Bio
Benjamin Woolf is a partner in the Corporate department and leads the Structured Finance practice.
Benjamin has significant experience within the structured finance sector representing issuers and investors alike on countless structured finance transactions, including primarily, CLOs, CRE CLOs, PACE securitisations and other structured lending transactions. He frequently works on securitisation, representing issuers and underwriters in both public and private offerings of securities backed by a variety of asset classes, including residential products and trade receivables.
Benjamin is a member of Appleby’s Scholarship & Student Committee mentoring students and assisting with their formal and informal training. Benjamin also volunteers at the Legal Befrienders Clinic providing pro bono advice in the Cayman Islands for the last eight years.
Before joining Appleby in 2011, Benjamin practised in London with Clifford Chance LLP and, subsequently, as a senior associate at Mayer Brown LLP where he worked primarily on securitisation.
Other experience includes restructuring and acquisition finance as well as public equity offerings and private placements in the oil and gas sphere.
Bio
Benjamin Woolf is a partner in the Corporate department and leads the Structured Finance practice.
Benjamin has significant experience within the structured finance sector representing issuers and investors alike on countless structured finance transactions, including primarily, CLOs, CRE CLOs, PACE securitisations and other structured lending transactions. He frequently works on securitisation, representing issuers and underwriters in both public and private offerings of securities backed by a variety of asset classes, including residential products and trade receivables.
Benjamin is a member of Appleby’s Scholarship & Student Committee mentoring students and assisting with their formal and informal training. Benjamin also volunteers at the Legal Befrienders Clinic providing pro bono advice in the Cayman Islands for the last eight years.
Before joining Appleby in 2011, Benjamin practised in London with Clifford Chance LLP and, subsequently, as a senior associate at Mayer Brown LLP where he worked primarily on securitisation.
Other experience includes restructuring and acquisition finance as well as public equity offerings and private placements in the oil and gas sphere.
Recognition
He is consistently ranked in Chambers Global as Band 1: Corporate & Finance. In 2025, he was praised as “the best Cayman lawyer in the CLO business. He is extremely commercial and provides great service to his clients.” Sources also noted, “I find Ben Woolf and his team to be very resourceful. They are an excellent partner on CLO dissolutions and do a great job guiding clients through the Cayman process.”
IFLR1000 rates Benjamin as ‘highly regarded’ in the capital markets: debt, capital markets: structured finance and securitisation, and M&A practice areas.
Legal 500 2022 recognised Benjamin as a ‘leading individual’ noting him as “highly responsive, pragmatic and commercial, yet extremely technical and capable of managing complex issues”. Legal 500 previously noted Benjamin as a “a smart lawyer who works tirelessly for his clients´ interests”. In the 2024 edition of Legal 500 Benjamin was ranked as a “Leading Partner”.
In 2018, he was identified among the world´s leading capital markets lawyers by Who´s Who Legal.
He is consistently ranked in Chambers Global as Band 1: Corporate & Finance. In 2025, he was praised as “the best Cayman lawyer in the CLO business. He is extremely commercial and provides great service to his clients.” Sources also noted, “I find Ben Woolf and his team to be very resourceful. They are an excellent partner on CLO dissolutions and do a great job guiding clients through the Cayman process.”
IFLR1000 rates Benjamin as ‘highly regarded’ in the capital markets: debt, capital markets: structured finance and securitisation, and M&A practice areas.
Legal 500 2022 recognised Benjamin as a ‘leading individual’ noting him as “highly responsive, pragmatic and commercial, yet extremely technical and capable of managing complex issues”. Legal 500 previously noted Benjamin as a “a smart lawyer who works tirelessly for his clients´ interests”. In the 2024 edition of Legal 500 Benjamin was ranked as a “Leading Partner”.
In 2018, he was identified among the world´s leading capital markets lawyers by Who´s Who Legal.
Qualifications & Education
Benjamin graduated from McGill University with an LL.B and B.C.L.
He was admitted as a Solicitor and called as a Barrister to the Alberta Bar in 2004 (non-practising), as a Solicitor in England and Wales in 2009 (non-practising) and as an Attorney-At-Law in the Cayman Islands in 2011.
Benjamin graduated from McGill University with an LL.B and B.C.L.
He was admitted as a Solicitor and called as a Barrister to the Alberta Bar in 2004 (non-practising), as a Solicitor in England and Wales in 2009 (non-practising) and as an Attorney-At-Law in the Cayman Islands in 2011.
“easily the best in the industry”
“Ben is the best Cayman lawyer in the CLO business. He is extremely commercial and provides great service to his clients.”