Manager of Customer Success - Mid Market

Hi, I’m Denise — Head of High Touch Customer Success at Ashby. One of our core principles is “Care Deeply About Our Customers,” and we hire people who are energized by helping customers succeed and delivering high-quality experiences. That’s why I’m excited to be hiring a Manager of Customer Success - Mid Market.

In this role, you’ll elevate the customer experience by coaching and developing a team of CSMs, while also helping them operate effectively at scale. Each CSM manages a large book of business (~60 customers), so a key part of this role is identifying what’s working, turning it into repeatable best practices, and building systems that allow the team to deliver consistently strong outcomes across many customers. You’ll partner closely with other leaders across High Touch CS, Startup CS, Implementation, as well as Support and Contract Management.

About the Role

As the Manager of High Touch Customer Success, you will play a pivotal role in ensuring our customers have a remarkable experience with Ashby as we continue to scale. You’ll lead — and continue to grow — a team of skilled and tenured CSMs focused on driving adoption, value realization, and long-term partnership post-onboarding.

In this role, you will:

• Lead and coach a team of CSMs who partner with customers across adoption, optimization, and ongoing success

• Uplevel team performance through 1:1 coaching, skill development, and strong operational rigor

• Drive scalable approaches to customer success, helping the team translate what’s working into repeatable best practices across a large portfolio

• Partner closely with Implementation, Support, and cross-functional teams to ensure a seamless customer experience across the lifecycle

• Be a key voice in evolving how we deliver consistent, high-quality experiences at scale

Role requirements:

• Team Leadership & Coaching: You have experience leading and developing Customer Success Managers in a SaaS environment supporting a complex product. You know how to foster a culture of empathy, accountability, and continuous growth.

• Customer Journey Expertise: You have deep experience driving adoption, retention, and long-term value realization. You understand how to help customers translate product usage into meaningful business outcomes.

• Operational Mindset: You’ve helped implement and improve team processes, and bring a structured approach to scaling what works. You’re comfortable building systems and playbooks that enable a team to deliver consistently across a large portfolio.

• Cross-functional Collaboration: You’re comfortable partnering with teams like Implementation, Sales, Product, and Support to ensure a seamless customer experience across the lifecycle.

• Problem-Solving Orientation: You don’t rely on “what worked before” — you’re thoughtful, pragmatic, and eager to find solutions that fit the evolving needs of your team and customers.

• Data-Driven: You’re comfortable using data and metrics to inform decisions, identify trends, and continuously improve both team performance and customer outcomes.

• Customer-First Thinking: You have a deep understanding of B2B customer needs and a track record of delivering high-quality, thoughtful customer experiences.

• Lifecycle Awareness: You understand the full customer lifecycle, and know how to effectively partner with cross-functional teams to ensure strong handoffs and sustained success.

You’ll Be a Great Fit If You:

• You communicate with clarity. You ask thoughtful, precise questions and can distill complex concepts into simple, actionable insights.

• You listen deeply. You act as both an advocate for your team and a strong voice of the customer, ensuring feedback meaningfully shapes internal decisions and product direction.

• You’re a structured problem solver. You tackle complex challenges with thoughtful, scalable solutions—not just one-off fixes.

• You value process and scale. You’re motivated to improve workflows and build systems that increase efficiency and consistency across the team.

• You operate with strong attention to detail. You bring rigor to internal operations and take pride in executing at a high standard.

• You’re a passionate coach. You seek opportunities to develop your team and elevate performance over time.

You Might Not Be a Fit If:

• 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, complex and evolving one.

• You prefer exclusively to build (rather than build, iterate, optimize)

• You have not done this work in a growing SaaS business

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! 🚀

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

30 min - Interview with Head of High Touch CS

Presentation Round - Global Head of Customer Success + 2 CS Leaders

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 work with 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.

• $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.

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