Chief Product & Technology Officer

About Us 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. 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. 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 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 Required: 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. Application Timeline and Details We anticipate the application window for this opening will close on: July 31, 2026. Submission does not guarantee selection, and Siftwell reserves the right to modify or close the hiring process at any time. Only shortlisted candidates will be contacted. All applications will be retained for future consideration. Candidates should be prepared to participate in a multi-stage interview process, which may include executive presentations, product and technology working sessions, and in-person meetings with key members of the leadership team. Disclosures Location & Hiring Eligibility This role is remote within the United States. We have an established presence in CO, FL, MA, MD, NC, NJ, NY, PA, and TN, and candidates in these states are encouraged to apply. If you're based elsewhere in the U.S., we'd still love to hear from you, we evaluate out-of-state candidates on a case-by-case basis. This role operates primarily during U.S. Eastern Time business hours. Benefits Overview At Siftwell, we hire Humble Killers — talented, mission-driven teammates who value impact, collaboration, and ownership. Our goal is to support that commitment through competitive pay, meaningful equity, and benefits that promote well-being, growth, and flexibility. Full-time Employment Opportunities include: Comprehensive health, dental, and vision insurance Short-term disability coverage 401(k) retirement plan with company matching Unlimited paid time off to rest and recharge Opportunities for ongoing professional development and learning Benefits may vary based on location and employment status. Equal Opportunity Statement Siftwell celebrates diversity and is proud to be an Equal Opportunity Employer. We consider all qualified applicants without regard to race, color, religion, sex, national origin, disability status, veteran status, or any other characteristic protected by law. Qualified applicants with arrest or conviction records will be considered in accordance with applicable laws, including the California Fair Chance Act. ADA Accommodation Statement If you require a reasonable accommodation during a selection process, please let us know through our general contact form or indicate this in your application. Security Requirements Adhering to the Company Security and Privacy Policies and the associated security standards Maintaining the security of the Information assets and resources to which they have been granted access Ensuring direct reports are aware of and adhere to Company Security and Privacy Policies Ensuring the security of information and managing risks to assets and resources owned by their functional area Ensuring that contractors, consultants, partners and other third parties under their sponsorship operate in compliance with Company policy Monitoring compliance related to business assets owned by their functional area and taking corrective action as necessary #Siftwell