VP, Head of Product

Vice President, Head of Product

PE-Backed | Legal & Dispute Resolution Services | Remote (U.S.)

Reports To: Chief Executive Officer

About the Opportunity

This is a greenfield product leadership opportunity inside a fast-scaling, PE-backed alternative dispute resolution platform. The company has established itself as one of the nation's leading providers of mediation and arbitration services — recruiting and retaining top-tier neutrals (former judges and senior legal professionals) and connecting them with law firms, businesses, and individuals seeking efficient resolution outside of litigation.

Having built a dominant position in its home market, the company is now executing an ambitious multi-market expansion strategy. Technology is central to that growth. A proprietary case management and workflow platform (internally built) underpins operations, and the company is now investing in senior product leadership to transform that platform into a true competitive advantage.

This role is a direct hire into the executive team — a hands-on leader who will own product strategy, manage external engineering partners, drive roadmap execution, and serve as the primary bridge between business priorities and technology delivery. It's built for someone who has done this before: owned a product, shipped it, and managed the people and vendors required to get there.

The Role

The VP, Head of Product owns the vision, roadmap, architecture, and execution of the company's proprietary platform and adjacent digital products. This is the senior-most technology product role in the organization — a seat at the leadership table with direct impact on the company's expansion trajectory.

Engineering work is currently performed by a third-party development partner. The VP owns that relationship and delivery outcomes. Over time, the role may evolve to include building internal engineering capability as the business scales. A path toward a CTO title exists for the right candidate.

Day-to-day IT operations, endpoint management, and security operations reside in a separate function. This role partners closely on enterprise architecture, security requirements, and business continuity.

Key Responsibilities

Product Strategy & Vision

• Define and execute a multi-year product strategy and roadmap aligned with business growth, geographic expansion, operational efficiency, and customer experience objectives.

• Evaluate build-versus-buy opportunities and develop business cases that support technology investment decisions based on ROI and long-term value.

• Establish product KPIs, success metrics, and governance processes to measure the impact of strategic initiatives.

• Lead the organization's AI strategy by identifying high-impact opportunities to improve workflows, productivity, automation, and customer experiences.

• Continuously assess emerging technologies, market trends, and competitive offerings to ensure the platform remains innovative and scalable.

Product Management & Business Partnership

• Build and lead a disciplined product management function, including intake, prioritization, roadmap planning, release management, and quarterly planning processes.

• Partner with business leaders across Operations, Finance, Case Management, and customer-facing teams to translate business needs into product requirements, user stories, and functional specifications.

• Oversee user acceptance testing (UAT), change management, and business readiness activities to ensure successful product releases.

• Communicate product priorities, investment strategies, and roadmap decisions to executive leadership and the Board of Directors.

Engineering Leadership

• Own software delivery outcomes, including quality, predictability, velocity, scalability, and platform reliability.

• Lead and manage third-party software development partners, establishing clear performance expectations and accountability for delivery.

• Improve software development methodologies, documentation standards, release management practices, and engineering governance.

• Leverage modern development tools and AI-assisted engineering practices to improve development efficiency and product quality.

• Define and monitor engineering performance metrics, including delivery timelines, sprint velocity, roadmap execution, and operational performance.

Platform Architecture & Technology Strategy

• Serve as the strategic technology leader responsible for the long-term architecture of the company's product ecosystem.

• Ensure the platform is designed for scalability, security, maintainability, extensibility, and future business growth.

• Establish modernization priorities, manage technical debt, and maintain comprehensive architecture documentation.

• Validate that the technology platform supports geographic expansion, acquisitions, product innovation, and evolving business requirements.

Vendor & Technology Management

• Serve as the executive owner for software development vendors and strategic technology partners.

• Manage vendor relationships, contract performance, delivery expectations, and ongoing service quality.

• Develop and oversee product and technology budgets while ensuring effective allocation of technology investments.

• Identify opportunities to optimize technology spend while maximizing business value and platform capabilities.

What You'll Bring

• 10 years of progressive leadership experience spanning Product Management, Software Engineering, Technology Strategy, or Digital Transformation.

• Proven success leading the strategy, development, and delivery of business-critical software platforms.

• Demonstrated ability to translate organizational strategy into successful technology solutions and product roadmaps.

• Experience managing external engineering partners, software vendors, and complex technology delivery programs.

• Strong understanding of modern software architecture, cloud technologies, application development, and enterprise platforms.

• Experience building or maturing product management organizations, governance processes, and cross-functional operating models.

• Outstanding executive communication and stakeholder management skills with experience presenting to senior leadership and Boards of Directors.

• Strong financial acumen with experience evaluating technology investments, budgets, and ROI.

Preferred Qualifications

• Experience supporting high-growth or private equity-backed organizations.

• Proven success modernizing proprietary software platforms or workflow management systems.

• Experience implementing AI-enabled products, automation strategies, or intelligent workflow solutions.

• Background within technology-enabled services, legal technology, professional services, healthcare, financial services, insurance, or other regulated industries.

• Experience leading technology organizations through rapid growth, geographic expansion, or mergers and acquisitions.

• Based in or willing to work from a U.S. coastal market, with preference given to candidates located in California, New York, or the Boston/New England region.

What Success Looks Like

This role is ideal for a leader who combines strategic thinking with operational execution. You are comfortable presenting a product vision to executive leadership one day and reviewing engineering delivery metrics the next. While you won't be writing code, you will own product outcomes, technology strategy, vendor performance, and the successful execution of the organization's technology roadmap.

If you're passionate about building scalable products, leading high-performing teams, and using technology—including AI—to transform business operations, we'd love to hear from you.