Vice President of Enterprise Sales

San Francisco, CA

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About Sentry

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster, so we can get back to enjoying technology.

With more than $127 million in funding and 80,000 organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

About Sales

The VP of Enterprise Sales will groom and expand our existing team of Enterprise Account Executives with the goal of quadrupling our Enterprise business over the course of the next 2 years. This will be done by systematically expanding the relationships with existing high-potential customers. She/he will do so by capitalizing on Sentry’s bottoms-up adoption in large Enterprises and expanding our footprint. In parallel, there will be a core focus on landing key accounts in verticals where offers extreme value.

In this role you will drive the following outcomes

  • Quadruple revenues from $10M ARR to $40M ARR in 24 months through executive-level engagements with Sentry’s highest potential accounts. Key is to leverage our existing bottoms-up adoption in intelligent ways.

  • Build, coach and topgrade the team of Enterprises Account Executives to support this motion;

  • Improve execution discipline and create a predictable sales motion that consistently delivers quarterly results with 90+% accuracy;

  • Co-develop the executive narrative required to drive larger transactions;

  • Roll out comprehensive sales training;


  • We need a builder - initially acting as a player-coach, assisting individual contributors with larger transactions, gradually building out a team of district managers across the US;

  • Ability to identify and recruit a team of top-notch Enterprise Sales Executives;

  • Executive sales and communication skills - ability to drive compelling Customer engagements with senior executives in Engineering and/or IT Operations;

  • A strong sense of curiosity to help identify and craft the narratives that compel senior executives to buy;

  • High integrity, transparent in internal communications;

  • Familiarity with key sales methodologies like MEDDPIC or Challenger;

  • Systematic implementer of rigorous sales processes. You have proven that rigorous adherence to sales stages leads to better-quality execution and higher forecast accuracy;

  • Experience with Product-Led-Growth not necessary, but eager to learn and capitalize on how PLG can help drive Enterprise sales.

  • A technical background is a plus.


  • Competitive salary and meaningful equity
  • 100% medical, dental, and vision coverage for employees, 75% company-paid for dependents
  • Monthly commuter subsidy
  • 401k program
  • Learning & Development stipend
  • Charitable matching program
  • Generous parental leave policy
  • Flexible working schedule and vacation policy, work from home policy, and real work/life balance
  • Catered lunches
  • Company events (Hack Weeks, All Hands, quarterly social events) and friends and family events
  • Relocation assistance - you are living in, or willing to relocate to the San Francisco Bay Area

COVID Vaccine Required - Reasonable Accommodations for Medical or Religious Reasons Considered

Sentry values diversity and inclusivity in our company and is an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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