VP, Transaction Counsel

Wilton Re; Norwalk (CT); On-site; USD 250,000 - 300,000; Full time

Job summary

Wilton Re seeks a seasoned VP, Transaction Counsel to join the Business Development team in Norwalk, CT. This role provides strategic legal leadership across complex in‑force and reinsurance transactions, reporting to the Co‑Head of Business Development.

The candidate will act as a hands‑on executor in drafting, risk analysis, and deal execution. The ideal candidate brings deep experience in life insurance/financial services transactions, strong drafting skills, and the ability to lead risk

Qualifications

• Minimum 6 years of legal experience in insurance or financial services.
• Strong drafting, negotiation and communication skills.
• Experience leading transaction diligence and coordinating external counsel.

Responsibilities

• Own all legal aspects of acquisitions and reinsurance transactions.
• Lead diligence, document drafting and risk assessment.
• Support contract negotiations and regulatory filings as needed.
• Coordinate with cross-functional teams and external counsel.

Skills

M&A experience

Insurance transactions

Drafting

Regulatory knowledge

Diligence management

Contract negotiations

Cross-functional collaboration

Risk analysis

Education

J.D.

Job description

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 holistically 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 derived 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