Topsail Re, a reinsurance company, has confirmed the promotion of Michael Swartz to Senior Vice President, Underwriting, and the appointment of Jason Callaway as Chief Information Officer and Executive Vice President, joining the firm’s Executive Team.
Michael Swartz, who has been with the organisation for more than two and a half years, steps into the Senior Vice President role following his contributions within the underwriting division.
Swartz has been recognised internally for his ability to handle complex assignments with a structured and disciplined approach, as well as for his detailed preparation and analytical perspective on transactions.
He is also known among brokers and clients for his professional conduct and measured approach, supporting the development of strong relationships and enhancing the company’s standing in the market.
Jason Callaway joins Topsail Re with more than two decades of experience across the global reinsurance and property and casualty sectors.
As Chief Information Officer and Executive Vice President, Callaway will lead the company’s technology strategy and contribute at the executive level.
He has previously held senior leadership roles at Swiss Re, XL Group (later AXA XL), and Vantage Risk, where he oversaw initiatives spanning cloud transformation, data strategy, and digital product development across underwriting, policy administration, billing and claims.
Callaway holds a degree in industrial engineering from the University of Wisconsin–Madison, along with a Certificate in Business Administration from the Grainger School of Business. He has built a track record of aligning technology initiatives with broader business objectives while developing collaborative, globally distributed teams. Outside of work, Callaway is active in community initiatives, including youth sports and volunteering with a nonprofit food bank.
Swartz said: “My time at Topsail Re has been an incredible experience. I work with extraordinary teammates and business partners every day and look forward to contributing to Topsail’s success in the years to come.”
Callaway added: “I’m honoured to join Topsail Re’s executive leadership team as Chief Information Officer. Topsail Re has built a strong reputation through the talent, collaboration, and dedication of its people, and I’m excited to partner with a talented IT team as we continue building and supporting a best‑in‑class technology platform together.”
