← All roles

VP of Sales

Rilla· Sales
Apply on company site
New York City$500k - $600kFull-timePosted 4mo ago

About the role

Senior leadership role responsible for the entire revenue organization (Enterprise, Mid-Market, SMB, and Customer Success) at Rilla, owning revenue generation, coaching leaders, designing segment-specific playbooks, and aligning product feedback with the roadmap.

Responsibilities

  • 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 feedback into sharp, prioritized roadmap inputs.
  • Partner with Growth, Sales, and Product to give buyers one seamless experience from first touch through close, renewal, and expansion, and clear internal friction.

Qualifications

  • A customer obsessive.
  • An infinite learner.
  • A team player.
  • Unafraid of failure.
  • Extremely focused.
  • Experience operating with a high-velocity, reinforcement-learning style in a startup context.

Skills

Required:Revenue leadership across multiple segments (Enterprise, Mid-Market, SMB, Customer Success)Forecasting and pipeline management

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
Last updated Oct 22, 2026. Interested? Apply on the company site.

About Rilla

The End of Ridealongs

Making offline commerce as searchable and easy to understand as the internet.

offline commercesalesAIanalyticssales conversations
Company profileWebsite

More open roles at Rilla