Careers

WaySky is hiring contractors who are sharp, honest, and comfortable with ambiguity. If you're interested, email michael@waysky.io with a short note on why you're a fit.

Reality Check Expert (Contractor)

  • Run 7-day evaluations and deliver evidence-based scorecards
  • Compare products vs competitors and produce a Readiness Score (0–100)
  • Must be decisive and comfortable saying ‘not ready’
  • Background: senior PMM / RevOps / sales-tech operator

Apply

Email michael@waysky.io

  • • Short note on why you're a fit
  • • Link to LinkedIn or portfolio
  • • Availability and rate expectations

Fix Pack Lead (Contractor)

  • Ship publish-ready assets in 30 days: positioning, pricing clarity, comparison page, integration page, case study draft
  • Strong B2B SaaS writing and packaging instincts
  • Works from a rubric and hits deadlines

Apply

Email michael@waysky.io

  • • Short note on why you're a fit
  • • Link to LinkedIn or portfolio
  • • Availability and rate expectations

Account Executive (Contractor)

  • Sell the Reality Check ($7,770) and close follow-on Fix Packs / Source Sprints
  • Comfortable talking to VP Marketing / Growth / PMM leaders
  • Can handle trust/ethics objections without sounding salesy

Apply

Email michael@waysky.io

  • • Short note on why you're a fit
  • • Link to LinkedIn or portfolio
  • • Availability and rate expectations