Head of AI

Alera Group•UNAVAILABLE, UNAVAILABLE

1d•Remote

About The Position

At Alera Group, our corporate teams play a critical role in supporting the success of colleagues and clients across the country. From Human Resources and Finance to Technology, Legal, Marketing, and Operations, these professionals ensure our organization runs efficiently while enabling our teams to deliver exceptional service. Founded in 2017, Alera Group has grown to become the 12th largest broker of U.S. business. We are passionate about our clients’ success in Employee Benefits, Property & Casualty Insurance, and Financial Services. With offices nationwide, our collaborative approach allows us to deliver national strength with local service. We are always looking to connect with talented professionals who want to contribute to a collaborative, high-growth environment and help drive strategic initiatives across a national organization. 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.

Requirements

MBA, Master's degree, or other advanced education in Business Administration, Technology Management, Data Science, Artificial Intelligence, Engineering, Organizational Development, or a related discipline
10-15 years of progressive leadership experience in enterprise strategy, business transformation, technology-enabled operations, consulting, financial services, insurance brokerage, or a related industry
Proven track record leading large-scale transformation initiatives that delivered measurable business outcomes, productivity improvements, operational efficiencies, or revenue growth
Executive leadership experience partnering with senior leaders and governance bodies to define strategy and drive enterprise execution
Strong business, financial, and strategic planning acumen with experience managing complex initiatives, budgets, and investment portfolios
Exceptional communication, stakeholder management, change leadership, and decision-making skills
Licensure (if applicable)
Relevant AI, technology, risk management, or business leadership certifications preferred

Nice To Haves

Experience leading AI, automation, digital transformation, innovation, or technology-enabled business initiatives at enterprise scale
Deep understanding of AI governance, responsible AI practices, data privacy, security, compliance, and technology risk management
Experience within the insurance, financial services, consulting, or regulated industry environment
Demonstrated success building high-performing teams, developing talent, and leading organizational change initiatives
Ability to translate complex technical concepts into business strategy, operational outcomes, and measurable value creation

Responsibilities

Serve as the organization's leading voice for AI strategy and innovation, helping transform how work gets done, how decisions are made, and how value is created across the enterprise.
Define and execute the organization's AI vision, strategy, governance framework, and investment roadmap to accelerate business transformation and long-term growth.
Lead a high-impact portfolio of AI initiatives, identifying, prioritizing, and scaling opportunities that deliver measurable business value, operational efficiency, and competitive advantage.
Partner with Executive Leadership across Finance, Operations, Technology, Legal, Compliance, Communications, and Learning & Development to embed AI into business strategies and drive enterprise-wide adoption.
Establish governance models that ensure the ethical, secure, compliant, and transparent use of AI while effectively managing organizational risk.
Foster AI readiness, advance digital skills, lead change management efforts, and empower employees to unlock new levels of productivity and innovation.
Develop compelling executive business cases, investment strategies, performance metrics, and value realization reporting that demonstrate AI's impact across the organization.
Monitor emerging technologies, industry trends, and evolving regulations to identify opportunities, mitigate risks, and maintain a leadership position in the market.
Build and inspire high-performing teams by cultivating a culture of innovation, accountability, continuous learning, and responsible experimentation that accelerates enterprise AI adoption.