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Legal Director – Insurance & Reinsurance

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Oliver James Associates Ltd.
Full Time position
Listed on 2026-01-16
Job specializations:
  • Law/Legal
    Legal Counsel, Business Law, Lawyer
Salary/Wage Range or Industry Benchmark: 200000 - 240000 USD Yearly USD 200000.00 240000.00 YEAR
Job Description & How to Apply Below
# Legal Director – Insurance & Reinsurance Legal Director – Insurance & Reinsurance Salary $200000 - $240000

Location Chicago, IL, USA Contract Permanent Industry Legal ---Contact Declan Frit
** LEGAL DIRECTOR – INSURANCE/ REINSURANCE
** Our client, a growing and leading Insure Tech are seeking their first Legal hire to come in as a Director of  this role, you will lead the companies legal strategy and operations. You will be a key partner to senior leadership, enabling the business to scale rapidly while maintaining strong risk-managed, rights-protected operations!
** LEGAL DIRECTOR – INSURANCE/ REINSURANCE
** Our Legal hiring team are excited to be working with a NEW CLIENT, a growing Insure Tech, who are seeking their 1st LEGAL HIRE for the business, to provide legal counsel to the c-suite, in a very imperative and broad role.

You will be working on business initiatives, product launches, partnerships, regulatory/licensing matters, fundraising, fronting carriers and re-insurers, corporate governance, contracts, and risk!

Our client, a growing and leading Insure Tech are seeking their first Legal hire to come in as a Director of  this role, you will lead the companies legal strategy and operations. You will be a key partner to senior leadership, enabling the business to scale rapidly while maintaining strong risk-managed, rights-protected operations.###
*
* Key Responsibilities:

*** Provide legal counsel to the SLT on business initiatives, product launches, partnerships, regulatory/licensing matters, fundraising, fronting carriers and re-insurers, corporate governance, contracts, and risk.
* Lead and oversee internal and external legal partners in areas such as commercial contracts, licensing, regulatory filings, corporate governance, intellectual property, data privacy and security, employment law, litigation management, and external counsel coordination.
* Assist the growth agenda: entering new states, new product lines, new jurisdictions – legal readiness, and enablement.
* Partner with Info Sec Officer and the Director of Compliance to ensure legal support for Insurance-related programs and operations, cyber, privacy, and data-governance risks.
* Act as a trusted advisor, translating complex legal/regulatory issues into business-friendly advice and decisions – enabling the business to move fast without compromising quality.
* Monitor relevant regulatory and legal developments (insurance law, P&C regulations, insurtech legislation, data/privacy) and proactively advise the business on emerging risk and opportunities.
* Interact directly with carriers, reinsurers, MGAs, wholesalers, partners, agencies, and vendors to reach amicable ‘red line’ resolutions
* Oversight of external legal spend; negotiate engagement terms; ensure cost-effectiveness and quality outcomes.###
** Qualifications &

Experience:

*** J.D. from a prestigious law school, admitted to practice in relevant jurisdictions.+ 5-8 years of legal experience, ideally in the insurance or insurtech industry, and significant experience advising high-growth companies.
* Deep familiarity with U.S. insurance regulation (state licensing, MGA/agency models, P&C underwriting, distribution/agent relationships), plus exposure to tech/data/privacy/regulatory matters.
* Strong commercial mindset: you thrive on partnering with business stakeholders (product, underwriting, marketing, operations, sales, partnerships) to enable growth while protecting the company.
* Track record of building and scaling legal teams and operating systems at a growth-stage company.

If interested, get in touch for a confidential conversation today!
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