We started Pairtu after years of fighting the system for our own families—Arian's mom is beating pancreatic cancer today because he learned to hack insurance rules nobody explains. Our vision: everyone deserves a fighter like that. Today we mix smart software with human advocates to guide Medicare patients through diagnoses, bills, and care plans. Investors from Omada, Oscar, and UnitedHealthcare believe in the mission—and in the scrappy team of <10 building it. Founded by experienced entrepreneurs with successful exits and deep healthcare + tech expertise. Backed by top-tier investors and advisors, including founders and executives from Oscar Health, Omada, Galileo, One Medical, Ro, United, Uber, and Postmates. We move fast and execute with purpose, operating with a lean, impact-driven mindset. We're guided by principles of conscious leadership, a commitment to getting things done (GSD), and a focus on achieving results through hard work, rapid iteration, and swift execution. Pairtu is a fast-moving, high-impact startup where chaos is the norm, and ownership is key. There's no playbook—some days, you'll put out fires; other days, you'll build from scratch. If you thrive in ambiguity, take initiative, and solve problems without waiting for direction, you'll fit right in. If you need structure and predictability or 'need to be a manager' this isn't for you. The upside? You'll level up and have growth, work with an elite, A+ team, and make a real impact as we scale. This isn't a corporate place, be advised.
Head of Sales
Location
United States
Posted
24 days ago
Salary
0
Seniority
Lead
Job Description
Head of Sales
Dearest Care
Role Description Dearest Care has established strong demand for its high-touch, AI-powered patient advocacy model in the direct-to-consumer market. Our next phase is focused on driving repeatable B2B growth by partnering with health systems, IDNs, regional provider groups, and adjacent care delivery organizations. We are seeking a senior, hands-on seller to help secure our first major contracts in this space. This is not a traditional management role. We want a self-starter who can independently source opportunities, navigate complex enterprise sales cycles, structure pilots, address internal blockers, and close deals. You’ll work directly with the founders to define and build our sales process from the ground up. What You’ll Do - Own the end-to-end sales cycle with providers: prospecting, discovery, pilot/POV design, stakeholder alignment, procurement, security review, contracting, and close - Independently build your pipeline: create account lists, initiate outreach, follow up, and schedule meetings - Target and win regional health systems, IDNs, large medical groups, and other provider organizations - Design thoughtful pilots with clear success metrics, stakeholder maps, workflows, and conversion plans - Navigate multi-stakeholder buying environments involving clinical, operational, financial, legal, IT, and procurement leaders - Collaborate with founders, product, and operations teams to refine messaging, package outcomes, and optimize our enterprise offering - Transform early wins and setbacks into a repeatable sales playbook (ICP, personas, objection handling, pilot templates, deal process) Qualifications - Have personally closed complex provider-side deals with health systems, IDNs, hospital networks, medical groups, or care delivery organizations - Built pipeline from scratch without strong brand pull, SDR support, or mature marketing resources - Structured pilots or proof-of-value programs that directly led to signed contracts - Sold into multiple stakeholders, including clinical, operational, and financial buyers - Navigated long enterprise sales cycles involving procurement, legal, security, and internal politics - Thrived in fast-paced, ambiguous startup environments where speed and ownership matter Bonus if you: - Have experience in care coordination, patient navigation, care management, transitions of care, population health, or value-based care - Are familiar with Medicare Advantage - Have strong relationships with provider-side executives or decision-makers - Have successfully positioned offerings seen as overlapping with internal teams as complementary What Success Looks Like in 12 Months - First provider contracts signed and implementation launched - 1–2 well-defined pilots converted into commercial agreements - Established, repeatable early sales motion for provider partnerships - Demonstrated operational and clinical value with strong customer proof points - Clear momentum to scale provider GTM beyond founder-led sales Why Join Us - Work directly with founders on one of the company’s most critical growth drivers - Influence product, GTM, and enterprise strategy in real time - Ownership and accountability for scaling Dearest Care's B2B platform - Join a high-energy team committed to fast, impactful execution - Help close a $60B+ healthcare navigation gap with a proven model backed by investors and payers - Directly impact our success in winning major contracts in the next 12 months - Be part of a high-trust, mission-driven, patient-first culture How to Apply - Submit your résumé or LinkedIn - Include a brief note describing a deal you personally closed into a health plan or health system, highlighting what made it successful Our Vision & Culture We envision a future where every American has access to a personal healthcare navigator. Our platform democratizes healthcare navigation, unlocking vital services for individuals often left to navigate complex medical systems alone. We value diverse perspectives and operate primarily within the Americas timezone. Excellence, integrity, and conscious leadership shape our every decision. - Prioritizing human connection within our team and in our work - Pursuing excellence in execution, communication, and creative problem solving - Practicing radical candor—addressing tough topics with honesty and empathy, uplifting each other - Competing smartly in the customer’s interest - Upholding the 15 commitments to conscious leadership
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