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Viewpoint: Insurers Are Automating the Front Office While Ignoring the Function That Determines Trust
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The $400,000 Chief of Staff Is the CEO’s Secret Weapon in the AI Age

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Viewpoint: The One Thing Holding Back Insurers’ AI Efforts
Finding Safer Ground: How Parcel-Level Data Is Redefining Wildfire Risk in California
When Builder’s Risk Coverage Doesn’t Reach the Finish Line
The Impact of Claims Experiences on Trust

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Content from John Swigart

John Swigart is the Co-Founder and Chief Executive Officer of Pie Insurance, a digitally native full-stack MGA serving small businesses. Swigart is responsible for overseeing all aspects of Pie since its establishment in 2017, and he brings with him more than 20 years of experience in tech-enabled insurance and financial services businesses. He started his career in the Financial Institutions Group at A.T. Kearney, a management consulting firm, and worked at Swiss Re in the U.S. Reinsurance business and global Capital Partners divisions. Prior to founding Pie, Swigart served on the Esurance executive team for 13 years, where he initially led all the financial functions and then became the company's first chief marketing officer. From there, he went on to serve as the chief marketing officer for RapidAdvance, a non-bank small business lender and part of the Quicken Loans family. Swigart is also a member of the Sixup PBC's board of directors and holds a B.A. in Economics from Haverford College.

Open for Business: Analytics Bring Workers Comp Cover to SMBs, Says Pie Insurance CEO

A small business owner sits down after a long day to buy workers compensation coverage online. It's 11:00 p.m. on a Tuesday, or maybe it's a Sunday evening. Either way, it isn't within normal ...

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  • The Latest Launches from Soteris, CLARA, Cozmo AI
  • Satellites Study Hurricanes During El Niño
  • Flock Safety Will Cut Several Hundred Jobs Amid Surveillance Backlash
  • Most Americans Think AI is Developing Too Fast: Poll
  • Viewpoint: The One Thing Holding Back Insurers’ AI Efforts
  • The Latest Launches From The Zebra, Sigo Seguros, Applied Systems
  • Be Mindful: How Workplace Hierarchy Can Shape Even Positive Interactions
  • Why Your Boss Matters More Than Remote or Hybrid Work When It Comes to Burnout and Job Satisfaction

Contributors

Kirk GarrettWhen Builder’s Risk Coverage Doesn’t Reach the Finish LineSean KevelighanFinding Safer Ground: How Parcel-Level Data Is Redefining Wildfire Risk in CaliforniaNeil SahotaViewpoint: Insurers Are Automating the Front Office While Ignoring the Function That Determines TrustSean HalversonFinding Safer Ground: How Parcel-Level Data Is Redefining Wildfire Risk in CaliforniaMary RimbeyWhy Organic Mentorship Is Insurance’s Best Retention Tool See Our Contributors

Features

  • Viewpoint: The One Thing Holding Back Insurers’ AI Efforts

  • Levers and Guardrails: How Growth Is Being Built at Hippo

  • AI Data Center Boom: Understanding How Risks Are Changing

  • Finding Safer Ground: How Parcel-Level Data Is Redefining Wildfire Risk in California

  • When Builder’s Risk Coverage Doesn’t Reach the Finish Line

  • The Impact of Claims Experiences on Trust

Insurance Top Gainers/Losers

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Company Symbol Close 1 Day Chg
Global Indemnity Group, LLCGBLI$24.46up+5.25%
Presurance Holdings, Inc.PRHI$8.28up+3.05%
Root, Inc.ROOT$49.13up+1.17%
Neptune Insurance Holdings Inc.NP$28.74up+1.05%
Trupanion, Inc.TRUP$26.06up+0.93%
Company Symbol Close 1 Day Chg
Goosehead Insurance, Inc.GSHD$43.51down-4.13%
Ategrity Specialty Insurance Company HoldingsASIC$25.93down-3.71%
TWFG, Inc.TWFG$24.76down-2.98%
Kingstone Companies, Inc.KINS$18.49down-2.89%
Universal Insurance Holdings, Inc.UVE$45.85down-2.38%
* As of October 9, 2026; Source: S&P Global Market Intelligence
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