Director of Customer Success

About the role

You are a customer-obsessed leader who believes that the best way to scale Customer Success is to build operators who obsess over customer outcomes. You will own the end-to-end success of the Rilla customer portfolio, designing the playbooks that turn new deployments into long-term strategic partnerships. You will combine hands-on account work with team leadership, coaching your CSMs to become trusted advisors who drive measurable business impact. You will set the standard for how data, intuition, and partnership come together to create exceptional customer experiences. You will be responsible for turning product adoption into revenue growth and proving that Customer Success is the engine of retention and expansion. You will build a culture of accountability, experimentation, and relentless learning within the team.

Key facts

What you'll do

• Lead, grow, and develop the CSM team at Rilla, setting a high bar for how deeply they know each customer, the health of every account, and the outcomes they drive, while coaching them hard to clear that bar.
• Design and own how Customer Success actually runs at Rilla, including the onboarding frameworks, coaching playbooks, and engagement models that get customers to real value and make your team the primary reason they stay.
• Turn your CSMs into real advisors, not ticket-takers, coaching them to manage the change that comes with a new habit, set honest expectations, and help customers rethink how they use the platform.
• Define the metrics that truly matter, such as adoption, ridealongs run, net revenue retention, and account health, and build the operating cadence and accountability to track and move them across the entire book of business.
• Be the clearest voice for what customers need from the product, turning your team's account-level insight into sharp, prioritized feedback that directly shapes the Rilla product 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 or creates unnecessary risk.
• Push your team to use AI in their own work, prioritizing accounts, catching risk early, and freeing up time for the high-touch activities that genuinely move a relationship forward.
• Experiment on purpose by testing new ways to deliver success, documenting what works, and turning those lessons into repeatable motions that scale as Rilla grows.
• Run the toughest QBRs and renewal conversations yourself, personally saving the accounts that others give up on and proving what is possible at the highest level.
• Hire great people, coach them intensely, and build a team that consistently gets every customer to value and keeps them growing over time.
• Maintain a bias for action, moving quickly to test ideas, learn from outcomes, and iterate on both process and people.
• Elevate the standard for how success is measured and communicated, ensuring every CSM understands the link between their work and business results.

Requirements

• You are a customer-obsessed leader who deeply cares about delighting customers and solving their pains, not about vanity metrics or surface-level activity.
• You are an infinite learner who is always looking to learn more and learn faster, and you feel uneasy when you get complacent, constantly seeking discomfort and new challenges.
• You are a team player who loves giving and receiving feedback, and who believes in learning and growing together as a cohesive unit.
• You are unafraid of failure, taking risks, seeing setbacks as opportunities to learn, grow, and improve, and you are excited by unconventional approaches to problem-solving.
• You are extremely focused, practicing extreme focus in everything you do, always prioritizing your time and resources for maximum efficiency and impact.
• You have built, scaled, and leveled up high-performing Customer Success teams, creating clear operating cadences, performance frameworks, and a culture of accountability.
• You have a track record of renewing and expanding accounts that others consider lost causes, demonstrating an ability to unlock value where it was not initially visible.
• You know what great consultative customer success looks like and can develop that in others by coaching CSMs to set accurate expectations, uncover customer goals, and drive results even when the path is not obvious.
• You have experience building 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 transforming how a team operates.
• You develop people intentionally, investing in each team member's growth, giving direct and actionable feedback, and creating the conditions for your team to thrive under pressure.
• You are comfortable making decisions with incomplete information and iterating based on real-world feedback rather than waiting for perfect data.
• You communicate clearly and persuasively at all levels, translating complex ideas into simple narratives that align stakeholders and drive alignment.

Nice to have

• Prior experience selling into enterprise customers in a consultative, multi-stakeholder environment.
• Hands-on experience using AI tools to augment customer workflows and internal productivity.
• A background in mobile or offline commerce environments where face-to-face selling is the primary motion.
• Experience building repeatable playbooks that standardize how success is delivered across a growing team.

Practical notes

• This role is full_time.
• The position is based in New York City.
• Candidates must be able to work onsite in the New York City office.
• There may be limited travel required as part of customer visits and team offsites.
• No visa sponsorship is available for this role at this time.
• The role reports to the leadership team and sits within the Customer Success organization.
• The successful candidate will be expected to move quickly, test hypotheses, and iterate based on feedback from customers and peers.