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
For Jason Bertoldi, Global Team Leader, Litigation & Contingent Risk Insurance at Alliant Insurance Services, litigation isn’t just a liability – it’s an asset. His expertise in law, insurance, and business has made Bertoldi an indispensable member of Alliant’s team, where he designs bespoke policies that unlock value from legal claims.
“Each of my placements involves multiple stakeholders – law firms, litigants, investors, insurance underwriters, external advisors, outside counsel, and others. My job is to make sure that all of us are rowing in the same boat,” Bertoldi notes.
“Juggling those roles is a challenge, and I address it by being rigorous with time management and always keeping my eyes on the end goal: What is everyone solving for?”
Bertoldi’s adaptability has been demonstrated through his work across a number of roles, including as a federal judicial law clerk, a litigator, and a front office finance analyst. By taking the skills and knowledge from each experience to his current position, Bertoldi has been able to leverage his time in different sectors to bring novel ideas to his current role.
“I’ve transitioned through those roles as the relationship between finance, law, and insurance has evolved. And at each transition, I felt confident making a career change because I’d learned from the best and was encouraged by my mentors and teammates to pursue new opportunities.”
He adds, “Not all of my career choices were on my bingo card when I graduated from law school, but I’m deeply grateful for how my career has ended up.”
Finding creative solutions for clients is the hallmark of a litigation and contingent risk broker, and Bertoldi prides himself on his ability to find unique placements that move the needle for clients.
“The challenge – and the fun – of my job is that I’m rarely in a position to offer an off-the-shelf solution. My clients know this, and when they work with me, I consider it a testament to my ability to think creatively and solve complex problems. I never take that responsibility lightly,” he says.
Clients and teammates are the everlasting priorities for Jason Bertoldi. By focusing on these two groups with a creative and results-driven mindset, he has been able to deliver exceptional results for Alliant’s clients.
“I’m part of a market-leading group at Alliant that sets an extraordinarily high bar for being an insurance broker,” he notes. “Seeing their hard work and the success that comes with it is a motivation and an inspiration for me.”
Ultimately, Bertoldi’s actions in his current role are guided by a mission of solving problems for clients while maintaining the highest standards of integrity possible.
“I follow two key tenets in my role at Alliant, and they’re the same tenets that have guided me throughout my career,” he explains.
“The first is to lead with integrity. Ethics – being honest and forthright with my counterparties and clients – are my lodestar. The second is to never identify a problem without also identifying at least one solution. Spotting issues is important; solving them is why clients hire me.”
101 Park Avenue, New York, NY 10178
jason.bertoldi@alliant.com
jason.bertoldi@alliant.com
linkedin.com/in/jason-bertoldi
alliant.com
Jason Bertoldi
Global Team Leader, Litigation and Contingent Risk Insurance
Alliant Insurance Services
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“You can’t control the outcome, but you can always control what version of you turns up every day”
Adam Rakowski,
Ortus Financial
2015–2017
2017–2019
2019–2022
2022–2024
2024–Present
2015–2016: Law Clerk for the Honorable Karen Nelson Moore, United States Court of Appeals for the Sixth Circuit
2016–2017: Law Clerk for the Honorable Katherine Polk Failla, United States District for the Southern District of New York
2015–2017
Associate at Susman Godfrey LLP
2017–2019
Analyst at the D. E. Shaw Group
2019–2022
Head of Contingent Risk Solutions at WTW
2022–2024
2024–2025: Band 1 Litigation Insurance Broker, Chambers and Partners
2024–Present: Global Team Leader, Litigation and Contingent Risk Insurance at Alliant Insurance Services
2024–Present
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.