Insurance · Deep dive

Counterpart

An AI-native managing general agent for management and professional liability, selling D&O, EPLI and E&O to small businesses through brokers — betting a proprietary risk score beats a legacy underwriting market that still runs on questionnaires, while renting the balance sheets it needs to grow.

emerging

The question that decides it: Counterpart's whole thesis is that its Digital Risk Score and 'agentic' underwriting produce a structurally better loss ratio on management liability than a legacy market pricing off static questionnaires. Does that edge hold up through long-tail claim development and the current soft D&O/EPLI market — and prove real enough that carrier partners keep supplying capacity and Counterpart can graduate to retaining risk on its own newly capitalized Counterpart Insurance Company — before a capacity partner reprices or pulls its paper, before 175%-a-year premium growth into a softening market surfaces adverse selection, or before Chubb, Travelers and Hartford simply copy the workflow at a scale a $106M MGA cannot match?

My take ★★ Very interesting ★ Interesting − Maybe ✗ Not interesting

Snapshot

Counterpart is a Los Angeles managing general agent, founded in 2019, that underwrites management and professional liability — D&O, EPLI, fiduciary, commercial crime and E&O — for small and mid-sized businesses, sold through wholesale and retail brokers. It carries no balance-sheet risk; it underwrites for A-rated carrier partners such as Markel, Aspen and Westfield Specialty for a commission plus profit share. Its differentiator is a proprietary “Digital Risk Score” and “Agentic Insurance” underwriting stack it claims prices and issues policies several times faster than the legacy market and at a better loss ratio. As of April 2026 it reported ~35,000 policies written, 250,000+ applications processed, ~2,800 brokers, and nearly 175% premium growth in 2025. It has raised $106M across four rounds, most recently a $50M Series C led by Valor Equity Partners. The bull case is a data edge in a stodgy line; the bear case is a thinly capitalized intermediary renting other people’s balance sheets into a softening market.

Founding story

Counterpart is a rare insurtech started by someone with no insurance background, made credible by a co-founder who has nothing but. Hackett had already co-founded Lazada’s Malaysian arm — later part of the group Alibaba bought for a reported $3.5B in 2018 — and Button, a mobile affiliate-commerce platform. An NYU Stern MBA, he approached management liability as a pricing problem obscured by paperwork: small businesses buy D&O and EPLI through brokers filling out static questionnaires, and carriers price off thin, backward-looking data — an inefficiency a data-native underwriter could exploit.

What made the idea bankable was Mike Levins, the co-founder and head of insurance, who had run broker relations and US MGA operations at Hiscox. An MGA lives or dies on two relationships — the wholesale brokers who bring business and the carriers who lend capacity — and Levins is why Counterpart could credibly ask an A-rated balance sheet to back an untested model. Founded in 2019, it launched publicly in 2020-2021 with Markel’s Evanston Insurance Company as first capacity partner.

How it works

An MGA is an outsourced underwriting department. Counterpart holds delegated authority from its carrier partners to quote, bind and service policies in their name within pre-agreed rules; the carriers and their reinsurers hold the risk and pay claims, while Counterpart earns a commission plus, if the book performs, a share of profit. It takes no balance-sheet risk on most of what it writes — which is why the Series C plan to capitalize its own carrier, Counterpart Insurance Company, matters.

Mechanically, a broker submits an application through Counterpart’s platform. Rather than routing it to a human underwriter with a questionnaire, Counterpart runs it through what it calls Agentic Underwriting, powered by the proprietary Digital Risk Score: the system pulls external data on the applicant — firmographics, litigation and regulatory exposure, employment patterns — scores the D&O/EPLI/E&O risk, and returns a quote, the company says, two-to-five times faster than the traditional market. The same data feeds risk mitigation (e.g. zeroHR, an HR-compliance toolkit given to EPLI policyholders to reduce the employment claims it insures) and claims, where Counterpart says prediction models and expense management close claims roughly 50% faster than the industry average at a 4.7 satisfaction score. The loop it sells investors: every application and claim trains the model, tightening pricing on the next account.

Product and business overview

Counterpart sells a suite of management and professional liability lines to small and mid-sized businesses: D&O, EPLI, fiduciary, commercial crime, professional liability/E&O, plus specialty extensions including allied healthcare and architects & engineers liability, and, more recently, professional liability for insurance agents, accountants and real estate professionals and excess coverage across all lines. In 2025 it launched Affirmative AI Coverage, insuring liability from a business’s use of AI tools — a wedge timed to a wave of AI-related employment and E&O litigation. Distribution is entirely through brokers; alongside the coverage it markets broker tooling — fast quoting, 20-plus API partnerships and programs, and support designed to win placements away from carriers’ slower legacy processes.

Business model and pricing

Counterpart’s revenue is MGA economics: a commission on the premium it writes for carrier partners, typically in the range of 15-25% for management liability MGAs, plus a contingent profit-share (a “profit commission”) if the book’s loss ratio beats an agreed threshold. It does not publish rates — pricing is per-account and quoted through brokers — so unit economics are opaque from outside. The number that governs the business is the loss ratio: the profit share, carriers’ willingness to keep supplying capacity, and the viability of its own balance sheet all hinge on the book paying out less than the model predicts. Counterpart claims “industry-leading” loss ratios, but that is self-reported and, in a long-tail line like D&O, unprovable for years. The Series C’s stated use of proceeds — capitalizing Counterpart Insurance Company to retain risk — is the tell: keeping risk earns underwriting profit rather than just fees, but also exposes Counterpart to losses it has so far passed to partners.

Traction over time

The growth is real but young and self-reported. A 175% premium jump in 2025 is fast, but off a small base and in a soft market where rates were falling — which makes rapid volume a flag as much as a triumph, since the easiest way to grow premium in a soft market is to loosen underwriting. Policy, broker and application counts are adoption metrics, not proof the book is profitable.

Market analysis

The addressable market is large and structurally attractive. Global business management liability insurance was estimated at roughly $11B in 2026 (Verified Market Reports), and private-company D&O alone at about $12.4B in 2025, growing ~7% a year to 2034 (Dataintelo). US MGAs wrote $114.1B in direct premiums in 2024, up 16% YoY — evidence carriers are increasingly comfortable delegating underwriting to specialists. The demand tailwind is litigation: EEOC pre-litigation recoveries hit a reported $528M in FY2025, and a new front of AI-hiring-discrimination suits (Mobley v. Workday, Kistler v. Eightfold) is pushing EPLI and E&O exposure up for the small employers Counterpart insures.

The countervailing force is the rate cycle. Management liability entered 2025 soft — ample capacity, declining D&O and EPLI premiums (Aon, 2025) — compressing the premium base an MGA earns commission on and rewarding discipline over growth. An MGA needing venture-scale growth into falling rates is fighting the cycle.

Competitive intel

The field splits into three (full profiles in the sidebar). Direct insurtech rivals — Embroker (>$150M raised, broader shelf, longer history) and Vouch (>$180M, tech-focused, post-layoff) — chase the same small-business buyer, mostly from the distribution side. Adjacent MGAs — Coalition (>$750M raised, multi-billion valuation) and At-Bay ($290M+) — proved the AI-underwriting-MGA model works at scale in cyber; they are both the template Counterpart is measured against and the better-capitalized players most able to enter its line. And the incumbents — Chubb, Travelers, The Hartford — already dominate small-commercial management liability with their own balance sheets, decades of loss data and digital platforms. Counterpart’s edge, if it exists, is underwriting depth in one specialty line and a real data-and-claims loop; its exposure is being out-capitalized by peers 3-7x and by incumbents by orders of magnitude, while its core capability — scoring risk from data — is what incumbents can build on data they already own.

History and evolution

• 2019 — Counterpart founded by Hackett and Levins.
• 2020-2021 — Public launch writing small-business management liability; Markel’s Evanston Insurance Company as first capacity partner.
• Mar 2021 — $10M Series A led by Valor Equity Partners.
• Mar 2022 — $30M Series B led by Vy Capital; Aspen added as a second A-rated carrier (May 2022), taking total funding to ~$40M.
• 2023-2024 — Expands product lines (fiduciary, crime, allied healthcare, A&E) and adds capacity (Westfield Specialty among later partners).
• 2025 — Rebrands the underwriting stack as “Agentic Insurance,” launches Affirmative AI Coverage, reports ~175% premium growth.
• Apr 2026 — $50M Series C led by Valor, total $106M; announces intent to capitalize its own carrier to begin retaining risk.

No public blow-up yet — but the hard chapters for any MGA (a loss-ratio disappointment, a capacity partner walking, a market turn) are cycle-dependent and still ahead of it.

What people say

The case for. Trade press treats Counterpart as a credible category-builder: The Insurer has repeatedly covered its capacity partnerships, and Forbes framed the Series C around a quantifiable litigation tailwind (rising EEOC recoveries, AI-hiring suits). Investors are top-tier and repeat — Valor Equity Partners (early in Tesla and SpaceX) led the A and the C, and Vy Capital led the B and re-upped — meaningful conviction across five years and a soft market. On Glassdoor it carries roughly 3.9/5 with about 70% recommending it, the recurring praise being the founding thesis made real: insurance veterans and technologists who respect each other, under high-trust leadership.

The complaints. The bear case is structural and sharp. First, capacity dependency: Counterpart writes on other companies’ paper, so a partner repricing or withdrawing capacity — as happened across the fronting/MGA world after the Vesttoo collateral scandal — could stall growth overnight; capitalizing its own carrier is an admission of that fragility, not a fix. Second, loss-ratio risk: “industry-leading” ratios are self-reported and, in long-tail D&O/EPLI, unknowable for years, and 175% growth into a softening market is the pattern that precedes adverse-selection surprises. Third, thin capitalization: at $106M, Counterpart is out-funded by Coalition, Vouch and Embroker and dwarfed by the incumbents that own the loss data it aims to out-underwrite. Fourth, sector skepticism: after the Lemonade, Root and Hippo public-market collapses, investors and carriers distrust insurtech loss-ratio and growth claims. And Glassdoor’s dissenting reviews are pointed — a “budget-driven to the extreme” culture, heavy workloads, and promotions to the underqualified while capable people are let go.

Outlook: the open question

Counterpart is a bet that data beats questionnaires in a line incumbents underwrite lazily, and that the resulting loss-ratio edge is durable enough to turn a fee-earning intermediary into a risk-bearing insurer. It works if the Digital Risk Score produces a loss ratio that genuinely leads the market and holds up as this year’s fast-written premiums mature into settled claims — proof that keeps carriers supplying capacity, justifies retaining risk on its own carrier, and converts self-reported growth into a compounding data-and-claims moat. It fails if the edge is an artifact of a benign soft market and long-tail claims come in worse than priced; if a capacity partner reprices or pulls paper before the balance sheet can stand alone; if 175%-a-year growth was bought with loosened underwriting; or if Chubb, Travelers and Hartford replicate the workflow on loss data Counterpart will never have. The growth and funding are visible now; the loss ratio — the only number that ultimately matters — reports last.

What settles it in Counterpart’s favor: maturing loss ratios that beat benchmarks, carrier partners expanding rather than trimming capacity, and a smoothly capitalized own-carrier that starts earning underwriting profit. What settles it against: a loss-development surprise, a capacity partner exit, or evidence that growth outran discipline. With $106M against rivals measured in the high hundreds of millions and incumbents in the tens of billions, Counterpart has to be right about its underwriting before the market cycle or a nervous carrier forces the question.

How a challenger would attack it

Attack the rented balance sheet before it becomes real. Counterpart’s economics run through four A-rated carriers’ paper, and the Series C’s plan to capitalize Counterpart Insurance Company means the next two years are its most fragile: half-fee-business, half-undercapitalized-carrier, with a self-reported loss ratio nobody can verify until long-tail D&O claims mature. A challenger with committed capacity — or its own rated paper from day one — pitches the same ~2,800 wholesale and retail brokers on the one thing Counterpart cannot promise: that the market won’t vanish mid-cycle the way capacity did across the MGA world after Vesttoo. The second vector is transparency-as-weapon: in a post-Lemonade market where carriers and brokers distrust insurtech claims, a challenger that publishes audited loss triangles quarterly makes “industry-leading loss ratios, trust us” untenable. Third, exploit the growth flag Counterpart itself created — 175% premium growth into a soft, falling-rate market is the classic adverse-selection setup, so a disciplined challenger cherry-picks the classes where Counterpart’s Digital Risk Score is loosest (the newest extensions: allied healthcare, A&E, real estate professionals, AI liability) and underprices only where its own data is deep, leaving Counterpart the residue.

Same playbook, new buyer

The scored-underwriting stack travels; the line and geography are choices. Counterpart proved that firmographic, litigation and employment data can price management liability without questionnaires — but it aimed the machine at US small-business D&O/EPLI in the softest part of the cycle. The more promising target is the buyer the incumbents underwrite even more lazily: nonprofit and public-entity management liability, where boards are volunteer-run, EPLI exposure is high, brokers are underserved, and Chubb-class carriers treat the segment as an afterthought. A second shift is upmarket-adjacent: the same zeroHR-style prevent-and-insure loop sold as an embedded product through PEOs and payroll platforms, reaching employers who never call a wholesale broker at all — a channel Counterpart’s broker-only distribution structurally cannot touch without alienating the 2,800 brokers who feed it. Counterpart won’t follow easily: its capacity agreements, Digital Risk Score training data and profit-share economics are all tuned to the broker-submitted small-business account, and with $106M against Coalition-scale rivals it cannot afford to fight on two fronts while capitalizing a carrier.

Sources and further reading

• Counterpart raises $50m Series C to tackle AI-era business risks (FinTech Global, April 29 2026)
• ‘Insurance Is Failing Small Businesses’ — SpaceX Backers Bet $50M On AI (Forbes, April 28 2026)
• Counterpart Expands Insurance Leadership Team as Demand Grows (BusinessWire, March 25 2026)
• Counterpart Introduces Agentic Insurance, AI-Powered Management and Professional Liability Systems (BusinessWire, March 12 2025)
• Markel-backed management liability insurtech Counterpart raises $10mn (The Insurer, March 2021)
• Counterpart Raises $30 Million in Series B Funding Round (Insurance Journal, March 1 2022)
• Counterpart Adds Additional A-Rated Carrier (Aspen) to Expand Management Liability (BusinessWire, May 10 2022)
• Management Liability Insurance Market in 2025: Stability Amid Evolving Risks (Aon, 2025)
• Private Company D&O Insurance Market Research Report (Dataintelo, 2025)
• Counterpart Reviews (Glassdoor, accessed 2026)