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Roosevelt Road Re hires Darren Bailey for ILS & Capital Markets role


Roosevelt Road Re, an expansive Bermuda based reinsurance company launched with a partnership with US MGA Tradesman, has announced the hiring of Darren Bailey, an executive with ILS and capital markets experience.

roosevelt-road-reRoosevelt Road Re has a significant focus on loss portfolio transfers and quota share reinsurance arrangements, working with clients as diverse as captives and risk retention groups.

But it’s clear the company has ambitions to partner with third-party capital investors as it grows, seeing an opportunity to leverage investor appetite for reinsurance-linked returns to help grow its business and diversify its capital base.

Darren Bailey most recently worked at legacy and run-off specialist R&Q as its Head of Business Development for M&A Legacy transactions. He joined R&Q in 2018 and departed around mid-2021.

Prior to that, Bailey had worked at specialist investment banking and insurance-linked securities (ILS) unit Aon Securities as Head of Capital Markets for Europe, before which he worked in the Aon Insurance Management team, leading ILS business development for the EMEA region.

So he has a diverse work-experience, with his recent roles all having a capital market and insurance-linked securities focus.

Roosevelt Road Re has hired Bailey as its Director of ILS and Capital Markets role with immediate effect and Bailey will be based in London for the company.

Commenting on his hire, Bailey said, “Roosevelt Road complements my hunger for continued success. Their leadership team has a dynamic strategy to business growth, employs an energetic approach to closing deals and demonstrates passion at all levels of the business that deliver year on year outstanding results.”

Dan Hickey, CEO of the company commented, “Appointing Darren to our growing and experienced team underlines our commitment to Roosevelt Road’s growth in 2022 and beyond. Darren was well known to our team, having worked closely with us during the Sandell Re transaction and subsequent restructuring with R&Q.

“Having a dedicated capital markets resource will no doubt enhance our visibility in the market via Darren’s vast network and global presence, and we look forward to strengthening our relationships in the ILS market. Recalling our main goal for Roosevelt Road, we strive to create a high-quality specialist reinsurance presence in Bermuda.”

Ken Randall, non-executive director of Roosevelt Road and well-known as the former head of R&Q, also said, “We continue to see high-calibre individuals such as Darren being attracted to Roosevelt Road and clearly highlights the continuation of the controlled expansion since inception in 2020. With Duncan King and Joe Bonanno joining the underwriting team in 2021, Dan Hickey is clearly demonstrating the foundations of building another successful entity in addition to the flourishing MGA business in Tradesman Program Managers.”

Roosevelt Road Re has a strategic partnership and is owned by Roosevelt Road Capital, a majority shareholder of the established US Managing General Agent (MGA) Tradesman Program Managers, LLC.

That relationship enables Roosevelt Road Re enhanced access to risk, so it will be interesting to see how the company can deliver on its clear ILS and capital market ambitions, in bringing third-party capital into its transactions.

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