Chief Product & Technology Officer

About the role

Siftwell is seeking a Chief Product & Technology Officer (CPTO) to lead our Product, Engineering, and Data Science organizations as we enter our next phase of growth. Reporting directly to the CEO, this executive will be responsible for defining our product vision, platform strategy, and technology investment priorities. The CPTO will ensure that customer needs, market opportunities, and business objectives are translated into a clear roadmap and aligned execution across Product, Engineering, and Data Science.

• Define and continuously evolve Siftwell's product vision, platform strategy, and long-term roadmap to support company growth, customer outcomes, and market differentiation.
• Own investment and resource allocation decisions across Product, Engineering, and Data Science, ensuring budgets, talent, and development capacity are focused on the initiatives that deliver the greatest customer, market, and business impact.
• Establish the roadmap and strategic priorities that guide Product, Engineering, and Data Science, ensuring execution remains aligned to customer needs, market opportunities, and business objectives.
• Create a disciplined product operating model that connects customer feedback, market intelligence, product strategy, and technology execution.
• Evaluate emerging market trends, competitive dynamics, regulatory developments, and payer industry needs to inform product strategy and future platform investments.
• Drive the evolution of the Siftwell platform, ensuring product capabilities, data assets, analytics, and AI-enabled solutions create measurable value for health plan customers.
• Partner closely with Customer Success, Growth, and executive leadership to ensure product priorities reflect market demand, customer needs, and commercial objectives.
• Align Product, Engineering, Data Science, Customer Success, and Growth around product priorities, investment decisions, success metrics, and long-term strategic objectives.
• Build, lead, and scale high-performing Product, Engineering, and Data Science organizations, including organizational design, workforce planning, executive hiring, succession planning, and leadership development.
• Lead, coach, and performance-manage Product, Engineering, and Data Science leaders, establishing clear expectations, accountability, and development plans that enable both individual and organizational growth.
• Serve as a key executive partner to the CEO in shaping company strategy, supporting fundraising efforts, and representing Siftwell's product vision, platform strategy, and technology roadmap to customers, partners, and investors.
• Establish the metrics, decision frameworks, and governance processes necessary to evaluate product investments, measure outcomes, and support data-driven prioritization across the organization.

Requirements

• Bachelor's degree required plus minimum 14 years relevant work experience; Master's degree preferred.
• 10+ years of progressive leadership experience spanning healthcare product management, software development, data platforms, and technology-driven solution delivery.
• Deep understanding of the payer healthcare market, including health plans, value-based care, healthcare analytics, population health, and related technology solutions.
• Understanding of healthcare data privacy, security, and regulatory requirements, including HIPAA compliance and the operational responsibilities associated with handling protected health information (PHI).
• Proven success defining product vision, platform strategy, and technology roadmaps that align customer needs, market opportunities, and business objectives.
• Experience leading Product, Engineering, and Data Science organizations and making executive-level prioritization, investment, and resource allocation decisions.
• Track record of building, scaling, hiring, and performance-managing high-performing Product and Technology teams.
• Experience partnering with executive leadership on company strategy, growth initiatives, and long-term business planning.

Preferred Qualifications

• Previous experience as a Chief Product Officer, Chief Product & Technology Officer, VP Product & Engineering, or equivalent executive leadership role.
• Experience scaling healthcare technology companies through Series A, Series B, or similar high-growth environments.
• Experience supporting fundraising efforts, investor presentations, board interactions, and strategic planning activities.
• Experience with AI/ML-enabled products, healthcare data platforms, analytics solutions, and modern cloud-based software architectures, including experience evaluating and prioritizing AI-driven product opportunities.