Shepherd
AI-native managing general underwriter (MGU) writing commercial casualty — general liability, commercial auto, workers' compensation, excess liability — for US construction contractors, with underwriting automation built on data feeds from Procore, Autodesk and other construction software.
www.shepherdinsurance.com ↗Score
- Traction (named carrier deployments)0 carrier deployment(s) with public source.
- n/a
- Maturity (years since founding)5 years since founding (2021).
- 2/5
- Coverage (insurance lines supported)2 line(s) supported: commercial, workers-comp.
- 2/5
- Analyst recognition (Celent / Gartner / Forrester / Everest / ISG)3 mention(s).
- 2/5
What it does
Shepherd is a San Francisco-based managing general underwriter for commercial construction casualty. It was founded in 2021 by Justin Levine, Mohamed El Mahallawy and Steve Buonpane, went through Y Combinator's Winter 2021 batch, and now writes general liability, commercial auto, workers' compensation and excess liability for US contractors.
What Shepherd actually is. This is not a piece of software a carrier buys. It is an MGU: Shepherd originates, underwrites and manages a book of construction risk on paper from licensed carrier and reinsurance partners. Brokers place business with it; carriers cede capacity to it. The "AI" lives inside Shepherd's own submission intake and portfolio pipeline — a reader shopping for an underwriting workstation should know that Shepherd is a risk carrier, not a tool they can license.
Funding and capacity. Cumulative disclosed funding is approximately $67M. The seed round was $6.15M in September 2021, led by Spark Capital with Susa Ventures, Y Combinator, Procore Technologies and Greenlight Re Innovations. A $13.5M Series A followed in February 2024, led by Costanoa Ventures with Intact Ventures, Era Ventures, Greenlight Re and Spark Capital. A $42M Series B was announced in March 2026, led by Intact Private Capital with Spark and Costanoa participating — Intact was simultaneously named a long-term capacity provider.
What the AI does. Shepherd's own Series B post describes the intake target as "email in, price out, no human intervention until the last mile", with a public claim of a 24-hour submission-to-indication turnaround and a two-year roadmap to take underwriter throughput from roughly 20 accounts a month to 200. Procore, Autodesk, OpenSpace, DroneDeploy and Samsara are named as data sources feeding underwriting.
Traction, with the usual MGU caveat. Shepherd has disclosed 1,500+ policies and 600+ customers covering over $400B of insured project value across the 24 months to March 2026. No specific contractor names appear in primary Shepherd press materials reviewed here — customer identification in construction MGU programs typically stays with the broker of record, not the underwriter.
Analyst gap. No Gartner, Celent or Forrester coverage surfaced in public search. Sourcing is trade press (The Insurer, Carrier Management, TechCrunch, Insurtech Insights) and Shepherd's own announcements.
Known limitations
- Shepherd is a Managing General Underwriter, not a software vendor. Carriers and brokers do not license a Shepherd product — they cede capacity to, or place business with, a Shepherd program. The AI underwriting workflow is internal to Shepherd's own book. (The Insurer)
- Shepherd writes commercial construction casualty only. Workers' compensation was added after the initial excess-liability launch and the company has publicly described workers' comp capacity as still expanding. (Insurtech Insights)
- Shepherd's Series B announcement (March 2026) described its automation target as 'the first fully agentic submission intake in commercial insurance' and framed full autonomous underwriting as a two-year roadmap, not a shipped capability. (Shepherd)