Nick DiMauro

ceo + co-founder @ daylii | Building the AI-Native Operating System for FSA & HSA Spend | Former Healthcare Operator (Exited) | On a Mission to Eliminate Healthcare Waste and Return Billions to Consumers

Boca Raton, Florida, United States

About

Building @daylii ----- 💡 I’ve spent the last 6 years building healthcare products that touched 10M+ lives, scaled past $100M in revenue, and partnered with 100+ payers nationwide. But the truth? The real lessons came from the nights we got it wrong. Like the time I gave out my personal cell phone to Medicare members….After a failed launch…listening call by call until we rebuilt trust. Those moments shaped my DNA: 👉 Listen harder than you talk. 👉 Adapt until trust is restored. 👉 Own the failures. 👉 Never get complacent. Now I’m carrying those lessons into the next chapter: Reimagining how healthcare works. Because here’s the problem: People are drowning in complexity. Systems feel intimidating and disconnected from real life. Trust is at an all-time low. The result? Billions wasted. Outcomes delayed. People left behind. That’s what I’m here to change. I believe healthcare should empower people, not frustrate them. So I’m building in the open......sharing wins, pivots, and lessons along the way. If you love healthcare as much as I do or simply someone who believes healthcare can (and should) be better 👉 Follow along @ godaylii.com. Because the future of healthcare won’t be built by the status quo. It’ll be built by those willing to break it. 🚀 godaylii.com

Experience

  • co-founder & ceo at daylii
    Sep 2025 - Present · 10 mos

    50M people. Outdated rules. Endless confusion. Fix loading…⏳

  • Chief Revenue Officer (United Medco aqcuired by Medline) at Medline Industries, LP
    2020 - Sep 2025 · 5 yrs 9 mos

    Joined Medline in January 2024 through acquisition. Prior to acquisition, launched and led direct to payer vertical, growing from $0 to over $100+ million in annual sales.

  • Vice President, Capital Markets at Sterling Organization
    2019 - 2020 · 1 yr

    Sterling Organization is a vertically integrated private equity real estate firm that has an established track record of providing exceptional risk-adjusted returns to its partners, in both relative and absolute terms. The company’s national platform is focused on investing in retail real estate assets across the risk spectrum in major markets within the United States on behalf of Sterling’s principals in partnership with the highest quality institutional investors. Mr. DiMauro serves as Vice President of Capital Markets for Sterling and its related companies. Mr. DiMauro is responsible for sourcing new and managing existing bank and alternative lending relationships. He works in conjunction with Sterling’s Asset Management and Investment teams with all financings on new and existing properties. Mr. DiMauro also assists in monitoring the firm’s liability management, which includes reviewing its interest rate risk exposure.

  • Director of Finance at BTI Partners
    2017 - 2019 · 2 yrs

    Responsible for all Finance related functions for BTI. Leads all debt and equity placement efforts for current and existing projects which includes sourcing new and existing bank and alternative lending relationships. Also responsible for all financial reporting and investor relations at BTI.

  • Finance and Performance Analytics at Florida Community Bank
    2014 - 2017 · 3 yrs