Director of Customer Success

What You'll Do

• Lead, grow, and develop the CSM team. Set a high bar for how deeply they know each customer, the health of every account, and the outcomes they drive, and coach them hard to clear it.
• Design and own how Customer Success actually runs at Rilla: the onboarding frameworks, coaching playbooks, and engagement models that get customers to real value and make your team the reason they stay.
• Turn your CSMs into real advisors, not ticket-takers. Coach them to manage the change that comes with a new habit, set honest expectations, and help customers rethink how they coach and sell.
• Define the metrics that matter (adoption, ridealongs run, net revenue retention, account health) and build the operating cadence and accountability to track and move them across the whole book.
• Be the clearest voice for what customers need from the product. Turn your team’s account-level insight into sharp, prioritized feedback that shapes the Rilla roadmap.
• Partner across Sales, Product, and Engineering to give customers one seamless experience from first demo through expansion, and clear the internal friction that slows accounts down.
• Push your team to use AI in their own work: prioritizing accounts, catching risk early, and freeing up time for the high-touch work that actually moves a relationship forward.
• Experiment on purpose. Test new ways to deliver success, write down what works, and turn it into a repeatable motion that scales as we grow.

Skills & Requirements

• You put your team first, always. Their growth is the scoreboard you actually care about, and you’d trade your own spotlight for their wins every time.
• You’ve built, scaled, and leveled up high-performing CS teams, creating clear operating cadences, performance frameworks, and a culture of accountability.
• You know what great consultative customer success looks like and can develop that in others: coaching CSMs to set accurate expectations, uncover customer goals, and drive results even when the path isn’t obvious.
• You’ve built teams that show up as credible, strategic partners at the executive level, and you can coach CSMs to earn that trust and manage the change that comes with getting a whole team to adopt a new way of working.
• You develop people intentionally: you invest in each CSM’s growth, give direct feedback, and create the conditions for your team to do the best work of their careers.

Nice to Haves

• You were an early hire at a fast-growing startup.
• You’ve worked with customers in construction, home improvement, or home services, or you’ve sold software into them (companies like ServiceTitan, Salesforce, Lasso, Buildertrend, BuildOps, or Housecall Pro).
• You’ve worked on software that sells to non-tech, offline, or blue-collar industries (companies like Flexport or Veeva).
• You’ve worked on a behavior-change, coaching, or enablement product, where success means customers build a new habit, not just flip a switch.
• You’ve already coached teammates on the side, and you want to do it for real.

Compensation & Benefits

• Compensation: $160,000-200,000 + 100-300K OTE + equity
• Medical, dental, and vision insurance
• Parental leave
• 401(k) retirement plan
• Fertility benefits
• Breakfast, lunch, dinner, and snacks 6 days a week in our NYC office
• Gym membership
• Commuter benefits
• Relocation assistance to NYC
• Unlimited PTO (not accrual-based — take what you need)
• $1,000 annual learning and development stipend
• Tech equipment