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