At Benepass we’re making benefits magical. We’re reinventing the way how companies take care of their people. We enable leading organizations to increase employee retention and satisfaction by offering flexible benefits that employees love.

We’re backed by leading VCs including Gradient (Google’s AI venture fund) and Y Combinator, and amazing angels like Aaron Levie (Box) and Jake Schwartz (General Assembly).

Our fintech based platform has been built from the ground up to natively support a wide range of organizations and different benefit program designs. Employees are empowered to use their benefits with easy access to a digital wallet and virtual/physical Visa card pre-loaded with all their benefits from their employer. Using Benepass, companies are seeing employee engagement rates of over 80% with their benefit programs.

Today, Benepass is in a period of hyper-growth. We’re looking for leaders to help us scale and bring our vision of flexible, employee-directed benefits to millions of people around the world.

As Head of Sales, you have an opportunity to join an exciting high-growth company at the ground floor and chart the growth trajectory for the next phase of company growth. You will work closely with the founder/CEO on building a winning GTM playbook. With the benefit of an exciting cohort of customers that love Benepass and a team of experienced Account Execs, you have a solid foundation on which to build. We’re looking for an entrepreneurial spirit to join the team and help scale our mission to many more cohorts of customers.


  • Managing the sales team on a day-to-day basis, including coaching, 1:1s, and advising reps on their current deals
  • Defining the appropriate amount of sales process to ensure
  • Defining strategy
  • Closing business


  • You are entrepreneurial and a self-starter. Whatever the challenge, you have an aptitude for figuring it out. You’re motivated by making a big impact on the trajectory of the company.
  • You learn quickly. You experiment and will try anything in pursuit of achieving goals.
  • You attract A players. You know how to run a productive sales team cadence and support your team in achieving their goals.
  • You’re a team player. You’re driven by team goals as well as individual goals. You learn from others, and you are excited your insights.


  • At least 2 years as a sales leader responsible for a team goal and hiring AEs
  • At least 5 years of full-funnel B2B sales experience with deal sizes in the mid five figures
  • Experience selling at an early stage startup or with underdog product
  • A desire to win and with a stellar attitude

Bonus skills:

  • Have sold into People/HR teams
  • Understanding of and/or curiosity about financial products

Not meeting all the requirements but still feel like you’d be a great fit? Tell us how you can contribute to our team in a cover letter or apply to our general opportunities.


  • Competitive compensation + equity
  • $430/month toward medical coverage (+$215/month for dependent)
  • 100% coverage of dental & vision for employees and 50% coverage for dependent
  • Fantastic benefits (of course 😃), including:
    • $500 WFH setup
    • $150/month cell phone + internet
    • $100/month Wellness
  • Team Onsites 3-4 times a year / next event in Chicago in August!
  • Flexible PTO
  • Work from anywhere (during standard US business hours)

At Benepass, we are working towards reimagining how companies take care of their people. We are committed to creating an inclusive environment for all our employees and are seeking to build a team that reflects the diversity of the people we hope to serve with our revolutionary products. Benepass is proud to be an equal opportunity employer.