Principal Product Manager, AI Strategy & Operations (Remote)

Since 1998, Businessolver has delivered market-changing benefits technology and services supported by an intrinsic responsiveness to client needs. The company creates client programs that maximize benefits program investment, minimize risk exposure, and engage employees with easy-to-use solutions and communication tools to assist them in making wise and cost-efficient benefits selections. Founded by HR professionals, Businessolver's unwavering service-oriented culture and secure SaaS platform provide measurable success in its mission to provide complete client delight.

**Please be aware of recruitment scams. Businessolver does not make job offers outside of our official hiring process or request payment or sensitive personal information. You will never receive an offer of employment without meeting a hiring authority and having a "live" and face-to-face conversation.**

Job Overview:

The Principal Product Manager, AI Strategy and Operations serves as the senior product and operating partner to the Chief AI Officer, helping translate AI strategy into execution across the portfolio. This role drives the management system for the AI function, including planning cadence, initiative tracking, portfolio visibility, investment logic, dependency management, and executive follow-through.

This leader works across product, engineering, governance, and executive stakeholders to ensure AI initiatives move with clear priorities, defined outcomes, and operating discipline. The role combines strategic thinking, product judgment, and operational rigor to help the organization scale AI efforts in a coordinated and measurable way.

The Gig:

AI Portfolio Strategy and Execution

• 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.

Operating Cadence and Governance

• 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.

Investment Logic and Prioritization

• 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.

Cross-Functional Alignment

• 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.

Measurement and Reporting

• 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.

Strategic Problem Solving

• 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.

What you need to make the cut:

Education

• Bachelor’s degree required in Business, Computer Science, Engineering, Information Systems, Economics, or a related field.

• Master’s degree preferred, including MBA or a relevant graduate degree in a technical or business discipline.

• Ongoing professional development in AI strategy, product operations, portfolio management, and executive communication expected.

Skills & Experience

• 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.

Preferred Qualifications

• 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.

The pay range for this position is $147,000 to $183,500 per year (pay to be determined by the applicant’s education, experience, knowledge, skills, and abilities, as well as internal equity and alignment with market data).

This role is eligible to participate in the bonus incentive plan.

Other Compensation: 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/

Dear Applicant.

At Businessolver, we take our responsibility to protect our clients, employees, and company seriously and that begins with the hiring process.

Our approach is thoughtful and thorough. We’ve built a multi-layered screening process designed to identify top talent and ensure the integrity of every hire. This includes quickly filtering out individuals who may attempt to misrepresent themselves or act in bad faith.

We also partner with trusted, best-in-class providers to conduct background checks, verify identities, and confirm references. These steps aren’t just about compliance, they’re about ensuring fairness, safety, and trust for everyone involved.

Put simply: we will always confirm that you are who you say you are. It's just one of the many ways we uphold the standards that matter most, to you, to us, and to the people we serve.

With heart,
The Businessolver Recruiting Team

Businessolver is committed to maintaining an environment that protects client data. We train our employees to maintain leading class security practices and expect all employees to adhere to policy, procedures and controls.

(Applicable to all roles at an AVP, DIR, VP, Head Of or SVP and above level):

Serve as a security contact for the business unit. Responsible for driving adoption and compliance with information security and privacy practices. Serve as a liaison with the information security team on security and privacy matters.

Equal Opportunity at Businessolver:

Businessolver is an Affirmative Action and Equal Opportunity Employer and is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and more. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements.

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