dearestcare - Head of Sales At Dearest
Requirements
• 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
Responsibilities
• 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 • 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
Benefits
• 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. • 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 • 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. • 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. • Conscious Leadership Values: 15 commitment to conscious leadership • https://vimeo.com/1188185714
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