Enterprise Account Executive

The Role

We're hiring an Enterprise Account Executive to own a named list of the largest provider organizations in the country: national MSOs, PE-backed platform groups, and multi-region specialty organizations.

This is the seat every enterprise seller says they want and rarely gets. The accounts are open, the whitespace is untouched, and the product wins in a bake-off. You're not inheriting a picked-over patch or a pipeline someone else already burned. You're picking the logos, building the plan, and running every cycle from first meeting to signature.

You'll have real air cover behind you. Founder-led sales that shows up on your calls, solutions and implementation teams that make pilots land, a product team that ships what your deals need, and a category with genuine urgency: every provider group in America is being asked what its AI strategy is, and most of them do not have an answer yet.

Revenue is up 5x on a lean team. This segment is our single largest expansion opportunity, and the person in this seat sets the ceiling on how fast we take it.

• Own a named account list end to end: account planning, prospecting, discovery, pilot, negotiation, close, and expansion

• Run long-cycle, multi-stakeholder deals across revenue cycle, finance, IT, security, compliance, clinical operations, and procurement, and hold every thread yourself

• Build durable relationships with the people who decide. The best enterprise sellers are trusted before they're needed. You'll invest in multi-year relationships with CFOs, COOs, CIOs, and VPs of Revenue Cycle, arriving with a point of view on their business rather than a pitch

• Author the ROI case. Every deal at Prosper is won on a quantified business case: cost-to-collect, denial rate, days in A/R, FTE hours redeployed, cash recovered. You'll build these models from the customer's own data and defend them in front of a CFO

• Navigate the enterprise gauntlet of RFPs, security reviews, HIPAA and BAA diligence, legal negotiation, and phased multi-site rollouts without losing momentum

• Convert pilots into platform commitments, designing land-and-expand paths from a single site or specialty to the full organization

• Direct the resources around your deals: outbound, marketing, solutions engineering, and founders all work against the plan you set for your accounts

• Codify what works into the battlecards, business-case templates, and qualification criteria the next five reps will run

What We're Looking For

• A track record of outperformance. You've consistently finished in the top tier of your team, and you can point to the numbers: quota attainment, President's Club, the year you closed the deal nobody thought was closable

• 6+ years of full-cycle closing experience, with at least 3 in enterprise or strategic accounts and $250K+ ACV deals

• Command of a real methodology. MEDDPICC, Command of the Message, Challenger, whichever you run, you qualify hard, you know where every deal stands, and your forecast is accurate

• Relationship-building as a core competency, not a byproduct. You build trust with senior operators over years, and people who've worked with you once seek you out again. You can win a room of C-suite executives and hold it

• Entrepreneurial eagerness and drive. You're eager to get scrappy, comfortable with getting in the mud, while at the same time being able to take a 10,000 foot view and have an ongoing strategy that adapts fast to new market signals

• Comfort with a technical product and the ability to translate AI capability into operational and financial outcomes

Bonus Points

• Healthcare provider, payer, or RCM selling experience

• Experience selling AI, automation, or voice technology into regulated industries

• Fluency with EHR and practice management ecosystems (Epic, athenahealth, ModMed, eClinicalWorks) and clearinghouse/RCM stacks

• An existing network across provider group leadership or PE-backed provider platforms

• Early-stage or hypergrowth startup background, especially as an early rep who helped build the motion