Head of Sales

🕒 July 28

🇺🇸 United States – Remote

⏰ Full Time

🔴 Lead

🤑 Sales

👻 Ghost score 50%

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Dearest

WebsiteLinkedInAll Job Openings

2 - 10 employees

🏥 Healthcare

👥 B2C

💰 Non Equity Assistance - Dearest on 2022-06

Healthcare • B2C

Dearest is a patient advocacy and care‑coordination service (branded as Dearest Care) that matches patients and caregivers with dedicated, experienced healthcare advocates—nurses, physicians, pharmacists, social workers, and care coordinators—to help navigate appointments, paperwork, insurance approvals, and next steps. The company supports a range of health needs (new diagnoses, chronic illness, cancer, dementia, senior care, disability support, equipment procurement, etc. ), is covered by Medicare and many Medicare Advantage plans nationwide, and emphasizes rapid access (avg. 24 hours to connect), large-scale experience (27,000+ patients served) and a team of trained advocates (103+). Dearest positions itself as an independent partner to patients and families, focused on care coordination, insurance navigation, and connecting people with appropriate doctors and services.

📋 Description

• 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)

🎯 Requirements

• 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 • Bonus if you are familiar with Medicare Advantage • Bonus if you have strong relationships with provider-side executives or decision-makers • Bonus if you have successfully positioned offerings seen as overlapping with internal teams as complementary

🏖️ Benefits

• 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