About Pear Suite

Pear Suite is a mission-driven healthcare technology company transforming how community-based care is delivered. Our platform empowers community health workers, doulas, and other frontline providers with tools to coordinate care, track outcomes, and improve health equity. We partner with organizations serving Medicaid and Medicare populations, delivering social and preventive care at scale.

Why Pear Suite?

We’re a mission-driven team committed to health equity and innovation in community-based care. You’ll thrive here if you’re eager to take initiative, value autonomy, and enjoy building structure where none exists. Join us to build scalable, human-centered technology that empowers frontline workers and improves lives across the U.S.

About the role

The Head of Growth, will own end-to-end strategy and execution for entering, scaling, and expanding in the payer/health plan market. This role will be responsible for revenue generation, market entry design, building strategic health plan relationships, and leading a team of sales professionals. Unlike a pure individual contributor, this role sits at the leadership level and requires both vision and hands-on execution.

What you'll do

Strategy & Market Entry

• Define and evolve Pear Suite’s payer go-to-market vision: target segments (Medicaid, Medicare Advantage, Duals, commercial), geographic priorities, and entry modes (direct contracts, pilots, network partnerships).
• Conduct competitive analyses, market sizing, payer gap assessments, and go/no-go decisions for new states or regions.
• Forecast and set annual growth targets, quotas, and KPIs for health plan revenue and penetration.

Sales & Revenue Generation

• Lead the full sales cycle: prospecting, deal qualification, proposal development, negotiation, contract execution.
• Secure new health plan clients and expand relationships in existing plans, including upsell, cross-sell, footprint expansion opportunities. Navigate complex payer procurement processes (RFPs, pilots, LOIs, direct contracting).
• Collaborate with Finance, Partnerships, Customer Success, and Operations to ensure financially sustainable contract structuring and risk-sharing models.

Relationship Building & Thought Leadership

• Build and sustain C-suite and VP-level relationships across health plans, including medical leadership, network, innovation, and SDOH arms.
• Serve as a public face of Pear Suite: speak at payer / industry events, publish or co-author thought leadership, participate in policy and payer consortiums.
• Engage with key stakeholders (state agencies, regulators, tradeshows) to maintain visibility and credibility.

Team Leadership & Cross-Functional Alignment

• Recruit, mentor, and manage a high-performing team of Strategic Accounts Managers, business development reps, and sales support staff.
• Work closely with Product, Marketing, Partnerships, and Customer Success to align product roadmap, messaging, and delivery to health plan needs.
• Drive internal enablement: create playbooks, training, collateral, ROI tools, negotiation guides, and sales processes tailored to payers.

Measurement & Execution

• Implement rigorous tracking of pipeline metrics, win rates, sales funnels, deal cycles, churn, and client satisfaction.
• Review performance regularly, diagnose pipeline bottlenecks, and iterate strategies.
• Own forecasts, reporting, and accountability to executive leadership.

Qualifications

• 10+ years of healthcare or health-tech business development, enterprise sales, or payer strategy experience, including 5+ years in leadership roles.
• Demonstrated track record closing multi-million-dollar deals with health plans or risk-bearing entities (Medicaid MCOs, Medicare Advantage, Duals).
• Deep familiarity with Medicaid, Medicare, managed care models, value-based contracting, SDOH/CHW programs, and payer reimbursement mechanisms.
• Experience with long, complex sales cycles, multi-stakeholder decision-making, and navigating procurement processes.
• Strong executive presence with ability to build credibility with C-level and senior payer executives.
• Experience building, mentoring, and scaling sales teams.
• Startup or high-growth experience, with agility and bias toward action.
• Willingness to travel (25%–40%) for meetings, conferences, and client engagements.

Preferred Skills & Attributes

• Experience in payer innovation units, quality/value-based care, or population health risk models.
• Experience working in multiple U.S. states and familiarity with state Medicaid markets and regulatory environments.
• Strong financial acumen, comfort modeling contract-level ROI, P&L, pricing, and negotiation strategies.
• Excellent communication and storytelling skills; ability to articulate clinical, operational, and social value to business audiences.
• Ability to thrive in ambiguity and lead through change.

What we offer

• The compensation range for this position is $130-150k + Commission and Performance Bonus
• A mission driven culture that values innovation, collaboration and growth
• Fully Remote
• Unlimited PTO
• Health, dental, and vision insurance
• Health and Wellness Stipend
• Tech Stipend
• Co-working Stipend