Skyward Specialty boosts regional Contract Surety teams with key hires

Property and casualty (P&C) insurer Skyward Specialty has bolstered its regional Contract Surety teams with a number of key appointments.

Firstly, in its Northeast region, the P&C insurer has appointed Gregg Callahan as regional vice president in New England, who has spent the last 27 years working at Liberty Mutual Insurance, specialising in Contract Surety.

His extensive expertise across the industry will help expand Skyward Specialty’s presence in the Northeast.

Next up, Larry Mastalski joins the firm from Markel, taking on the role of regional vice president in the Texas and Midwest territories. Boasting more than 33 years of specialised surety expertise, Mastalski is well-equipped to take on the role. In his most recent position at Markel he served as Vice President Branch Manager. He also previously held senior positions at Chubb.

Also joining Skyward Specialty is Sam Allison, who has been appointed to the role of assistant regional vice president in Texas. Overall, Allison has 21 years of experience in the Texas surety market, having most recently served as Regional Bond Manager for Main Street America Group (MSA).

Meanwhile, in the Pacific Northwest region, Skyward Specialty has hired Sean Fallows as regional assistant vice president to develop the firm’s western contract surety portfolio.

Fallows brings more than 18 years of specialised surety expertise towards the role. Most recently, he served as the PNW Branch Manager for Intact Insurance Specialty Solutions.

Skyward Specialty has also added two new underwriters to strengthen its underwriting bench in select regions, with Joe Waynauskas, a 22-year surety veteran, joining as senior underwriter in the north-central region, and Joe Michalewsky, ASFB, joining the Northeast region as an underwriter.

Michalewsky joins the firm following two years of Surety experience at Sompo International.

Matt Semeraro, president of Surety, commented on the appointments: “We are thrilled to welcome these six highly skilled individuals to our accomplished team of underwriting professionals. With their addition, we are well positioned to capitalize on market opportunities as we reinforce our regional growth strategy with their outstanding contract surety expertise.

“We’ve built a best-in-class surety and our ability to continue to recruit top talent is essential to our success in providing exceptional service, resources and solutions to our agency partners.”

In related news, Skyward Specialty recently entered the mortgage re/insurance market and announced that Jean-Philippe “JP” Latour will lead the new unit.

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