Homeoffice Head of Growth (Health Plans) na Pear Suite's Career Page

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