Lead AI Product Manager

Jobtailor; Connecticut; On-site; USD 140,000 - 190,000; Full time

Job summary

Jobtailor in Connecticut is seeking an experienced Senior Product Manager to lead the AI product strategy and a 12–18 month roadmap across participant engagement, advisor enablement, plan administration, and investment-related experiences.

You will translate business needs into clear product requirements, partner with engineering for rapid iteration, ensure fiduciary compliance, and drive go‑to‑market plans with measurable adoption and impact.

Qualifications

• Bachelor’s degree in a quantitative field is required; advanced degree preferred.
• 8+ years of product management experience, with at least 4 years in AI or ML roles.
• Proven track record delivering AI-powered products from discovery through launch.
• Strong knowledge of LLM-based products and retrieval-augmented generation.
• Experience working in regulated environments with compliance, legal, and risk stakeholders.
• Understanding of retirement, wealth, or financial services products.
• Excellent communication and stakeholder management, capable of influencing senior leaders.

Responsibilities

• Define and lead AI product strategy and 12–18 month roadmap.
• Identify AI opportunities using research, data, and insights.
• Establish success metrics and own key business outcomes.
• Lead discovery with advisors and participants to translate needs into specs.
• Collaborate with engineering to evaluate prototypes and guide trade-offs.
• Ensure compliance with fiduciary standards in a regulated setting.
• Drive go-to-market planning, rollout sequencing, and adoption measurement.
• Align senior stakeholders across business, tech, compliance, and investment teams.

Skills

AI product strategy

AI opportunities

stakeholder management

regulatory compliance

requirements writing

go-to-market planning

cross-functional collaboration

strong communication

Education

Bachelor’s degree in Computer Science, Engineering, Finance, Economics, Mathematics, or a related quantitative field

Advanced degree preferred

Job description

Responsibilities

• Define and lead the AI product strategy and 12-18 month roadmap across participant engagement, advisor enablement, plan administration, and investment-related experiences.
• Identify, assess, and prioritize AI opportunities using customer research, behavioral data, workflow analysis, and competitive insights.
• Establish clear success metrics and own business outcomes such as engagement, adoption, operational efficiency, and retirement readiness improvements.
• Lead discovery with advisors, plan sponsors, administrators, and participants to translate business needs into clear product requirements and technical specifications.
• Partner closely with engineering teams to evaluate prototypes, guide product trade-offs, and support rapid iteration through launch.
• Ensure solutions meet compliance, legal, risk, and fiduciary standards within a regulated financial services environment.
• Drive go-to-market planning, rollout sequencing, stakeholder communication, and adoption measurement for AI-enabled products.
• Build alignment across senior stakeholders in business, technology, compliance, and investment teams while influencing without direct authority.

Requirements

• Bachelor’s degree in Computer Science, Engineering, Finance, Economics, Mathematics, or a related quantitative field required; advanced degree preferred.
• 8+ years of product management experience, including at least 4 years in AI or machine learning product roles within technology, fintech, or financial services.
• Proven experience delivering AI-powered products from discovery through launch and measurable adoption.
• Strong knowledge of LLM-based products, retrieval-augmented generation, agentic workflows, model evaluation frameworks, experimentation methods, and data-informed product development.
• Ability to write high-quality product requirements and technical specifications for engineering teams.
• Experience working in regulated environments and partnering with compliance, legal, and risk stakeholders.
• Strong understanding of retirement, wealth, or financial services products, including fiduciary considerations and participant or advisor workflows.
• Excellent communication, prioritization, and stakeholder management skills, with the ability to influence senior leaders and cross-functional teams.