Head of Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Take charge of the complete sales cycle with providers: prospecting, discovery, pilot/POV design, stakeholder alignment, procurement, security review, contracting, and closing.

• Proactively develop your pipeline by creating account lists, initiating outreach, following up, and scheduling meetings.

• Aim to secure regional health systems, IDNs, large medical groups, and various provider organizations.

• Create well-structured pilots that feature clear success metrics, stakeholder mappings, workflows, and conversion strategies.

• Navigate complex multi-stakeholder purchasing environments involving clinical, operational, financial, legal, IT, and procurement leaders.

• Work collaboratively with founders, product, and operations teams to enhance messaging, package outcomes, and refine our enterprise offering.

• Convert early successes and challenges into a repeatable sales playbook (ICP, personas, objection handling, pilot templates, deal processes).

⛳️ Requirements

• Have successfully closed intricate provider-side deals with health systems, IDNs, hospital networks, medical groups, or care delivery organizations.

• Developed a pipeline from the ground up without strong brand recognition, SDR support, or established marketing resources.

• Structured pilots or proof-of-value initiatives that directly resulted in signed agreements.

• Engaged with multiple stakeholders, including clinical, operational, and financial buyers.

• Managed lengthy enterprise sales cycles that involved procurement, legal, security, and internal politics.

• Excelled in dynamic, ambiguous startup settings where speed and ownership are essential.

• Bonus if you possess experience in care coordination, patient navigation, care management, transitions of care, population health, or value-based care.

• Bonus if you are knowledgeable about Medicare Advantage.

• Bonus if you maintain strong relationships with provider-side executives or decision-makers.

• Bonus if you have effectively positioned offerings perceived as overlapping with internal teams as complementary.

🏝️ Benefits

• Collaborate directly with founders on one of the company's key growth drivers.

• Influence product, go-to-market, and enterprise strategies in real-time.

• Enjoy ownership and accountability for scaling Dearest Care's B2B platform.

• Become part of a high-energy team dedicated to prompt, impactful execution.

• Contribute to closing a $60B+ healthcare navigation gap with a proven model supported by investors and payers.

• Have a direct impact on our success in securing major contracts within the next 12 months.

• Join a high-trust, mission-driven, patient-first culture.