WorkStep is looking for a VP of Sales to drive the next phase of growth, taking us to $50M ARR and beyond.

Our VP of Sales will own and support the Sales organization (Enablement, RevOps, Account Executives, and BDR team), and report directly to the CEO. The teams in place are highly performant, our product is sticky, and our NRR is top decile. This hire will serve as an accelerant to that success.


  • Align the sales organization to maximize revenue growth
  • Foster a culture of progressive personal development and mentoring
  • Develop plans, strategies, and tactics for increasing new business and exceeding revenue goals
  • Successfully ramp new hires with onboarding and training
  • Collaborate with the CEO and Leadership Team to refine the sales strategy
  • Foster strong partnerships with the CX and Marketing teams to build enthusiastic advocates and generate customer references
  • Identify opportunities to meaningfully increase revenue from our existing customers
  • Implement and adjust team performance metrics and hold the team accountable to milestones and objectives



  • 10+ years in SaaS sales and demonstrated success selling into the enterprise segment
  • 3+ years managing enterprise AE teams responsible for achieving quota
  • Track record of effectively executing a ‘land and expand’ strategy
  • Experience in high-growth organizations with ARR ranging from $5 million to $50 million
  • Passion for the WorkStep mission


Preferred experience 

  • Experience working with HR and Operations buyers
  • Proven track record of successfully selling technology solutions to non-technology companies


  • Competitive compensation
  • Flexible PTO
  • Top-notch technology
  • Annual team building on-sites
  • Work space stipend
  • Competitive company-sponsored health, vision, and dental benefits package
  • Opportunity to join a passionate, motivated, and fun team at an early stage to help shape and execute on our mission
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