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).

NEW: Looking for digital banks, lenders, payment providers, insurance or digital accounting for small businesses? Check out our latest lists: SMB Savings & Treasury Accounts (8) | SMB online lenders (33) | SMB challenger banks (12) | SMB insurers (15) | SMB charge cards/expense management (16) | Billpay & invoicing (16)| Payment processors (7) | Subscription processors (7) | SMB digital accounting/bookkeeping (21) | Equity crowdfunding (7)

The FAB Score Ranking (Fintech Attention Barometer) is a proxy for the size of a private fintech company.

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

Rank Was (July) Company FAB Score* Reviewed Founding HQ Funding ($M)** Visits
(Oct ’23)
1 2 Next Insurance 392 17 Nov 23 2016 SF $1,146 510,000
2 1 Coalition 349 17 Nov 23 2017 SF $770 130,000
3 3 Pie Insurance 250 17 Nov 23 2017 DC $621 87,000
4 4 Newfront 118 17 Nov 23 2017 SF $310 30,000
5 5 Cowbell Cyber 82 17 Nov 23 2019 SF $148 40,000
6 6 Embroker 67 17 Nov 23 2015 SF $142 100,000
7 7 INSHUR 48 17 Nov 23 2016 NYC $63 140,000
8 8 Vouch Insurance 44 17 Nov 23 2016 SF $160 15,000
9 10 Thimble 18 17 Nov 23 2015 NYC $29 120,000
10 11 Glow 16 17 Nov 23 2018 SF $27 2,000
11(t) 9 Insureon 12 17 Nov 23 1997 Chicago $31 210,000
11(t) 14 Layr 12 17 Nov 23 2016 Atlanta $26 600
13 13 Simply Business (Travelers) 11 17 Nov 23 2005 London $0 170,000
14 12 CoverWallet 9 17 Nov 23 2015 NYC $28 46,000
15(t) 15 Cake Insure (Pinnacol) 4 17 Nov 23 2017 Denver $10 6,900
15(t) 17 (t) Bizinsure 4 17 Nov 23 2012 SF $7 48,000
17 Zeguro 3 17 Nov 23 2016 SF $7 7800
18(t) 17 (t) InsuranceBee 0 17 Nov 23 2010 Boston $0 6,700
18(t) FounderShield 0 17 Nov 23 2012 NYC 0 23000

 

Source: FintechLabs, Pitchbook, Crunchbase, SimilarWeb, SEMrush; 17 November 2023
“Was” is rank on 27 June 2023

Profiles of Digital SMB Insurtech Startups

1. Next Insurance
FAB Score: 392 (up 133 since July)

  • 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 (Oct 2023): 510,000 (SimilarWeb)
    – Employees: 700 648 (Pitchbook), up 52 since July, down 100 since April
    – Articles: 93 (Crunchbase)
  • Social
    – Linkedin: 37,000 followers (684 employees, up 6 since July)
    – Trustpilot: 2.5 (Note: Only 5 reviews)
    – YouTube: 59M views (up 8M since July); 5,500 subscribers

2. Coalition
FAB score: 349 (up 3 since July)

  • 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), up 102 since July, up 200 since April
    – Website visits (Oct 2023): 130,000 (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: 29,000 followers (620 employees, up 35 since July)
    YouTube: 22,000 views, 1,000 subscribers
    TrustPilot: NA (no reviews)
    Articles: 651 (Crunchbase)

3. Pie Insurance
FAB score: 250 (unchanged)

  • 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: 460 (Pitchbook), unchanged
    – Insurance agency partners: 1,000+
    – Website visits (Oct 2023): 87,000 (SimilarWeb)
    – Number of articles: 60 (Crunchbase)
  • Social
    Linkedin: 15,000 followers (436 employees, down 16 since April)
    YouTube: 3.5M views (470 subscribers)
    Instagram: 2,400 followers
    TrustPilot: 4.6 (513 reviews)
  • Founders:
    – John Swigart, CEO (previously CMO at Esurance)
    – Dax Craig, President (previously co-founded Valen Analytics)

4. Newfront
FAB score: 118 (unchanged)

  • HQ: San Francisco
  • Founded: 2017
  • Traction:
    – Raised: $310M (Crunchbase) including $200M in 2022
    – Employees: 762 (Pitchbook), down 88 since July, down 10 since Oct 2022
    – Website visits (Oct 2023): 30,000 (SimilarWeb)
    – Number of articles: 29 (Crunchbase)
  • Social
    Linkedin: 15,000 followers (755 employees, down 33 from July)
    YouTube: NA
    Instagram: 476 followers
    TrustPilot: NA
  • Founder: Spike Lipkin, CEO

5. Cowbell Cyber
FAB score: 82 (up 12)

  • HQ: SF Bay Area (Pleasanton)
  • Founded: 2019
  • Traction:
    – Raised: $148M (Crunchbase) including $20M in 2021, $100M in Aug 2022 and $25M in Nov 2023
    – Employees: 310 (Pitchbook), up 68 from July
    – Website visits (Oct 2023): 40,000 (SimilarWeb)
    – Number of articles: 911 (Crunchbase)
  • Social
    Linkedin: 9,400 followers (307 employees, up 6)
    YouTube: 5,200 views, 97 subscribers
  • TrustPilot: No reviews
  • Founders: Jack Kudale, Prab Reddy, Rajeev Gupta, Trent Cooksley

6. Embroker
FAB score: 67 (unchanged)

  • 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 (Oct 2023): 130,000 visits (SimilarWeb)
    – Number of articles: 45 (Crunchbase)
  • Social
    Linkedin: 14,000 followers (229 employees, up 5 since July)
    YouTube: 11,000 views, 270 subscribers
    Instagram: 3,500 followers
  • TrustPilot: No reviews
  • Founders: Matt Miller, Sean X Cummings, Yotam Shacham

7. INSHUR
FAB score: 48 (down 7)

  • HQ: NYC
  • Founded: 2016
  • Traction:
    – Raised: $63M (Crunchbase) including $26M April 2023 and $25M in 2021
    – Employees: 133 (Pitchbook), up 12 from July
    – Website visits (Oct 2023): 140,000 visits (SimilarWeb)
    – Number of articles: 21 (Crunchbase)
  • Social:
    Linkedin: 11,000 followers (146 employees, up 23)
    YouTube: 31,000 views, 127 subscribers
    Instagram: 244 followers
  • TrustPilot: 4.5 (5,720 reviews, up 1,030 since July)
  • Founders: Dan Bratshpis, David Daiches, Mathew Donfrancesco, Matthew Tomlinson, Richard Anderson

8. Vouch 
FAB score: 44 (down 1)

  • HQ: SF
  • Founded: 2018
  • Traction:
    – Raised: $160M (Crunchbase) including $60M in 2021
    – Employees: 227 (Pitchbook), up 7 from July, up 77 from April
    – Website visits (Oct 2023): 15,000 visits (SimilarWeb)
    – Number of articles: 11 (Crunchbase)
  • Social
    Linkedin: 10,000 followers (227 employees, up 1 since July)
    Instagram: 945 followers
  • TrustPilot: No reviews
  • Founders: Sam Hodges, Travis Hedge

9. Thimble (Acquired by Arch Insurance)
FAB score: 18 (up 1)

  • HQ: NYC
  • Founded: 2015
  • Traction:
    – Raised: $28.9M (Crunchbase)
    – Employees: 40 (Pitchbook), unchanged
    – Website visits (Oct 2023): 120,000 visits (SimilarWeb)
    – Number of articles: 16 (Crunchbase)
  • Social
    Linkedin: 6,300 followers (48 employees, up 2 over July)
    YouTube: 3.3M views (unchanged), 127 subscribers
    Instagram: 1,300 followers
  • TrustPilot: 4.4 (1,520 reviews, up 200)
  • Founders: Eugene Hertz, Jay Bregman

10. 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), up 12 since April
    – Website visits (October 2023): 2,000 (SimilarWeb)
    – Number of articles: NA (too generic)
  • Social
    LinkedIn: 1,400 followers (132 employees, up 17 from July, up 100 from April)
    TrustPilot: No reviews
  • Founder: Samad Wahedi

11 (tie). Insureon
FAB score: 12 (down 6)

  • HQ: Chicago
  • Founded: 1997
  • Traction:
    – Raised: $31M (Crunchbase)
    – Employees: 128 (Pitchbook), unchanged
    – Website visits (Oct 2023): 210,000 visits (SimilarWeb)
    – Number of articles: 45 (Crunchbase)
  • Social
    Linkedin: 4,200 followers (129 employees, up 3)
    YouTube: 37,000 views, 772 subscribers
    Instagram: 45 followers
  • TrustPilot: 4.2 (569 reviews, up 197)
  • Founders: Jim Cochran, Michael Cline, Ted Devine

11 (tie). Layr
FAB score: 12 (up 5)

  • 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 (Oct 2023): 600 visits (SEMrush)
    – Number of articles: 97 (Crunchbase)
  • Social
    Linkedin: 2,400 followers (56 employees, up 3 since July)
    YouTube: 400 views, 15 subscribers
    Instagram: 87 followers
  • TrustPilot: No reviews
  • Founders: Andrew Egenes, Phillip Naples

13. Simply Business (acquired by Travelers in 2017)
FAB score: 11 (up 3)

  • 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 (Oct 2023): 660,000 visits to .uk (SimilarWeb); 170,000 to .com (SimilarWeb)
    – Number of articles: 49 (Crunchbase)
  • Social
    Linkedin: 14,900 followers (919 employees, down 8 since July)
    YouTube: 1.1M views (3,900 subscribers)
    Instagram: 11,000 followers
  • TrustPilot: 4.2 (3,400 reviews, up 560 from July)
  • Founders: Brad Liebmann, Chris Slater, Deno Fischer, Jim Nelson, Ralph Arnold

14. CoverWallet (acquired by AON, Nov 2019)
FAB score: 9 (down 2)

  • HQ: NYC
  • Founded: 2015
  • Acquired by AON in Jan 2020
  • Traction:
    – Raised: $28.3M (Crunchbase)
    – Employees: 300 (Pitchbook), unchanged
    – Website visits (Oct 2023): 46,000 visits (SimilarWeb)
    – Number of articles: 22 (Crunchbase)
  • Social
    Linkedin: 24,000 followers (415 employees, down 26 from July)
    YouTube: 39,000 views, 72 subscribers
  • TrustPilot: 2.4 (14 reviews)
  • Founders: Inaki Berenguer, Rashmi Melgiri

15 (tie). Cake Insure (Pinnacol)
FAB score: 4 (up 1)

  • HQ: Denver, CO
  • Founded: 2017
  • Subsidiary of Pinnacol Assurance
  • Traction:
    – Raised: $10.1M (Crunchbase)
    – Employees: 6 (Linkedin), unchanged
    – Website visits (Oct 2023): 6,900 visits from 4,300 uniques (SEMrush)
    – Number of articles: 0 (Crunchbase)
  • Social
    Linkedin: 680 followers (7 employees, up 1 since July)
    YouTube: 1.2M views, 14 subscribers
    Instagram: 122 followers
  • TrustPilot: No reviews
  • Founder: Robert Norris

15 (tie). BizInsure
FAB score: 4 (up 4)

  • HQ: SF Bay Area (Oakland)
  • Founded: 2012
  • Traction:
    – Raised: $6.6M (Crunchbase)
    – Employees: 12 (Linkedin)
    – Website visits (Oct 2023): 48,000 visits from 46,000 uniques (SEMrush)
    – Number of articles: 3 (Crunchbase)
  • Social
    Linkedin: 800 followers (12 employees, unchanged)
    YouTube: 19,000 views, 4 subscribers
  • TrustPilot: No reviews
  • Founder: Greg Morris

18(tie). InsuranceBee
FAB score: 0 (unchanged)

  • HQ: Maynard, MA
  • Founded: 2010
  • Traction:
    – Premiums written (gross): $20M Q1 2021
    – Raised: Unknown (Crunchbase)
    – Employees: 13 (Linkedin), up 1 from July
    – Website visits (May 2023): 6,700 visits from 5,600 uniques (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.