VP, Mid-Market Sales at Checkr
San Francisco, CA, US

Checkr’s mission is to build a fairer future by improving the understanding of the past. Since graduating Y-Combinator in 2014, Checkr’s product has shifted the on-demand economy and has continued to scale by serving enterprise companies across various industries. As a company that provides modern and compliant background checks for global enterprises and startups, Checkr knows first hand how difficult it may be for individuals with prior criminal history to find employment and we want to help provide fair chances for the formerly convicted. A career with Checkr provides the opportunity to make an impact on the professional lives of millions of people and we encourage all qualified individuals to apply for our roles.

As the VP, Mid-Market Sales, you will be responsible for managing the Mid-Market Sales team to drive greenfield, mid-market opportunities through your prospecting, deal and pipeline management, and closing abilities. You will be part of an elite, professional, and rapidly growing team that succeeds through collaboration, tenacity, and constant improvement.


  • As the leader on Mid-Market sales team, you will be responsible for building, hiring, and training a world class sales organization from the ground up. Current sales headcount is 20 employees including 2 first line managers. 
  • Take a very hands on approach to management/deal flow, including shadowing/running sales calls at the senior executive level within Fortune 1000 accounts across a wide variety of vertical markets
  • You will implement sales process, forecasting, etc in order to consistently exceed revenue targets by applying modern sales techniques and processes to efficiently manage sales opportunities through your team’s funnel to a successful close
  • You will use your creativity and tenacity to develop and improve how we target and penetrate new vertical markets
  • Build a team of hunters

What you bring: 

  • Minimum of 10+ years of successful Mid-Market/Enterprise software sales experience, w/ 7+ years of management experience
  • Demonstrable track record of above target performance for the team, especially in a startup environment
  • Ability to recruit A players
  • Bring enablement/mentoring process
  • Forecasting consistency
  • Managed at least 8 direct reports including ICs and First Line Managers
  • Prefer experience selling business applications
  • Understand and use a specific sales methodology
  • Deep prospecting experience and methodology
  • Experience managing team through Salesforce

What you get:

  • A fast-paced and collaborative environment where we leverage the latest technology
  • Hands-on coaching and professional development
  • Competitive compensation and opportunity for advancement – a true meritocracy
  • 100% medical, dental and vision coverage
  • Unlimited PTO policy
  • Gym membership, transportation reimbursements
  • Catered lunch, dinner, and snacks

Equal Employment Opportunities at Checkr

Checkr is committed to hiring talented and qualified individuals with diverse backgrounds for all of its tech, non-tech, and leadership roles. Checkr believes that the gathering and celebration of unique backgrounds, qualities, and cultures enriches the workplace.   

Checkr also welcomes the opportunity to consider qualified applicants with prior arrest or conviction records. Checkr’s commitment to diversity extends to hiring talented individuals in spite of a prior criminal history (in accordance with San Francisco’s Fair Chance Ordinance as well as state and/or federal laws).