# Alera Group — Head of AI

- Generated: 2026-09-15 10:48:11 PM EDT
- Original/canonical posting: https://wellfound.com/jobs/4700197-head-of-ai
- Provider: Wellfound
- Posted: Not disclosed
- Elapsed since posting: represented by the provider's relative posting label and approximate Eastern timestamp when available
- Applicants: Not disclosed
- Work model/location: Remote — United States
- Compensation: $250,000-$300,000 base plus performance bonus
- Travel: Occasional; exact percentage should be confirmed against Keith's 5% maximum
- Positioning track: Executive leader
- Fit outcome: PASS — 95%

## Direct-match strengths

Enterprise AI strategy, portfolio prioritization, executive partnership, Responsible AI, privacy and compliance, workforce transformation, change leadership, investment planning, measurable value, regulated financial-services experience, and team building.

## Hard or material gaps

Travel is described only as occasional and should be confirmed at 5% or less. Keith's direct insurance-brokerage experience is limited, but he has strong regulated financial-services, privacy, AI-governance, and enterprise transformation evidence; brokerage depth is preferred rather than required.

## Evidence map

1. Define enterprise AI vision, strategy, governance, and roadmap (weight 3, evidence 3/3) — Direct strategy-through-production AI, cloud, data, and governance leadership.
2. Lead a portfolio of measurable AI initiatives (weight 3, evidence 3/3) — Prioritized 50+ enterprise use cases and built a platform supporting 70+ automations across 20+ workflows.
3. Partner with executives and governance bodies (weight 3, evidence 3/3) — Advised 200+ enterprises and led cross-functional executive transformations.
4. Responsible AI, privacy, security, and compliance (weight 3, evidence 3/3) — Led five privacy and AI-governance initiatives in regulated financial services.
5. Workforce transformation and change leadership (weight 3, evidence 3/3) — Built teams and global communities and led enterprise adoption and enablement.
6. Business cases, budgets, investments, and value reporting (weight 3, evidence 3/3) — Owned budgets up to $900,000 and quantified delivery, adoption, reliability, and cycle-time outcomes.
7. Build high-performing teams (weight 2, evidence 3/3) — Built and led organizations up to 25, including managers.
8. Insurance, financial services, or regulated industry (weight 2, evidence 3/3) — Direct MassMutual financial-services, privacy, governance, and regulated-platform experience.
9. Advanced degree (weight 1, evidence 3/3) — Ph.D. plus extensive executive and technical leadership.

## Keyword diagnostic

Exceptional enterprise AI strategy, governance, portfolio, adoption, investment, executive, transformation, and regulated-environment coverage.

## Full normalized job description

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Alera Group
Actively Hiring
Risk management, insurance & financial service solutions
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Head of AI
$250k – $300k
|
Remote (
United States
)
|
15 years of exp
|
Full Time
Posted:
7 days ago
• Recruiter recently active
Hires remotely
in
United States
Remote Work Policy
Remote only
Company Location
Deerfield
Visa Sponsorship
Not Available
Relocation
Allowed
Skills
Strategy
Change Management
Innovation
Emerging Technologies
Investment Strategies
Ethical
Performance Metrics
AI Strategy
Secure
Digital Skills
INDUSTRY TRENDS
AI Readiness
Responsible AI Practices
AI Vision
Governance Models
AI Initiatives
Governance Framework
Compliant
Evolving Regulations
Organizational Risk
Investment Roadmap
Transparent Use of AI
Executive Business Cases
Value Realization Reporting
About the job
Overview
Head of Artificial Intelligence (AI)
Overview
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.
About Alera Group
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.
Responsibilities
What You'll Do
In this role, you will 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.
Shape the Future of AI Across the Enterprise by defining and executing 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.
Champion Responsible AI Practices by establishing governance models that ensure the ethical, secure, compliant, and transparent use of AI while effectively managing organizational risk.
Drive Workforce Transformation by fostering AI readiness, advancing digital skills, leading change management efforts, and empowering employees to unlock new levels of productivity and innovation.
Translate Vision into Business Results through compelling executive business cases, investment strategies, performance metrics, and value realization reporting that demonstrate AI's impact across the organization.
Stay Ahead of What's Next by monitoring 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.
Qualifications
Required Qualifications
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
Preferred Qualifications
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
Compensation
Salary Range - $250,000 - $300,000 annually
Bonus Eligible - Yes (Performance Based)
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
Additional Information
Work Arrangement
This position is
Remote
Travel Requirements -
Occasional travel may be required to support office implementations, training, and collaboration with project teams.
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.
,, #Nationwide
Location Type
Remote
Apply Now
About the company
Alera Group
Actively Hiring
Risk management, insurance & financial service solutions
501-1000
Employees
Deerfield
501-1000
Financial Services
B2B
Learn more about
Alera Group
Funding
AMOUNT RAISED
$1B
FUNDED OVER
1
round
Round
S
$1000000000
Seed
-
May 2025
View
Alera Group
's funding history
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## Artifact metadata

- Resume: https://bit.ly/4hsZI2t
- Cover letter: https://bit.ly/4751mkQ
- Validation: PASS — 2-page resume (913 words), 1-page cover letter (219 words); PDF geometry, bounds, annotations, links, and visual pages verified.
- Google Drive used: No