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 a Senior Manager of High Touch Customer Success In this role, you’ll have the opportunity to elevate the customer experience to the next level, working alongside our Strategic, Startup, Support, Contract Management, and Professional Service leaders.
As Senior Manager, you’ll play a pivotal role in shaping how Ashby supports our upper Mid Market and lower Enterprise customers as we continue to scale. You’ll lead the High Touch CS function — overseeing a talented team of CSMs and managing the current Manager of High Touch CS (a recent internal promotion). Together, you’ll ensure every customer experience reflects Ashby’s high standards of partnership, product expertise, and strategic impact.
You’ll own both strategy and execution: refining how we deliver consistent, high-quality experiences across onboarding, adoption, and long-term success. You’ll drive process improvements, particularly post-onboarding, to ensure customers realize full value from Ashby. And as a key product advocate, you’ll work closely with Product, Sales, and Customer Education to champion improvements that best serve our High Touch customer base.
The ideal candidate is deeply product-oriented — someone who enjoys getting into the details alongside their team, understands how customers use Ashby day-to-day, and can translate customer needs into actionable product and process improvements.
We have open jobs posted to lead different segments within customer success, High Touch and Strategic. Please read the job description carefully and only apply to one, the role that suits your skills best. You know your skillset better than us! If during an interview we think there is stronger alignment for the other segment, we’ll let you know then.
Role requirements:
Proven Leadership & Coaching: You have a track record of successfully growing, leading and developing high-performing Customer Success Teams in a SaaS environment. You know how to give clear, actionable feedback, and you build a culture where your team can grow and succeed.
Strategic & Operational Excellence: You proactively identify opportunities to strengthen how we serve customers — bringing structure, clarity, and scalability to the way our team operates. 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 escalate, when to collaborate, 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 cutting edge 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.
Customer-First Thinking: You have a deep understanding of B2B customer needs and have a history of ensuring outstanding support experiences.
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 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 High Touch CSMs.
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 on ideas and strategies without owning their execution.
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 want to move away from in-product work. While there is plenty of programmatic and operational work, this role requires genuine interest in diving into product nuances (and you’ll use the product yourself as you grow the team).
You prefer exclusively to build (rather than build, iterate, optimize).
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.
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
30 min – Interview with VP of Customer Success
60 min – Hiring Manager Interview with Head of Dedicated CS
60 min Presentation & Interview with our Manager of High Touch, Head of Startup & Head of Professional Services
Final Round:
30 min – Cross Functional Interview with Support Leader
30 min – Interview with CEO
10 min – Closing Questions with Hiring Manager
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 sell 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.
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