Chief AI Strategy & Transformation (Remote)

Alera Group, Inc.; United States; On-site; USD 250,000 - 300,000; Full time

Benefits offered by this job

Medical, dental, and vision insurance

Life and disability coverage

401(k)

Generous paid time off

Professional development

Job summary

Alera Group, Inc. is seeking a visionary Head of Artificial Intelligence to drive enterprise-wide AI strategy, governance, and an investment roadmap that accelerates business transformation.

You will partner with executive leadership across Finance, Operations, Technology, Legal, Compliance, and Learning to embed AI into business plans, lead a high-impact portfolio, and champion responsible AI practices. This role is remote and nationwide within the United States.

Qualifications

• MBA or advanced education in business, technology management, or related
• 10–15 years of progressive leadership experience in enterprise strategy, business transformation, or related field
• Proven track record leading large-scale transformation initiatives with measurable outcomes
• Executive leadership experience partnering with senior leaders to define strategy and drive execution
• Strong business, financial, and strategic planning acumen with complex initiatives and budgets
• Exceptional communication, stakeholder management, change leadership, and decision-making skills

Responsibilities

• Define and execute the enterprise AI vision, strategy, governance, and investment roadmap
• Lead a high-impact portfolio of AI initiatives delivering measurable business value
• Partner with executive leadership to embed AI into business strategies and drive adoption
• Champion Responsible AI governance ensuring ethical, secure, compliant practices
• Drive workforce transformation by advancing AI readiness and digital skills
• Translate vision into business results with compelling business cases and metrics
• Monitor emerging tech and regulations to maintain leadership in the market
• Build high-performing teams through a culture of innovation and accountability

Skills

Executive leadership

Strategic planning

Stakeholder management

Change leadership

Decision making

Communication

Education

MBA / Master's degree

Job description

Alera Group, Inc. is seeking a visionary Head of Artificial Intelligence to drive enterprise-wide AI strategy, governance, and an investment roadmap that accelerates business transformation.

You will partner with executive leadership across Finance, Operations, Technology, Legal, Compliance, and Learning to embed AI into business plans, lead a high-impact portfolio, and champion responsible AI practices. This role is remote and nationwide within the United States.