Ashby

The Staff Product Designer will take ownership of larger product features, focusing on various aspects of design including navigation, information architecture, and interaction. They will also consult with engineers and use customer feedback to propose projects for improvement. | Candidates should have over 10 years of product design experience, particularly in desktop SaaS, and be able to manage ambiguous projects effectively. They should possess strong skills in design craft and be able to influence cross-functional teams. | Hi! 👋 I'm Chris, head of Product Design at Ashby. We're looking for a versatile, intrinsically motivated designer who is excited to contribute to rethinking how modern software is designed. At Ashby, you'll be part designer, part product manager, part consultant, and part design system manager (or some combination of the 4!). We do design differently here, and if that excites you, read on. Our unique approach is working - we're growing >100% year-over-year and have notable customers like Notion, Linear, Shopify, and Snowflake. Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, very low churn, and many years of runway. We're backed by amazing investors like Y Combinator, Elad Gil, Lachy Groom, and many more! We’ll share more details once we meet. How We Work In my previous roles, product teams always consisted of a product manager, a designer, and ~4-5 engineers. This may sound familiar to you! The product manager briefs the designer who then designs. After designing, mocks are handed to the engineers. We take a more principled approach here at Ashby. If you've been designing software enough, you'll realize in actuality, design is required in varying degrees on each project. Sometimes in the past, I'd be asked to design yet another settings page, when really all that was needed was an engineer to reuse existing components and just follow some documentation I had written. Other times, I felt I should effectively be the product manager and own a project from beginning to end. In these latter cases, it made sense that I was even the one providing project updates and managing resources rather than constantly being pinged by a separate product manager. This principled approach is now what we do here, and it is part of what has allowed Ashby to take down incumbents in multiple verticals all at once. We don't settle for the status quo—we actively resist reversion to the mean. Currently, I report to Benji, the co-founder & CEO. Both Abhik and Benji (our founders) care deeply about design, which at first glance may seem counterintuitive given the number of full-time designers that we employ. The belief is not that design is unimportant, but rather that it should be owned by the product team collectively, not solely by a group of full-time designers who happen to have the job title. The design department’s job at Ashby is not to make every single design decision but to equip our entire product team to make better decisions themselves, as well as edit decisions that PMs/Engineers choose to make. That, while tackling the biggest design challenges ourselves. Separate from design, you may also be excited by the fact that we maintain a near seed-stage-like culture with fuzzy lines between functional roles, as much autonomy as you can handle, and a focus on IC-work with an almost-no-meeting culture. While you get the product-market fit and scale of a growth-stage startup, you also get the agency and no-nonsense, no-red-tape culture of a seed-stage startup. What We’re Building Talent teams aspire to build a hiring process that identifies great candidates, moves them quickly through the interview process, and provides an excellent experience for the candidate. To accomplish this, recruiters perform thousands of daily tasks to coordinate and relay information between candidates, interviewers, and hiring managers. Teams struggle to keep up! Scheduling a final round is an excellent example of our customers' challenges. A recruiter needs to collect availability from the candidate, identify potential interviewers, perform “Calendar Tetris” to find who is available to interview the candidate, schedule on the earliest date possible, and perform any last-minute adjustments as availability changes. They must perform this while considering the interview load on each individual and whether interviewers need to be trained and shadowing others. Ashby provides talent teams with 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 put a lot of effort into designing products that are approachable to beginners but mastered and extended by power users. In many ways, spreadsheets set the bar here (and are what we often replace!). Why you should or shouldn’t apply Your qualifications: 10+ years of product design experience, with the majority being in desktop SaaS Able to take huge, ambiguous projects and break them down into actionable parts Able to speak to patterns of the highest functioning design teams and how to create an environment of high performance Able to leverage designers' superpowers to influence engineering, product, and the rest of the company Able to create standards and principles that will help improve the quality of design across the product org Able to think from first principles instead of simply applying the “standard” UX processes. Enough experience that your intuition can solve most usability problems without having to rely solely on data & metrics or conducting user research. Curious & resourceful enough to come up with creative solutions and de-risk them appropriately. Best-in-class skills in layout, navigation, IA, UI, and interaction design. Obsession with craft & details. You have experience at an early-stage startup or have spent time as a solo designer on a team. You may want to apply if you’re excited about: Creating leverage and impact far and above what you'd see in a typical EPD product team structure. You won’t be a cog in the wheel, the wheel is not very big! Getting to work on all parts of a massive product surface area - spanning many user types, JTBDs, usability challenges, etc. Unlike in other organizations, you won’t be stuck working on one problem for many years. Helping reinvent the design model for modern enterprise software—you don’t have to build wireframes, user journeys, personas, etc. What matters is solving a customer’s problem; what tools you use are up to you. Covering all parts of the design process with a focus on design craft. You'll still be doing the occasional user research interview but will be focused on using heuristics & experience to improve our IA, navigation, interactions, UI patterns, and more. Helping build our design system from (almost) the ground up. Conversely, you may not want to apply if: You feel uncomfortable designing independently without much guidance from a PM or design management. You’re uncomfortable having your decisions and process being challenged constantly by engineering & product. You prefer an in-person role over remote (Ashby operates remotely). You dislike written documentation. You want a set structure and rhythm to your projects. PM gives you a brief, you do wireframes, then mocks, then pass off work to engineers. Rinse and repeat. You prefer a narrow job scope - interaction design only, design system only, etc. On a weekly basis you will find yourself: Consulting for engineers who need help structuring layout, typography, flows, etc. Digging into problems by consulting GTM, talking to customers, asking for data requests, and more in order to present confident assumptions about your proposals. Using Figma to draw out your ideas and create visual artifacts for stakeholder alignment. Writing specification docs (we call them specs!) that detail your design proposals. These documents are meant to get stakeholder alignment on the biggest decisions you want to make and are a core part of how we work at Ashby. Taking ownership of larger product features and thinking through Jobs-To-Be-Done, navigation, information architecture, layout, interaction, etc. Taking in customer feedback and using heuristics to build your own usability backlog and propose projects for engineers to take on. Consolidating and refining our design system to be functional, aesthetic, and best-in-class. 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 and talking through decisions. Our interview process is four rounds with some casual Zoom coffee in between to get to know each other: 30-minute introduction call to discuss Ashby and your experience 45-minute portfolio review 135-minute design exercise, portfolio deep dive, and meet the CEO. The exercise will be a live whiteboarding exercise where we provide a prompt and you show us how you'd break down problems and come up with solutions. The portfolio review is a repeat but you'd have more time and a different audience. 90-minute meet the team + an app teardown I'll be your main point of contact and prepare you for interviews. You’ll meet other engineers and product managers as well (with 15 minutes in each interview to ask them questions). If we don’t give an offer, I'll provide feedback as to why if you'd like it (I'm serious!). 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. This is one of the reasons I joined personally - not a lot of startups do this. 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. If you’re in the US, top-notch health insurance for you and your dependents with all premiums 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.

Managing a high volume of inbound and outbound sales opportunities, conducting product demos, and building relationships with startup clients. | 2+ years of full-cycle SaaS sales experience, proficiency in outbound prospecting, and ability to manage multiple opportunities concurrently. | About Ashby • We’re building the next generation of enterprise software, starting with products that help talent leaders, recruiters, and managers unlock hiring excellence • Raised our Series D earlier this year, and we’re growing ARR >100% YoY • Have over 3,000 amazing customers including OpenAI, Ramp, Deliveroo, Notion and Reddit • Built multiple products to win both land-and-expand and material new business deals • Rapidly moving up-market with no signs of slowing down • Implemented AI throughout the platform • Known for our pace of innovation and advanced analytics About this Role We're hiring an Account Executive in North America (East) to continue to scale Ashby's fast growing Startup segment! In this role, you'll help play a key role on a small team, helping us win new business with growth companies of up to 100 employees. We receive a steady stream of inbound leads in this segment, which means our Startup AEs need to be highly organized and capable of managing a high volume of opportunities. You'll also do outbound pipeline development to some of the fastest growing and exciting venture-backed startups in the market to accelerate our growth. To ensure a smooth review process, please apply to only one territory (East or West) that best aligns with your background and time preferences. You could be a great fit if • 📣 You practice clear, concise communication. You write short, effective emails. You are skilled at executing outbound strategies that target high growth startup accounts and want the opportunity to lead the team in pipeline creation. • 🕘 You’re highly organized and diligent with your time. You know where to focus your efforts to produce the best results. • 🤓 You love becoming an expert. You enjoy learning about new fields of interest, and can distill information down to its essence to share with others. • 🔍 Your peers describe you as detail oriented. You send crisp follow-up emails, on time. You take pride in internal operations, like real-time CRM updates. • ⚡️ You move fast. You leverage tools/technology to maximize your selling time. You are comfortable managing a pipeline of 15+ opportunities concurrently. • 🎧 You are an excellent listener. You consistently seek to understand both the technical pain and the business impact, hearing the nuance and detail in what others have to say. • 🧑‍💼 You are a collaborative team player, dedicated to supporting your colleagues and contributing to the team's overall success. You thrive in a cooperative environment where growth and team success are valued. Requirements • 🤝 You have 2+ years of full-cycle SaaS sales experience • 📢 You source sales meetings from outbound prospecting activities • 📈 You have consistently achieved stretch targets by being both creative and organized Bonus Points • You were previously a recruiter or RecOps professional and have used Ashby or other tools like Greenhouse or Lever • You have previously sold to TA professionals • Or, you were a top performing inbound and outbound BDR before becoming an AE Reasons not to apply: • You are uncomfortable running your own product demonstrations • You only want to work on a small number of big deals • You would rather not have your day to day to consist of 4+ meetings per day Our Philosophy Here are a few key points that should give you an idea of what it is like to work with us: • We invest in building best-in-class products with strong product development velocity since we believe a highly differentiated product is easier to sell. • We aim to offer deep expertise whenever we interact with prospects and customers. • We strongly believe that small teams of talented people (and the right work environment) deliver much better performance than teams with large headcount. We hire and compensate accordingly. Interview Process: Our interview process is thorough — we aim to ensure each person that joins the team is the right fit for Ashby and will provide ample information for you to assess if Ashby is the right fit for you. The process for this role is as follows: • Recruiter Screen -30 min • Sales Writing Take Home • Hiring Manager Interview - 60 min • Sales Demo and Revenue Operations Conversation - 1.15 hr Benefits • Sell a product that our customers are truly excited about. • Fairly set, achievable quotas. Typically, greater than 65% of AEs are at or above quota. • Unlimited PTO with four weeks recommended per year • Generous equipment, software, and office furniture budget. Get what you need to be happy and productive! • 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. • $100/month education budget with more expensive items (like conferences) covered with manager approval. • If you’re in the US, top-notch health insurance for you and your dependents with 100% of all premiums covered by us, Flexible Spending Accounts and 401K match. We also offer up to 12 weeks of fully paid family/parental leave for all caregivers. We're in the talent acquisition software business. We run the end-to-end hiring process through our own platform, and ensure a level playing field for all candidates. Reaching out to hiring managers or recruiters directly won't improve your odds of success. Please focus your energy on the quality of your application. 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.

Supporting SaaS sales through technical expertise, managing product development, and leading teams. | Proven experience in SaaS sales, outbound prospecting, and achieving sales targets, with excellent communication and organizational skills. | About Ashby We’re building the next generation of enterprise software, starting with products that help talent leaders, recruiters, and managers unlock hiring excellence Raised our Series D earlier this year, and we’re growing ARR >100% YoY Have over 3,000 amazing customers including OpenAI, Ramp, Deliveroo, Notion and Reddit Built multiple products to win both land-and-expand and material new business deals Rapidly moving up-market with no signs of slowing down Implemented AI throughout the platform Known for our pace of innovation and advanced analytics About this Role We're hiring an Account Executive in North America (East) to continue to scale Ashby's fast growing Startup segment! In this role, you'll help play a key role on a small team, helping us win new business with growth companies of up to 100 employees. We receive a steady stream of inbound leads in this segment, which means our Startup AEs need to be highly organized and capable of managing a high volume of opportunities. You'll also do outbound pipeline development to some of the fastest growing and exciting venture-backed startups in the market to accelerate our growth. To ensure a smooth review process, please apply to only one territory (East or West) that best aligns with your background and time preferences. You could be a great fit if 📣 You practice clear, concise communication. You write short, effective emails. You are skilled at executing outbound strategies that target high growth startup accounts and want the opportunity to lead the team in pipeline creation. 🕘 You’re highly organized and diligent with your time. You know where to focus your efforts to produce the best results. 🤓 You love becoming an expert. You enjoy learning about new fields of interest, and can distill information down to its essence to share with others. 🔍 Your peers describe you as detail oriented. You send crisp follow-up emails, on time. You take pride in internal operations, like real-time CRM updates. ⚡️ You move fast. You leverage tools/technology to maximize your selling time. You are comfortable managing a pipeline of 15+ opportunities concurrently. 🎧 You are an excellent listener. You consistently seek to understand both the technical pain and the business impact, hearing the nuance and detail in what others have to say. 🧑‍💼 You are a collaborative team player, dedicated to supporting your colleagues and contributing to the team's overall success. You thrive in a cooperative environment where growth and team success are valued. Requirements 🤝 You have 2+ years of full-cycle SaaS sales experience 📢 You source sales meetings from outbound prospecting activities 📈 You have consistently achieved stretch targets by being both creative and organized Bonus Points You were previously a recruiter or RecOps professional and have used Ashby or other tools like Greenhouse or Lever You have previously sold to TA professionals Or, you were a top performing inbound and outbound BDR before becoming an AE Reasons not to apply: You are uncomfortable running your own product demonstrations You only want to work on a small number of big deals You would rather not have your day to day to consist of 4+ meetings per day Our Philosophy Here are a few key points that should give you an idea of what it is like to work with us: We invest in building best-in-class products with strong product development velocity since we believe a highly differentiated product is easier to sell. We aim to offer deep expertise whenever we interact with prospects and customers. We strongly believe that small teams of talented people (and the right work environment) deliver much better performance than teams with large headcount. We hire and compensate accordingly. Interview Process: Our interview process is thorough — we aim to ensure each person that joins the team is the right fit for Ashby and will provide ample information for you to assess if Ashby is the right fit for you. The process for this role is as follows: Recruiter Screen -30 min Sales Writing Take Home Hiring Manager Interview - 60 min Sales Demo and Revenue Operations Conversation - 1.15 hr Benefits Sell a product that our customers are truly excited about. Fairly set, achievable quotas. Typically, greater than 65% of AEs are at or above quota. Unlimited PTO with four weeks recommended per year Generous equipment, software, and office furniture budget. Get what you need to be happy and productive! 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. $100/month education budget with more expensive items (like conferences) covered with manager approval. If you’re in the US, top-notch health insurance for you and your dependents with 100% of all premiums covered by us, Flexible Spending Accounts and 401K match. We also offer up to 12 weeks of fully paid family/parental leave for all caregivers. We're in the talent acquisition software business. We run the end-to-end hiring process through our own platform, and ensure a level playing field for all candidates. Reaching out to hiring managers or recruiters directly won't improve your odds of success. Please focus your energy on the quality of your application. 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.

Leading and developing a high-performing customer success team for enterprise clients, optimizing customer lifecycle processes, and collaborating cross-functionally to enhance product and customer outcomes. | Proven leadership in SaaS customer success, enterprise B2B experience, strategic and operational skills, deep product understanding, cross-functional collaboration, and data-driven mindset. | Head of Strategic Customer Success Hi, I'm Casey — Head of Dedicated Customer Success; I look after our upmarket customers in the Strategic and High Touch segments. One of my favorite aspects of Ashby is our operating principle of Continuous Improvement. 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 Head of Strategic Customer Success! In this role, you’ll have the opportunity to elevate the customer experience to the next level, working alongside our High Touch, Startup, Support, Contract Management, and Professional Service leaders. Our product and growth are exceptional. Ashby’s All-in-One solution is powerful, easy to use, and often replaces 4-5 disparate solutions (ATS, scheduling, analytics, sourcing and CRM). We have several thousand customers, including notable organizations like Shopify and Snowflake. Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, we’re growing >100% year over year, with very low churn. About this role: As Head of Strategic Customer Success, you will lead our Strategic Customer Success segment and help define how Ashby serves our Enterprise customers. This role is pivotal in ensuring that, as we continue to move upmarket, our customers consistently have a remarkable experience. You’ll oversee and continue to grow a highly skilled team of tenured Strategic CSMs, guiding how they partner with some of our most sophisticated and complex organizations. You’ll work alongside our High Touch Customer Success leaders, applying programmatic frameworks where they fit, while also facilitating bespoke engagements for Enterprise customers who require a more tailored approach. Success in this role requires a deep product focus: we’re looking for a leader who is comfortable getting into the details of the product alongside the team, and who can partner with internal stakeholders to advocate for the product changes that matter most. Ultimately, you will shape how Strategic Customer Success evolves at Ashby and ensure our largest customers achieve meaningful outcomes with our platform. Role requirements: Proven Leadership & Coaching: You have a track record of successfully growing, leading and developing high-performing Customer Success Teams in a complex B2B SaaS environment. You know how to deliver clear, actionable feedback, and you build a culture where your team can grow and succeed. Customer-Centricity with an Enterprise Focus: You bring proven experience working with upmarket B2B companies (1,000+ employees) and understand the unique opportunities of enterprise adoption. You ensure customers realize value across their lifecycle and achieve their objectives with Ashby, balancing hands-on support with scalable approaches. Strategic & Operational: You proactively identify opportunities to strengthen how we serve customers — whether through process improvements, new frameworks, or fresh approaches to engagement. You balance big-picture strategy with hands-on execution, driving process improvements and frameworks that deliver measurable results. Customer Impact & Product Mastery: You excel at quickly learning and navigating robust, complex products to design programs that improve the customer journey at scale. Your work drives measurable impact across onboarding, adoption, and retention — ensuring customers realize value quickly and sustain success over time. Cross-functional Collaboration: You partner effectively with Sales, Product, Engineering, and Operations to align on customer needs and deliver solutions. You understand when to collaborate, when to escalate, and how to influence outcomes across teams. Innovative & Principled Approach: You proactively address thematic customer opportunities and improve our processes accordingly; you’re comfortable leveraging fresh technologies to enhance the efficiency and efficacy of our team. You don’t rely on ‘I’ve seen this done’ but instead think critically to problem solve. Analytical Mindset & Continuous Improvement: You use data to guide decisions and improve performance. You’re comfortable measuring what matters — both for your team and your customers — and iterating to drive better results. You could be a great fit if: 📣 You communicate with clarity. You ask precise questions and can distill complex concepts into simple themes. 🎧 You see your role as both 1) an advocate for the Customer Success team, and 2) the voice of the customer to internal stakeholders so the product roadmap continues to evolve in an optimal direction. 📈 You are a strategic problem solver. You thrive at solving complex challenges with principled, scalable solutions. ⚡️You know process matters. You’re eager to improve workflows and operational details that enhance efficiency and consistency. 🔍 Your peers know you for your follow-through, detail orientation, and pride in strong internal operations. 🧑‍🏫 You love to coach. Whether through call shadowing, real-time feedback, or structured development, you see every moment as an opportunity to help your team grow. 🛠 You get into the weeds. You’re energized by diving into the product alongside your team, learning deeply, and modeling the type of engagement we expect from Strategic CSMs. You might not be a great fit if: You’re not eager to roll up your sleeves and get into the weeds — whether that’s shadowing calls, digging into the product, or iterating directly with your team. You prefer to focus solely on strategic priorities. We expect that even our most senior leaders are able to ‘traverse the elevation’ and be in the particulars as necessary. You’re uncomfortable with a writing-heavy culture. We rely on clear, concise proposals and documentation, and written communication is core to how we operate. You’re most comfortable with a simpler product rather than a highly configurable, technical platform. You prefer exclusively to build (rather than build, iterate, optimize). Your upmarket experience involves working with organizations that have fewer than 1,000 employees. 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 a lot easier to sell. We want to offer deep expertise whenever we interact with prospects and customers. We strongly believe that small teams with very talented people (and the right work environment) deliver much better performance than teams with large headcount. We hire and compensate accordingly. We value a strong sense of ownership, principled thinking over experience, and thoughtful communication (we put a lot of effort into using the right communication channels) - we’ll get into these and other values during the hiring process. 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 90 min - Interviews with VP of CS and Head of Dedicated CS - 30 min, then 60 min pending previous conversation 60 min - Presentation & Interview with Strategic CSM(s), Head of Startup, & Head of Professional Services 30 min - Interview with CEO 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 If you’re in the US, we offer top-tier health insurance for you and your dependents, with 100% of premiums covered by Ashby. We also offer a 3% 401k match. 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.

Lead and manage the revenue enablement team to develop and execute programs that improve sales and customer success team performance, onboarding, and adoption of frameworks to drive revenue growth and retention. | Proven experience leading enablement teams in SaaS companies scaling to $100M+ ARR, strong cross-functional partnership skills, program development expertise, LMS management, and ability to measure enablement impact. | About Ashby • We’re building the next generation of enterprise software, starting with products that help talent leaders, recruiters, and managers unlock hiring excellence • Raised our Series D earlier this year, and we’re growing ARR >100% YoY • Have over 3,000 amazing customers including OpenAI, Ramp, Deliveroo, Notion and Reddit • Built multiple products to win both land-and-expand and material new business deals • Rapidly moving up-market with no signs of slowing down • Implemented AI throughout the platform • Known for our pace of innovation and advanced analytics About this role As the Head of Revenue Enablement, you will be the business partner to our VP Sales and VP Customer Success to ensure consistently high caliber execution to support revenue growth and customer retention. You will play a pivotal role in developing and, with your team, executing programs that foster excellence in our Sales and CS organizations. Success in this hands-on leadership role is measured by the overall effectiveness of our customer-facing Sales & CS teams — this includes but isn’t limited to: fast time-to-ramp for new hires, consistent adoption of our frameworks and methodologies, strategic business partnership with GTM leadership and ultimately delightful customer experiences that drive growth. In 2026, Revenue Enablement will be a team of three. You will lead and manage two practitioners, one for each Sales and Customer Success. You will operate in a player-coach capacity, with an eagerness to roll up your sleeves to support program delivery and ensure execution against company priorities. Sales & CS will be close to 200 people by the end of next year, and so you and your team will have a high impact role on Ashby’s growth trajectory to $100M ARR and well beyond. Role Scope & Requirements • 🤝 Business Partnership: You are innately curious about the work and priorities of our Sales and CS Leaders. You ask the hard questions to understand the nuances of the business to identify how you can have the greatest impact. You partner effectively with stakeholders including Product Marketing, Revenue Operations and Senior Leadership to deliver comprehensive programs in support of our go-to-market strategy. • ⚙️ Program Development: You understand business needs and identify gaps in knowledge or skills. You’re a quick learner who is at home creating and curating materials for go-to-market teams. You collect disparate information through quantitative and qualitative approaches (e.g. interviews, internal documentation, and recorded customer calls) to create tailored learning paths that drive behavior change. You actively elicit feedback for program improvement. • 🧑‍🏫 New Hire Onboarding: You have experience developing onboarding programs for GTM teams that ensure new hires ramp quickly. You have a knack for simplification and prioritization—sometimes less is more. You can be the master architect for role and segment specific onboarding tracks. • 💻 Systems: You’ve managed an LMS and have perspective on which software capabilities best support learning outcomes and in-field execution. You closely follow AI-native enablement vendors and can separate marketing fluff from powerful new features. • 🚀 Scaling: You’ve helped a SaaS company scale to over $100M ARR where you lead an enablement team. You thrive in a high growth, dynamic environment and are familiar with reinforcement learning techniques to support organizations of this scale. • 📈 Impact: You use both analytics and observations to assess the impact of your enablement programs. You have a proven track record of achieving measurable improvements in team performance and productivity. You iterate on your approach based on results, evolving company goals, and changing market conditions. • 👷 Team Management: You are highly organized and have managed an enablement team who deliver multiple projects concurrently. You’re an “in the details” leader who ensures the success of your team’s work. You know when to advocate for additional resources to maximize impact. Out of Scope Since every organization thinks about Revenue Enablement a little bit differently, we intend to be clear about what we currently view as out of scope for this role, while also acknowledging that things may evolve, and your perspective also counts. • Technical Enablement / Ashby Product: We have an expansive product surface area as a full-suite talent acquisition platform. Our Support, CS and Solutions Engineering teams especially need to develop deep product acumen to be effective in their jobs. We anticipate you being a partner to other owners of Technical Enablement but it is not your primary responsibility. • Competitive Intelligence: You would not be expected to become the subject matter expert on our competitive landscape, but would partner with our PMM and Solutions Engineering teams on the creation of competitive enablement programs, leveraging existing knowledge and frameworks. You Might Love This Role If • You have a desire to build a world-class GTM practice. • You’re a systems thinker with experience scaling enablement programs. • Your peers would describe you as operationally excellent. • You excel in cross-functional collaboration. This Role Might Not Be for You If • You are uncomfortable rolling up your sleeves and executing. This is not a role for hands-off delegators. • You prefer working independently vs as part of an interdisciplinary team. • You love meetings! We’re a documentation first, async friendly team that values written communication as a core mode of communication. (We’re not anti-meeting but highly value the written word). Our Philosophy Here are a few points relevant to go-to-market that should give you an idea of what it is like to work with us: • We believe a highly differentiated product is a lot easier to sell, so we continually invest in product innovation and this has proven to be a sustainable source of competitive differentiation • We always aim to show up well prepared and with deep industry acumen. This caliber of customer experience is another way we differentiate. • We strongly believe that small teams with very talented people (and the right work environment) deliver much better performance than teams with large headcount. We hire and compensate accordingly. We value a strong sense of ownership, principled thinking over experience, and thoughtful communication (we put a lot of effort into using the right communication channels) - we’ll get into these and other values during the hiring process. 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, but equally move with precision and urgency • Competitive compensation, including 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 with four weeks is recommended per year. • 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.

Lead and grow a team of Customer Success Managers to enhance onboarding, adoption, and long-term customer partnerships while driving process improvements and advocating for product enhancements. | Experience leading Customer Success teams in a B2B SaaS environment, expertise in customer lifecycle management, operational process improvement skills, strong cross-functional collaboration, and data-driven problem solving. | Head of High Touch Customer Success 👋 Hi, I’m Casey — Head of Dedicated Customer Success at Ashby; I look after our upmarket customers in the Strategic and High Touch segments. One of my favorite aspects of Ashby is our operating principle of Continuous Improvement. 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 my backfill: the Head of High Touch Customer Success! In this role, you’ll have the opportunity to elevate the customer experience to the next level. You’ll join our Dedicated CSM leadership team, working alongside our Heads of Strategic and EMEA Customer Success, as well as leaders from our Startup CS, Support, Customer Education and Contract Management teams. About the Role As Head of High Touch Customer Success, you’ll play a critical role in ensuring our customers continue to have an exceptional experience with Ashby as we scale. You’ll grow a talented team of CSMs, lead the current Manager of High Touch Customer Success (a recent internal promotion), and drive the overall strategy and execution of our High Touch CS function. In this role, you will: • Lead and coach both the current Manager of High Touch CS and your own team of CSMs supporting customers across onboarding, adoption, and long-term partnership • Drive process improvements across the customer journey, with a focus on post-onboarding and adoption • Help evolve how we deliver consistent, high-quality customer experiences at scale • Serve as a key product advocate — partnering closely with internal teams to champion improvements that better support our upper mid-market and lower enterprise customers Role requirements: • Team Leadership & Coaching: You have experience leading and developing Customer Success Managers in a B2B SaaS environment. You know how to foster a culture of empathy, accountability, and continuous growth. • Customer Journey Expertise: You understand the customer lifecycle and have helped improve onboarding, adoption, and retention through thoughtful, repeatable approaches. • Operational Mindset: You’ve helped implement and improve team processes, and you bring a structured lens to scaling what works while staying adaptable. • Cross-functional Collaboration: You’re comfortable partnering with teams like Sales, Product, and Support to align around customer needs and elevate the experience. • Problem-Solving Orientation: You don’t rely on “what worked before” — you’re thoughtful, pragmatic, and eager to find solutions that fit the unique needs of your team and customers. • Data-Driven: You are comfortable using data and metrics to drive decision-making, continually improving both the team and customer experience. • Customer-First Thinking: You have a deep understanding of B2B customer needs and have a history of ensuring outstanding support experiences. • Lifecycle Awareness: You’re familiar with key stages like onboarding and adoption, and you’ve supported efforts that drive product engagement and help customers achieve their goals. You’ll Be a Great Fit If You: • 📣 You demonstrate clear communication. You ask clarifying questions with precision and can distill complex concepts into simple themes. • 🎧 You are a great listener. You see your role as 1) Advocate for the Customer Success Team as well as 2) Voice of the customer to internal stakeholders so we can ensure that our product roadmap continues to evolve. • 📈 You are a problem solver. You thrive at solving complex challenges with innovative, scalable solutions. • ⚡️You know process matters. You are eager to improve processes and workflows to enhance efficiency and efficacy. • 🔍 Your peers describe you as detail oriented. You take pride in internal operations. • ⚙️ You’re an advocate for the team. We’ll be looking for your help when it comes to defining resourcing and headcount planning. • 🧑‍🏫 You love to coach. You see every teaching moment as an opportunity and are excited to help teams grow. You Might Not Be a Fit If: • You prefer an in-person role over remote. • You’re not eager to roll up your sleeves and get into the weeds (e.g. call shadowing isn’t interesting to you). • You are accustomed to defining ideas and strategies, yet not responsible for their execution. • You thrive in environments where you lead a simple, established product rather than a dynamic, evolving one. • You prefer exclusively to build (rather than build, iterate, optimize) 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 a lot easier to sell. • We want to offer deep expertise whenever we interact with prospects and customers. • We strongly believe that small teams with very talented people (and the right work environment) deliver much better performance than teams with large headcount. We hire and compensate accordingly. We value a strong sense of ownership, principled thinking over experience, and thoughtful communication (we put a lot of effort into using the right communication channels) - we’ll get into these and other values during the hiring process. 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 • 60 min - Hiring Manager Interview with Global Head of Dedicated CS • 60 min Presentation & Interview with our Manager of High Touch, Head of Startup & Head of Strategic • Final Round: • 30 min - Interview with VP of Customer Success • 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 represent a product that our prospects & customers are truly excited about. • 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. • $100/month education budget with more expensive items (like conferences) covered with manager approval • Extended health benefits for you and your dependents (subject to availability with our Employer of Record) • Generous equipment, software, and office furniture budget. Get what you need to be happy and productive! 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.