Head of Product

The Role

This is a rare opportunity to own the product function at a high-growth vertical SaaS and payments company with strong product-market fit, 2,500+ dental offices on the platform, and top tier unit economics.

You’ll be the first dedicated product leader reporting directly to the CEO with autonomy to define forward-looking roadmap, drive execution, and commercialize Pearly’s expanding platform across billing, payments, and patient engagement.

Getting there requires two distinct and related efforts. The first is expanding new product capabilities that deepen the value we deliver and increase ACV. The second is scaling through self-serve distribution, product-led growth, tight feedback loops, and integrations.

This is not a traditional product management role. You’ll operate as an entrepreneurial leader, driving the product strategy and rapidly building new capabilities that solve real problems for the dental industry. You'll act with ownership of commercial outcomes of what you build and working shoulder-to-shoulder with the CTO on engineering velocity and AI tool adoption. If you’re energized by building rather than managing at a company with real traction, and think about product decisions in terms of revenue and unit economics—not just features and sprints—this is your role.

What You'll Own

Product Strategy & Commercialization

• Own product strategy and roadmap across A/R automation, payments, patient engagement, and analytics aligned with revenue and profitability impact.

• Define pricing, packaging, and commercialization for new products in partnership with Sales, CS, and Marketing (both SaaS and payments revenue streams)

• Experiment with product-led growth motions that drive adoption, usage, and expansion revenue across private practices, groups, and DSOs.

Execution & Engineering Partnership

• Hands-on product leader: operate at all altitudes from strategy to writing specs and generating prototypes. Compartmentalize to deliver iteratively, not in 6-month batches.

• Partner with the CTO on engineering velocity, AI-augmented development workflows, and build/buy/partner decisions across PMS systems, payment processors, and other solutions.

Payments & Platform

• Hone integration and data strategy across dental PMS platforms, payment processors, and channel partners to drive scalability, expand market reach, and deepen value for customers

• Build partner enablement frameworks that allow channel partners and integration partners to accelerate distribution.

UX, Data & Self-Serve

• Enhance patient UX as a differentiator and build segmented experiences for DSO executives vs. office managers. Drive self-serviceability and scale distribution as the product suite grows.

• Leverage our healthcare record data set to up-level analytics, insights, and ROI across the customer journey form first touch to raving customer advocate.

Team & Leadership

• Be an engaged partner to the CEO and leadership team to shape Pearly’s culture and model our values.

• Establish product feedback loops between CS, Sales, Marketing and Engineering that inform roadmap prioritization and improve adoption.

• Build and grow the product function over time: metrics, team, systems, AI.

What You Bring

• 5-7+ years in Product within growth-stage B2B SaaS and/or payments, with experience as the sole or lead product person at a company scaling from early traction to $20M+ ARR

• B2B payments or fintech experience: understands payment facilitation, merchant onboarding, processing economics, and/or embedded payments strategy

• Segmented strategy: has built segmented product strategies across different customer types (enterprise/DSO, mid-market groups, SMB/private practice)

• UX depth: experience designing both B2B and consumer-level experiences in multi-product environments across software, hardware, and/or other technologies.

• PLG upsell / cross-sell: has built product-led growth motions that drive cost-efficient in-app expansion and measurably increase ACV (and/or sales-assisted motions).

• Data & analytics: expertise productizing reporting, ROI tools, and analytics to enhance product stickiness and demonstrate value across the customer journey.

• Self-serve distribution: has enabled high-volume, high-retention distribution and servicing with minimal human touch (direct and/or indirect)

• Partner and integration experience: has built scalable integration frameworks and successfully leveraged partner ecosystems

• Based in Atlanta, GA, New York or Santa Barbara, CA. Remote considered for an exceptional candidate with regular travel to Atlanta, NYC, and Santa Barbara.

Benefits

• Competitive salary, equity, and healthcare benefits

• Meeting-light culture

• Work with an A+ smart and passionate team

• Flexible vacation/time-off policy

• Opportunity to make your mark at an accelerating company with great product-market fit