is a set of common components (analytics modeling and query language, policy engine, workflow engine, design system) that we constantly improve. Each improvement to a common component cascades throughout our app (short video below).

• AI-powered tooling. We think of AI as a way to automate the mundane parts of building and maintaining high-quality software. We use a combination of third-party and internally built tools that, for instance, auto-triage customer issues, suggest fixes, prototype ideas, generate production-ready code, and conduct code reviews. Engineers have an unlimited token budget (but are not measured on it). We write in detail about our philosophy, current use of AI, and future plans for AI in Engineering .

Here’s an impromptu quote from Arjun in our company Slack of what it’s like to build a feature at Ashby:

And a demo of one of these building blocks:

Put Effort into Diversity

Diverse teams drive innovation and better outcomes. Having seen my mother and partner build their careers as minority women in non-diverse fields, I want to make sure Ashby creates opportunities for the next generation of engineers from underrepresented groups.

Today, 25% of engineers and 50% of our engineering leaders at Ashby are from underrepresented groups. We are taking conscious steps to improve, like sourcing diverse candidates, providing generous paid family leave, no leetcode interviews, and more.

Interview Process

At Ashby, our team and interview process want to help you show your best self. We’ll dive into past projects and simulate working together through pair programming, designing, writing design system specs collaboratively, and discussing decisions. There are no leetcode or whiteboard exercises.

Our interview process is three rounds:

• Introduction call with me (30m, live). Be prepared to screen-share examples of your work.

• A second round where we either do a technical screen (1h, live) or a design take-home (~3h async, 30m live)

• Three interviews, a deep dive into a past design system or design project, a design system interview, and the interview we didn’t do in the second round: technical screen or design take-home. (3h, live)

Depending on our leadership team’s bandwidth, we may start with an additional 30m screen with a recruiter.

I will be your main point of contact and prep you for interviews. Each round will have written guidance so you know what to expect. You’ll meet 3-4 people in Design Engineering (with 5-15 minutes in each interview to ask them questions). If we don’t give an offer, we’ll provide feedback!

Your First Three Months at Ashby

We want an exceptional onboarding experience for every new hire. At Ashby, your dev environment is set up with a single script, you push your first product change on day one, and you spend the rest of your time shipping product changes that give you a tour of our codebase and best practices. The product changes increase in scope and ambiguity from simple copy changes to the delivery of a prominent, impactful feature. Your manager will do a 30, 60, and 90-day review to give feedback and calibrate on how we work together.

It’s a team effort to get you successfully onboarded; you’ll have a peer paired with you to answer questions, pair program, and check in often to see if you need help. The rest of the team will run training sessions on our culture, product, engineering process, and technical architecture.

Technology Stack

Our tech stack is TypeScript (frontend & backend), React, GraphQL API, Node.js, Postgres, and Redis. Depending on the level you’re applying for and your past experience, we expect, at a minimum, good proficiency with TypeScript, React, and CSS. Proficiency with backend technologies is a plus, as it allows you to work without coordinating with Product Engineers.

Benefits

• Competitive salary and equity.

• 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable.

• Unlimited PTO, and we will encourage you to take it.

• A minimum of 12 weeks of fully paid parental leave, covered by Ashby. For folks outside the US, it may be longer to be in line with regional requirements.

• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!

• $100/month education budget with more expensive items (like conferences) covered with manager approval.

• If you’re in the US, we offer top-tier health insurance for you and your dependents, with 100% of premiums covered by Ashby. In other countries, we provide high-quality supplemental health insurance for you and your dependents, also fully covered by us.

Ashby’s success hinges on hiring great people and creating an environment where we can be happy, feel challenged, and do our best work. We’re being deliberate about building that environment from the ground up. I hope that excites you enough to apply.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.

Hi, I’m , Head of Contract Management (Renewals) at Ashby. Our Contract Management team plays a critical role in helping customers navigate renewal and commercial conversations thoughtfully, strategically, and with a high degree of trust. We are building a team that takes pride in delivering exceptional customer experiences while also protecting the long-term health of the business, and I am excited to be hiring a Manager of Contract Management (Renewals) to help scale and evolve this function.

In this role, you’ll lead and develop a team of Startup Contract Managers responsible for guiding customers through renewals, pricing conversations, negotiations, and long-term partnership planning. A key part of this role is helping the team navigate increasingly complex commercial conversations while building scalable processes, operational rigor, and repeatable frameworks that elevate both the customer experience and the effectiveness of the Contract Management organization.

You’ll partner closely with leaders across Customer Success, Sales, RevOps, Product, Legal, Finance, and Support to help shape how Ashby approaches renewals and long-term customer growth as we continue to scale upmarket.

About the Role

As the Manager of Contract Management, you’ll lead a team of global Startup Contract Managers responsible for renewal strategy, customer retention, and commercial partnership management across Ashby’s customer base. You’ll act as a coach, operator, and strategic thought partner — helping the team grow their commercial acumen, negotiation capabilities, and customer judgment while also building scalable systems and processes that allow the organization to operate effectively at scale.

In this role, you will:

• Lead and coach a team of 6 Startup Contract Managers (4 in America and 2 in EMEA) responsible for renewals, contract negotiations, and commercial partnership conversations. These individuals do high volume - about

• Up-level team performance through thoughtful coaching, operational discipline, and skill development across negotiation strategy, forecasting, customer communication, and stakeholder management

• Help build scalable renewal processes, systems, and operational workflows that improve efficiency while preserving a high-touch customer experience

• Partner cross-functionally with Customer Success, Sales, Product, Finance, Legal, Support, and RevOps to align on customer strategy and commercial outcomes

• Drive consistency in renewal execution, forecasting accuracy, CRM hygiene, and pricing governance across the team

• Support the team in navigating complex negotiations involving procurement, legal, executive stakeholders, pricing transitions, and multi-product commercial conversations

• Translate successful negotiation strategies and customer patterns into repeatable frameworks, playbooks, and enablement materials for the broader organization

• Help shape the long-term vision and operational strategy for the Contract Management function as Ashby continues to scale

Role Requirements

Team Leadership & Coaching

You have experience leading and developing high-performing customer-facing teams in a b2b SaaS environment. You know how to foster a culture centered around empathy, accountability, creativity, and transparency, while helping individuals grow through thoughtful coaching and continuous feedback.

Commercial Acumen & Negotiation Strategy

You have deep experience managing or overseeing complex renewals, pricing conversations, and contract negotiations. You understand how to balance customer partnership with commercial integrity, and can coach teams through nuanced negotiation scenarios with confidence and sound judgment.

Renewal Strategy & Forecasting

You understand how to proactively manage renewal risk, expansion opportunities, forecasting accuracy, and long-term account planning. You bring structure and discipline to renewal operations while remaining adaptable in dynamic customer situations.

Operational Mindset

You have experience building or improving scalable systems, workflows, and processes that allow teams to operate effectively at scale. You value operational excellence, data accuracy, and thoughtful process design.

Cross-Functional Collaboration

You are comfortable partnering across Sales, Customer Success, Product, RevOps, Legal, Finance, and Support to align around customer needs, pricing strategy, and long-term business outcomes.

Customer & Executive Communication

You are an excellent communicator who can navigate challenging conversations with empathy, professionalism, and clarity. You know how to build trust with both customers and internal stakeholders while maintaining transparency throughout the renewal process.

Problem-Solving Orientation

You don’t rely solely on “what worked before.” You are thoughtful, adaptable, and solutions-oriented — able to navigate ambiguity and develop creative approaches to complex commercial challenges.

Data-Driven & Strategic

You are comfortable using data, trends, customer insights, and operational metrics to drive decision-making and improve both team performance and customer outcomes.

You’ll Be a Great Fit If You:

• You communicate with clarity and empathy. You ask thoughtful questions, simplify complex concepts, and build trust through transparent communication.

• You enjoy coaching. You see every negotiation, renewal, and customer interaction as an opportunity to help your team learn and grow.

• You are highly operational. You value strong internal systems, accurate forecasting, clean data, and scalable process design.

• You thrive in dynamic environments. You are energized by solving complex problems and adapting processes as the business evolves.

• You balance customer advocacy with business integrity. You can empathize deeply with customer needs while confidently protecting Ashby’s long-term commercial interests.

• You are a strategic problem solver. You know how to navigate ambiguity, identify creative solutions, and align multiple stakeholders toward a shared outcome.

• You enjoy building. You are excited about helping shape the future of the Contract Management organization and scaling its impact across Ashby.

You Might Not Be a Fit If:

• You prefer highly rigid, unchanging processes and environments.

• You are uncomfortable navigating pricing conversations, negotiations, or commercial ambiguity.

• You prefer operating independently rather than through cross-functional collaboration and team development.

• You are more interested in defining high-level strategy than owning execution alongside your team.

• You avoid operational detail, forecasting rigor, or system/process improvement work.

• You are uncomfortable balancing customer empathy with accountability and commercial discipline.

• You prefer transactional customer interactions over long-term strategic partnership building.

Our Philosophy

Here are a few key points (relevant to the go-to-market side) that should give you an idea of what it is like to work with us:

• We spend a lot of time building best-in-class products since we believe a highly differentiated product is easier to position and support in commercial conversations.

• We believe deeply in pairing customer empathy with accountability and operational excellence.

• We value thoughtful communication, principled decision-making, and strong ownership across every function.

• We strongly believe that small teams with very talented people deliver significantly better outcomes than large teams with unclear ownership or low accountability.

• We care deeply about helping customers succeed while also building a sustainable, scalable business.

We value a strong sense of ownership, principled thinking over experience, and thoughtful communication — we’ll get into these and other values throughout the interview process.

Interview Process

At Ashby, our interview process is designed to help you show your best self while also giving you insight into how we operate as a team. The process typically includes:

• Recruiter Screen - 30 minutes

• Hiring Manager Interview - 45 minutes

• Strategic Exercise - Take-home assignment

• Final Round - 2 hours

  • Rather than a traditional panel interview with a large group, we structure our panel into a series of smaller conversations. This gives you the opportunity to meet with multiple team members in a more conversational setting focused on specific topics, instead of a formal Q&A. You'll discuss how you approach problem solving, how you work with sales, and dive into a product complexity exercise.

Benefits

• You’ll get the time to do things the right way; we put a lot of emphasis on high quality work and avoid quick hacks as much as possible.

• 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby - do it when you feel financially comfortable.

• Unlimited PTO with four weeks is recommended per year. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅

• Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise.

• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!

• $100/month education budget with more expensive items (like conferences) covered with manager approval.

  Ashby’s success hinges on hiring exceptional people and creating an environment where they can do their best work. We’re being intentional about building that environment from the ground up, and we hope that excites you enough to apply.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.