Principal Product Manager, AI Strategy & Operations (Remote)

Businessolver has been delivering market-changing benefits technology and services since 1998. They are seeking a Principal Product Manager to lead AI strategy execution across their portfolio, ensuring alignment with business priorities and operational discipline.

Responsibilities:

• Partner with the Chief AI Officer to translate enterprise AI priorities into a clear execution model across products, platforms, and enabling functions
• Maintain visibility into the AI initiative portfolio, including status, dependencies, risks, investment needs, and expected outcomes
• Help ensure the portfolio is aligned to business priorities, product strategy, and technical capacity
• Design and run the operating cadence for the AI organization, including planning cycles, reviews, decision forums, and executive updates
• Drive clear follow-through on strategic initiatives by coordinating actions, owners, milestones, and escalation paths
• Establish consistent mechanisms for tracking progress, surfacing tradeoffs, and supporting decision-making
• Support investment planning for AI initiatives by helping define sequencing, expected impact, resource tradeoffs, and portfolio balance
• Partner with Finance, Product, and Engineering leaders to frame initiative value, cost, and execution readiness
• Help leaders make informed prioritization decisions grounded in business impact and execution constraints
• Coordinate across Product, Engineering, Security, Legal, Privacy, Compliance, and executive stakeholders to keep major initiatives aligned and moving
• Identify gaps in accountability, sequencing, or communication and drive resolution
• Ensure portfolio-level decisions are reflected in roadmap planning and operating commitments
• Define and maintain the core reporting structure for AI strategy execution, including initiative health, milestone progress, value realization, and operating risks
• Produce clear materials for executive stakeholders, board-level discussions, and cross-functional leadership reviews
• Improve the quality and consistency of portfolio reporting across AI-related workstreams
• Support the Chief AI Officer on special projects, strategic analyses, operating model decisions, and cross-functional initiatives
• Develop recommendations that connect business goals, product choices, technical realities, and execution risk
• Act as a force multiplier for leadership by driving clarity, structure, and action across ambiguous problem spaces

Requirements:

• Bachelor's degree required in Business, Computer Science, Engineering, Information Systems, Economics, or a related field
• 10+ years of experience in product management, strategy, business operations, technical program leadership, or portfolio operations, including work with senior executives
• Proven experience translating strategy into execution across cross-functional organizations with multiple stakeholders and dependencies
• Strong product and business judgment, with the ability to evaluate initiative value, readiness, and tradeoffs
• Demonstrated experience building operating cadences, portfolio management systems, executive reporting, and decision support processes
• Strong written and verbal communication skills, including the ability to prepare materials for executive audiences
• Ability to operate effectively in ambiguous environments and drive alignment across technical and non-technical teams
• Ongoing professional development in AI strategy, product operations, portfolio management, and executive communication expected
• Master's degree preferred, including MBA or a relevant graduate degree in a technical or business discipline
• Experience supporting AI, data, platform, or enterprise transformation initiatives
• Background in product operations, strategic planning, chief of staff work, or transformation leadership
• Familiarity with governance, risk, and compliance considerations for AI-enabled capabilities
• Experience working in SaaS, enterprise software, or regulated environments