Director of Enterprise Sales

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