Founding Account Executive

Job Description About Plena Plena is building the AI operating layer for specialty medical practices. Healthcare practices still run huge parts of their operations through phone calls, faxes, manual data entry, spreadsheets, and repetitive EHR work. We automate those workflows end to end across fax management, referrals, scheduling, patient calls and texting, intake, and procedure prep, integrating directly into the EHRs and practice management systems practices already use. We work across specialties including gastroenterology, orthopedics, urology, ophthalmology, cardiology, and dermatology, and sell into independent medical practices, MSOs, and private equity-backed specialty groups. We’re backed by Y Combinator and already working with some of the largest specialty medical groups in the country. We’re hiring our first dedicated Founding Account Executive to help scale our sales engine. The Role You’ll own the full sales cycle, from prospecting through signed contract, selling into independent practices, MSOs, and PE-backed specialty groups. You’ll navigate practice administrators, CEOs, COOs, physicians, and VPs/Directors of Practice Management. This is a hunter’s role. We have a sales playbook, strong customer traction, and a clear market. We need someone who can take that foundation, aggressively build pipeline, and close business. You won’t be waiting for meetings to land on your calendar. You’ll go create them. What You’ll Do • Build and manage your own pipeline through outbound prospecting, conferences, referrals, and industry relationships • Run discovery to understand how a practice operates today and where Plena creates real operational and financial value • Lead product demos tailored to each prospect’s workflows and priorities • Close six-figure ACV deals, with upside as accounts expand into additional workflows and locations • Navigate multi-stakeholder sales processes across operational, executive, clinical, and technical teams • Travel regularly to prospect sites, customer sites, and industry conferences • Partner with implementation, product, and engineering to scope opportunities accurately and ensure clean handoffs • Maintain pipeline discipline, CRM hygiene, and forecast accuracy • Expand initial deployments into additional workflows, departments, locations, and practices • Bring market feedback back to the team to sharpen messaging, demos, and process What We’re Looking For • 4–6+ years of quota-carrying sales experience, ideally in healthcare technology or vertical SaaS • Direct experience selling into physician practices, specialty medical groups, MSOs, or similar healthcare organizations • Familiarity with GI, orthopedics, urology, or cardiology practices and their specialty group landscapes is a strong plus • Existing familiarity with practice administrators, operational leaders, CEOs, COOs, and physicians as buyers • A strong track record of sourcing and closing your own opportunities, with a consistent history of hitting or exceeding quota • A true hunter mentality, energized by prospecting and opening doors • High urgency, follow-through, and strong CRM/forecast discipline • Comfortable operating with a high degree of ownership in a fast-moving startup • Willing and able to travel regularly Experience selling AI, automation, patient access, practice management, revenue cycle, scheduling, communications, or other operational technology into U.S. healthcare practices is a strong advantage. What Makes This Role Different This isn’t a traditional AE role where marketing and SDRs fill your calendar. You’ll have full autonomy to build relationships across the industry and directly influence Plena’s growth, from first outreach through signed contract. Compensation & Benefits • OTE: $225K–$325K • 60/40 base/variable split • Uncapped commission with additional upside for overperformance • Meaningful equity in a fast-growing, venture-backed company • Comprehensive health, dental, and vision coverage • Paid time off • Remote-first, based in the United States