Why This Role Exists

Dearest has proven strong demand for its high-touch, AI-powered patient advocacy model in the direct-to-consumer market. Our next chapter is building repeatable B2B growth through health systems, IDNs, regional provider groups, and adjacent care delivery organizations.

We’re hiring a senior, hands-on seller to help us win those first contracts.

This is not a pure management role. We want someone who can source opportunities, run complex enterprise sales cycles, structure pilots, navigate internal blockers, and close deals. You’ll work directly with the founders to build the motion from the ground up.

A bit about Dearest

We started Dearest 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 <15 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.

Dearest 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.

What You’ll Do: Strategize and own the B2B Sales Cycle with Cofounder

Own the full sales cycle into provider organizations: prospecting, discovery, pilot/POV design, stakeholder alignment, procurement, security review, contracting, and close
Build pipeline yourself with minimal support: account lists, outreach, follow-up, and meeting creation
Target and win regional health systems, IDNs, large medical groups, and similar provider-side buyers
Design pilots with clear success metrics, stakeholder maps, workflows, and conversion plans
Navigate complex buying environments involving clinical leaders, population health, care management, quality, finance, legal, IT, and procurement
Partner with founders, product, and ops to sharpen messaging, package outcomes, and improve the enterprise offering
Turn early wins and losses into a repeatable sales playbook: ICP, personas, objection handling, pilot templates, and deal process

You’re a Fit If You…

Personally closed complex provider-side deals into health systems, IDNs, hospital networks, medical groups, or care delivery organizations
Built pipeline yourself in environments without strong brand pull, SDR support, or mature marketing infrastructure
Structured pilots or proof-of-value programs that led to real contracts
Sold across multiple stakeholders, including clinical, operational, and financial buyers
Navigated long enterprise cycles that include procurement, legal, security, and internal politics
Thrived in a startup or high-ambiguity environment where speed, judgment, and ownership matter

Strong pluses

Experience in care coordination, navigation, care management, transitions of care, discharge workflows, population health, or value-based care
Medicare Advantage familiarity
Existing relationships with provider-side executives or decision-makers
Experience positioning an offering that could be perceived as overlapping with internal teams, and successfully reframing it as complementary

This role is probably not for you if

You mainly managed teams and no longer like carrying a bag
You relied heavily on brand, inbound demand, conferences, or large SDR support
Your background is primarily employer or payer sales and you have limited provider-side deal experience
You prefer polished structure over building in ambiguity
You like strategy discussions more than sourcing, follow-up, and closing

What Success Looks Like in 12 Months

First provider contracts signed and launched
At least 1–2 well-scoped pilots converted into commercial agreements
A repeatable early sales motion for provider partnerships
Strong proof points around operational and clinical value
Clear signal that Dearest can scale provider-side GTM beyond founder-led sales

Why Join Us

You’ll work directly with the founders on one of the most important growth motions in the company
You’ll shape product, GTM, and enterprise strategy in real time
You’ll have meaningful ownership over whether Dearest becomes a scaled B2B platform
You’ll join a mission-driven team that moves quickly and cares deeply about execution
We’re tackling a $60B+ healthcare navigation gap with a model investors and payers already believe in.
This is not a “corporate healthcare” role—your work will directly decide if we win major contracts in the next 12 months.
You’ll join a high-trust, mission-first culture that moves fast and cares deeply about patients.

How to throw your hat in the ring

How to Apply

Email [email protected] with subject line “B2B Sales – [Your Name]” and:

Your résumé or LinkedIn.
A short note on a deal you personally closed into a health plan or health system and what made it successful.
(Optional) Any relevant warm intros you could make tomorrow to payer/provider decision-makers.

Dearest celebrates diversity and is committed to equal opportunity. If you’re passionate about helping people and meet most of the role, please apply. We care more about grit and heart than perfect résumés.

Our Vision + Culture:

We envision a future where every American has access to a personal healthcare navigator. Our platform is designed to democratize healthcare navigation, offering tools and resources that were previously unavailable to many. By addressing the challenges faced by patient advocates and those navigating chronic diseases or healthcare illiteracy, we're paving the way for a more inclusive and accessible healthcare system.

Culture:

We have a distributed culture, mainly working out of the Americas timezone. We strive to be diverse in thinking, in hiring, and in how we tackle problems. We believe that operating excellently for our clients is our number one priority and building great products is critical.

Human connection: We’re bringing healthy human relating into the world as a healing modality, and we prioritize healthy relating within our team and in everything we do.
Excellence: in executing, thinking, writing, and communicating.
Stop the ego: hard conversations and ripping the band-aid earlier than later. Uplift each other.
Work smartly, competitive for our customers: Impact is driven and measured by delivering benefit to the end customer.

Head of Sales At Dearest