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Director of Sales — Player​/Coach (Enterprise SaaS, Remote, Unlimited PTO

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listing for: Cayuse
Remote/Work from Home position
Listed on 2026-08-18
Job specializations:
  • Sales
    Director of Sales
  • Management
Salary/Wage Range or Industry Benchmark: 180000 - 240000 USD Yearly USD 180000.00 240000.00 YEAR
Job Description & How to Apply Below
Position: Director of Sales — Player/Coach (Enterprise SaaS, Remote, Unlimited PTO)

Cayuse is seeking an experienced Director of Sales to lead and scale our commercial sales organization, while continuing to directly drive new business. Reporting to the VP of Sales, this player/coach will own a defined territory and revenue target, coach a team of Account Executives, and partner with cross-functional teams to maximize outcomes.

The ideal candidate will close complex enterprise opportunities, build durable pipelines, and drive disciplined execution across MEDDPICC, procurement,

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