Fractional Sales Expert

About the Role

* This role begins as a part-time contract position, with the possibility of transitioning to full-time for the right candidate. You will need to be San Francisco or New York-based (3 days/week in-office).

This is a founder-facing, in-the-trenches role supporting our founders in landing their first few dozen customers. This isn’t armchair advising; it’s getting your hands dirty alongside (largely technical, largely B2B) founders. You’ll be both a strategist and an operator. Here’s what we mean by that:

• As a strategist, you might recommend whether a company should go with a value-based pricing strategy or a competitive pricing strategy based on their business, competition, product etc. As an operator, you’ll help them actually build their value-based model in Excel.

• As a strategist, you might teach a founder best practices in running discovery calls. As an operator, you might listen to 5 of their calls and provide tactical feedback on a live call.

• As a strategist, you might help a founder prepare for a big pilot wrap up call by giving them a recommended agenda. As an operator, you might build their pilot structure from the ground up in Notion.

• We’ve been supporting founders in this way for many years. With demand at an all-time high, we’re looking for additional experts to pinch-hit as early GTM hires until our companies hire one of their own.

• Build the foundation
  :
  Figure out the early sales process steps, build enablement materials, test out pricing models etc.

• Ride along on big opportunities: Help founders work big opportunities step by step to close by prepping with them, listen to calls and providing feedback and sometimes joining calls

• Run fast paced engagements
  :
  Lead end-to-end projects through live working sessions and async follow-up work to unblock founders and help them accelerate sales

• Typical projects:

  • Listen to founder’s sales calls and provide tactical feedback

  • Help founders design their sales motion – their sales processes, pilot programs, pricing models, commission plans etc.

  • Help founders build enablement materials – decks, pilot documents, proposals, business cases etc.

  • Ride along on important sales calls (and follow ups) with founders

  • Interview founding SDR/AE candidates to help founders find the perfect fit for their early hires

• At least 5 years in a Founding GTM / Founding AE / Founding Head of Sales role

• At least 5 years of new business quota carrying experience

• Have worked in at least 2 different startups that achieved several million in ARR (you’ve “seen the movie” more than once)

• Experience closing deals of varying sizes, but primarily $25K - $300K ACV

• You have a minimum of 5 years of experience supporting early stage (