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Posted August 20, 2026

VP, Transaction Counsel

Wilton Re
Stamford, CT Full Time
Compensation: $230,000 to $260,000 Annually
Reference: wiltonre34

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VP, Transaction Counsel


We are searching for an experienced VP, Transaction Counsel at our Connecticut office.

VP, Transaction Counsel
Norwalk, CT

About the Company:
Wilton Re is an industry leader in the life (re)insurance space, specializing in the acquisition of in-force life insurance and annuity (as well as long term care) blocks and run-off entities. We are experienced industry specialists focused on the risk, capital and operational needs of our clients’ businesses. We provide our clients with the services they need from in-force transactions and product development to underwriting and new business strategies.

Wilton Re has the resources and expertise to pursue and successfully manage materially complex life and annuity transactions in the market.

Position Summary
Wilton Re is seeking a seasoned transaction attorney to join its Business Development team as VP, Transaction Counsel reporting to the Co-Head of Business Development. This role will serve as an integrated member of our M&A team and a key legal advisor to the deal team and senior management, providing support for complex reinsurance transactions, acquisitions and strategic partnerships. This person will be both a strategic thinker and a hands-on executor—able to advise at a high level while also rolling up their sleeves and engaging directly in detailed analysis and document drafting.
The ideal candidate will bring deep experience in insurance or financial services transactions with strong technical drafting skills and interest in wholistically managing legal matters from transaction inception through in-force management. The ideal candidate thrives in a fast-paced, collaborative environment and has experience driving legal analysis and risk evaluation as well as experience materially independently drafting transaction documents.

Key Responsibilities

Own materially all legal aspects of transactions (acquisition and reinsurance)
Primary responsibility and ownership for legal diligence, legal risk identification and evaluation and drafting of all applicable transaction documents (e.g., NDAs, coinsurance agreements, master transaction agreements and ancillary agreements such as administrative services and transition services agreements)
Support (and in certain instances lead) contract negotiations
Point for transaction legal diligence, including diligence materials review, tracker question development, management meeting agenda and question preparation and derivate risk and contract considerations arising from diligence
Develop and manage internal and external legal and regulatory risks and issues lists
Collaborate cross functionally with subject matter experts and risk managers to identify and analyze legal and regulatory risks
Work with deal manager and broader deal team to present risks/issues to risk committee
Collaborate with the finance/investment in-house attorney as to trust and IMA matters in connection with transaction executions
Collaborate with operations, actuarial, and risk teams to support deal execution
Oversee and coordinate external counsel to ensure efficient and cost-effective delivery
Assist with regulatory filings and interactions with insurance departments and other regulatory bodies in connection with transactions
Develop and maintain templates, playbooks, and best practices for transaction execution

Basic Qualifications
Minimum 6 years of relevant legal experience, preferably at a top law firm and/or in-house at an insurance or financial services company
Strong experience with insurance/reinsurance transactions and/or M&A
Familiarity with life insurance products and regulatory frameworks
Proven ability to manage complex transactions independently
Excellent drafting, negotiation, and communication skills
Strong business acumen and ability to provide practical, risk-based advice
Ability to manage multiple priorities in a dynamic environment

Required Education / Certifications:
J.D. from an accredited law school and active bar membership in good standing

Pay/Location
Norwalk, CT
Hybrid Structure
Travel Required

Base salary/hourly rate range for this position in Connecticut is between $230,000 and $260,000 Please note that specific compensation decisions are based upon a variety of job-related factors as permitted by law, including geographic location, credentials, skills, education, training, and experience.
Base salary is just one component of Wilton Re’s total compensation package for employees. Additional compensation includes annual performance-based bonus, 401K with employer contribution, and profit-sharing program. Employee may also be eligible for long-term incentives (equity). All incentives and benefits are subject to the applicable plan terms.


What We Offer:
Competitive vacation and sick time, including company-paid holidays, floating holidays and early closing days
401(k) plan with employer contribution - US Employees Only
Profit Sharing Program
Competitive parental leave
Health, vision, dental, and life insurance, including access to health and wellness programs
Actuarial Development Program (ADP) for Actuarial employees taking exams
Employee Assistance Program (EAP)
Current hybrid working environment
Employee Engagement Events and various committees on site to join

Wilton Re strives to attract, develop, and retain a diverse workforce. We are committed to providing an inclusive and accessible work environment where all associates feel valued, respected, and supported. Our commitment to inclusivity is reflected in the safeguards, policies, and commitments we have in place to remove barriers and provide equal opportunities to prospective and current associates, without discrimination. A Human Resources representative is available to consult with applicants who require accommodation in the application or recruitment process. Any information shared by the applicant about an accommodation will be treated as confidential.
To All Recruitment Agencies: Please do not send any resumes or solicitations regarding open positions to Wilton Re employees unless you have been requested to work on this position or other positions with Wilton Re; please reach out to your main point of contact. Wilton Re is not responsible for any fees related to unsolicited resume


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