Head of Sales

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.

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 United Healthcare, 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

• 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)

• 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