Chief Product & Technology Officer

About the role

Siftwell Analytics is a fast-growing company that combines healthcare operator expertise and artificial intelligence to equip managed care health plans with better insights to drive earlier and more precise health interventions for members. Siftwell was founded with a fundamental commitment to address the unique challenges faced by health plans, beginning with Medicaid, Marketplace, and Medicare plans, who are entrusted with the care of our most vulnerable and complex populations. At Siftwell, we hire "Humble Killers" - individuals with a deep commitment to the mission, high ownership, and low ego. We are committed to providing a mutually respectful work environment where diversity and inclusion are critical to our success. We seek to recruit, develop, and retain talented professionals from a broad range of backgrounds, and to foster a culture where individuals can grow, contribute meaningfully, and thrive. 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. This role requires a product-led executive with a proven track record of building and scaling healthcare technology platforms, ideally within the payer ecosystem. The successful candidate will define Siftwell's long-term product and platform strategy, establish the roadmap and investment priorities that guide Product, Engineering, and Data Science, and make the critical tradeoff decisions required to scale the business. Beyond roadmap ownership, they will bring an external market perspective to the organization, challenge assumptions, identify emerging opportunities, and ensure resources remain focused on the initiatives that create the greatest value for customers and the company. Working in partnership with Siftwell's cofounder who leads the company's core AI models, proprietary algorthims and agentic AI / digital-workforce program, the CPTO will help translate the company's advanced analytics and artificial intelligence capabilities into differentiated products that address evolving market and customer needs. Success in this role means creating the operating discipline that connects market needs, product strategy, technology execution, and investment decisions. As a key member of the executive team, the CPTO will serve as a strategic partner to the CEO and help articulate a differentiated platform vision that translates AI, analytics, and healthcare technology into measurable value for customers, partners, and investors. This position reports to the CEO, is remote within the United States and operates on U.S. East Coast hours, with occasional travel for client engagement and team collaboration. All new hires are subject to a one-time drug screening in accordance with Siftwell's PHI compliance policies.

Responsibilities

• 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.
• Serve as the ultimate executive decision-maker for product and technology prioritization, making disciplined tradeoff decisions regarding new product investments, platform capabilities, technical debt, scalability initiatives, and organizational resources.
• 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 o

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