At least 7 out of 10 small businesses (SMB) lack basic business insurance coverage in one or more critical areas. And lack of transparency, along with just plain bad customer experience, are big contributors to this insurance gap.

Enter the digital insurance challengers aiming to fill the gaps through simple online/mobile interfaces. Here are the biggest players in the United States ranked by our FAB score (Fintech Attention Barometer).

Resources: Looking for digital banks, lenders, payment providers, insurance or digital accounting for small businesses? Check out our latest lists: Small Business (SMB) savings/treasury accounts (7) | SMB online lenders (33) | SMB challenger banks (15) | SMB insurers (15) | SMB credit cards/expense management (16) | Billpay & invoicing (16)| Payment processors (7) | SMB digital accounting/bookkeeping (21)

The FAB Score (Fintech Attention Barometer) is a proxy for the size and growth of fintech companies founded since 1999. 

Leading USA Digital Small Business Insurers
ranked by our FAB score (Fintech Attention Barometer*)

Rank Company FAB Score* Reviewed Founding HQ Funding ($M)** Visits (Feb’26)
1 Next Insurance 307 11 Mar 26 2016 SF $1,146 610,000
2 Coalition 208 11 Mar 26 2017 SF $800 76,000
3 Pie Insurance 78 11 Mar 26 2017 DC $621 60,000
4 INSHUR 63 11 Mar 26 2016 NYC $117 120,000
5 Cowbell Cyber 50 11 Mar 26 2019 SF $208 12,000
6 Simply Business (Travelers) 39 11 Mar 26 2005 London $0 350,000
7 Newfront 38 11 Mar 26 2017 SF $310 22,000
8 Vouch Insurance 33 11 Mar 26 2016 SF $185 21,000
9 Embroker 23 11 Mar 26 2015 SF $142 55,000
10 Thimble 19 11 Mar 26 2015 NYC $29 130,000
11 Berxi 9 11 Mar 26 2017 Boston $0 63000
12 Insureon 8 11 Mar 26 1997 Chicago $31 110,000
13 Layr 7 11 Mar 26 2016 Atlanta $26 0
14 Bizinsure 6 11 Mar 26 2012 SF $7 54,000
15 Glow 5 11 Mar 26 2018 SF $27 2,600
16 CoverWallet 4 11 Mar 26 2015 NYC $28 9,200
17t Cake Insure (Pinnacol) 3 11 Mar 26 2017 Denver $10 11,000
17t Stable Insurance 3 11 Mar 26 2018 NYC $3 0
17t FounderShield 3 11 Mar 26 2012 NYC 0 34,000
20 InsuranceBee 0 11 Mar 26 2010 Boston $0 2,400

Source: FintechLabs, Pitchbook, Crunchbase, SimilarWeb, LinkedIn, YouTube, Instagram, TrustPilot; 19 Mar 2026

Profiles of Digital SMB Insurtech Startups

1. Next Insurance (acquired by Ergo Group, March 2025 for $2.6 billion)
FAB Score: 307 (down 6 since Dec ’25)

  • Founded: 2016
  • HQ: SF
  • Traction
    – Exit value: $2.6B
    – Raised: $1.1B (Crunchbase) including $265M Nov 2023, 250M in 2021,
    – American Express invested in the B-round (July 2018)
    – Website visits (Feb 2026): 610,000 (SimilarWeb)
    – Employees (Pitchbook): 550 vs. 709 in July ’24; 700 in Oct ’23; 648 July ’23; 800 in April ’23
    – Articles: 153 (Crunchbase)
  • Social
    – Linkedin: 52,000 followers (721 employees; vs 730 in July ’24; 684 in Oct ’23; 678 in July ’23)
    – Trustpilot: 4.5 (1,370 reviews; vs 179 in July. ’24; 5 in Oct. ’23)
    – YouTube: 6,300 subscribers vs.5,800 in July ’24

2. Coalition
FAB score: 208 (up 8)

  • HQ: San Francisco, California
  • Founded: 2017
  • Traction:
    – Valuation: $5.0B (based on July 2022 round)
    – Raised: $800M (Crunchbase) including $30M Mar 2025, $250M in 2022 and $380M in 2021
    – Employees (Pitchbook): 733 vs. 700 in July ’24 through Oct. ’23; 598 in July ’23; 500 in April ’23
    – Website visits (Feb 2026): 76,000 (SimilarWeb)
    – $325M run rate (gross written premiums), up 9-fold over 2020 (TechCrunch, Sep 2021)
    – $500M combined annual run rate after acquiring Attune with a combined customer base of 130,000 (InsurTechInsights, Oct 2021)
  • Social
    LinkedIn: 212,000 followers (728 employees vs. 680 in July ’24; 620 in Oct ’23; 595 since July ’23
    YouTube: 650 subscribers vs 1,000 in July ’24
    TrustPilot: NA (no reviews)

3. Pie Insurance
FAB score: 78 (down 122)

  • HQ: Washington DC & Denver, CO
  • Founded: 2017 (first policy sold in 2018)
  • Traction:
    – Premiums written (gross): $100M lifetime (Dec 2021)
    – Raised: $621M (Crunchbase) including $118M in 2021 (co-led by Allianz Group) & $315M in Sep 2022
    – Employees (Pitchbook): 422 vs. 431 in July ’24; 460 Oct. ’23 through July ’23
  • – Insurance agency partners: 1,000+
    – Website visits (Feb 2026): 60,000 (SimilarWeb)
    – Number of articles: 87 (Crunchbase)
  • Social
    LinkedIn: 41,000 followers (440 employees vs. 414 in July ’24; 436 in Oct. ’23; 452 in April ’23
    YouTube: 730 subscribers vs. 500 in July ’24
    Instagram: 2,600 followers vs 2,500 in July ’24
    TrustPilot: 2.7 (644 reviews vs. 597 in July ’24; 513 in Oct. ’23)
  • Founders:
    – John Swigart, CEO (previously CMO at Esurance)
    – Dax Craig, President (previously co-founded Valen Analytics)

4. INSHUR
FAB score: 63 (up 24)

  • HQ: NYC
  • Founded: 2016
  • Traction:
    – Raised: $116M (Crunchbase) including $35M in July 2025, $19M in Oct 2024; $26M April 2023 and $25M in 2021
    – Employees (Pitchbook): 167 vs. 158 in July ’24; 133 in Oct. ’23; 121 in July ’23
    – Website visits (Feb 2026): 120,000 visits (SimilarWeb)
    – Number of articles: 23 (Crunchbase)
  • Social:
    LinkedIn: 19,000 followers (170 employees vs. 163 in July ’24; 146 in Oct. ’23; 123 in July ’23)
    YouTube: 160 subscribers vs. 130 in July ’24
    Instagram: 260 followers, unchanged since July ’24
  • Trustpilot: 4.3 (8,500 reviews vs. 6,900 in July ’24; 5,700 in Oct ’23)
  • Founders: Dan Bratshpis, David Daiches, Mathew Donfrancesco, Matthew Tomlinson, Richard Anderson

5. Cowbell Cyber
FAB score: 50 (down 54)

  • HQ: SF Bay Area (Pleasanton)
  • Founded: 2019
  • Traction:
    – Raised: $208M (Crunchbase) including $60M in July 2024, $20M in 2021, $100M in Aug 2022 and $25M in Nov 2023
    – Employees: 310 (Pitchbook), unchanged since Oct ’23; was 242 in July ’23
    – Website visits (Feb 2026): 12,000 (SimilarWeb)
    – Number of articles: 911 (Crunchbase)
  • Social
    Linkedin: 30,000 followers (366 employees vs. 307 in July ’24; 346 in Oct. ’23; 340 in July ’23)
    YouTube: 135 subscribers vs. 110 in July ’24
  • TrustPilot: No reviews
  • Founders: Jack Kudale, Prab Reddy, Rajeev Gupta, Trent Cooksley

6. Simply Business (acquired by Travelers in 2017)
FAB score: 39 (up 21)

  • HQ: London
  • Founded: 2005
  • Acquired by Travelers in 2017 for $490M
  • Traction:
    – Raised: Unknown (Crunchbase)
    – Employees: 1,000 (Pitchbook), unchanged since July ’24; was 800 July ’23
    – Website visits (Feb 2026): 530,000 visits to .uk (SimilarWeb); 350,000 to .com (SimilarWeb)
    – Number of articles: 62 (Crunchbase)
  • Social
    Linkedin: 20,000 followers (876 employees vs. 902 in July ’24; 919 in Oct. ’23; 927 in July ’23)
    YouTube: 4,600 subscribers vs. 4,100 in July ’24
    Instagram: 16,200 followers vs. 12,400 in July ’24
  • TrustPilot: 4.2 (7,100 reviews vs. 4,600 in July ’24; 3,400 in Oct. ’23)
  • Founders: Brad Liebmann, Chris Slater, Deno Fischer, Jim Nelson, Ralph Arnold

7. Newfront
FAB score: 38 (down 80)

  • HQ: San Francisco
  • Founded: 2017
  • Traction:
    – Raised: $310M (Crunchbase) including $200M in 2022
    – Employees (Pitchbook): 706 vs. 733 in July ’24; 762 in Oct. 23; 850 in July ’23; 772 in Oct ’22
    – Website visits (Feb 2026): 22,000 (SimilarWeb)
    – Number of articles: 35 (Crunchbase)
  • Social
    Linkedin: 25,000 followers (650 employees vs. 733 in July ’24; 755 in Oct. ’23; 788 in July ’23)
    YouTube: NA
    Instagram: 550 followers vs. 509 in July ’24
    TrustPilot: NA
  • Founder: Spike Lipkin, CEO

8. Vouch 
FAB score: 33 (up 4)

  • HQ: SF
  • Founded: 2018
  • Traction:
    – Raised: $185M (Crunchbase) including $25M in Mar 2024, $60M in 2021
    – Employees (Pitchbook): 205 vs. 206 in July ’24; 227 in Oct ’23; 220 in July ’23; 150 in April ’23
    – Website visits (Feb 2o26): 21,000 visits (SimilarWeb)
    – Number of articles: 11 (Crunchbase)
  • Social
    Linkedin: 16,000 followers (141 employees vs. 201 in July ’24; 227 in April ’23; 226 in July ’23)
    Instagram: 967 followers
  • TrustPilot: No reviews
  • Founders: Sam Hodges, Travis Hedge

9. Embroker
FAB score: 23 (down 7)

  • HQ: SF
  • Founded: 2015
  • Traction:
    – Premiums written (gross): $20M Q1 2021
    – Raised: $142M (Crunchbase) including $100M in 2021
    – Employees (Pitchbook): 145 vs. 223 in July ’24; 194 in April ’23
    – Website visits (Feb 2026): 55,000 visits (SimilarWeb)
    – Number of articles: 59 (Crunchbase)
  • Social
    LinkedIn: 20,000 followers (109 employees vs. 173 in July ’24; 229 in Oct. ’23; 224 in July ’23)
    YouTube: 295 subscribers vs. 280 in July ’24
    Instagram: 3,200 followers vs. 3,400 in July ’24
  • TrustPilot: No reviews
  • Founders: Matt Miller, Sean X Cummings, Yotam Shacham

10. Thimble (Acquired by Arch Capital, April 2023)
FAB score: 19 (unchanged)

  • HQ: NYC
  • Founded: 2015
  • Traction:
    – Raised: $28.9M (Crunchbase)
    – Employees: 40 (Pitchbook), unchanged since Oct ’23
    – Website visits (Feb 2026): 130,000 visits (SimilarWeb)
    – Number of articles: 16 (Crunchbase)
  • Social
    Linkedin: 7,500 followers (64 employees vs. 56 in July ’24; 48 in Oct. ’23; 46 in July ’23)
    YouTube: 23M views vs. 3.5M in July ’24; 3.3M in Oct. ’23), 198 subscribers
    Instagram: 1,320 followers vs. 1,300 in July ’24
  • TrustPilot: 4.2 (2,300 reviews vs. 1,900 in July ’24; 1,500 in Oct. ’23)
  • Founders: Eugene Hertz, Jay Bregman

12. Insureon
FAB score: 8 (down 4)

  • HQ: Chicago
  • Founded: 1997
  • Traction:
    – Raised: $31M (Crunchbase) prior to 2016
    – Employees (Pitchbook): 250 vs. 128 in July ’24 through July ’23
    – Website visits (Feb 2026): 110,000 visits (SimilarWeb)
    – Number of articles: 46 (Crunchbase)
  • Social
    Linkedin: 5,000 followers (134 employees vs. 128 in July ’24; 129 in Oct. ’23; 126 in July ’23)
    YouTube: 88,000 views vs. 56,000 in July ’24 (572 subscribers)
    Instagram: 42 followers
  • TrustPilot: 4.6 (2,100 reviews vs. 1,100 in July ’24; 650 in Oct. ’23)
  • Founders: Jim Cochran, Michael Cline, Ted Devine

13. Layr
FAB score: 7 (down 5)

  • HQ: Atlanta, Georgia
  • Founded: 2016
  • Traction:
    – Raised: $25.6 including $10M in 2022 and $10M in Oct 2023 (Crunchbase)
    – Employees (Pitchbook): 51, unchanged since July ’23; was 45 in April ’23
    – Website visits (Feb 2026): INA (Similarweb)
    – Number of articles: 100 (Crunchbase)
  • Social
    Linkedin: 2,900 followers (58 employees vs. 66 in July ’24; 56 in Oct. ’23; 53 in July ’23)
    YouTube: 290 views, 18 subscribers
    Instagram: 82 followers
  • TrustPilot: No reviews
  • Founders: Andrew Egenes, Phillip Naples

14. BizInsure
FAB score: 6 (up 2)

  • HQ: SF Bay Area (Oakland)
  • Founded: 2012
  • Traction:
    – Raised: $6.6M (Crunchbase) prior to 2017
    – Employees: 12 (Linkedin)
    – Website visits (Feb 2026): 54,000 (Similarweb)
    – Number of articles: 4 (Crunchbase)
  • Social
    Linkedin: 850 followers (13 employees vs. 12 in July ’24 and July ’23)
    YouTube: 2.1M views, 253 subscribers
  • TrustPilot: No reviews
  • Founder: Greg Morris

15. Glow
Fab score: 5 (down 11)

  • HQ: SF
  • Founded: 2018
  • Products: Worker’s compensation
  • Traction:
    – Raised: $28.5M (Crunchbase), including $24M in Oct 2022
    – Employees: 49 (Pitchbook), unchanged since Oct. ’23; was 37 in April ’23
    – Website visits (Feb 2026): 2,600 (SimilarWeb)
    – Number of articles: NA (too generic)
  • Social
    LinkedIn: 11,000 followers (282 employees vs. 178 in July ’24; 132 in Oct. ’23; 115 in July ’23; 32 in April ’23)
    TrustPilot: No reviews
  • Founder: Samad Wahedi

16. CoverWallet (acquired by AON, Nov 2019)
FAB score: 4 (down 5)

  • HQ: NYC
  • Founded: 2015
  • Acquired by AON in Jan 2020
  • Traction:
    – Raised: $28.3M (Crunchbase) prior to 2019
    – Employees: 300 (Pitchbook), unchanged since July ’23
    – Website visits (Feb 2026): 9,200 visits (SimilarWeb)
    – Number of articles: 32 (Crunchbase)
  • Social
    Linkedin: INA (was 27,000 followers in July ’24), (265 employees vs.  379 in July ’24; 415 in Oct. ’23; 441 in July ’23)
    YouTube: 39,000 views, 77 subscribers
  • TrustPilot: 1.7 (25 reviews vs. 20 in July ’24; 14 in Oct. ’23)
  • Founders: Inaki Berenguer, Rashmi Melgiri

17(t). Cake Insure (Pinnacol)
FAB score: 3 (unchanged)

  • HQ: Denver, CO
  • Founded: 2017
  • Subsidiary of Pinnacol Assurance
  • Traction:
    – Raised: $10.1M (Crunchbase) prior to 2018
    – Employees: 5 (Linkedin)
    – Website visits (Feb 2026): 11,000 (SimilarWeb)
    – Number of articles: 3 (Crunchbase)
  • Social
    Linkedin: 780 followers (3 employees vs. 5 in July ’24; 7 in Oct. ’23; 6 in July ’23)
    YouTube: NA
    Instagram: 109 followers
  • TrustPilot: No reviews
  • Founder: Robert Norris

19. InsuranceBee
FAB score: 0 (unchanged)

  • HQ: Maynard, MA
  • Founded: 2010
  • Traction:
    – Premiums written (gross): $20M Q1 2021
    – Raised: Unknown (Crunchbase)
    – Employees: 13 (Linkedin), unchanged since Oct. ’23, up 1 from July ’23
    – Website visits (Feb 2026): 3,000
    – Number of articles: 1 (Crunchbase)
  • Social
    LinkedIn: 220 followers (13 employees unchanged from Oct ’23; 12 in July ’23)
  • TrustPilot: No reviews

Appears to be shuttered (19 March 2026)

Stable Insurance
FAB score: 3 (unchanged)

  • HQ: NYC
  • Founded: 2018
  • Traction:
    – Raised: $3.3M including $3M in 2022 and $300k in 2021 (Crunchbase)
    – Employees: 12 (Pitchbook), unchanged since July ’24
    – Website visits (Feb 2026): INA (SEMrush)
    – Number of articles: 29 (Crunchbase)
  • Social
    Linkedin: 1,300 followers (2 employees, down 1 since July)
  • TrustPilot: No reviews
  • Founders: Douglas Ver Mulm, Stephen Dekker

 

Notes:
* The FAB score, Fintech Attention Barometer, is a proxy for the overall size of a private company since they typically do not release traditional metrics (# customers, deposits, AUM, etc). The score is based on VC funding, website traffic, mobile downloads, and the number of employees. It’s a work in progress, so expect changes in the formula.
**Funding: Includes equity and debt funding per Crunchbase.

Disclaimer:
Our business model depends on revenue from referrals and sponsors. When you see a referral link in the URL, we may earn a fee when a new account is started (thanks!). This can improve visibility on our website, but does not impact the company’s FAB score.