Manager, Startup Customer Success

👋 Hi, I’m Jared — Head of Startup Customer Success at Ashby. Over the past few years, I’ve had the privilege of growing our Startup CS team with thoughtful, process-oriented, and customer-obsessed CSMs. Today, we’re a team of fourteen spanning across the US and EMEA.

As we scale, I’m looking for a Manager to partner with me on day-to-day leadership and help drive our broader strategic initiatives within our segment. If you’re excited by the idea of supporting a team that operates at the intersection of high-quality support, scalable programs, and startup customer impact, I’d love to speak with you.

About the Role

As the Manager of Startup Customer Success, you’ll help lead a team of about 7 CSMs who support Ashby’s early-stage customers. Our Startup segment is special; we work with fast-moving founders and hiring teams who are often learning both how to use Ashby and how to build great recruiting habits. The team’s mission is to help them do both, through a combination of scalable onboarding, proactive enablement, and thoughtful human touch.

You’ll be responsible for coaching and developing our CSMs, scaling effective practices, and ensuring our customers get the right help at the right time. You’ll partner closely with leaders from our Support, Contract Management, and High Touch Customer Success teams to deliver an excellent and consistent customer experience.

As Manager of Startup Customer Success, you’ll:

• Lead and coach a team of Startup CSMs who serve customers across onboarding and enablement to deliver great outcomes

• Foster team growth through 1:1s, skill-building, and thoughtful feedback

• Support team operations and quality assurance for our shared inbox, live customer engagements, and project work

• Scale our programmatic success model across the customer journey while maintaining empathy and precision in each customer touchpoint

• Collaborate cross-functionally to evolve how Ashby supports its startup customers

• Represent the Startup CS perspective in internal planning around resourcing, tooling, and product roadmap

Role Requirements:

• Team Leadership & Coaching: You have experience managing or mentoring CSMs in a scaled or pooled CS model in a 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.

• Customer Success at Scale: You bring a structured approach to scaling what works, but value staying flexible in the face of new needs. You are comfortable balancing 1:many engagement strategies with strong judgment around when dedicated support matters most.

• Operational Excellence: You are energized by operations: you care about process quality, internal tools, and smooth execution.

• Leading from the Front: You enjoy rolling up your sleeves (e.g. inbox reviews, shadowing, quality checks) to uplevel the team and, when necessary, jumping in to help out yourself.

• Data-Driven: You are comfortable using data and metrics to inform decision-making and continually improve the team and customer experience.

• Great Communicator: You communicate clearly and with care, especially in fast-moving or ambiguous situations.

• 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.

You’ll be a great fit if:

• 🧑‍🏫 You take pride in helping others succeed. You find energy in supporting others’ growth through 1:1s, shadowing, and candid feedback.

• ⚙️ You think like a builder. You’re excited to improve what exists, create what doesn’t, and iterate quickly without sacrificing quality.

• ⭐ You bring calm to complexity. When things get busy or messy, you bring clarity, structure, and a level head.

• 📣 You enjoy context switching. From 1:1s to tooling workflows to strategy docs, you thrive in a high-variety environment.

• 🛠️ You find joy in systems. You enjoy creating clean processes, clear documentation, and consistent execution. On top of that, you love helping others see it too.

• 📈 You believe in high standards, delivered kindly. You hold the bar high while leading with empathy, curiosity, and care.

• 🔍 You believe “How we’ve always done it” isn’t good enough. You ask good questions, challenge stale assumptions, and welcome better ways.

• 🧩 You feel ownership over the whole. You see customer success as a team sport. One that includes Product, Support, and beyond.

You might not be a good fit if:

• You prefer direct ownership over customers, rather than managing those who do

• You’re more drawn to a traditional 1:1 CS model than a scaled, programmatic one

• You’d rather focus exclusively on vision than execution — this role blends both

• You prefer an in-person role over a remote one

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

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 Interview

• 60 min - Hiring Manager Interview

• Take-Home Assignment/Presentation

• Final Round

  • Rather than a traditional panel interview with a large group, we structure our panel into a series of smaller conversations. This gives you the opportunity to meet with multiple team members in a more conversational setting focused on specific topics, instead of a formal Q&A. You'll connect with the VP of CS, some leaders in CS, and some others across the business.

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 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.

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.