Remote 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 principles 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, 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

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:

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 which requires a deep understanding of the Ashby product, even leadership roles.

• 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

45 min – Hiring Manager Interview with Head of Strategic Customer Success

Presentation Round

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.