Five Sigma
AI-native claims management software that insurers run on top of Guidewire and similar systems.
On the record
Checkpoint: Guidewire's expected launch of an in-platform AI Claims Agent with early carrier adoption
The call
Five Sigma has real customers and live AI claims workflows, but it is running low on funding runway while Guidewire and AI-native peers close in on the same ground.
Five Sigma makes software that uses AI to handle insurance claims faster and more accurately. It works on top of Guidewire's system, which is the main program that insurance companies use to manage claims. The problem is that Guidewire itself is adding AI features directly into its own software, and other AI claims companies like Shift and Snapsheet are competing too, so Five Sigma's advantage could disappear quickly. The biggest question mark is whether the company has enough money left in the bank to survive: it has not raised a major funding round in four and a half years, which could mean either the business is lean and profitable, or it is running low on cash and cannot raise more money from investors.
Why
01
AI pressure: Shift Technology, Snapsheet, Tractable, and CCC's AI claims agents. Rival AI-native claims tools are shipping similar automation, competing for the same carriers before Five Sigma locks in share. Could AI do the core job? Only partly.
02
Bigger players: Guidewire. Guidewire owns the system of record Five Sigma sits on top of and is adding its own AI claims features directly into ClaimCenter. Could a giant copy it? Yes, easily.
03
What protects it. Deep workflow integration and a regulated action layer make ripping Five Sigma out of a live claims process costly once carriers go live.
What would change this call
Guidewire announces an in-platform AI Claims Agent with tier-1 carrier adoption within 12-18 months. Would show the incumbent is closing the gap Five Sigma relies on for differentiation.
Five Sigma closes a Series B round or discloses current ARR, growth rate, and cash runway. Would show whether the company is capital-efficient or running low on funding.
A top-15 P&C carrier goes live on Five Sigma's Clive as a system-of-record replacement rather than an overlay. Would show the platform can win core business, not just niche add-on deals.
Five Sigma closes a Series B round or discloses current ARR, growth rate, and cash runway. Would show whether the company is capital-efficient or running low on funding.
A top-15 P&C carrier goes live on Five Sigma's Clive as a system-of-record replacement rather than an overlay. Would show the platform can win core business, not just niche add-on deals.
Key numbers
- Est. $10.1M ARR after 9 years operating
- $18M-$20M total funding raised since 2019
- Caplight momentum score dropped 23 points in 30 days
Named risks
- No Series B closed since January 2022 extension despite 4.5 years passing, raising runway concerns.
- Caplight recorded a -23 point momentum drop in 30 days before 2026-06-21, signaling weakening investor sentiment.
- Core positioning as an AI layer atop Guidewire is directly threatened by Guidewire's own ProNavigator AI launch (2026-04-16).
- Crowded competitive field of better-funded AI-native rivals (Shift, Tractable, Snapsheet, CCC) contesting the same niche.
- Conflicting third-party data on HQ, revenue, and headcount signals limited transparency for evaluators.
Rivals, as read in July 2026
| Rival | Direction | Evidence |
|---|---|---|
| Guidewire | gaining on | Launched ProNavigator AI insights into ClaimCenter on 2026-04-16, eroding Five Sigma's overlay differentiation |
| Shift Technology | contesting | Described as bigger or far better-funded AI claims rival as of 2025-07-11 |
| Tractable | contesting | Larger, better-funded AI damage assessment competitor per 2025-07-11 source |
| Snapsheet | contesting | Configurable no-code claims platform competing directly in AI-native claims space |
| CCC Intelligent Solutions | contesting | Larger auto claims AI ecosystem player, named among better-funded rivals in 2025-07-11 source |
| Duck Creek, Sapiens, Majesco | losing to | Legacy CMS incumbents Five Sigma overlays; risk they add native AI and cut overlay need |
Questions people ask
- Is Five Sigma profitable in 2026?
- Five Sigma has not disclosed profitability. Third-party estimator Latka put 2024 ARR at roughly $10.1M as of 2024-11-29, and no independent source confirms breakeven or profit. With no new funding round since a January 2022 Series A extension, its financial health remains unverified publicly.
- Could Guidewire replace Five Sigma's platform?
- Yes, that's the main threat. Five Sigma's Clive AI layer sits atop Guidewire ClaimCenter, but Guidewire launched ProNavigator on 2026-04-16, embedding its own AI insights directly into claims workflows, narrowing the gap Five Sigma relies on for differentiation.
- Who owns Five Sigma?
- Five Sigma is privately held, founded in 2017 by CEO Oded Barak, CTO Michael Krikheli, and VP R&D Dror Sholomon. Investors include 83North, Aquiline Technology Growth, F2 Venture Capital, and others, per a $12M Series A announced 2021-09-12 and a January 2022 extension.
- Who are Five Sigma's biggest competitors?
- Five Sigma competes with AI-native claims rivals Shift Technology, Tractable, Snapsheet, and CCC Intelligent Solutions, described as bigger or far better-funded as of 2025-07-11, while also depending on and competing against incumbent systems of record Guidewire, Duck Creek, Sapiens, and Majesco.
- Has Five Sigma raised a Series B?
- No public Series B has been announced. Five Sigma's last disclosed raise was a Series A extension backed by Aquiline Technology Growth on 2022-01-19, bringing total disclosed funding to roughly $18M to $20M, with no later-stage round confirmed as of July 2026.
- What is Clive, Five Sigma's AI product?
- Clive is Five Sigma's multi-agent AI Claims Expert, launched 2024-07-17 and marketed as the insurance industry's first AI claims adjuster. It can sit atop CMS platforms like Guidewire or Duck Creek, or run natively, automating intake, communications, and claims triage.
Timeline
- 2026-07-07L+M Development Partners (self-insured real estate) goes live on Five Sigma and Clive
- 2026-06-30Company reports 33% efficiency gain at Resorts World Las Vegas
- 2026-06-21Caplight records -23 point momentum score drop over prior 30 days
- 2026-04-16Guidewire launches ProNavigator, embedding AI insights into ClaimCenter workflows
- 2026-02-17Loadsure deploys Five Sigma's AI claims platform for freight claims
- 2025-09-30Five Sigma named to FinTech Global's InsurTech100 list for second year
- 2024-07-17Five Sigma launches Clive, its multi-agent AI Claims Expert
- 2022-01-19Series A extension announced, backed by Aquiline Technology Growth
- 2021-09-12Five Sigma raises $12M Series A led by 83North
- 2017-01Five Sigma founded by Oded Barak, Michael Krikheli, and Dror Sholomon
Revision history
23 July 2026
First assessed. Losing its protection. The text above is fixed as of this date and is not edited afterwards.
In the same band
Sources
- Insurtech startup Five Sigma raises $12 million Series A (2021-09-12)
- Five Sigma Announces Extension of Series A Investment From Aquiline Technology Growth (2022-01-19)
- Five Sigma 2026 Company Profile
- $10.1M ARR, $20M Raised (2024-11-29)
- Management and Employees List
- L+M Development Partners Goes Live (2026-07-07)
- InsurTech100: Five Sigma Recognized as a Leading Insurance Technology Innovator (2025-09-30)
- Products, Competitors, Financials, Employees, Headquarters Locations (2025-10-01)
- Valuation, Funding Rounds & Stock Price (2026-07-05)
- Introducing Clive: The Insurance Industry's First AI Claims Adjuster (2024-07-17)
- Five Sigma Clive page (2026-07-02)
- Loadsure Uses Five Sigma AI to Accelerate Freight Claims (2026-02-17)