Job Description

Vice President of Legal Affairs

Location: Mount Prospect, IL

Salary: $275,000-$325,00 annually (based on experience) plus annual performance bonus

American Freedom Insurance Company (AFIC), a growing, A+ (Superior) rated non-standard automobile insurer, is seeking a strategic legal professional to lead and manage our in-house Legal and Claim Defense Department. The Vice President of Legal Affairs will serve as the primary legal advisor to the company’s leadership team, oversee legal strategy, manage litigation and claims-related legal issues, as well as ensure regulatory compliance. This executive role will be based in our headquarters where we prefer in-person attendance to foster close collaboration with executive leadership and operational teams; however a hybrid schedule is available for this position. The ideal candidate will not only serve as the company’s chief legal advisor but will also build and scale a high-performing legal department that supports a dynamic, compliance-driven insurance operation.

As AFIC expands in new markets, we are looking for an attorney who thrives in a collaborative environment and has extensive negotiating, coverage and excess loss avoidance experience.

Your Responsibilities

• Serve as a trusted legal advisor to senior management.
• Develop and implement a comprehensive legal strategy aligned with the company’s goals.
• Oversee, negotiate and process attorney-represented losses.
• Directly manage litigation in multiple jurisdictions.
• Oversee complex litigation and manage outside counsel for matters including bodily injury claims, bad faith allegations, coverage disputes, fraud investigations, and class actions.
• Deliver thorough and timely coverage opinions, liability evaluations, and litigation assessments.
• Collaborate with internal stakeholders to assess and mitigate legal and reputational risks across operations.
• Work cross-functionally with Claims to respond to regulatory inquiries and ensure compliance with all applicable insurance laws, particularly those impacting non-standard auto insurance operations.
• Evaluate the current legal function and design a forward-looking organizational structure that aligns with the company’s growth, compliance, and risk priorities.
• Recruit, mentor, and develop legal talent—both attorneys and adjusters—ensuring the team is appropriately resourced and aligned for success.
• Establish clear internal workflows, accountability structures, and legal operations protocols.
• Develop and enforce best practices for excess loss mitigation, including monitoring of policy limits and out-of-state claims as well as responding to time-limited demands.
• Stay abreast of regulatory, judicial and legal trends impacting bad faith litigation and claims-handling standards.
• Cultivate a culture of integrity, legal awareness, and proactive risk management throughout the organization.

Requirements

• Juris Doctor (JD) from an accredited law school and active license to practice law, preferably in the states of Illinois, Indiana, Pennsylvania, or Tennessee.
• 10+ years of progressive legal experience, with at least five years in a senior legal role in the insurance industry, ideally including experience in insurance defense as well as non-standard auto insurance experience.
• Deep familiarity with auto insurance regulations and non-standard auto complaints and market dynamics.
• Demonstrated ability to lead legal teams and engage with executives, regulators, and outside counsel effectively.
• Demonstrated success preventing excess loss exposure.
• Exceptional legal judgment, negotiation skills, and attention to detail.
• Deep understanding of claim dynamics and litigation strategies.
• Significant experience supervising attorneys, legal adjusters, and support staff.
• Strong technical writing and policy interpretation skills.

Why AFIC?

Compensation & Benefits

• Competitive base salary
• Annual performance bonus potential
• 401(k) with up to 6% company match

Health & Wellness

• Blue Cross Blue Shield medical plans (PPO, HMO, HSA)
• Dental & vision insurance

Growth & Stability

• Over 26 years of consistent profitability
• A+ rated by A.M. Best
• Expansion across 5 states

Professional Development

• Paid CLEs, licensing renewals, and training
• Opportunities for advancement

Culture

• Business casual dress
• Friendly, high-integrity workplace

Interested?

Join a company that values strategic thinking, hard work, legal experience, and your skills protecting carriers.

Apply today and shape the legal future of a rapidly growing insurer.

Learn more at

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