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[Remote] Principal Product Manager, AI Strategy & Operations (Remote)

Worldwide Salaried Open

Note: The job is a remote job and is open to candidates in USA. Businessolver is a company that has been delivering innovative benefits technology and services since 1998. The Principal Product Manager for AI Strategy and Operations will partner with the Chief AI Officer to translate AI strategy into execution, ensuring alignment across product and engineering teams while managing the AI initiative portfolio.

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

Skills

  • 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

Benefits

  • This role is eligible to participate in the bonus incentive plan.
  • If this position is full-time or part-time benefit eligible, you will receive a comprehensive benefits package which can be viewed here: https://businessolver.foleon.com/bsc/job-board-businessolver-virtual-benefits-guide/

Company Overview

  • Businessolver is an employee benefits administration technology company. It was founded in 1998, and is headquartered in West Des Moines, Iowa, USA, with a workforce of 1001-5000 employees. Its website is https://www.businessolver.com.
  • Company H1B Sponsorship

  • Businessolver has a track record of offering H1B sponsorships, with 2 in 2025, 3 in 2024, 3 in 2023, 2 in 2022, 3 in 2021, 1 in 2020. Please note that this does not guarantee sponsorship for this specific role.
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