Manager of Strategic Customer Success

Hi, I’m Loren, the Head of Strategic Customer Success here at Ashby. My team is dedicated to building deep, consultative partnerships within the Enterprise space. One of our operating principals is “Aim High” and I'm excited to find a Manager of Strategic Customer Success who can identify gaps, drive meaningful change, and bring a creative vision to this segment as we scale.

In this role, you'll lead a team of CSMs who serve Ashby's largest and most complex customers. A key part of this role is helping your team navigate the nuances of enterprise partnerships — building the depth of engagement these customers expect while identifying what's working and translating it into repeatable approaches that scale across a sophisticated book of business. You'll partner closely with other leaders across Product, Implementation, Support, and Contract Management.

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