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 Was (10/23) Company FAB Score* Reviewed Founding HQ Funding ($M)** Visits (Jul ’24)
1 1 Next Insurance 313 13 Aug 24 2016 SF $1,146 650,000
2 3 Pie Insurance 204 13 Aug 24 2017 DC $621 87,000
3 2 Coalition 200 13 Aug 24 2017 SF $770 120,000
4 4 Newfront 118 13 Aug 24 2017 SF $310 27,000
5 5 Cowbell Cyber 104 13 Aug 24 2019 SF $208 40,000
6 7 INSHUR 39 13 Aug 24 2016 NYC $63 140,000
7 6 Embroker 30 13 Aug 24 2015 SF $142 110,000
7 8 Vouch Insurance 30 13 Aug 24 2016 SF $160 15,000
9 9 Thimble 19 13 Aug 24 2015 NYC $29 130,000
10 13 Simply Business (Travelers) 18 13 Aug 24 2005 London $0 220,000
11 10 Glow 16 13 Aug 24 2018 SF $27 2,400
12 11 Insureon 12 13 Aug 24 1997 Chicago $31 210,000
12 11 Layr 12 13 Aug 24 2016 Atlanta $26 1,600
14 14 CoverWallet 8 13 Aug 24 2015 NYC $28 39,000
15 15 Cake Insure (Pinnacol) 3 13 Aug 24 2017 Denver $10 2,300
16 15 Bizinsure 0 13 Aug 24 2012 SF $7 14,000
16 17 InsuranceBee 0 13 Aug 24 2010 Boston $0 1,600
16 18 FounderShield 0 13 Aug 24 2012 NYC 0 17000

Source: FintechLabs, Pitchbook, Crunchbase, SimilarWeb, SEMrush; 13 Aug 2024
“Was” is rank on 15 Nov 2023

Profiles of Digital SMB Insurtech Startups

1. Next Insurance
FAB Score: 313 (down 79 since Oct ’23)

  • Founded: 2016
  • HQ: SF
  • Traction
    – Valuation: $4B (based on March 2021 round)
    – Raised: $1.1B (Crunchbase) including $250M in 2021, $265M Nov 2023
    – American Express invested in the B-round (July 2018)
    – Website visits (July 2024): 650,000 (SimilarWeb)
    – Employees: 709 (Pitchbook), up 9 since Oct ’23, up 61 since July ’23, down 91 since April ’23
    – Articles: 153 (Crunchbase)
  • Social
    – Linkedin: 43,000 followers (730 employees, up 46 since Oct ’23, up 52 since July ’23)
    – Trustpilot: 4.0 (179 reviews, up 174 since Oct. ’23)
    – YouTube: 75 million views (up 16M since Oct. 23); 5,800 subscribers

2. Pie Insurance
FAB score: 204 (down 46)

  • 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: 431 (Pitchbook), down 29 since Oct. ’23 and July ’23
    – Insurance agency partners: 1,000+
    – Website visits (July 2024): 38,000 (SimilarWeb)
    – Number of articles: 87 (Crunchbase)
  • Social
    LinkedIn: 26,000 followers (414 employees, down 22 since Oct. ’23, down 38 since April ’23)
    YouTube: 12.8M, up 9.3M since Oct. 23 (500 subscribers)
    Instagram: 2,500 followers
    TrustPilot: 4.0 (597 reviews, up 84 since Oct. ’23)
  • Founders:
    – John Swigart, CEO (previously CMO at Esurance)
    – Dax Craig, President (previously co-founded Valen Analytics)

3. Coalition
FAB score: 200 (down 149)

  • HQ: San Francisco, California
  • Founded: 2017
  • Traction:
    – Valuation: $5.0B (based on July 2022 round)
    – Raised: $770M (Crunchbase) including $250M in 2022 and $380M in 2021
    – Employees: 700 (Pitchbook), unchanged since Oct. ’23, up 102 since July ’23, up 200 since April ’23
    – Website visits (July 2024): 120,000 (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: 51,000 followers (680 employees, up 60 since Oct ’23; up 95 since July ’23)
    YouTube: 20,000 views, 1,000 subscribers
    TrustPilot: NA (no reviews)
    Articles: 659 (Crunchbase)

4. Newfront
FAB score: 118 (unchanged)

  • HQ: San Francisco
  • Founded: 2017
  • Traction:
    – Raised: $310M (Crunchbase) including $200M in 2022
    – Employees: 733 (Pitchbook), down 29 since Oct. 23, down 117 since July ’23, down 39 since Oct ’22
    – Website visits (July 2024): 27,000 (SimilarWeb)
    – Number of articles: 35 (Crunchbase)
  • Social
    Linkedin: 18,000 followers (733 employees, down 22 since Oct. 23, down 55 from July ’23)
    YouTube: NA
    Instagram: 509 followers
    TrustPilot: NA
  • Founder: Spike Lipkin, CEO

5. Cowbell Cyber
FAB score: 104 (up 22)

  • 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 from Oct ’23, up 68 from July ’23
    – Website visits (July 2024): 24,000 (SimilarWeb)
    – Number of articles: 911 (Crunchbase)
  • Social
    Linkedin: 18,000 followers (268 307 employees, down 39 from Oct. ’23, down 33 from July ’23)
    YouTube: 6,200 views, 112 subscribers
  • TrustPilot: No reviews
  • Founders: Jack Kudale, Prab Reddy, Rajeev Gupta, Trent Cooksley

6. INSHUR
FAB score: 39 (down 9)

  • HQ: NYC
  • Founded: 2016
  • Traction:
    – Raised: $63M (Crunchbase) including $26M April 2023 and $25M in 2021
    – Employees: 158 (Pitchbook), up 25 since Oct. ’23, up 37 from July ’23
    – Website visits (July 2024): 140,000 visits (SimilarWeb)
    – Number of articles: 23 (Crunchbase)
  • Social:
    LinkedIn: 15,000 followers (163 employees, up 17 from Oct. ’23, up 40 from July ’23)
    YouTube: 31,000 views, 131 subscribers
    Instagram: 260 followers
  • Trustpilot: 4.3 (6,900 reviews, up 1,200 since Oct ’23)
  • Founders: Dan Bratshpis, David Daiches, Mathew Donfrancesco, Matthew Tomlinson, Richard Anderson

7 (tie). Embroker
FAB score: 30 (down 37)

  • HQ: SF
  • Founded: 2015
  • Traction:
    – Premiums written (gross): $20M Q1 2021
    – Raised: $142M (Crunchbase) including $100M in 2021
    – Employees: 223 (Pitchbook), unchanged since July, up 29 since April
    – Website visits (July 2024): 110,000 visits (SimilarWeb)
    – Number of articles: 59 (Crunchbase)
  • Social
    LinkedIn: 17,000 followers (173 employees, down 56 since Oct. ’23, down 51 since July ’23)
    YouTube: 12,000 views, 280 subscribers
    Instagram: 3,400 followers
  • TrustPilot: No reviews
  • Founders: Matt Miller, Sean X Cummings, Yotam Shacham

7 (tie). Vouch 
FAB score: 30 (down 14)

  • HQ: SF
  • Founded: 2018
  • Traction:
    – Raised: $185M (Crunchbase) including $25M in Mar 2024, $60M in 2021
    – Employees: 206 (Pitchbook), down 21 since Oct ’23, down 14 from July ’23, up 56 from April ’23
    – Website visits (July 2024): 15,000 visits (SimilarWeb)
    – Number of articles: 11 (Crunchbase)
  • Social
    Linkedin: 13,000 followers (201 employees, down 26 since April ’23, down 25 since July ’23)
    Instagram: 967 followers
  • TrustPilot: No reviews
  • Founders: Sam Hodges, Travis Hedge

9. Thimble (Acquired by Arch Capital)
FAB score: 19 (up 1)

  • HQ: NYC
  • Founded: 2015
  • Traction:
    – Raised: $28.9M (Crunchbase)
    – Employees: 40 (Pitchbook), unchanged since Oct ’23
    – Website visits (July 2024): 130,000 visits (SimilarWeb)
    – Number of articles: 16 (Crunchbase)
  • Social
    Linkedin: 7,000 followers (56 employees, up 8 since Oct. ’23, up 10 over July ’23)
    YouTube: 3.5M views (up 200,000 since Oct. ’23), 140 subscribers
    Instagram: 1,300 followers
  • TrustPilot: 4.5 (1,900 reviews, up 400 since Oct. ’23)
  • Founders: Eugene Hertz, Jay Bregman

10. Simply Business (acquired by Travelers in 2017)
FAB score: 18 (up 7)

  • HQ: London
  • Founded: 2005
  • Acquired by Travelers in 2017 for $490M
  • Traction:
    – Raised: Unknown (Crunchbase)
    – Employees: 1,000 (Pitchbook), up 200 since July
    – Website visits (July 2024): 720,000 visits to .uk (SimilarWeb); 220,000 to .com (SimilarWeb)
    – Number of articles: 62 (Crunchbase)
  • Social
    Linkedin: 16,000 followers (902 employees, down 17 since Oct. ’23, down 25 since July ’23)
    YouTube: 1.6M views (4,100 subscribers)
    Instagram: 12,400 followers
  • TrustPilot: 4.3 (4,600 reviews, up 1,200 from Oct. ’23)
  • Founders: Brad Liebmann, Chris Slater, Deno Fischer, Jim Nelson, Ralph Arnold

11. Glow
Fab score: 16 (unchanged)

  • 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, up 12 since April ’23
    – Website visits (July 2024): 2,400 (SimilarWeb)
    – Number of articles: NA (too generic)
  • Social
    LinkedIn: 3,000 followers (178 employees, up 46 since Oct. ’23, up 63 from July ’23, up 146 from April ’23)
    TrustPilot: No reviews
  • Founder: Samad Wahedi

12 (tie). Insureon
FAB score: 12 (unchanged)

  • HQ: Chicago
  • Founded: 1997
  • Traction:
    – Raised: $31M (Crunchbase)
    – Employees: 128 (Pitchbook), unchanged
    – Website visits (July 2024): 210,000 visits (SimilarWeb)
    – Number of articles: 46 (Crunchbase)
  • Social
    Linkedin: 4,200 followers (128 employees, down 1 since Oct. ’23, up 2 since July ’23)
    YouTube: 56,000 views, 425 subscribers
    Instagram: 43 followers
  • TrustPilot: 4.5 (1,100 reviews, up 450 since Oct. ’23)
  • Founders: Jim Cochran, Michael Cline, Ted Devine

12 (tie). Layr
FAB score: 12 (unchanged)

  • HQ: Atlanta, Georgia
  • Founded: 2016
  • Traction:
    – Raised: $25.6 including $10M in 2022 and $10M in Oct 2023 (Crunchbase)
    – Employees: 51 (Pitchbook), unchanged since July, up 6 from April
    – Website visits (July 2024): 1,600 visits (Similarweb)
    – Number of articles: 100 (Crunchbase)
  • Social
    Linkedin: 3,000 followers (66 employees, up 10 since Oct. ’23, up 13 since July ’23)
    YouTube: 150 views, 21 subscribers
    Instagram: 84 followers
  • TrustPilot: No reviews
  • Founders: Andrew Egenes, Phillip Naples

14. CoverWallet (acquired by AON, Nov 2019)
FAB score: 8 (down 1)

  • HQ: NYC
  • Founded: 2015
  • Acquired by AON in Jan 2020
  • Traction:
    – Raised: $28.3M (Crunchbase)
    – Employees: 300 (Pitchbook), unchanged since July ’23
    – Website visits (July 2024): 39,000 visits (SimilarWeb)
    – Number of articles: 32 (Crunchbase)
  • Social
    Linkedin: 27,000 followers (379 employees, down 36 since Oct. ’23, down 62 from July ’23)
    YouTube: 39,000 views, 75 subscribers
  • TrustPilot: 2.2 (20 reviews, up 6 since Oct. ’23)
  • Founders: Inaki Berenguer, Rashmi Melgiri

15. Cake Insure (Pinnacol)
FAB score: 3 (down 1)

  • HQ: Denver, CO
  • Founded: 2017
  • Subsidiary of Pinnacol Assurance
  • Traction:
    – Raised: $10.1M (Crunchbase)
    – Employees: 5 (Linkedin)
    – Website visits (July 2024): 2,300 (SimilarWeb)
    – Number of articles: 3 (Crunchbase)
  • Social
    Linkedin: 720 followers (5 employees, down 2 since Oct. ’23, down 1 since July ’23)
    YouTube: NA
    Instagram: 118 followers
  • TrustPilot: No reviews
  • Founder: Robert Norris

16 (tie). BizInsure
FAB score: 0 (down 4)

  • HQ: SF Bay Area (Oakland)
  • Founded: 2012
  • Traction:
    – Raised: $6.6M (Crunchbase)
    – Employees: 12 (Linkedin)
    – Website visits (July 2024): 14,000 (SEMrush)
    – Number of articles: 4 (Crunchbase)
  • Social
    Linkedin: 820 followers (12 employees, unchanged since July ’23)
    YouTube: 140,000 views, 7 subscribers
  • TrustPilot: No reviews
  • Founder: Greg Morris

16 (tie). 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 (July 2024): 1,600 (SEMrush)
    – Number of articles: 1 (Crunchbase)
  • Social
    LinkedIn: 200 followers (13 employees)
  • TrustPilot: No reviews

Defunct

Stable Insurance (URL unreachable 17 Nov 2023)

  • HQ: NYC
  • Founded: 2018
  • Traction:
    – Raised: $3.3M including $3M in 2022 and $300k in 2021 (Crunchbase)
    – Employees: 12 (Pitchbook), unchanged
    – Website visits (Oct 2023): NA (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.