VP of 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.

The Role

You will own all of revenue at Rilla: Enterprise, Mid-Market, SMB, and Customer Success. Every new logo, every renewal, and every expansion runs through your org.

This role is for someone who has done both. Closed at the top of the board and taken a team to numbers it had never touched. You know the difference between carrying a quota and building the engine that blows past one. Now you want to build and lead the whole engine here.

You want to pass on everything you've learned, build something real at a startup, and grow an org in your image. You're on the way up, with everything to prove, and you'll outwork anyone in the room.

You get your hands dirty.

You 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 hire great leaders and great reps, coach them hard, and build an org that wins.

What You'll Do

• Own the number. Net new ARR, net revenue retention, and gross retention across Enterprise, Mid-Market, SMB, and Customer Success are yours.
• Lead, grow, and develop the leaders of each segment and the reps. Set a high bar for pipeline, deal quality, quota attainment, and retention, and coach the org hard to clear it.
• Design how each segment runs. Enterprise, Mid-Market, and SMB need different sales processes, playbooks, and deal motions. Build each one, and know when a motion belongs in one segment and not another.
• Run Customer Success as a revenue team. Own onboarding, adoption, renewals, and expansion, and make sure every customer sees the behavior change they bought.
• Stay in the biggest deals yourself. Run the toughest enterprise closes and the hardest renewals alongside your leaders 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, NRR, GRR) and build the pipeline reviews, QBRs, and accountability to move them.
• Set comp plans and capacity plans for every segment, and hire ahead of the number.
• Be the clearest voice for what customers need from the product. Turn what you hear across every segment into sharp, prioritized feedback that shapes the Rilla roadmap.
• Partner with Growth, Sales, and Product to give buyers one seamless experience from first touch through close, renewal, and expansion, and clear the internal friction that slows deals down.

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.

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 led a multi-segment sales org before, with second-line leaders reporting to you, and taken it well past the number it was handed.
• 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've owned retention and expansion, not just new logo. You know how to multiply teams as a revenue function.
• You know what great selling looks like at every deal size and can develop it in others: velocity motions in SMB, structured discovery in Mid-Market, long cycles, procurement, and security reviews in Enterprise.
• You've built the machinery: forecasting, comp plans, territory and capacity planning, pipeline reviews, and the hiring engine behind them.
• You build trust with executives and the C-suite, and you can coach your leaders to earn that same trust.
• You develop people intentionally: you invest in each leader's and rep's growth, give direct feedback, and create the conditions for your org to do the best work of their careers.
• You're in NYC, or ready to relocate. This role is in-office.

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
• Wellness / Gym Benefits
• 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