Director of Customer Success

Rilla•New York, NY

6d•$160,000 - $200,000•Onsite

About The Position

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.

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.

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.
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.