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 clarity. You ask precise questions and can distill complex concepts into simple themes.

• 🎧 You see your role as both 1) an advocate for the Customer Success team, and 2) the voice of the customer to internal stakeholders so the product roadmap continues to evolve in an optimal direction.

• 📈 You are a strategic problem solver. You thrive at solving complex challenges with principled, scalable solutions.

• ⚡️You know process matters. You’re eager to improve workflows and operational details that enhance efficiency and consistency.

• 🔍 Your peers know you for your follow-through, detail orientation, and pride in strong internal operations.

• 🧑‍🏫 You love to coach. Whether through call shadowing, real-time feedback, or structured development, you see every moment as an opportunity to help your team grow.

• 🛠 You get into the weeds. You’re energized by diving into the product alongside your team, learning deeply, and modeling the type of engagement we expect from Strategic CSMs.

You might not be a great fit if:

• You’re not eager to roll up your sleeves and get into the weeds — whether that’s shadowing calls, digging into the product, or iterating directly with your team.

• You prefer to focus solely on strategic priorities. We expect that even our most senior leaders are able to ‘traverse the elevation’ and be in the particulars as necessary.

• You’re uncomfortable with a writing-heavy culture. We rely on clear, concise proposals and documentation, and written communication is core to how we operate.

• You’re most comfortable with a simpler product rather than a highly configurable, technical platform.

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

• Your upmarket experience involves working with organizations that have fewer than 1,000 employees.

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

• 90 min

• Interviews with VP of CS and Head of Dedicated CS - 30 min, then 60 min pending previous conversation

• 60 min

• Presentation & Interview with Strategic CSM(s), Head of Startup, & Head of Professional Services

• 30 min

• Interview with CEO

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.

• 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.

• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!

• $100/month education budget with more expensive items (like conferences) covered with manager approval

• If you’re in the US, we offer top-tier health insurance for you and your dependents, with 100% of premiums covered by Ashby. We also offer a 3% 401k match.

Ashby’s success hinges on hiring great people and creating an environment where we can be happy, feel challenged, and do our best work. We’re being deliberate about building that environment from the ground up. I hope that excites you enough to apply.

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.