Vice President, Legal - Reinsurance & Strategic Transactions

Everlake•Northbrook, IL

2d•Hybrid

About The Position

Everlake, a leading life insurance company headquartered in Northbrook IL with offices in Chicago IL and Lincoln NE, is conducting a search for an attorney to join our growing team. If you have a passion for the insurance business, value working in a dynamic team environment and are ready to roll up your sleeves to help us achieve best in class results, then this may be the role for you. At Everlake, you will find the dynamics of a small entrepreneurial organization and the strength of a big corporation rolled into one. We think big and evolve quickly, backed by a collaborative mindset and a solid financial foundation. The Vice President, Legal will serve as a senior legal advisor for Everlake’s reinsurance and strategic transactions and provide support for other areas, as needed. The role will provide practical, business-oriented legal guidance on complex insurance growth and risk management initiatives, including those involving flow and block reinsurance, pension risk transfer reinsurance, captive financing, funding agreement-backed products, investment-related matters, collateral trust arrangements, and related commercial contracts. This attorney will be expected to lead significant legal workstreams with limited oversight from the Chief Legal Officer, partnering closely with senior management and cross-functional leaders to evaluate, structure, negotiate, and execute complex transactions while appropriately managing legal, regulatory, operational, and conflict risks. This role requires a highly skilled, commercially minded attorney with substantial experience in life insurance, annuities, reinsurance, and financial services transactions, together with strong judgment, transaction execution discipline, and the ability to advise on emerging business initiatives. The successful candidate must be able to build strong working relationships, communicate effectively with senior leaders, and operate effectively in a fast-paced transactional environment. The attorney must be comfortable advising on sensitive strategic matters, escalating material issues appropriately, and driving alignment among legal, actuarial, investment, risk, finance, tax, operations, compliance, and business development stakeholders. The successful candidate will be capable of leading external counsel, negotiating directly with sophisticated counterparties, and helping Everlake advance strategic growth while protecting the company’s interests. The role reports directly to the Chief Legal Officer and will operate as a senior member of the Legal department, with responsibility for leading major transaction workstreams, coordinating internal and external legal resources, and advising executive leadership on legal risks and opportunities.

Requirements

Juris Doctor degree from an accredited law school and active membership in good standing with at least one U.S. state bar.
10+ years of relevant legal experience.
Familiarity with the Model Holding Company Act.
Strong transactional background, including drafting, negotiating, and executing complex reinsurance, financing, investment, and commercial agreements.
Deep understanding of flow and block reinsurance, pension risk transfer transactions, and related regulatory and operational considerations.
Demonstrated ability to lead multiple high-priority transaction workstreams in a fast-paced environment with limited oversight and strong accountability for outcomes.
Excellent executive presence, judgment, communication, and influencing skills, with the ability to advise senior leaders and build alignment across legal, business development, finance, risk, actuarial, investment, compliance, and operations teams.
Proven ability to manage outside counsel and other advisors effectively, balancing quality, speed, cost, and commercial practicality.
Strong research, analytical, drafting, negotiation, and problem-solving skills, with a commitment to accuracy, clarity, and high-quality work product.
High ethical standards, sound professional judgment, and demonstrated ability to maintain confidentiality on sensitive strategic and transaction matters.

Responsibilities

Serve as senior legal lead and an integral member of the core deal teams supporting reinsurance and other insurance growth transactions, including flow and block reinsurance, captive financings, and other arrangements.
Support all phases of reinsurance and insurance growth transactions, from preliminary bids and indications of interest through closing.
Advise on transaction structure and manage required regulatory filings and approvals.
Lead the drafting, review, and negotiation of reinsurance, confidentiality, trust, investment, and other transaction-related agreements.
Partner with business development, actuarial, investments, risk, finance, tax, operations, compliance, and senior leadership to structure and execute transactions aligned with Everlake’s strategic objectives.
Manage outside counsel and other advisors to ensure high-quality and efficient support on complex transactions and other matters.
Monitor legal, regulatory, and industry developments affecting Everlake’s business.
Prepare legal memoranda, executive summaries, risk assessments, board or committee materials, and transaction status updates for senior stakeholders.
Develop and enhance templates, playbooks, procedures, controls, and documentation standards for transaction intake, review, approval, execution, and ongoing contractual compliance.
Support insurance-related litigation, disputes, regulatory inquiries, and counterparty matters as needed, working closely with internal stakeholders and external counsel.