Founding Enterprise Account Executive

About Pretty Good AI

Pretty Good AI runs voice agents for specialty practices on athenaOne. We handle the calls a clinic actually struggles with: inbound patient calls, scheduling, refills, referral conversion, after-hours coverage, appointment-gap recovery, and patient win-back. Everything runs natively inside athenaOne.

We're profitable, founder-led, and have prior exits in mobile and AI. Growth is customer-pulled, not burn-funded. We're members of the athenaConnect Innovators program, and compliance and usability shape every decision we make.

Why This Role Exists

We've figured out our edge. Customers tell us, in their own words, that what we do is different, and they feel it inside the first ten minutes of a demo. The product sells itself when it's pitched right. Our constraint isn't the product, the category, or pricing. It's getting in front of the right buyer at the right moment.

A few things about how we operate, because they shape what this job actually feels like:

• We sell month-to-month, by choice. We refuse long-term contracts even when customers ask for them, because we don't believe a customer will walk away once they're live. That confidence is earned, and it sets the tone for every sales conversation you'll run.

• “Too good to be true” is the most common first reaction. Buyers tell us out loud that what we're describing can't be real. Then they pilot it and find out it is. Every customer we have is a reference customer, and most go out of their way to send us new ones.

That's the job: get into the rooms, run the diagnostic, let the product do the heavy lifting, and convert.

The Role

This is our founding go-to-market hire. You'll own the full revenue motion for our athenaOne Marketplace solution: move active pilots to signed customers, convert inbound demand into closed business, and land larger multi-location specialty groups.

This is not a “spray demos and close logos” job. Our buyers are smart operators: practice administrators, COOs, RCM leaders, and physician-owners. They expect a partner who can look at their practice and tell them where the funnel is actually leaking, then right-size a solution that works for both sides. We scope honestly up front, and our pilots convert at a rate we're proud of. You'll carry that standard forward.

Your first 90 days are about velocity: move in-flight pilots toward signed contracts and get fully ramped on inbound. Net-new pipeline matters too, but advancing the funnel we already have comes first.

What You'll Do

• Own the full cycle — diagnosis, demo, pilot scoping, pilot-to-close, and expansion — focused on multi-location specialty groups on athenaOne.

• Run consultative discovery. Profile a practice before the first call (provider count, locations, call volume, funnel gaps) and lead with insight, not a feature list.

• Move active pilots to signed customers and shorten time-to-go-live.

• Convert inbound and event-sourced demand into closed business.

• Navigate multi-stakeholder buying (physician-owners, operations, RCM) and the MSO/IPA approval processes that govern many of our target accounts.

• Right-size and disqualify honestly. We'd rather lose a bad-fit deal than churn a customer.

• Partner closely with our founders and product team, and bring the field signal back in.

Who You Are

• 5+ years of B2B sales in healthcare SaaS, EHR/practice-management software, RCM, or patient-engagement / workflow automation.

• You know the athenahealth ecosystem. You've sold athenaOne practices, ideally an athenahealth Marketplace solution. You understand the buyer, the lead-flow process, the integration go-live path, and who you're up against.

• You're AI-native in your daily work. You already use tools like Claude for research, account planning, and discovery prep, and you can profile a practice in real time. If you've been at a slower-moving or legacy vendor and want to sell an AI-native stack, we especially want to talk to you.

• You sell consultatively. You can run the diagnostic, not just the pitch, and you're comfortable talking referral conversion, scheduling throughput, no-show recovery, and ROI math.

• You're a builder. A founding-seller role at a small, profitable company is upside and ambiguity in equal measure, and that excites you.

• Excellent communication, presentation, and negotiation skills. Self-starter. Honest.

Why Pretty Good AI

• Founding GTM seat at a profitable, fast-growing company. Your work directly moves revenue.

• A product with real, defensible advantages that customers feel on the first call. Your job is to get the meetings; the product handles the close.

• A real customer-onboarding team that owns implementation and go-live. You won't be implementing it alone after the signature.

• Founders with real exits who are building this one to last.

• Competitive base plus uncapped commission, with OTE set based on your experience and accelerators tied to pilot conversion. Your incentives match what moves the business; we'll share the band on our first call.

• Fully remote and flexible. Travel isn't required day-to-day — expect a few key industry conferences a year, such as athenahealth's Thrive Summit.

• A team that ships, on a stack built with the best AI available.

Apply

If you know the athenahealth world, sell by diagnosing rather than pitching, and want a founding seat at a profitable healthcare AI company, send us a note.