Ashby

Manage contract renewals, support customer success, and collaborate with sales and internal teams to ensure customer satisfaction. | Experience in sales, customer success, or contract management, with strong communication and administrative skills. | Hello! I am Alex, Head of Contract Management at Ashby. I am thrilled to be expanding our Contract Management team, as this function serves an important role in the success of our customers and the business. Having a Contract Management team at Ashby allows our Sales team to focus on supporting prospective buyers on their journey to becoming an Ashby customer and existing customers expanding further into the product, while simultaneously allowing our Customer Success team to focus on the growth and success of our existing customers. With this harmonious relationship across the internal teams, we are able to make renewal and contract conversations meaningful and relevant to the needs of our customers, providing a top tier experience with Ashby. About The Role As an Ashby Contract Manager for Startup accounts, you will play a key role in supporting our revenue function and customer satisfaction with customers who are up to 100 employees. You will manage annual customer renewals, month-to-month customer subscriptions, contract questions, and will collaborate closely with a number of internal teams across Ashby’s largest customer segment. As a trusted guide to quickly growing and steady-state startups, you will need to secure early customer loyalty, guide non-recruiting personas through the renewal process, and provide hands-on assistance to customers. Attention to detail on a high volume of accounts will be essential, with an agile approach to secure continuing customers swiftly and solve for these smaller businesses creatively. With a focus on helping small startups begin to meaningfully grow their businesses, you will identify opportunities to support these businesses and identify high growth accounts. Your work as a Contract Manager directly impacts our broader business goals, with Ashby’s Operating Principles woven into our processes. This position requires expertise in core contract management competencies: • Navigating pricing and negotiation discussions with empathy and tact, while upholding a high level of respect for the value of Ashby and the services we render • Leading the renewal process with customers, ensuring timely and successful contract renewals, with terms that align to both the broader business goals and solve for the customer’s needs • Building and maintaining trust with customers, proactively addressing concerns and ensuring their subscription needs are met at time of renewal and throughout the customer lifecycle • Managing day-to-day administrative tasks, such as customer outreach, generating order forms, and CRM maintenance • Understanding contract terminology and how to communicate these terms to customers Our ideal candidate will have a strong background in a combination of sales, customer success, and renewal management, with a proven ability to drive contract renewals and enhance customer relationships. In this role, you will work closely with our customers to ensure they receive maximum value from our offerings, ultimately contributing to customer retention and satisfaction. You will work in partnership with Sales and Customer Success to ensure that the right resources are engaged to maximize customer growth, driving expansion and renewal. Ashby takes tremendous pride in our software; as such, we encourage all employees to have rich product knowledge. While the scope of your role does not require technical product aptitude, we will empower you with product knowledge to ensure you’re well-positioned for customer conversations (e.g. should tech stack pricing efficiency surface in a renewal, you are comfortable communicating our differentiators). You could be a great fit if: • You enjoy finding creative solutions for complex situations – this in turn will allow you to successfully solve for both the customer and Ashby • You are solutions-oriented – there is a solution to every problem or challenge we may face in Contracts • You are detail-oriented – we work across many different systems, with fact-checking and record-keeping a paramount priority for this contracts role • You are adaptable – you are able to be continuously learning and applying these learnings to your daily work • You excel at cross-functional collaboration, leveraging the right teams and colleagues to provide a top tier experience and solution for each customer, while being respectful of other individuals time, priorities, and goals • You have excellent communication skills over phone and email, and are able to navigate high pressure situations with ease and professionalism (strong public speaking skills translate well to this role) • You delight in having autonomy over your schedule — there is a high level of accountability at Ashby, and we rely on you to complete your work; while all of your work will be visible to the entire company, you will be responsible for managing your time • You display empathy in situations that require it – you understand where our customers are coming from and strive to find a solution accordingly • You value transparency – there is clarity and honesty in every step of our renewal process, and within Ashby as a company You might not be a great fit if: • You avoid taking ownership, and prefer to hand off various tasks • Dynamic situations make you uncomfortable • You find pricing conversations and negotiations demanding and taxing • You do not enjoy admin work and prefer to be in face-to-face meetings all day • You find it challenging to devise creative solutions for complex situations, which may hinder your ability to effectively address the needs of both the customer and Ashby. • You prefer to work independently and not collaboratively • You prefer a rigid schedule with limited autonomy, as you find accountability challenging • You have difficulty working remotely full time Our Culture Our co-founders have written authentic pieces about Ashby’s communication and operating principles. As a company, we hire fewer, stronger people and provide them with clear ownership over a specific scope of work. Our Customer Success team, in particular, prioritizes solving for the customer. Our hope is to hire a driven Contract Manager who embodies empathy and curiosity to join the team. Interview Process • Recruiter Interview: 30 minutes • Hiring Manager Interview: 30-45 minutes • Take-Home Assignment: 30-45 minutes • Final Panel: • Cross-Functional Interview with Sales and Customer Success: 30-45 minutes • Contract Management at Ashby: 30-45 minutes • Negotiation and Stakeholder Management: 30 minutes • Closing Questions: 15 minutes About Ashby We’re building the next generation of recruiting software and we’re starting with a suite of products that helps talent leaders, recruiters, and hiring managers run an efficient and data-driven hiring process. We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier (and many others who we cannot name!). Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. In short, it's the perfect time to join! 🚀 Benefits • Competitive salary and equity. • Opportunity to work with a talented and passionate team. • 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. • 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.

Manage and execute end-to-end implementation projects for SaaS clients, ensuring positive customer experiences and timely delivery. | Extensive experience in managing complex SaaS implementations, strong technical understanding of SaaS products, excellent communication, and change management skills. | Strategic Implementation Specialist Hi! I’m Morgan, the Implementation Manager here at Ashby. Our customers are at the center of everything we do, and that’s especially true during implementation. We take pride in being responsive, collaborative partners who focus not just on delivery, but on doing things thoughtfully. This role plays a critical part in ensuring our new customers start off with a strong foundation and a clear path forward. I’m thrilled to be hiring our next Implementation Specialist. As part of our growing Professional Services team within Ashby’s Customer Success organization, you’ll play a key role early in the customer journey—ultimately helping to elevate the entire customer experience. About this role: As our Implementation Specialist, you will be responsible for managing and executing the end-to-end implementation of Ashby’s solution for many of our new customers. You will work directly with customers in our Strategic (predominantly Enterprise) segment, developing and executing implementation plans to ensure a positive customer experience and expedited time to value. Your goal is to support our customers, helping them get up and running swiftly with Ashby so they can achieve their desired outcomes. Role requirements: • Implementation & Project Management: You have extensive experience managing and executing several complex implementation and onboarding projects concurrently in a high-growth B2B SaaS org (defining the work, aligning with stakeholders, communicating the project plan, and ultimately delivering results in accordance with the agreed-upon expectations). You keep the team on track to ensure milestones are met. You work effectively in a remote-first setting, with the ability to travel <10% as needed for strategic customer engagements. • Technical Proficiency: You have a strong understanding of complex, configurable B2B SaaS products and their technical intricacies. By "complex", we mean platforms with multi-step workflows, supporting several core workflows, and integrations with other systems. You're technically curious and creative. Ashby or ATS experience is a plus, not required. • Customer Centricity: You deeply understand customer needs and tailor implementations to meet their specific requirements. You build strong customer relationships by maintaining high levels of engagement and communication; you’re the customer’s proactive guide and advocate throughout the implementation period. • Change Management: You are experienced in navigating change management processes and helping customers adapt to new systems and a refreshed approach. • Best Practices & Recommendations: You take pride in advising customers on best practices specific to their usage of software to ensure optimal value. • Critical Thinking & Solutions Orientation: You proactively address thematic customer opportunities and improve our processes accordingly. You don’t rely on ‘I’ve seen this done,’ but instead think critically to solve problems. • Cross-functional Collaboration: You effectively partner with cross-functional stakeholders across Customer Success, Sales, Product, Engineering, and Operations to align and define progress. You could be a great fit if: • 📣 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 the voice of the customer to internal stakeholders so we can ensure that our offerings continue to evolve in accordance with customer needs. • 📈 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 and technically proficient. You take pride in internal operations. • 📊 You are data-driven. You use metrics and analytics to inform decisions and measure success. • 🌍 You are adaptable. You can navigate changes in a fast-paced, evolving environment. • 🧑‍🏫 You love to coach. You see every teaching moment as an opportunity and are excited to help our customers grow. You might not be a great fit if: • You prefer an in-person role over remote. • You are less interested in customer-facing roles that require both technical and interpersonal skills. • You are accustomed to defining ideas and strategies, yet not responsible for their execution. • You prefer working with a simple product (such as a point solution). • 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 with Talent Team • 45 min - Interview with Hiring Manager • 60 min- Mock Call with 2 Implementation Specialists • Final Round: • 30 min - Customer Adoption with Head of Dedicated CS & one of our Strategic CSMs • 30 min - Interview with VP of Customer Success & Head of PS • 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 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 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.

Guide and support enterprise SaaS customers to maximize product adoption and retention, leveraging technical knowledge and stakeholder management. | Extensive experience in SaaS customer success, supporting complex technology adoption, managing a strategic customer portfolio, and working with cross-functional teams. | About this Role Our Customer Success Team is passionate about shaping and scaling an exceptional upmarket customer experience across the Enterprise Segment. We’re thrilled to be hiring our next Strategic CSM in the EST time zone as we continue to grow the team. In this role, you'll guide Ashby's biggest customers - focusing on improved product adoption and increased customer health. You will shape how we serve customers ranging from high growth organizations to public companies. Ashby is designed to be powerful and flexible, allowing users to adjust it to their needs. This means that there is a lot to learn. You will become a product and domain expert in order to enable our customers to make the best use of Ashby to drive hiring excellence. Role Requirements: • You have a strong track record of customer success experience in B2B SaaS (at least five years), supporting the implementation and adoption of complex technologies through the customer journey. • You’re comfortable managing a book of ~20 strategic customers, exceeding $2m in total ARR. You enjoy multi-threading, developing relationships across a broad set of stakeholders while supporting existing teams to drive adoption and retention. • You have experience working closely with cross-functional stakeholders across Sales, Marketing, Product, and Operations. • You love becoming a product and industry expert. You create ‘Ah ha!’ moments by tailoring configuration, driving product adoption, and crafting training to address a customer’s specific challenges so they achieve their intended business outcomes. • You’ve worked with technically complex products and show a strong curiosity to explore details and understand how things work. You Should Apply If: • 📣 You communicate with precision and clarity. You can take something complex (like a multi-layered report or a nuanced workflow) and explain it simply and confidently. • 🎧 You are a listener first. You seek to understand what customers actually need and then advocate for them internally to shape how Ashby evolves for enterprise use cases. • ⚙️You thrive in complexity. Ashby is powerful and highly configurable; you’re energized by learning a product with depth, and you can translate that knowledge into creative solutions for your customers. • 🧑‍🏫 You’re excited to help shape a new segment. Our Strategic customer motion is still evolving; you’ll be iterating on playbooks, helping us learn what works, and turning those learnings into repeatable processes for the team. • 🔍 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 are always looking for ways to improve your work through data. • 👥You may have been a recruiter, hiring manager, or interviewer before. That experience helps you quickly connect Ashby’s workflows to real-world hiring problems (though it’s not required). Why you shouldn’t apply: • You prefer managing a broad book of business (if so, see our High Touch or Startup roles). • You're interested in managing customer accounts with infrequent and well-defined touchpoints (rather than excited by the fluidity required of early stage CS work). • You shine as an exclusively commercial CSM, motivated by variable compensation. While our team's north star metric is revenue retention, we focus on adoption and engagement as leading indicators. For renewal negotiation and upsell, we have a remarkable team of Contract Managers. As such, this role does not currently include variable pay, aligning with our strategy to hire product-oriented CSMs rather than adhering to the conventional Account Manager model. • You’re afraid of rolling up your sleeves. If the idea of getting in the weeds with a customer about the nuance between a time in process report and a time to hire report feels too granular, or project managing a workflow change for offer approvals isn’t interesting, this job isn’t going to be for you. About Ashby We’re building the next generation of enterprise software, and we’re starting with a suite of products that help talent leaders, recruiters, and hiring managers run their hiring process significantly better. We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier (and many others who we cannot name!). Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. In short, it's the perfect time to join! 🚀 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: • Intro Call with Ashby Recruiting - 30 Minutes • Hiring Manager Interview - 45 Minutes • Take-Home/Presentation - 45 Minutes • Panel Interview - 2 hours 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 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.

Guide and support enterprise customers in adopting and maximizing the value of complex SaaS products, fostering strong relationships and driving retention. | At least five years of SaaS customer success experience, managing a significant book of strategic accounts, with strong technical and communication skills. | About this Role Our Customer Success Team is passionate about shaping and scaling an exceptional upmarket customer experience across the Enterprise Segment. We’re thrilled to be hiring our next Strategic CSM in the EST time zone as we continue to grow the team. In this role, you'll guide Ashby's biggest customers - focusing on improved product adoption and increased customer health. You will shape how we serve customers ranging from high growth organizations to public companies. Ashby is designed to be powerful and flexible, allowing users to adjust it to their needs. This means that there is a lot to learn. You will become a product and domain expert in order to enable our customers to make the best use of Ashby to drive hiring excellence. Role Requirements: • You have a strong track record of customer success experience in B2B SaaS (at least five years), supporting the implementation and adoption of complex technologies through the customer journey. • You’re comfortable managing a book of ~20 strategic customers, exceeding $2m in total ARR. You enjoy multi-threading, developing relationships across a broad set of stakeholders while supporting existing teams to drive adoption and retention. • You have experience working closely with cross-functional stakeholders across Sales, Marketing, Product, and Operations. • You love becoming a product and industry expert. You create ‘Ah ha!’ moments by tailoring configuration, driving product adoption, and crafting training to address a customer’s specific challenges so they achieve their intended business outcomes. • You’ve worked with technically complex products and show a strong curiosity to explore details and understand how things work. You Should Apply If: • 📣 You communicate with precision and clarity. You can take something complex (like a multi-layered report or a nuanced workflow) and explain it simply and confidently. • 🎧 You are a listener first. You seek to understand what customers actually need and then advocate for them internally to shape how Ashby evolves for enterprise use cases. • ⚙️You thrive in complexity. Ashby is powerful and highly configurable; you’re energized by learning a product with depth, and you can translate that knowledge into creative solutions for your customers. • 🧑‍🏫 You’re excited to help shape a new segment. Our Strategic customer motion is still evolving; you’ll be iterating on playbooks, helping us learn what works, and turning those learnings into repeatable processes for the team. • 🔍 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 are always looking for ways to improve your work through data. • 👥You may have been a recruiter, hiring manager, or interviewer before. That experience helps you quickly connect Ashby’s workflows to real-world hiring problems (though it’s not required). Why you shouldn’t apply: • You prefer managing a broad book of business (if so, see our High Touch or Startup roles). • You're interested in managing customer accounts with infrequent and well-defined touchpoints (rather than excited by the fluidity required of early stage CS work). • You shine as an exclusively commercial CSM, motivated by variable compensation. While our team's north star metric is revenue retention, we focus on adoption and engagement as leading indicators. For renewal negotiation and upsell, we have a remarkable team of Contract Managers. As such, this role does not currently include variable pay, aligning with our strategy to hire product-oriented CSMs rather than adhering to the conventional Account Manager model. • You’re afraid of rolling up your sleeves. If the idea of getting in the weeds with a customer about the nuance between a time in process report and a time to hire report feels too granular, or project managing a workflow change for offer approvals isn’t interesting, this job isn’t going to be for you. About Ashby We’re building the next generation of enterprise software, and we’re starting with a suite of products that help talent leaders, recruiters, and hiring managers run their hiring process significantly better. We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier (and many others who we cannot name!). Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. In short, it's the perfect time to join! 🚀 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: • Intro Call with Ashby Recruiting - 30 Minutes • Hiring Manager Interview - 45 Minutes • Take-Home/Presentation - 45 Minutes • Panel Interview - 2 hours 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 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 coach a SaaS sales team to achieve revenue targets, hire and develop talent, and refine sales processes. | Proven experience managing SaaS sales teams with high ARR contributions, strong coaching skills, and operational mindset. | About Ashby We’re building the next generation of enterprise software and we’re starting with a suite of products that empower talent leaders, recruiters, and hiring managers to be a driving force for revenue & efficiency via a holistic, data-centric talent strategy. We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have over 2,500 amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier (and many others who we cannot name!). We have a clear buyer persona and large target market. Plus, we already have multiple products to sell. Revenue is growing >100% Y/Y and we've only taken the first steps towards a much larger opportunity. In short, it's the perfect time to join! 🚀 We have multiple products with more to come and our sales process allows us to both land-end-expand and win material new business deals. We've only taken the first step towards a large market opportunity, and are looking for our next dedicated sales leader for our SMB Segment (1-100) in the Americas to help us maximize our opportunity with high growth early stage companies. About this Role We are seeking an experienced SaaS Sales Manager in North America to lead our Startup Sales team. There are three primary responsibilities that this sales leader will take on: Be accountable for the revenue results of the segment. Understand the primary revenue drivers for the segment, focus your team's energy on high-impact activities, and partner with Marketing on pipeline generating initiatives. Provide consistent coaching to enable all sales reps to achieve their full potential. Identify themes for improvement with individuals and at the team level. Help reps grow in their sales career. Make high quality hires in lock step with market demand. We believe that smaller, high caliber teams can achieve remarkable results. In this role, you’ll report to our Head of Americas Sales and have a significant impact in defining our go-to-market strategy for the SMB segment. If we are even moderately successful relative to our ambition, we'll have an incredible growth story to tell in just a few years! You could be a great fit if: 💰 You’ve managed a team of Account Executives delivering $5M/yr+ of ARR contribution at a growth-stage SaaS company. 🥇 You have a proven track record of hiring and onboarding new sales reps who quickly become top performers. You challenge and support them to continue to grow their careers. 👩‍🏫 You’re a teacher and a coach who loves helping reps hone their craft. You can quickly identify skill or knowledge gaps and deliver coaching that is empathetic and drives tangible improvement. 📊 You have a strong mental model for what sales excellence looks like. At the same time, you're a lifelong learner and are open to new ideas and experimentation. 🤝 You are comfortable jumping into deals to establish executive relationships with customers. You do so without ‘boxing out’ your team. ⚙️ You have an operational mindset and have identified bottlenecks and implemented solutions to accelerate deal flow. You love working with Revenue Ops to continually refine processes and tools. 🤓 You become a product and industry expert. You connect the dots quickly. Customers and your team trust you to provide practical advice and relevant stories. Bonus: You have run sales teams in both sales-led and product-led go to market motions You have sold platform applications to Talent and/or People leaders You Shouldn’t Apply If: You are a high performing individual contributor. We’re seeking a leader with people management experience for this position. You don’t love coaching. This role is all about supporting and developing early sales career talent. 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 aim to offer deep domain 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 decades of experience, and thoughtful communication both internally and with customers. Interview Process Our interview process is designed so you can showcase your achievements and points of learning and apply those in a practical exercise. We'll provide you with some Ashby-specific data so you can develop a well informed perspective on our business and solutions engineering involvement. You’ll have opportunities to ask questions of our team throughout. The interview process for this role is four rounds in the following order: Intro Call (30 min) - You'll meet with one of our Sales Recruiters to discuss your fit for the role and address questions about our market and solution Experience Deep Dive (1 hr) - You'll walk Leigh (Head of AMER Sales) through your career journey in some detail to highlight your experience, achievements, and points of learning to understand how you've developed into the leader you are today Presentation (1 hr) - We’ll give you some Ashby data, and have you present a perspective on our business and your approach to sales leadership. Final Round (2 hrs) - You'll have a set of four interviews with cross-functional partners, our CEO and a few members of the team. Benefits A product that our prospects & customers are truly excited about Competitive salary, commission 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 with four weeks recommended per year. 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 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 customer support teams, designing processes, and analyzing data to improve customer satisfaction and operational efficiency. | Extensive experience in customer support management, process improvement, and data analysis, with leadership skills; SaaS experience is preferred but not explicitly mentioned. | Role Overview In this CSSO role, you will drive the strategy, processes, and data-driven insights that empower our Customer Success Team to deliver exceptional outcomes for our customers. Reporting to the Head of Revenue Operations, and partnering closely with Customer Success leadership, you will define strategies and execute improvements that optimize customer health, retention, and revenue growth. Our Customer Success team is consistently praised by our customers for their deep expertise, responsiveness, and dedication—a testament to how much we Care Deeply About Customers, one of our core Operating Principles. As we continue to scale, it’s critical that we preserve and enhance this high standard of customer care while ensuring our processes, tools, and insights evolve to support sustainable growth. You will play a crucial role in our operations, including process improvements, planning, and reporting. This is both a strategic and tactical role in which you’ll design frameworks and programs, uncover actionable insights, and create data-informed recommendations across our Customer Success functions. What you'll do at Ashby: • Operationalize CS Strategy: Develop and refine processes, tools, and workflows to scale Customer Success operations. This includes customer segmentation, onboarding workflows, lifecycle mapping, and playbook development. • Analyze Business Dynamics: Partner with internal stakeholders on reporting & analysis of metrics such as NRR, GRR, churn, product adoption, health score, and customer sentiment. Use these insights to provide early warnings and refine CS strategies. • Optimizate the Customer Journey: Enhance the end-to-end customer journey, ensuring smooth transitions across all post-sales touch points from onboarding through support and renewal. • Support Strategic Planning: Collaborate with Finance and CS leadership on planning cycles, including headcount planning, capacity modeling, and quota setting. Provide relevant historical data for informed decision making. • Drive Process Improvements: Identify inefficiencies and implement improvements to CS workflows, customer onboarding, account transitions, and renewal processes. Implement & deploy KPIs to measure performance against strategic initiatives. • Optimize CS Systems: Define the business requirements to improve Customer Success efficiency, efficacy, and scalability. Partner with RevOps teammates to implement changes to tools (CRM, health scoring platforms, etc) • Collaborate Cross-functionally: Ensure alignment with Sales, Product, and other teams to align resources with customer needs and forecasted growth. • Support Change Management: Lead the roll-out and adoption of new processes or workflows to the CS team. Partner with Enablement on larger scale change programs. You could be a great fit if you: • Are a self-starter, innately curious in your approach • Bring both SaaS & financial literacy, offering an informed perspective on CS benchmarks (e.g.ideal book sizes) • Have a strategic mindset, with the ability to distill data into actionable recommendations • Are detail-oriented and committed to data accuracy and process quality • Have experience in fast-growth SaaS environments, ideally in a Customer Success or Revenue Operations role • Are skilled in CRM reporting, with preference for HubSpot experience • Work autonomously, managing multiple tasks and deadlines effectively • Are an excellent communicator, both verbally and in writing This role may not be a fit if: • You’re unwilling to manage both high-level strategy and hands-on execution • You’re uncomfortable with ambiguity and prefer structured, predefined assignments • You prefer focused work on a single project at a time • You prefer working within a single team rather than across multiple teams Interview Process Our interview process is thorough — we aim to ensure each person joining the team is the right fit for Ashby and will provide ample information to assess if Ashby is the right fit for you. The process for this role is as follows: • Recruiter Screen with Talent Acquisition Team - 30 minutes • Hiring Manager Interview / Career Deep Dive - 60 minutes • Challenge Interview - 45 Minutes • Final Round / Virtual Onsite - 2 hours About Ashby We’re building the next generation of enterprise software, and we’re starting with a suite of products that help talent leaders, recruiters, and hiring managers run their hiring process significantly better. Learn more on our website: https://www.ashbyhq.com/ We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier (and many others who we cannot name!). Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. In short, it's the perfect time to join! 🚀 Benefits • 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. • If you’re in the US, top-notch health insurance for you and your dependents, with all premiums covered by us. 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.