Founding Senior Account Executive

Location: Indianapolis, Indiana preferred, but open to the right person anywhere in the US.

Right now, Pragmatico's new revenue mostly runs through its founder. That works until it becomes the thing holding growth back, and we are there.

This is the role that makes new-client revenue founder-independent. You will close bookings against a quota by selling AI transformation to C-suite buying committees. You will co-sell with our founder-CEO on the hardest deals at first, and then, quickly, close them without the CEO in the room. As you go, you will build the sales playbook that captures what actually works, and you will earn the chance to build and lead the team that runs it.

Two things are true here at the same time. The number is the scoreboard. A repeatable, founder-independent motion is the win. If one of those excites you and the other bores you, this is the wrong seat.

We sell AI Transformation Management: the full system that gets a mid-market workforce to actually adopt AI and ties the work to the P&L, measured to the board. It is services plus software, people plus process. You are not selling a feature list, and the buyer can tell the difference.

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.

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.)

We would rather be honest about the shape of this role than pretend it needs someone who does not exist.

You do not need deep vertical expertise across every industry. You sell cross-industry, and we will get you fluent in the verticals that matter.

You do not need to be a marketing operator. Marketing is a peer you partner with, not a function you run.

You do not need to be technically deep in AI or ML. You need enough to be credible and to know when to pull in solutions engineering. We are not hiring an engineer.

You do not need big-company forecasting rigor and process polish on day one. Early, this is about deals closed and a motion built. The rigor comes as we scale, and you help build it.

Pragmatico installs a client's AI Transformation Department, embedded and fractional. The software half is a platform that measures every user, benchmarks them against vertical peers, distributes what the best users discover, and keeps the score that ties the work to the P&L. The human half is a bench: an AI Transformation Partner leading trainers, coaches, forward-deployed engineers, and process-improvement leads. No mid-market company can afford that bench on its own, and no hiring plan buys the platform. They rent both from us as one system. That is the category, and we are defining it.

This is an early founding team hire, and the seat carries the leverage to match it. You will work shoulder to shoulder with the founder-CEO/CRO, own the motion that decides whether the company scales, and have a path you earn to building and leading the team that comes after you. What you build here is yours to run.

Compensation is competitive ($200-300k ote), with uncapped variable, so the ceiling on what you earn is the ceiling on what you close. You will receive meaningful equity befitting a founding hire. We generously reward high performers.

Equal Opportunity

Pragmatico is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to gender, age, race, religion, or any other classification protected by applicable law.