Head of High Touch Customer Success

Head of High Touch Customer Success

👋 Hi, I’m Casey — Head of Dedicated Customer Success at Ashby; 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 my backfill: the Head of High Touch Customer Success!

In this role, you’ll have the opportunity to elevate the customer experience to the next level. You’ll join our Dedicated CSM leadership team, working alongside our Heads of Strategic and EMEA Customer Success, as well as leaders from our Startup CS, Support, Customer Education and Contract Management teams.

About the Role

As Head of High Touch Customer Success, you’ll play a critical role in ensuring our customers continue to have an exceptional experience with Ashby as we scale. You’ll grow a talented team of CSMs, lead the current Manager of High Touch Customer Success (a recent internal promotion), and drive the overall strategy and execution of our High Touch CS function.

In this role, you will:

• Lead and coach both the current Manager of High Touch CS and your own team of CSMs supporting customers across onboarding, adoption, and long-term partnership

• Drive process improvements across the customer journey, with a focus on post-onboarding and adoption

• Help evolve how we deliver consistent, high-quality customer experiences at scale

• Serve as a key product advocate — partnering closely with internal teams to champion improvements that better support our upper mid-market and lower enterprise customers

Role requirements:

• Team Leadership & Coaching: You have experience leading and developing Customer Success Managers in a B2B SaaS environment. You know how to foster a culture of empathy, accountability, and continuous growth.

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

• 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’re familiar with key stages like onboarding and adoption, and you’ve supported efforts that drive product engagement and help customers achieve their goals.

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 themes.

• 🎧 You are a great listener. You see your role as 1) Advocate for the Customer Success Team as well as 2) Voice of the customer to internal stakeholders so we can ensure that our product roadmap continues to evolve.

• 📈 You are a 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 internal operations.

• ⚙️ You’re an advocate for the team. We’ll be looking for your help when it comes to defining resourcing and headcount planning.

• 🧑‍🏫 You love to coach. You see every teaching moment as an opportunity and are excited to help teams grow.

You Might Not Be a Fit If:

• You prefer an in-person role over remote.

• You’re not eager to roll up your sleeves and get into the weeds (e.g. call shadowing isn’t interesting to you).

• You are accustomed to defining ideas and strategies, yet not responsible for their execution.

• You thrive in environments where you lead a simple, established product rather than a dynamic, evolving one.

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

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

• 60 min - Hiring Manager Interview with Global Head of Dedicated CS

• 60 min Presentation & Interview with our Manager of High Touch, Head of Startup & Head of Strategic

• 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 represent a product that our prospects & customers are truly excited about.

• 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.