We are a small team of renegades, entrepreneurs, and underdogs dedicated to helping fix the American healthcare system.

CRESTONEASSOCIATES

Sales Development Representative

Help America's small businesses get the healthcare their people deserve.

And stop the insurance companies from taking advantage of the underdog. Crestone Associates is the PEO brokerage that knows what companies should be paying. We are hiring three people who can get a CFO on the phone and earn twenty minutes. Read this before you apply.

From Lucas Siegel, Founder & CEO

Who this role is not for

  • People who want a 9-to-5 with clear boundaries.
  • People who need a script to pick up the phone.
  • People who see sales as a stepping stone to something else.
  • People who want to be managed closely.
  • People who let their ego get in the way of learning and feedback.

Who should apply

  • You are obsessive about outbound craft: subject lines, openers, objection handling, the ask.
  • You can talk to a CFO about money without flinching, and you would rather learn the numbers than fake them.
  • You want to be early at something, on a team where everyone is elite or working toward it.
  • You are ready to be measured, coached, and pushed harder than anywhere you have worked.
  • You want to win and get heavily compensated for it, while helping people at the same time.

How the application works

  1. Foundation: who you are, a few honest questions, a short selfie video. About 20 minutes.
  2. Writing: learn our pitch from a short read and five short films, then three outreach emails on a clock, plus how you use AI.
  3. A live cold call with an AI prospect. One shot, recorded, scored.
  4. Systems, resilience, and values.
  5. References, then a conversation with Lucas.

Remote. You work US Central business hours from wherever you are. Your progress saves as you go, and you can finish across several sittings.

If that sounds like you, enter your email below. The application itself is the first test.