Profile
“Being true to who we are is key; we are purely a referral-based business. There is zero marketing or advertising”
Adam Rakowski,
Ortus Financial
Dave Roberts brings nearly 20 years of industry experience, having held several regional and national leadership roles prior to joining Westchester in 2014.
Before this most recent appointment, he served as executive vice president at Westchester, with executive operating responsibility in small business underwriting, middle market underwriting, programs underwriting, operations, and information technology.
Roberts holds CPCU and RPLU industry designations. He earned a Bachelor of Science degree in management, with a minor certification in Spanish, from Pennsylvania State University.
3 Country View Road, Malvern, PA
484 321 4180
david.roberts@westchester.com
https://www.linkedin.com/in/ewa-maj-b2888928
westchester.com/en
Dave Roberts
Chief Operating Officer
Westchester, A Chubb Company
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Milestones
“You can’t control the outcome, but you can always control what version of you turns up every day”
Adam Rakowski,
Ortus Financial
2007–2012
2014–2019
2021–2022
2023–2024
2025
2007: Started insurance career at USLI
2012: Promoted to Regional Underwriter Leader at USLI
2007–2012
2014: Joins Westchester
2015: Promoted to Vice President at Westchester
2019: Promoted to Senior Vice President at Westchester
2014–2019
2021: Promoted to Head of Westchester Small Business
2022: Westchester Big Audacious Goal Award
2021–2022
2023: Promoted to Executive Vice President of Westchester Digital & Middle Market, Westchester Business Unit of the Year
2024: Westchester Business Unit of the Year
2023–2024
Promoted to COO of Westchester
2025
Milestones
Milestones
ELITE WOMEN 2024 JUDGE
“You can’t control the outcome, but you can always control what version of you turns up every day,” he says.
While at the helm of a rapidly growing business and a family that includes two young children at home, Rakowski has learned to manage what he calls a “never-ending list of commitments” that consists of a new team member each month, a new interstate office and two to three new referral partners monthly.
“Our business is a human business, so investing genuine time in every person can be draining on a personal level. Balancing it all is a challenge,” he says. “Simply put, do what you say you will do, and act at all times with honesty and integrity, being respectful and empathetic. The financial outcomes are a byproduct of the human interactions we have.”
Attracting, retaining and delivering exceptional client outcomes and service starts with a sincere interest in their journey and remaining relevant to them as their lives and needs evolve, notes Rakowski. He points out that he and his team put in most of the work upfront in building meaningful relationships, which is a testament to its 99% client retention rate.
He says, “We are clear in the types of clients we work best with and our value proposition. We also look for a cultural alignment with all of our referral partners, and we are acutely aware of our strengths and how different we are from our industry peers.”
Rakowski recently opened a Queensland business and plans a foot in every other capital city. He strives to establish the brokerage as a national business with on-the-ground representation in every state by the end of 2025.