Head of Sales

Why This Role Exists

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.

About Dearest Care

Dearest Care was founded after personal journeys navigating the healthcare system for our own families—Arian’s mom beat pancreatic cancer because we learned to hack insurance rules nobody explains. Our vision is that everyone deserves a fighter like that.

Today, we combine intelligent software with human advocates to guide Medicare patients through diagnoses, bills, and care plans. Backed by investors from Omada, Oscar, and UnitedHealthcare, we’re a dedicated team of fewer than 15 people with big ambitions.

• Founded by seasoned entrepreneurs with a track record of successful exits and deep expertise in healthcare and technology

• Supported by top-tier investors and advisors, including founders and executives from Oscar Health, Omada, Galileo, One Medical, Ro, United, Uber, and Postmates

• We operate with speed and intention, guided by conscious leadership and a bias for action

• We thrive in a fast-paced, high-impact environment where ownership is essential and ambiguity is the norm

• If you take initiative and solve problems proactively, you’ll fit right in. If you thrive in structured, hierarchical environments, this might not be the best fit

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)

You’re a Fit If You…

• 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

Dearest Care celebrates diversity and is an equal opportunity employer. If you’re passionate about helping people and meet most of the requirements, we encourage you to apply—we value grit and drive over perfect backgrounds.

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.

Our principles:

• 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

Watch our story

Dearest Care is an equal opportunity employer committed to diversity and inclusion. Join us in transforming healthcare navigation for the better.