Manager of Strategic Customer Success

About the Role

As the Manager of Strategic Customer Success, you'll lead a tenured team of skilled CSMs while helping shape how Ashby delivers value as we scale upmarket. You'll be the team's coach, sounding board, and champion — helping CSMs grow, building systems that scale, and advocating cross-functionally — all in service of helping customers drive exceptional outcomes with a rapidly evolving product.

As our Manager of Strategic Customer Success, you’ll:

• Lead and coach a team of CSMs who serve as the primary point of contact for customers post-onboarding and throughout the partnership

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

• Drive process optimization across the customer journey — with a particular focus on adoption and optimization

• Advocate for the CSM team cross-functionally across Product , Support , Sales , RevOps , and Contract Management

• Balance building scalable process with delivering the bespoke experiences our most complex customers expect

• Be a key voice in evolving how we deliver consistent, high-quality outcomes for our Enterprise customers

Role requirements:

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

• Customer Journey Expertise : You understand the enterprise customer lifecycle and have helped improve onboarding, adoption, and retention through thoughtful, repeatable approaches.

• Up Market Motion : You have worked with enterprise customers and scaled their use case as they grow in complexity.

• 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 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 demonstrate clear communication. You ask clarifying questions with precision and can distill complex concepts into simple, actionable themes.

• You listen deeply. You see your role as both an advocate for the Customer Success team and a voice of the customer to internal stakeholders — ensuring our product roadmap continues to evolve in the right direction.

• You advocate for your team. You engage actively in resourcing and headcount planning conversations and bring a clear point of view.

• You love to coach. You see every teaching moment as an opportunity and are excited to help your team grow and develop.

• You are a structured 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 strong internal operations.

You Might Not Be a Fit If:

• Getting into the details isn't your thing. Call shadowing, hands-on troubleshooting, and doing the work alongside your direct reports isn't appealing.

• You're more comfortable generating broad ideas than owning their execution.

• You prefer established, stable processes and find frequent change frustrating.

• You want to build something once and move on, rather than continuously iterate and improve on it.

• You primarily work with simple products, not highly configurable complex products

• You have not spent the last few years leading an upmarket Customer Success team in a growing B2B SaaS business