Enterprise Account Executive

THE VOICE AI WORKFORCE FOR HEALTHCARE Healthcare runs on phone calls and loses $450B a year to the administration around them. Patients wait on hold, staff spend hours calling insurers, and revenue leaks at every handoff. At Prosper, we're building the AI workforce that runs healthcare operations end to end. Our voice AI agents answer patient calls, schedule appointments directly in the EHR, verify insurance benefits, automate billing, and get payors on the phone when humans would otherwise wait on hold. We've grown revenue 5x in the last year, partnered with 100+ healthcare organizations covering more than 150,000 providers, and raised $35M, including a $30M Series A led by Andreessen Horowitz. 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. WHAT YOU'LL DO - 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 WHY PROSPER - A trillion-dollar problem, real customers, and revenue growing 5x - Greenfield named accounts with no legacy pipeline and no internal competition for logos - Direct access to founders, product, and engineering. Deals get unblocked in hours, not quarters - Backed by the best investors in the world. Andreessen Horowitz manages $90B and sits behind OpenAI, Databricks, and Coinbase