Director of Customer Success

About the role

This role is for an exceptional individual contributor who's ready to make the leap into leadership. Someone who's been the best CSM, account manager, or success-minded seller in the room. The one at the top of the leaderboard, who renews and expands the accounts everyone else gives up on, and who is now hungry to build and lead a team of their own.

Responsibilities

• 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.
• 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.
• 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.

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.

Skills & Requirements

• Nice to have:
• 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.

Benefits

• Compensation: $160,000-200,000 + 200-300K OTE + equity
• Mental health days
• 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
• Commute benefits
• Relocation assistance to NYC
• Unlimited PTO (not accrual-based — take what you need)
• $1,000 annual learning and development stipend
• Tech equipment