Note: The job is a remote job and is open to candidates in USA. Pragmatico is seeking a founding-stage sales leader to make new-client revenue independent of the founder by selling AI transformation solutions to executive buying committees. The role owns quota-carrying new business, pipeline generation, complex deal execution, and the creation of a repeatable sales playbook, with a path to building and leading the sales team.
Responsibilities
- Close net-new client bookings against quota. The target is $1M in net-new bookings in your first 12 months, ramping to closing on your own between day 90 and day 120
- Sell into a CEO-led buying committee. The CEO is your primary buyer. The committee usually pulls in the CIO and the CHRO, and it is often handed to a COO who has been told to "go figure out this AI thing." The CFO is sometimes in the room, but you still have to speak their P&L and ROI language to get a CEO or COO to yes. These deals are committee-based and moderately complex. They are not six-month enterprise sagas
- Take the founder out of the room. You co-sell the hardest deals early to learn the motion, then you own them. By month 6, at least 75% of your won deals close without the founder-CEO on the decision call, measured over the trailing quarter
- Build the playbook from first principles. ICP, discovery, multi-threading the committee, pricing and packaging objection handling, close plans. The test is not that a document exists. The test is that a second rep uses it to source and advance their own qualified deals
- Generate your own pipeline. By month 3, you are sourcing half of your own qualified pipeline in partnership with marketing, not living on inbound
- Feed the field back into the company. What you learn in live deals sharpens the packaging, the pricing, and the playbook. Our market moves weekly, and so do we
Skills
- You have sold to a CEO-led buying committee and won
- You know how to multi-thread a CIO and a CHRO, work alongside a COO who owns the evaluation, and build a CFO-grade business case even when the CFO never joins a call
- You generate your own pipeline
- Outbound is a muscle you use now, not one you have outsourced or let atrophy
- You sell transformation, not features
- You are comfortable carrying an intangible outcome, delivered through people-plus-process change (services and software), and making it concrete enough that an executive will sign for it
- You build
- You codify what works from first principles, write it down, and hand it to another rep who can run it
- You are a founding-stage operator
- High agency, high ownership
- You do your best work without a finished playbook, iterating weekly on incomplete information
- You are a true AI practitioner
- You use AI to make your own work sharper, and you learn constantly on your own time
- The bar is not how much AI you use, it is whether AI makes you better. AI that produces slop counts against you. (Strong preference. We will waive it for an otherwise elite seller.)
Benefits
- Uncapped variable compensation
- Meaningful equity befitting a founding hire
Company Overview