Co-Founder, New Reign Capital
Director of Operations & Integration, LINK Fund I
Creator, Escaping the Claims Desk & Power Circles
Founder, WorkComp Blitz
Josh Diggs is the Chief Operating Officer of LINK Fund I and a Founding Partner at New Reign Capital. He brings over a decade of hands‑on experience in workers’ compensation claims management, private equity operations, and business integration. As Director of Claims at Modern Reign Insurance Brokers, Josh has honed his expertise in underwriting, risk analysis, and client advocacy, skills he now leverages to optimize and scale each addition to the LINK Fund I portfolio.
Integration Architect & Operational Leader
Josh designed and leads our overlapping integration framework, ensuring that each acquisition, from TPA roll‑ups to fintech ventures, aligns seamlessly with LINK Fund I’s three pillars: Connect, Distribute, and Facilitate. He oversees end‑to‑end deal execution and post‑close operations, implementing KPI dashboards, performance benchmarks, and continuous‑improvement initiatives that drive synergies and unlock value across the fund’s ecosystem.
Fundraising & Investor Relations Partner
In collaboration with Zach Brown, Josh plays a pivotal role in LP engagement, crafting data‑driven updates, guiding due diligence discussions, and translating complex operational metrics into clear, investor‑ready narratives. His deep industry network (“power circles”) and reputation as a “Work Comp Ninja” have been instrumental in sourcing high‑quality deal flow and forging strategic partnerships.
Education & Background
Josh earned his Bachelor’s degree in Business Administration from California State University, Fullerton, where he cultivated his passion for leadership and community engagement. Based in Orange County, CA, he balances his professional drive with mentorship, regularly speaking at industry panels and career‑day events to empower the next generation of insurance and finance talent.
Whether architecting seamless acquisitions or guiding investor conversations, Josh’s blend of operational rigor, strategic vision, and hands‑on industry know‑how ensures LINK Fund I delivers premium returns and lasting impact in the traditionally fragmented workers’ compensation space.
Director of Operations & Integration, LINK Fund I
Creator, Escaping the Claims Desk & Power Circles
Founder, WorkComp Blitz
Josh Diggs is the Chief Operating Officer of LINK Fund I and a Founding Partner at New Reign Capital. He brings over a decade of hands‑on experience in workers’ compensation claims management, private equity operations, and business integration. As Director of Claims at Modern Reign Insurance Brokers, Josh has honed his expertise in underwriting, risk analysis, and client advocacy, skills he now leverages to optimize and scale each addition to the LINK Fund I portfolio.
Integration Architect & Operational Leader
Josh designed and leads our overlapping integration framework, ensuring that each acquisition, from TPA roll‑ups to fintech ventures, aligns seamlessly with LINK Fund I’s three pillars: Connect, Distribute, and Facilitate. He oversees end‑to‑end deal execution and post‑close operations, implementing KPI dashboards, performance benchmarks, and continuous‑improvement initiatives that drive synergies and unlock value across the fund’s ecosystem.
Fundraising & Investor Relations Partner
In collaboration with Zach Brown, Josh plays a pivotal role in LP engagement, crafting data‑driven updates, guiding due diligence discussions, and translating complex operational metrics into clear, investor‑ready narratives. His deep industry network (“power circles”) and reputation as a “Work Comp Ninja” have been instrumental in sourcing high‑quality deal flow and forging strategic partnerships.
Education & Background
Josh earned his Bachelor’s degree in Business Administration from California State University, Fullerton, where he cultivated his passion for leadership and community engagement. Based in Orange County, CA, he balances his professional drive with mentorship, regularly speaking at industry panels and career‑day events to empower the next generation of insurance and finance talent.
Whether architecting seamless acquisitions or guiding investor conversations, Josh’s blend of operational rigor, strategic vision, and hands‑on industry know‑how ensures LINK Fund I delivers premium returns and lasting impact in the traditionally fragmented workers’ compensation space.
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