AI Product Lead - Employee Benefits, Financial Services & Sales

AI Product Lead - Employee Benefits, Financial Services & Sales

At Alera Group, our people, and the way we empower them, are our greatest competitive advantage. We are seeking an AI Product Lead to define and execute the AI and operational excellence strategy for our Employee Benefits and Financial Services practices, with additional AI support for Sales. In this role, you will own the AI roadmap for both practices. You will turn emerging capabilities into practical solutions that improve efficiency, support growth, enhance the client experience, and advance One Alera.

If you are energized by translating new technology into measurable business results, partnering with senior leaders across the enterprise, and helping teams work smarter, this is your opportunity to lead.

Founded in 2017, Alera Group is one of the nation's leading independent insurance and financial services firms. We combine the strength of a national organization with the personalized service of local experts to help clients succeed across Employee Benefits, Property & Casualty Insurance, Retirement Plan Services, Wealth Services, and Human Capital Solutions.

Why Join Alera Group?

• Collaborate with purpose – Work alongside colleagues who believe the best results come from strong partnerships, shared expertise, and supporting one another.
• Build your career – Expand your expertise through meaningful work, continuous learning, and opportunities to grow across a national organization.
• Make an impact – Help clients navigate complex challenges while contributing to solutions that make a difference for their businesses, employees, and communities.

What You'll Do

• Develop and execute the AI strategy and roadmap for Employee Benefits and Financial Services, aligned to practice objectives, systems, enterprise standards, and growth goals
• Partner with Employee Benefits and Financial Services leaders to identify, prioritize, and deliver practical AI use cases for each practice
• Support AI adoption for Sales teams, helping improve productivity and client engagement
• Run the AI operating approach: initiative intake, prioritization, budget recommendations, and progress reporting
• Manage the AI initiative portfolio, deciding what to prioritize, scale, redesign, or discontinue
• Translate AI-enabled productivity gains into measurable outcomes for client experience, efficiency, colleague capacity, and growth
• Represent Employee Benefits, Financial Services, and Sales needs in decisions on AI platforms, licensing, vendors, integrations, data readiness, and build-versus-buy
• Lead AI enablement across supported teams, including communication, upskilling, and adoption
• Apply enterprise responsible AI standards covering privacy, security, compliance, and vendor risk, including requirements specific to employee benefits and financial services
• Build business cases and track adoption, productivity, financial, and client impact metrics
• Monitor AI, insurance, Employee Benefits, financial services, and regulatory trends, and turn them into recommendations
• Manage relationships with AI vendors, consultants, and strategic partners
• Participate in enterprise AI councils, champion networks, and cross-functional working groups

What You'll Bring

• Bachelor's degree in Business Administration, Technology, Data Science, AI, Engineering, Organizational Development, or a related field (master's degree or relevant certification preferred)
• 7+ years of progressive experience, including 3+ years in Employee Benefits or Financial Services
• 2+ years in AI or automation, including building prototypes, defining evaluation and acceptance criteria, and managing vendors, solution architecture, and budgets
• Experience in business transformation, technology-enabled operations, consulting, or insurance brokerage, including leading cross-functional initiatives
• A record of AI, operational improvement, or technology-enabled change initiatives that delivered measurable results
• Working knowledge of evolving AI regulations, ethical AI, data governance, and privacy and security requirements
• Strong business, insurance, and financial acumen, including business cases, budgets, and ROI tracking
• The ability to influence senior stakeholders and build consensus across a matrixed organization
• Excellent communication skills, with the ability to turn complex technical concepts into clear business recommendations

Licensure (if applicable)

• Relevant AI, technology, risk management, or business leadership certifications preferred

Compensation

• Salary Range: $200,000 - $260,000 annually + Bonus

Benefits

Eligible colleagues enjoy a comprehensive benefits package including:

• Medical, dental, and vision insurance
• Life and disability coverage
• 401(k)
• Generous paid time off
• Professional development and career growth opportunities

Work Arrangement

This position is Remote

Travel Requirements: Frequent travel to other offices and client meetings is expected.

We're an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status, or any other protected class.

Alera Group is committed to protecting your privacy. Please review our Privacy Policy to understand what personal information we may collect and use as part of your application process.

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