Head of Product

Pearlyplan Inc.

Job Overview

Location

Indiana, USA

Job Type

Full-time

Full Job Description

📋 Description

• Pearlyplan Inc. is seeking a visionary and entrepreneurial Head of Product to spearhead our product strategy and execution in the rapidly growing vertical SaaS and payments space. This is a unique opportunity to take ownership of the entire product function at a company that has already achieved significant product-market fit, serving 2,500 dental offices with exceptional unit economics. Reporting directly to the CEO, you will have the autonomy to define our forward-looking roadmap, drive the execution of new initiatives, and commercialize Pearly's expanding platform across billing, payments, and patient engagement.
• This role is designed for a hands-on leader who thrives on building and innovating. You will be instrumental in two critical, interconnected efforts: first, expanding new product capabilities to deepen customer value and increase Annual Contract Value (ACV); and second, scaling our platform through self-serve distribution, product-led growth (PLG) strategies, robust feedback loops, and strategic integrations.
• As the first dedicated product leader, you will operate as an entrepreneurial force, shaping the product strategy and rapidly developing new capabilities that address the core challenges faced by the dental industry. Your responsibilities will extend beyond feature development; you will own the commercial outcomes of your work, collaborating closely with Sales, Customer Success (CS), and Marketing teams on go-to-market strategies. You will also work hand-in-hand with the CTO to optimize engineering velocity and explore the adoption of AI tools to enhance development processes.
• If you are energized by the prospect of building and scaling a product from the ground up at a company with proven traction, and if you approach product decisions with a keen eye on revenue and unit economics rather than just features and sprints, this role is an ideal fit. Your impact will be directly tied to the commercial success and strategic direction of Pearlyplan.
• **Product Strategy & Commercialization:**
• Own and define the overarching product strategy and roadmap, encompassing areas such as Accounts Receivable (AR) automation, payments, patient engagement, and advanced analytics. Crucially, each initiative will have a clear, measurable link to revenue and profitability impact.
• Develop and refine pricing, packaging, and commercialization strategies for all new products, working collaboratively with Sales, CS, and Marketing to maximize both SaaS and payments revenue streams.
• Experiment with and implement product-led growth (PLG) motions designed to drive adoption, increase usage, and foster expansion revenue across our diverse customer base, including private practices, group practices, and Dental Support Organizations (DSOs).
• **Execution & Engineering Partnership:**
• Act as a hands-on product leader, actively involved in writing detailed specifications, defining requirements, generating prototypes, and making critical trade-off decisions.
• Operate effectively at all levels, from high-level strategic planning down to sprint-level execution, ensuring iterative delivery rather than large, infrequent batch releases.
• Collaborate closely with the CTO to enhance engineering velocity, integrate AI-augmented development workflows, and make informed build vs. buy vs. partner decisions concerning Dental Practice Management Systems (PMS), Electronic Health Records (EHR) systems, payment processors, and terminal hardware.
• **Payments & Platform Architecture:**
• Architect and implement robust integration and data strategies across various dental PMS platforms, payment processors, and channel partners to ensure scalability, broaden market reach, and enhance customer value.
• Develop and refine partner enablement frameworks to empower channel and integration partners to accelerate distribution and adoption of Pearlyplan's solutions.
• **User Experience, Data & Self-Serve:**
• Elevate the patient user experience (UX) to serve as a key differentiator, while also building segmented experiences tailored to the distinct needs of DSO executives versus office managers.
• Drive the enhancement of self-service capabilities as the product suite continues to grow, empowering users to manage their needs independently.
• Leverage our rich healthcare record data set to develop sophisticated analytics, actionable insights, and demonstrable ROI across the entire customer journey, from initial engagement to becoming a loyal advocate.
• Design and execute product strategies aimed at fostering high-volume, high-retention distribution, service, and support models.
• **Team & Leadership:**
• Serve as an engaged and strategic partner to the CEO and the broader leadership team, contributing to the shaping of Pearlyplan's culture and embodying our core values.
• Establish and refine product feedback loops that effectively integrate insights from CS, Sales, Marketing, and Engineering to inform roadmap prioritization and enhance product adoption.
• Build and grow the product function over time, establishing key metrics, developing the team, implementing necessary systems, and championing AI adoption.

🎯 Requirements

• Proven experience as a product leader in a growth-stage B2B SaaS and/or payments company, with a track record of scaling from early traction to significant ARR (e.g., $20M+).
• Demonstrated ability to own or significantly influence pricing, packaging, and go-to-market commercialization strategies, with a strong understanding of revenue and unit economics.
• Hands-on product management experience, including writing specifications, defining requirements, prototyping, and making trade-off decisions, coupled with a builder mentality and a bias for action.
• Experience with product-led growth (PLG) motions, specifically in driving cost-efficient in-app expansion, increasing ACV, and enabling self-serve distribution and servicing with minimal human touch.
• Experience in B2B payments or fintech, understanding payment facilitation, merchant onboarding, processing economics, and/or embedded payments strategy.
• Ability to design and implement segmented product strategies for different customer types (e.g., enterprise DSOs, mid-market groups, SMB private practices) and experience designing both B2B and consumer-level experiences.

🏖️ Benefits

• Competitive salary and equity package.
• Comprehensive healthcare benefits.
• A meeting-light culture that prioritizes focused work and efficiency.
• Opportunity to collaborate with a highly intelligent and passionate team.
• Flexible vacation time-off policy to support work-life balance.
• The chance to make a significant impact at an accelerating company with strong product-market fit.

Skills & Technologies

Remote

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Pearlyplan Inc.

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About Pearlyplan Inc.

Pearlyplan is a tech company focused on simplifying financial planning and wealth management for individuals. Their platform offers tools for budgeting, saving, investing, and retirement planning, aiming to make complex financial concepts accessible and actionable. By leveraging technology, Pearlyplan provides personalized insights and guidance to help users achieve their financial goals. The company operates in the fintech industry, catering to a broad audience seeking to improve their financial literacy and build long-term wealth. Their services are designed to be user-friendly, empowering individuals to take control of their financial future with confidence.

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