Risk Strategies acquires trucking insurance program manager Winter Group in CA

Risk Strategies has acquired Winter Group – a specialty insurance program manager focused on serving the trucking industry.

Terms of the transaction were not disclosed.

Winter Group, founded 1995, is an insurance wholesaler based in San Diego, CA. The firm offers national insurance solutions for essentially all aspects of the trucking and transportation industry – in particular, Winter Group strongly specializes in cross-border transportation risks. At present, it serves over 17,000 customers, helping brokers deal with NAFTA transportation risk management and compliance.

In addition to its San Diego office, Winter Group also has a presence in Texas, Florida, Washington, South Carolina, Atlanta, North Carolina, and Ohio. The firm also serves as a program administrator for a number of national trucking associations.

“Strong, continued economic growth is driving rapid expansion in the US transportation sector at a time when technological and road safety advances are creating new opportunities for differentiation and specialization,” said Risk Strategies senior managing director of wholesale Matthew Power. “More than ever, brokers serving this industry need more than access, they need a specialist like Winter Group on their side.”

“Risk Strategies is a highly collaborative and innovative firm,” added Winter Group managing director Phillip Winter. “Its focus on distinctly differentiated niche areas of our industry, and an acquisition strategy centered on specialty wholesale organizations, is a perfect foundation on which our team, customers and stakeholders can grow and thrive.”

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Lisa Kelly: From tomboy to celebrity trucker

DALLAS, Texas – In an episode of Ice Road Truckers, Lisa Kelly jumps off her moving 22-wheeler to save herself as the ice begins to splinter on a remote Alaskan highway.

That is the only way truckers can make a quick escape in such harsh conditions on roads where the maximum posted speed is 10 km/h with no stopping allowed.

Although that is reality TV, real trucking life in the wilderness of Alaska is not much different.

In fact, according to Kelly, 38, what she does on the show “is real life.”

That is exactly why she likes her job, a job she has been enjoying for the past 15 years.

“I love trucks,” she summed up her passion for trucking in three words in an interview at last month’s Great American Truck Show (GATS) in Dallas, Texas.

Lisa Kelly on the Delo flyer.

Kelly was there as the brand ambassador of Delo, a line of heavy-duty engine oils developed by the lubricants giant Chevron Products Co.

A longtime user of the product, she signed Delo flyers for fans at the show.

“When I open my toolbox door, it’s always Delo,” Kelly says in a Chevron commercial.

She has been working for Chevron for about three years, and she says she goes wherever the company needs her to go.

“Mostly GATS and MATS (the Mid-America Trucking Show in Louisville, Ky).”

Kelly was born in Grand Rapids, Mich., but raised on a small farm in Sterling, Alaska, about 220 kilometers southwest of Anchorage.

She was a bit of tomboy with a can-do attitude, and “really liked getting out of the building and driving around town.”

Kelly drove a delivery van and a school bus before realizing her dream of “driving a big truck someday,” according to a bio posted on her website.

The trucker’s job also catapulted her to stardom and fame.

On History Channel’s Ice Road Truckers, simply called IRT, she and five male drivers ferry freight on big rigs through Alaska’s frozen lakes and rivers. The show premiered in 2007, and the 11th season aired in late 2017.

She also starred in the IRT spinoff IRT Deadliest Roads. A few episodes of that show were filmed in some of the deadliest roads in India, Bolivia and Peru. In one, shot in the Indian Himalayas, Kelly hauls supplies through “pretty wild” roads.

“(It was) unlike anything I have ever experienced,” she said.

Image courtesy: Lisa Kelly

Kelly is the biggest and most popular star of the IRT. She was once called “the sexiest trucker alive” by the men’s magazine Esquire.

She has more 66,000 followers on Twitter, but fame doesn’t affect her work as a trucker.

Kelly works and lives in the truck for a couple of months before taking a break and going home to Wasilla, Alaska. One time, she said, she was able to go home only after three or four months.

“I have a very understanding husband,” she said, giggling.

“He gives me the freedom to go away for so many months, and it is amazing.”

An avid dirt biker, Kelly met her future husband Traves Kelly while buying a Kawasaki 125 motorcycle in 2004. They married four years later.

“He was motorcycle mechanic. He is a plumber now. It’s a weird life,” Kelly said.

She said her best experience as a truck driver was the “cool places” she was able to go.

Kelly is aware of the fact that not many women are working in the trucking industry, but she thinks it is changing.

“Feels like it’s been going up, a lot.”

She said many people watching the TV show or meeting her at trade shows often comment that she doesn’t look like a truck driver.

“Stereotypical ones. You don’t have to fit a stereotype. You can just do whatever you like.”

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