FORTY Under 40: Josh Kalmikoff
Josh Kalmikoff, member relationship director, Accelerant.
Kalmikoff has been in specialty insurance for 15 years. He brings a unique perspective, having worked extensively in both alternative markets and programme insurance.
He worked previously at Arch Insurance, where he utilised contractual liability policies (CLIPs) to reinsure warranties and service contracts into producer-owned reinsurance companies (PORCs). Then he moved to be director of specialty underwriting programmes at IMA Financial Group, developing affinity and A-fund / B-fund group captive P&C programmes.
Kalmikoff is now a founding leader in the captive practice and a member relationship director at Accelerant, a data-driven global insurance risk exchange that connects specialty underwriters with risk capital and provides paper, capacity and infrastructure to support captive and guaranteed cost insurance programmes. He is a self-professed captive wizard, lover of people, soccer and Taco Bell.
Looking back at your journey over the past year, what accomplishment are you most proud of, and how has becoming a FORTY Under 40 finalist influenced your perspective on that achievement?
Captives have been a priority at Accelerant. Successfully creating both group captive and single-parent captive transactions, each designed with delegated authority in mind, reflects our commitment to pushing decision-making to the experts. Being named a finalist for FORTY Under 40 is meaningful validation and recognition of these accomplishments.
What key challenge did you face in your work this year? How did you overcome it and what did it teach you about leadership at this stage of your career?
As a bootstrapped start-up division within Accelerant, our captive practice faced resource constraints and operational complexity while building something ambitious from the ground up. Rather than becoming monolithic, we leaned into being nimble, which allowed us to be creative, fast, thoughtful and technically sharp in how we structured transactions and deployed capacity.
I believe strongly that delegated authority and outsourcing expertise are the future of the captive space, and we are building the infrastructure to usher in that reality.
In what ways have you tried to push innovation or rethink traditional approaches within your sector, and what impact has that had on your team or organisation?
I’m privileged to have significant experience in both the MGA programme and captive sectors. This has given me a broader perspective and insight into where the captive sector can go. I believe strongly that delegated authority and outsourcing expertise are the future of the captive space, and we are building the infrastructure to usher in that reality.
How do you see your role evolving over the next three to five years, and what initiatives are you most excited to pursue as you continue to grow professionally?
Over the next few years, I see my leadership role within the captive practice and across Accelerant continuing to expand as we broaden our capabilities. I’m particularly excited to launch and scale our workers’ compensation capability and to further infuse agentic AI into our operating model.
By leveraging AI thoughtfully, we can build cutting-edge, data-driven experiences for captives, enhancing underwriting precision, operational efficiency and decision-making while preserving the human expertise that defines our platform.
Many of the FORTY Under 40 winners are recognised for both business success and broader impact – how do you balance professional excellence with contributions to your community or industry landscape?
Finding balance requires a lot of energy, especially while being married with three kiddos and managing my career. Time is my most precious commodity, and I count myself fortunate to be mindful that my time “under 40” is limited, especially with my young kids. I take every opportunity to coach my kids’ sports teams, attend their school concerts, go on field trips, etc. and enjoy life before it’s too late. I’m also a deeply spiritual person and am passionate about soul care. I volunteer, when time allows, in the care ministry at our church, working with men who struggle with various forms of addiction and with couples, alongside my wife, who are navigating relationship challenges.
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