About Us

Meet the XN Captive team

Leadership
Gabriel Weiss
CEO & Co-Founder
  • Previously Entrepreneur-In-Residence at Point72
  • 7+ years insurance experience, Russell Reynolds Alum
  • Co-Founder of successfully acquired claims-focused AI Insurtech
  • Captain & Airborne Ranger, US Army, 101st Airborne Division
LinkedIn
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  • Previously Entrepreneur-In-Residence at Point72
  • 7+ years insurance experience, Russell Reynolds Alum
  • Co-Founder of successfully acquired claims-focused AI Insurtech
  • Captain & Airborne Ranger, US Army, 101st Airborne Division
Sam Espinosa
CMO & Co-Founder
  • Previously VP of Marketing at Pindrop
  • 16+ years experience, B2B

Sales & Marketing

  • Head of Marketing for successfully acquired YC

Tech startup

  • Yale University
LinkedIn
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  • Previously VP of Marketing at Pindrop
  • 16+ years experience, B2B

Sales & Marketing

  • Head of Marketing for successfully acquired YC

Tech startup

  • Yale University
Rachel Jenkins
COO & Co-Founder
  • Previously Managing Director

at Founder Shield

  • 12+ years insurance experience, Marsh and AIG Alum
  • 2023 RISE Awards Winner,

35 under 35

  • Wharton School of Business
LinkedIn
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  • Previously Managing Director

at Founder Shield

  • 12+ years insurance experience, Marsh and AIG Alum
  • 2023 RISE Awards Winner,

35 under 35

  • Wharton School of Business
Jonathan York
CTO
  • Previously Head of Digital Transformation & Client Technology at Bridgewater Associates
  • 25 years leadership experience in financial services technology
  • Business Insider’s Top 8 POWER PLAYERS in Tech Innovation
  • Oxford University Alum
LinkedIn
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  • Previously Managing Director

at Founder Shield

  • 12+ years insurance experience, Marsh and AIG Alum
  • 2023 RISE Awards Winner,

35 under 35

  • Wharton School of Business
Judah Max Dobrinsky
Director of Risk Finance
  • Previously Director of Operations at Graph Group, managing $200M+ in admitted and captive assets
  • Founder & President of Magnet Insurance Agency, with $1.5B in insurable value
  • Deutsche Bank Alum, advising  $1.35B+ in transactions
LinkedIn
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  • Previously Director of Operations at Graph Group, managing $200M+ in admitted and captive assets
  • Founder & President of Magnet Insurance Agency, with $1.5B in insurable value
  • Deutsche Bank Alum, advising  $1.35B+ in transactions
Allison Ammirato
Senior Accountant
  • Previously Senior Accountant
    at Brown & Brown
  • 7+ years insurance experience in Captive Accounting
  • Captive Insurance Times Emerging Talent April 2020 Issue
  • Bachelor of Science in Mathematics, Union College
LinkedIn
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  • Previously Senior Accountant
    at Brown & Brown
  • 7+ years insurance experience in Captive Accounting
  • Captive Insurance Times Emerging Talent April 2020 Issue
  • Bachelor of Science in Mathematics, Union College
Chris Boedeker
Head of Claims
  • Previously Head of Claims for Waymo and Uber
  • Senior Leader at Marsh managing Airbnb and Tesla
  • 30 years of multi-line claims experience
  • Expertise in complex regulatory, tax, and reinsurance transactions
LinkedIn
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  • Previously Head of Claims for Waymo and Uber
  • Senior Leader at Marsh managing Airbnb and Tesla
  • 30 years of multi-line claims experience
  • Expertise in complex regulatory, tax, and reinsurance transactions
XN Captive, a privately held company and headquartered in New York City, is venture-backed by investors, led by Caffeinated Capital.
Expertise
XN Captive is supported by a team of world-class experts across multiple disciplines, including:
Advisory
Regulatory
Legal
Claims
Actuary
Audit
Investment
Reinsurance
XN is our abbreviation for the Latin phrase Ex Nihilo, meaning   “Out of Nothing.”
We create opportunity for capital growth where none existed before.
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