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VP, Legal Entity Leader

Alera Group

Chicago, Illinois(remote)

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JOB DETAILS
SKILLS
Accounting, Billing, Brokerage, Business Strategy, Business Transformation, Communication Skills, Cross-Functional, Customer Support/Service, Finance, Insurance, Leadership, Legal, Operational Strategy, Organizational Skills, Problem Solving Skills, Project Planning, Project/Program Management, Risk Analysis, Risk Management, Team Player
LOCATION
Chicago, Illinois
POSTED
Today
OVERVIEW

VP, Legal Entity Leader
Location: Remote
Department: Enterprise Transformation Office
Reports To: SVP, Enterprise Transformation
Status: Full-Time | Exempt
About the Role
Alera Group is seeking a VP, Legal Entity Leader to drive enterprise-wide legal entity and carrier consolidation initiatives as part of our broader Business Transformation strategy. This role partners closely with regional leadership, operations, finance, legal, and carrier teams to execute complex transitions while minimizing operational disruption and maintaining continuity across servicing, billing, commissions, and revenue flow.

This is a highly visible role for a hands-on transformation leader who can balance strategy, execution, stakeholder management, and operational problem solving.

About Alera Group
Founded in 2017, Alera Group has grown to become the 14th 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.
Why Join Alera Group?
This role offers the opportunity to help shape enterprise transformation initiatives that directly impact the future growth and operational strategy of Alera Group while partnering with leaders across the organization.

Alera Group is an equal opportunity employer committed to creating an inclusive environment for all colleagues.

RESPONSIBILITIES

What You'll Do
  • Lead legal entity and carrier consolidation initiatives across the organization
  • Translate enterprise transformation priorities into practical regional and office-level execution plans
  • Partner with regional leaders, shared services, and carrier teams to coordinate transitions and resolve operational challenges
  • Identify and mitigate risks related to commissions, billing, revenue flow, and client servicing continuity
  • Manage project plans, milestones, dependencies, governance updates, and execution tracking
  • Help simplify and standardize consolidation processes to support long-term scalability

QUALIFICATIONS

What You Bring
  • 5+ years leading complex cross-functional initiatives or transformation programs
  • Strong understanding of insurance brokerage operations, carrier relationships, commission accounting, or legal entity structures
  • Experience supporting enterprise transformation, consolidation, operational integration, or large-scale business initiatives
  • Proven ability to balance strategic leadership with hands-on execution
  • Strong communication, organizational, and stakeholder management skills

ADDITIONAL INFORMATION

Compensation:
Salary range: $150,000 - $200,000 per year
Eligible for performance-based bonus: Yes

Benefits:
Alera Group offers comprehensive benefits including medical, dental, vision, life and disability coverage, 401(k), generous PTO, and more.

Work Model:
This role is Remote

Professional Development - Alera Group Academy
At Alera Group, growth isn't left to chance. Through Alera Group Academy, we provide structured development opportunities designed to help you expand your expertise and build a meaningful career.

You'll have access to:
  • Role-specific learning paths
  • Leadership development programs
  • Technical and compliance training
  • Industry certifications and continuing education support
  • Peer learning and knowledge-sharing communities
Whether you're deepening technical expertise or preparing for leadership, we're invested in helping you grow.

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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Location Type

Remote

About the Company

A

Alera Group

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