Director of Customer Success

A Foundational Company Rilla builds the leading conversation intelligence software for offline commerce. Salespeople talk, our mobile app records the conversation, and our AI transcribes and analyzes it to make them better at their jobs. We’re bringing the technology of the 21st century’s most innovative companies to the more than 10 million salespeople who work face to face. We’ve grown from zero to $55M+ in ARR in four years, and we’re profitable. We sell to enterprises like The Home Depot, KKR, Neighborly, and PulteGroup. We’re backed by Google Ventures, Bessemer Venture Partners, Crew Capital, and Broom Ventures. We hire people with high agency and high urgency. We’re in-office because the best work happens when ambitious people are in the same room. Who You Are A customer obsessive. You deeply care about delighting customers and solving their pains, not about vanity metrics. An infinite learner. You’re always looking to learn more and learn faster. You feel uneasy when you get complacent, and you’re constantly seeking discomfort. A team player. You love giving and receiving feedback, and learning and growing as a team. Unafraid of failure. You take risks. You see failure as an opportunity to learn, grow, and be better the next time. You’re excited by the unconventional. Extremely focused. You practice extreme focus in everything you do. You’re always prioritizing your time and resources for maximum efficiency. Our operating principle is that we try to run Rilla like a high speed reinforcement learner: a machine learning algorithm that plays a game a million times over and becomes invincible in a short amount of time. 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. You want to pass on everything you’ve learned, help build something at a startup, and grow a team in your image. You’re on the way up, with everything to prove, and you’ll outwork anyone. You will get your hands dirty. You’ll still own accounts yourself, run the toughest QBRs, and personally save the renewals that matter most. You will lead by example. At Rilla, leaders are second-class citizens. You work for your team, not the other way around. Your job is to clear their obstacles, make everyone around you better, and put them first. You’ll hire great people, coach them hard, and build a team that gets every customer to value and keeps them growing. 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. A signed contract that doesn’t change anyone’s behavior is just churn on a delay. 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 + 200-300K 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