Head of Strategic Customer Success - Americas

Head of Strategic Customer Success

Hi, I'm Casey — Head of Dedicated Customer Success; 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 our Head of Strategic Customer Success! In this role, you’ll have the opportunity to elevate the customer experience to the next level, working alongside our High Touch, Startup, Support, Contract Management, and Professional Service leaders.

Our product and growth are exceptional. Ashby’s All-in-One solution is powerful, easy to use, and often replaces 4-5 disparate solutions (ATS, scheduling, analytics, sourcing and CRM). We have several thousand customers, including notable organizations like Shopify and Snowflake. Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, we’re growing >100% year over year, with very low churn.

About this role:

As Head of Strategic Customer Success, you will lead our Strategic Customer Success segment and help define how Ashby serves our Enterprise customers. This role is pivotal in ensuring that, as we continue to move upmarket, our customers consistently have a remarkable experience. You’ll oversee and continue to grow a highly skilled team of tenured Strategic CSMs, guiding how they partner with some of our most sophisticated and complex organizations.

You’ll work alongside our High Touch Customer Success leaders, applying programmatic frameworks where they fit, while also facilitating bespoke engagements for Enterprise customers who require a more tailored approach.

Success in this role requires a deep product focus: we’re looking for a leader who is comfortable getting into the details of the product alongside the team, and who can partner with internal stakeholders to advocate for the product changes that matter most.

Ultimately, you will shape how Strategic Customer Success evolves at Ashby and ensure our largest customers achieve meaningful outcomes with our platform.

Role requirements:

• Proven Leadership & Coaching: You have a track record of successfully growing, leading and developing high-performing Customer Success Teams in a complex B2B SaaS environment. You know how to deliver clear, actionable feedback, and you build a culture where your team can grow and succeed.

• Customer-Centricity with an Enterprise Focus: You bring proven experience working with upmarket B2B companies (1,000+ employees) and understand the unique opportunities of enterprise adoption. You ensure customers realize value across their lifecycle and achieve their objectives with Ashby, balancing hands-on support with scalable approaches.

• Strategic & Operational: You proactively identify opportunities to strengthen how we serve customers — whether through process improvements, new frameworks, or fresh approaches to engagement. You balance big-picture strategy with hands-on execution, driving process improvements and frameworks that deliver measurable results.

• Customer Impact & Product Mastery: You excel at quickly learning and navigating robust, complex products to design programs that improve the customer journey at scale. Your work drives measurable impact across onboarding, adoption, and retention — ensuring customers realize value quickly and sustain success over time.

• Cross-functional Collaboration: You partner effectively with Sales, Product, Engineering, and Operations to align on customer needs and deliver solutions. You understand when to collaborate, when to escalate, and how to influence outcomes across teams.

• Innovative & Principled Approach: You proactively address thematic customer opportunities and improve our processes accordingly; you’re comfortable leveraging fresh technologies to enhance the efficiency and efficacy of our team. You don’t rely on ‘I’ve seen this done’ but instead think critically to problem solve.

• Analytical Mindset & Continuous Improvement: You use data to guide decisions and improve performance. You’re comfortable measuring what matters — both for your team and your customers — and iterating to drive better results.

You could be a great fit if:

• 📣 You communicate with c