Director of Enterprise Sales

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 enterprise closer in the room. The one who carried the biggest number, won the deals everyone else wrote off, and 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 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 reps, coach them hard, and build a team that wins.

What You'll Do

• Lead, grow, and develop a team of enterprise AEs. Set a high bar for pipeline, deal quality, and quota attainment, and coach the team hard to clear it.

• Design and own how enterprise sales runs at Rilla: the sales process, playbooks, and deal motions that turn complex, multi-stakeholder deals into predictable wins.

• Coach your reps into trusted advisors to enterprise buyers. Help them run long sales cycles, win over multiple stakeholders, get through procurement and security, and sell outcomes instead of features.

• Stay in the biggest deals yourself. Run the toughest closes alongside your reps and show them how it’s done.

• Own the forecast. Define the metrics that matter (pipeline coverage, win rate, cycle time, ACV, net new ARR) and build the pipeline reviews and accountability to move them.

• Be the clearest voice for what enterprise prospects need from the product. Turn what you hear in deals into sharp, prioritized feedback that shapes the Rilla roadmap.

• Partner across Marketing, SDRs, Customer Success, and Product to give buyers one seamless experience from first touch through close and expansion, and clear the internal friction that slows deals down.

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’re a proven top enterprise closer. You carried a big number and beat it, again and again, winning complex, multi-stakeholder deals that other reps couldn’t.

• You’re ready to step into leadership and build a team, and you want to pass on the playbook that made you great.

• You know what great enterprise selling looks like and can develop it in others: coaching reps through long cycles, multiple stakeholders, procurement, and security reviews.

• You build trust with executives and the C-suite, and you can coach your reps to earn that same trust.

• You develop people intentionally: you invest in each rep’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 sold a behavior-change, coaching, or enablement product, where the win is getting a whole team to work differently, not just signing a contract.

• You’ve already mentored or coached reps on the side, and you want to do it for real.

Benefits

• Medical, dental, and vision insurance

• 401(k) retirement plan

• Parental leave

• 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 + unlimited Claude spend