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 or corporate charge/credit cards serving small businesses?
Check out our latest lists: SMB online lenders (26) | SMB charge/credit cards (15) | SMB challenger banks (10) 

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

Rank Company FAB Score Reviewed  Founding HQ Funding ($M) Visits (10/21)
1 Next Insurance 230 2 Dec ’21 2016 SF $881M 770,000
2 Coalition 122 2 Dec ’21 2017 SF $520 73,000
3 Pie Insurance 80 2 Dec ’21 2017 DC $306 77,000
4 Simply Business (Travelers) 63 2 Dec ’21 2005 London Unknown 550,000
5 Embroker 39 2 Dec ’21 2015 SF $142 71,000
6 Vouch Insurance 32 2 Dec ’21 2016 SF $184 14,000
7 INSHUR 25 2 Dec ’21 2016 NYC $37 100,000
8 Insureon 24 2 Dec ’21 1997 Chicago $31 290,000
9 CoverWallet 20 2 Dec ’21 2015 NYC $28 130,000
10 Thimble 18 2 Dec ’21 2015 NYC $29 110,000
11 Cowbell Cyber 10 2 Dec ’21 2019 SF $24 1,000
12 Cake Insure (Pinnacol) 4 2 Dec ’21 2017 Denver $10 4,400
13 Stable Insurance 3 2 Dec ’21 2018 NYC Unknown 1,100
14 Layr 3 2 Dec ’21 2016 Atlanta $6 7,700
15 Bizinsure 1 2 Dec ’21 2012 SF $7 6,300
16 InsuranceBee 1 2 Dec ’21 2010 Boston Unknown 6,100

Source: FintechLabs, Pitchbook, Crunchbase, SimilarWeb, SEMrush; 2 Dec 2021
*As nerds do, we are developing a proprietary score measuring the adoption of private digital financial services companies that do not release traditional metrics (# customers, deposits, AUM, etc). We are calling it the FAB score, standing for Fintech Attention Barometer. It’s a work in progress, so expect changes in the formula.

Profiles of Digital SMB Insurtech Startups (coming soon)

1. Next Insurance
FAB Score: 230

  • Founded: 2016
  • HQ: SF
  • Traction
    – Valuation: $4B (based on March 2021 round)
    – Raised: $881M (Crunchbase) including $250M in 2021
    – American Express invested in the B-round (July 2018)
    – Website visits (Oct 2021): 770,000 (SimilarWeb)
    – Employees: 660 (Pitchbook)
    – Articles: 68 (Crunchbase)
  • Social
    – Linkedin: 24,400 followers
    – Twitter: 9,800 followers
    – Trustpilot: NA (2 reviews)
    – YouTube: 19M views; 3,100 subscribers

2. Coalition
FAB score: 122

  • HQ: San Francisco, California
  • Founded: 2017
  • Traction:
    – Valuation: $3.5B (based on Sep 2021 round)
    – Raised: $520M (Crunchbase) including $380M in 2021
    – Employees: 265 (Techcrunch)
    – Website visits (Oct 2021): 73,000 (SimilarWeb)
    – $325M run rate (gross written premiums), up 9-fold over 2020 (TechCrunch, Sep 2021)
    – $500M combined annual run rate after acquiring Attune with combined customer base of 130,000 (InsurTechInsights, Oct 2021)
  • Social
    Linkedin: 11,700 followers
    Twitter: 800 followers
    YouTube: 1,300 views, 27 subscribers
    TrustPilot: NA (no reviews)

3. Pie Insurance
FAB score: 80

  • HQ: Washington DC & Denver, CO
  • Founded: 2017 (first policy sold in 2018)
  • Traction:
    – Premiums written (gross): $100M lifetime
    – Raised: $306M (Crunchbase) including $118M in 2021 (co-led by Allianz Group)
    – Employees: More than 300 full-time
    – Insurance agency partners: 1,000+
    – Website visits (Oct 2021): 77,000 from 52,000 unique visitors (SEMrush)
    – Number of articles: 35 (Crunchbase)
  • Social
    Linkedin: 6,500 followers (313 employees)
    Twitter: 840 followers
    YouTube: 2.6M views, 193 subscribers
    Instagram: 2,200 followers
  • TrustPilot: 4.6 (298 reviews)
  • Founders:
    – John Swigart, CEO (previously CMO at Esurance)
    – Dax Craig, President (previously co-founded Valen Analytics)

5. Embroker
FAB score: 39

  • HQ: SF
  • Founded: 2015
  • Traction:
    – Premiums written (gross): $20M Q1 2021
    – Raised: $142M (Crunchbase) including $100M in 2021
    – Employees: 177 (Pitchbook)
    – Website visits (Oct 2021): 71,000 visits (SimilarWeb)
    – Number of articles: 27 (Crunchbase)
  • Social
    Linkedin: 4,600 followers (186 employees)
    Twitter: 3,400 followers
    YouTube: 8,300 views, 44 subscribers
    Instagram: 3,600 followers
  • TrustPilot: No reviews
  • Founders: Matt Miller, Sean X Cummings, Yotam Shacham

9. CoverWallet (acquired by AON)
FAB score: 20

  • HQ: NYC
  • Founded: 2015
  • Acquired by AON in Jan 2020
  • Traction:
    – Raised: $28.3M (Crunchbase)
    – Employees: 300 (Pitchbook)
    – Website visits (Oct 2021): 130,000 visits (SimilarWeb)
    – Number of articles: 20 (Crunchbase)
  • Social
    Linkedin: 14,500 followers (367 employees)
    Twitter: 4,120 followers
    YouTube: 36,000 views, 43 subscribers
  • TrustPilot: 2.6 (only 4 reviews)
  • Founders: Inaki Berenguer, Rashmi Melgiri

10. Thimble
FAB score: 18

  • HQ: NYC
  • Founded: 2015
  • Traction:
    – Raised: $28.9M (Crunchbase)
    – Employees: 177 (Pitchbook)
    – Website visits (Oct 2021): 110,000 visits (SimilarWeb)
    – Number of articles: 16 (Crunchbase)
  • Social
    Linkedin: 5,600 followers (58 employees)
    Twitter: 770 followers
    YouTube: 4.3M views, 115 subscribers
    Instagram: 1,250 followers
  • TrustPilot: 4.6 (718 reviews)
  • Founders: Eugene Hertz, Jay Bregman

7. INSHUR
FAB score: 25

  • HQ: NYC
  • Founded: 2016
  • Traction:
    – Raised: $36.6 (Crunchbase) including $25M in 2021
    – Employees: 100 (Pitchbook)
    – Website visits (Oct 2021): 100,000 visits (SimilarWeb)
    – Number of articles: 11 (Crunchbase)
  • Social:
    Linkedin: 8,100 followers (152 employees)
    YouTube: 30,000 views, 114 subscribers
    Instagram: 176 followers
  • TrustPilot: 4.5 (2,145 reviews)
  • Founders: Dan Bratshpis, David Daiches, Mathew Donfrancesco, Matthew Tomlinson, Richard Anderson

8. Insureon
FAB score: 24

  • HQ: Chicago
  • Founded: 1997
  • Traction:
    – Raised: $31M (Crunchbase)
    – Employees: 160 (Pitchbook)
    – Website visits (Oct 2021): 290,000 visits (SimilarWeb)
    – Number of articles: 44 (Crunchbase)
  • Social
    Linkedin: 3,100 followers (163 employees)
    Twitter: 2,300 followers
    YouTube: 9,300 views, 325 subscribers
    Instagram: 48 followers
  • TrustPilot: 1.7 (235 reviews)
  • Founders: Jim Cochran, Michael Cline, Ted Devine

6. Vouch 
FAB score: 32

  • HQ: SF
  • Founded: 2018
  • Traction:
    – Raised: $184M (Crunchbase) including $60M in 2021
    – Employees: 125 (Pitchbook)
    – Website visits (Oct 2021): 14,000 visits from 7,900 unique visistors (SEMrush)
    – Number of articles: 8 (Crunchbase)
  • Social
    Linkedin: 5,700 followers (149 employees)
    Twitter: 620 followers
    Instagram: 830 followers
  • TrustPilot: No reviews
  • Founders: Sam Hodges, Travis Hedge

11. Cowbell Cyber
FAB score: 10

  • HQ: SF Bay Area (Pleasonton)
  • Founded: 2019
  • Traction:
    – Raised: $23.6M (Crunchbase) including $20.3M in 2021
    – Employees: 105 (Pitchbook)
    – Website visits (Oct 2021): 1,000 visits from 1,000 uniques (SEMrush)
    – Number of articles: 432 (Crunchbase)
  • Social
    Linkedin: 2,500 followers (124 employees)
    Twitter: 300 followers
    YouTube: 18,000 views, 44 subscribers
  • TrustPilot: No reviews
  • Founders: Jack Kudale, Prab Reddy, Rajeev Gupta, Trent Cooksley

4. Simply Business (Travelers)
FAB score: 63

12. Cake Insure (Pinnacol)
FAB score: 4

  • HQ: Denver, CO
  • Founded: 2017
  • Subsidiary of Pinnacol Assurance
  • Traction:
    – Raised: $10.1M (Crunchbase) including $100M in 2021
    – Employees: 32 (Pitchbook)
    – Website visits (Oct 2021): 4,400 visits from 4.400 uniques (SEMrush)
    – Number of articles: 0 (Crunchbase)
  • Social
    Linkedin: 610 followers (7 employees)
    Twitter: 120 followers
    YouTube: 1.2M views, 15 subscribers
    Instagram: 130 followers
  • TrustPilot: No reviews
  • Founder: Robert Norris

13. Stable Insurance
FAB score: 3

  • HQ: NYC
  • Founded: 2018
  • Traction:
    – Raised: Unknown (Crunchbase)
    – Employees: 5 (Pitchbook)
    – Website visits (Oct 2021): 1,100 visits from 1,100 uniques (SEMrush)
    – Number of articles: 8 (Crunchbase)
  • Social
    Linkedin: 350 followers (11 employees)
    Twitter: 83 followers
  • TrustPilot: No reviews
  • Founders: Douglas Ver Mulm, Stephen Dekker

14. Layr
FAB score: 3

  • HQ: Atlanta, Georgia
  • Founded: 2016
  • Traction:
    – Raised: $5.9 (AngelList)
    – Employees: 24 (Pitchbook)
    – Website visits (Oct 2021): 6,900 visits from 3,700 uniques (SEMrush)
    – Number of articles: 91 (Crunchbase)
  • Social
    Linkedin: 900 followers (23 employees)
    Twitter: 250 followers
    YouTube: 53,000 views, 9 subscribers
    Instagram: 81 followers
  • TrustPilot: No reviews
  • Founders: Andrew Egenes, Phillip Naples

15. BizInsure
FAB score: 1

  • HQ: SF Bay Area (Oakland)
  • Founded: 2012
  • Traction:
    – Raised: $6.6M (Crunchbase) including $100M in 2021
    – Employees: 8 (Linkedin)
    – Website visits (Oct 2021): 6,300 visits from 5,700 uniques (SEMrush)
    – Number of articles: 3 (Crunchbase)
  • Social
    Linkedin: 550 followers (8 employees)
    Twitter: 140 followers
    YouTube: 18,000 views, 3 subscribers
  • TrustPilot: No reviews
  • Founder: Greg Morris

5. InsuranceBee
FAB score: 77

  • HQ: Maynard, MA
  • Founded: 2010
  • Traction:
    – Premiums written (gross): $20M Q1 2021
    – Raised: Unkown (Crunchbase)
    – Employees: 8 (Linkedin)
    – Website visits (Oct 2021): 6,100 visits from 6,100 uniques (SimilarWeb)
    – Number of articles: 1 (Crunchbase)
  • Social
    Linkedin: 150 followers (8 employees)
    Twitter: 290 followers
  • FeeFo: 4.6 (103 reviews) (No reviews on TrustPilot

5. InsuranceBee
FAB score: 77

  • HQ: SF
  • Founded: 2015
  • Traction:
    – Premiums written (gross): $20M Q1 2021
    – Raised: $142M (Crunchbase) including $100M in 2021
    – Employees: 177 (Pitchbook)
    – Website visits (Oct 2021): 71,000 visits (SimilarWeb)
    – Number of articles: 27 (Crunchbase)
  • Social
    Linkedin: 4,600 followers (186 employees)
    Twitter: 3,400 followers
    YouTube: 8,300 views, 44 subscribers
    Instagram: 3,600 followers
  • TrustPilot: No reviews
  • Founders: Matt Miller, Sean X Cummings, Yotam Shacham