Pie Insurance review: small business insurance

Peer comparison

How Pie Insurance compares

Side-by-side against the 4 carriers we score most similarly.

Carrier	Our score	Positioning	Starting price	Coverage	AM Best
	7.9	Single-carrier program for SMBs	GL $68/mo	9.0/10	A+
	7.2	Berkshire-backed contractual umbrella	GL $28/mo	8.0/10	A++
	8.1	Broad-ladder primary carrier	GL $42/mo	9.0/10	A++
	7.0	Professional services E&O focus	GL $30/mo	7.5/10	A

• 
  7.9

  Positioning

  Single-carrier program for SMBs

  Starting price

  GL $68/mo

  Coverage

  9.0/10

  AM Best

  A+

• 
  7.2

  Positioning

  Berkshire-backed contractual umbrella

  Starting price

  GL $28/mo

  Coverage

  8.0/10

  AM Best

  A++

• 
  8.1

  Positioning

  Broad-ladder primary carrier

  Starting price

  GL $42/mo

  Coverage

  9.0/10

  AM Best

  A++

• 
  7.0

  Positioning

  Professional services E&O focus

  Starting price

  GL $30/mo

  Coverage

  7.5/10

  AM Best

  A

Pie Insurance is one of the few monoline workers' compensation specialists in the direct-to-business market. The carrier was founded in 2017 by Dax Craig and John Swigart around the thesis that small-business WC — historically sold through brokers on paper priced for mid-market exposure — was structurally underserved by generalist commercial insurers.¹ For the first six years of Pie's operating history, WC was the entire product. In 2024-2025, Pie extended into a business owner's policy (BOP) offering available in a subset of states.² Writing on its own admitted paper — primarily Pie Casualty Insurance Company (NAIC 10997, Illinois-domiciled) and The Pie Insurance Company (NAIC 21857, Ohio-domiciled), pooled affiliates under the Pie Insurance Group umbrella — the carrier carries an A- (Excellent) rating from A.M. Best, affirmed March 27, 2025.³⁴⁵

Within workers' comp specifically, Pie's product is category-leading in three dimensions that broad-ladder carriers struggle to match: instant AI-driven quote-to-bind (most WC placements through broker channels take days or weeks), pay-as-you-go payroll billing tied to actual payroll rather than estimated annual payroll (no annual audit-bill surprise), and state-specific rate transparency published in per-$100-of-payroll format rather than as a monthly "from $X" figure.¹⁶ Rates range from roughly $0.57/$100 of payroll in Texas to $2.32/$100 of payroll in Alaska, depending on class code and state, per Pie's own published data. For a WC-primary buyer — restaurants with hourly servers, light-contracting businesses with crews, fitness studios with employee trainers — that product depth is the reason to choose Pie over Hartford's WC line or NEXT's annual WC offering.

The structural caveats are three. First, Pie is monoline-plus — WC is the core product; BOP is a newer, less operationally mature extension. Second, the A- rating is below the A+/A++ of most peers in our coverage set and Pie's AM Best rating sat under-review-with-negative-implications briefly in March 2024 before being affirmed at A- in March 2025, which is a recent credit-quality event sophisticated buyers should know about.³⁷⁸ Third, Pie's AI-driven underwriting is fast for standard class codes but thins at the edges — non-standard or high-hazard operations that a Hartford or Travelers broker could place through underwriter discretion may get declined by Pie's rule-based model. We land the overall rating at 7.6.

Our quick verdict

Pie Insurance earns 7.6 out of 10 as a workers' compensation specialist whose product depth in WC is category-leading on three dimensions broad-ladder competitors struggle to match: instant AI-driven quote-to-bind in minutes, pay-as-you-go billing tied to actual rather than estimated payroll, and state-specific rate transparency published in per-$100-of-payroll format. Best for small businesses whose primary insurance need is workers' compensation — restaurants, light-contracting, fitness studios, and service businesses with hourly employees — especially buyers with variable headcount that benefits from pay-as-you-go billing and buyers who value instant quote-to-bind over broker-channel WC placement. Not the right fit for businesses seeking a bundled GL plus BOP plus WC program on one carrier, WC-only buyers in the eleven states where Pie is unavailable, or non-standard high-hazard operations outside Pie's automated underwriting appetite. Pricing is payroll-percentage rather than flat-monthly: roughly $0.57 per $100 of payroll in Texas to $2.32 in Alaska.

• Our rating: 7.6 / 10 (Good)
• Scoring category: A — direct carrier with mature NAIC volume (methodology)
• Best for: small businesses whose primary insurance need is workers' compensation — restaurants, trades, light contracting, service businesses with hourly employees — especially buyers who value pay-as-you-go payroll billing and instant quote-to-bind
• Not for: businesses looking for a bundled GL + BOP + WC program on one carrier; WC-only buyers in the 11 states where Pie's WC isn't available; non-standard or high-hazard operations outside Pie's automated underwriting appetite
• Pricing structure: payroll-percentage rates, not a flat monthly figure — roughly $0.57/$100 payroll (TX) to $2.32/$100 payroll (AK) by class code and state⁶
• A.M. Best rating: A- (Excellent), affirmed March 27, 2025 — Pie Casualty Insurance Company (NAIC 10997) and pooled affiliate The Pie Insurance Company (NAIC 21857)³
• NAIC complaint index: NAIC CIS did not return a commercial liability filter for Pie Casualty Ins. Co. (NAIC 10997) in our 3-year (2023–2025) extraction — consistent with Pie's workers' compensation specialty; see Complaint history and claims experience below

What Pie is

Pie Insurance Holdings, Inc. is an independent, venture-backed insurance carrier founded in 2017, headquartered at a dual hub in Washington, DC and Denver, CO.¹ As of 2025, Pie reports roughly 55,000 policies in-force across its workers' compensation and BOP books, with recent geographic expansion including a WC launch in Connecticut in August 2025.⁹¹⁰

The primary risk-bearing entities are pooled affiliates under the Pie Insurance Group umbrella:

• Pie Casualty Insurance Company (NAIC 10997, Illinois-domiciled, Chicago-based) — the more frequently cited underwriting entity.⁴
• The Pie Insurance Company (NAIC 21857, Ohio-domiciled, Columbus-based) — pooled affiliate.⁵

Both entities carry the A- (Excellent) rating from A.M. Best with the long-term issuer credit rating at a- (Excellent).³ Unlike biBerk's multi-entity Berkshire group or Hartford's multi-entity structure, Pie's pooled affiliates are specifically named — Pie Casualty (primary) and The Pie Insurance Company (affiliate). A policy may be issued by either entity depending on state and product, with both pool members contributing to reserves.

The March 2024 AM Best under-review event worth knowing about. On March 11, 2024, A.M. Best placed both Pie entities' ratings under review with negative implications — signaling potential downgrade pending further evaluation of Pie's financial performance and reserve adequacy.⁷⁸ A.M. Best subsequently removed the ratings from under-review status and affirmed the A- (Excellent) rating on March 27, 2025.³ The affirmation is the current rating, but the under-review episode is a material recent event — buyers evaluating Pie should understand that the A- rating was recently defended rather than simply held. Our Financial Strength scoring reflects both the current A- affirmation and the recency of the review event.

Structurally, Pie is a direct admitted insurance carrier — not an MGA, not a broker. Policies are issued on Pie paper; claims are handled by Pie's own claims operation; indemnity dollars come from the pool members' balance sheets. This is the same Category A framework we apply to Hartford, Travelers, Hiscox, and biBerk, adapted for the smaller scale and narrower product focus that a 2017-founded monoline specialist carries.

Policies Pie offers

Pie writes two commercial lines:²

• Workers' compensation — the core product since 2017. Native WC on Pie paper, payroll-based pricing, pay-as-you-go monthly billing tied to actual reported payroll rather than estimated annual payroll. Available in 39 states plus DC, with ongoing expansion; August 2025 added Connecticut to the footprint.⁶¹⁰
• Business owner's policy (BOP) — a newer product extension launched in 2024-2025 alongside continued WC expansion. Available in a subset of states; pricing not publicly published.²

Eight commercial lines that Pie does not write: general liability (standalone), professional liability, commercial auto, cyber liability, commercial property (standalone), commercial umbrella, directors and officers, and employment practices liability.^1112131415 Businesses that need any of these will need to pair Pie with another carrier or choose a broader writer like Hartford or Travelers.

State availability for WC. Pie's workers' comp is available in 39 states plus DC.⁶ It is not available in:

• Monopolistic-fund states (OH, ND, WA, WY) — structural, applies to every carrier.
• Additional carrier-choice exclusions — Hawaii, Idaho, Massachusetts, Maine, Minnesota, Montana, South Dakota. For small businesses in any of those seven states, Pie's WC simply isn't an option regardless of other fit.

What Pie actually costs

Pie's pricing model is structurally different from monthly-starting-price direct carriers like NEXT or Hiscox. The carrier publishes payroll-percentage rates rather than a uniform "from $X/mo" figure:⁶

• Range across states and class codes: approximately $0.57 per $100 of payroll (Texas, low-risk classes) to $2.32 per $100 of payroll (Alaska, higher-risk classes).
• What this means in dollars: a small restaurant with $200,000 in annual payroll might pay $1,140/year at the Texas floor rate or $4,640/year at the Alaska top rate — roughly $95 to $387 per month. Real quotes depend on class code, state, and historical claims.
• No uniform monthly "from $X" floor. Pie doesn't publish a single number because WC rates genuinely vary by factor of 4x or more across states and class codes; any single "starting at" figure would mislead buyers.

That pricing-transparency approach is more honest than a monthly starting floor for workers' comp specifically. Insureon's aggregated WC benchmark for small business is roughly $45/mo median across its marketplace,¹¹ and WC rates vary by a factor of three or more across states per Insureon's state-by-state comparison.¹⁶ Publishing a single "$14/mo" floor (as some direct carriers do for WC) compresses that variance into a misleading number; publishing the per-$100-payroll rate range across states is more informative for a buyer who can actually compute their own estimate.

Pay-as-you-go billing. Pie bills monthly WC premium based on actual reported payroll rather than estimated annual payroll.¹ Traditional WC policies estimate payroll upfront, collect the full estimated premium across the year, then audit at renewal — resulting in either a large audit-bill surprise (if actual payroll exceeded estimate) or a refund (if it fell short). Pie's model ties premium to actual payroll month-by-month, which means no year-end audit surprise and better cash-flow predictability for businesses with variable headcount. NEXT and Hartford also offer pay-as-you-go WC,¹⁷¹⁸ but Pie was built around the model rather than adding it as a feature later.

BOP pricing — not publicly published. The newer BOP extension does not publish starting prices.² Buyers need to complete a quote form to see a BOP number. For a buyer comparing Pie BOP against Hartford BOP (~$141/mo average) or biBerk BOP (starting price not published), Pie BOP pricing transparency is narrower than the WC product's.

Our Pricing score of 7.5 reflects: honest payroll-percentage transparency on the core WC product (positive, more useful than a flat monthly floor for a payroll-based line); pay-as-you-go billing as a model advantage (positive); BOP pricing opacity as a single-line gap (negative offset).

See full cost analysis: Our workers' compensation insurance cost guide, and business owners policy (bop) cost guide break down typical pricing across industries and states.

Coverage breadth: where Pie is strong and where it's thin

A note on scoring a monoline specialist. Pie writes two lines. Scoring Pie on breadth against a ten-line direct carrier like Hartford or Travelers would mismeasure the product — Pie is a deliberate WC specialty, not a generalist carrier that failed to expand. Our Coverage Breadth score of 8.0 reflects category-leading depth within workers' comp specifically, adjusted downward for the BOP extension's newer operational maturity (methodology).

Where Pie is strong — within WC. The workers' comp product is the deepest direct-bind SMB WC offering we cover:

• Payroll-based pricing transparency.⁶ Per-$100-of-payroll rates published across states and class codes — more informative than a single monthly floor for a payroll-variable line.
• Pay-as-you-go billing tied to actual payroll.¹ Monthly reporting, no annual audit-bill surprise, cash-flow predictable.
• Instant AI-driven quote-to-bind. Online quote in minutes rather than the days-to-weeks broker-channel WC placement cycle.
• Industry-specific class code optimization.² Pie's underwriting model is tuned specifically for SMB WC class codes rather than treating WC as one line in a broad commercial book.
• Geographic expansion pattern. Adding states incrementally with state-specific rate filings rather than blanket rollout, which tends to produce more accurate state-level pricing.¹⁰

Where Pie is thin. Three structural gaps drive our Coverage score to 8.0 rather than higher.

First, monoline plus early-stage BOP.² For the dominant period of Pie's operating history, WC was the entire product. The BOP extension launched in 2024-2025 is a newer, less-mature offering. A buyer placing BOP with Pie is buying a product with meaningfully shorter operational and claims-handling track record than the WC line. For BOP-primary buyers, Hartford, Travelers, or biBerk's older BOP products are more-tested options.

Second, 11-state WC unavailability.⁶ Monopolistic states (OH, ND, WA, WY) are structural — no private carrier writes WC there. But Pie also excludes HI, ID, MA, ME, MN, MT, SD by carrier choice. For small businesses in any of the seven carrier-choice-excluded states, Pie WC simply isn't available.

Third, underwriting appetite narrows for non-standard risks. Pie's AI-driven instant-quote model works well for standard class codes and typical SMB profiles; non-standard operations, high-hazard classes (heavy construction, roofing, long-haul trucking with loss history), or businesses with unusual exposure patterns may get declined by the rule-based underwriting where a Hartford or Travelers broker could place the risk through underwriter discretion. For a non-standard-profile SMB, broker-placed WC with a generalist carrier is often more accessible than Pie's direct flow.

Industry-specific strengths. Pie writes well in SMB classes where WC is a material exposure:² general contractors, restaurants, fitness and wellness, landscapers, cleaners, electricians, plumbers, HVAC, accountants, marketing agencies, consultants, e-commerce and retail, real estate, and photographers. The class-code specialization is the operational backbone of the product.

Complaint history and claims experience

Scoring category note. Pie Insurance is a Category A carrier under our methodology — direct carrier with mature NAIC volume (methodology). We attempted to retrieve a 3-year commercial liability complaint index for Pie Casualty Ins. Co. (NAIC 10997) from NAIC CIS. The commercial liability filter did not return data at the entity level in our 2023–2025 extraction — consistent with Pie's workers' compensation specialty positioning and the absence of a material commercial liability book outside of WC-adjacent coverages. With no CL ratio to read, we cannot score on CIS evidence and the sub-threshold volume rule does not formally apply either — the dimension is structurally absent for this entity on this line. We retain a 7.0 neutral baseline on Complaint History and disclose the data state directly. This is a reliability call about the data, not a finding about the carrier's complaint handling; readers evaluating Pie on WC-specific complaint patterns should consult state DOI reports, which we checked for material enforcement actions and found none.¹⁹

The March 2024 under-review-negative event. Worth surfacing directly in the claims-history context. On March 11, 2024, A.M. Best placed both Pie entities under review with negative implications — indicating a potential downgrade if financial or reserve concerns were not addressed.⁷⁸ A.M. Best affirmed the A- rating on March 27, 2025, lifting the under-review status.³ The episode is a recent credit-quality event — not a finding that Pie was insolvent, but a signal that the rating authority flagged concerns that required active management to resolve. Our Financial Strength scoring reflects both the current A- affirmation and the recency of the review event (which is why Pie scores 7.5 rather than 7.0 on FS despite the A- band — the affirmation is the forward-looking signal).

Claims process. Pie operates its own WC claims organization, specialized for the single line.¹ WC-specific claims expertise is different from general commercial claims — return-to-work programs, modified-duty coordination, medical case management, and state WC regulatory compliance all benefit from specialist operational depth. Pie's claims team is smaller in absolute scale than Hartford's or Travelers' commercial claims org, but focused entirely on WC.

Regulatory actions. We checked public state DOI enforcement records for material market-conduct or solvency actions against Pie Casualty Insurance Company and The Pie Insurance Company. No recent enforcement action is on file as of our research date.

Net. The 7.0 Complaint History score is a Category A baseline, held because the NAIC CIS commercial liability cut does not return data at the entity level for Pie Casualty — the carrier is WC-specialty, and the CL slice is structurally thin for this writer. Our Claims Experience score of 7.5 reflects the WC-specialty operational focus (positive) offset by smaller scale than generalist peers and the under-review-negative episode affecting the broader operational track record (slight negative). The CIS gap does not pull either direction — we simply decline to score on a dimension the primary-source instrument does not cover for this entity.

The honest take

What works well.

1. Category-defining workers' comp product within our direct-bind coverage set.²¹ Instant AI-driven quote-to-bind, payroll-percentage pricing transparency, pay-as-you-go monthly billing tied to actual payroll. Hartford and NEXT also offer pay-as-you-go; Pie was built around it as the core model rather than adding it as a feature to a broader product.
2. Transparent payroll-percentage pricing.⁶ Publishing rates from $0.57/$100 payroll (TX) to $2.32/$100 payroll (AK) by class code and state is more informative than a misleading single "from $X/mo" floor for a payroll-based line.
3. Direct admitted carrier structure.⁴ Not an MGA, not a broker. Pie Casualty Insurance Company (NAIC 10997) and The Pie Insurance Company (NAIC 21857) are the risk-bearing entities; claims flow through Pie's own operation.
4. A.M. Best A- (Excellent) affirmed March 2025.³ The rating authority explicitly affirmed A- after a year of under-review-negative status — that's a forward-looking credit signal worth more than the rating itself.
5. Geographic expansion discipline.¹⁰ Adding states with state-specific rate filings rather than blanket rollout produces better-calibrated pricing; Connecticut added August 2025, suggesting ongoing state-specific underwriting investment.

What doesn't work.

1. Monoline plus early-stage BOP.² For buyers who need a bundled GL + BOP + WC program on one carrier, Pie is structurally limited to WC (plus a newer, less-mature BOP). The eight commercial lines Pie doesn't write means any business with broader needs will have to pair Pie with another carrier.
2. A- rating with recent under-review-negative episode.⁷³ The A- is below A+/A++ peers (Travelers, biBerk, Hartford, NEXT post-acquisition), and the March 2024 under-review-negative status is a recent credit-quality event that buyers should understand even though the rating was affirmed.
3. 11-state WC unavailability.⁶ Monopolistic states (4) plus carrier-choice exclusions (HI, ID, MA, ME, MN, MT, SD — 7 more). For small businesses in any of those 11 states, Pie isn't an option for WC.
4. Underwriting appetite thin for non-standard risks. AI-driven instant quote works for standard class codes; non-standard operations or unusual loss history profiles may be declined where broker-placed Hartford or Travelers could place the risk through underwriter discretion.
5. BOP product is newer and less operationally mature than WC.² A buyer placing Pie BOP is buying a product with meaningfully shorter operational track record than the WC line. BOP-primary buyers should understand this caveat before choosing Pie over Hartford, biBerk, or Travelers BOP offerings.

Who should skip Pie.

• Businesses needing a bundled multi-line program (GL + BOP + WC + PL) on one carrier — Hartford or Travelers is structurally better.
• WC buyers in the 11 states where Pie doesn't write.⁶
• Businesses with non-standard or high-hazard operations outside Pie's automated underwriting appetite.
• Buyers who need BOP as their primary product (vs. WC) — BOP is newer and less mature than the WC line.
• Buyers who weight financial strength heavily and want A+/A++ paper, not A-.

Who Pie is best for

Pie is a strong fit in three specific scenarios:

1. Small businesses whose primary insurance need is workers' comp. Restaurants with hourly servers, general contractors with crews, fitness studios with employee trainers, landscapers, cleaners, electricians, plumbers, HVAC businesses.² Businesses where WC is the dominant insurance exposure by cost and operational complexity benefit most from a WC-specialist carrier.
2. Businesses with variable headcount. Pay-as-you-go payroll billing tied to actual rather than estimated payroll is genuinely operationally useful for businesses with seasonal, part-time, or contractor-heavy staffing models.¹ No annual audit-bill surprise; cash flow matches actual payroll.
3. Direct-to-business WC buyers who want instant quote-to-bind. The AI-driven underwriting model is among the fastest WC placements in the market for standard class codes, measured against broker-channel WC placements that typically take days or weeks.

Business size: Small (micro through small-to-mid). business_size_focus is "small" — Pie writes across the small-business range but doesn't target mid-market or enterprise.

Alternatives to consider

If Pie's monoline focus, state gaps, or A- rating doesn't fit, three alternatives — each addressing a different Pie limitation:

1. The Hartford — If you want WC as part of a broader ten-line program on one carrier, Hartford writes native WC alongside GL, BOP, PL, commercial auto, cyber, property, umbrella, D&O, and EPLI on A+ paper.²⁰¹⁸ Hartford's WC average is ~$86/mo; Pie's payroll-based pricing may be cheaper or more expensive depending on class and state, but Hartford wins on program completeness if you need multiple lines on one carrier.
2. NEXT Insurance — If you want a digital direct-bind carrier with WC available alongside GL, BOP, PL, commercial auto, cyber, and property on A+ paper (post-ERGO acquisition), NEXT is the closer direct-digital peer to Pie on UX and pricing.¹⁷²¹ NEXT's WC starts from $14/mo on a monthly floor rather than Pie's payroll-percentage model — NEXT is faster to quote a headline number; Pie is more accurate once you compute against your actual payroll.
3. Travelers Small Business — If you want A++ paper (vs. Pie's A-) with the same broad-ladder completeness as Hartford and can tolerate enterprise-tuned digital UX, Travelers is the broader direct-bind alternative. Travelers writes WC in 44 states plus DC with Insureon-reported median pricing around $45/mo.

Different choices for different priorities. Monoline WC specialty with pay-as-you-go payroll billing — stay with Pie. Bundled multi-line program including WC — Hartford (A+ broad ladder). Digital direct-bind with WC plus broader lines — NEXT. Strongest paper with broad ladder — Travelers.

How to get a Pie quote

Pie is direct-to-business via the carrier's website and through agent channels that appoint Pie for WC placements.²¹ For direct placement:

1. Start at pieinsurance.com and initiate the WC quote flow (BOP is available in a subset of states through the same flow).
2. Answer questions about your business: entity type, state, industry class code, employee count, annual payroll estimate, prior claims history, specific operations.
3. Payroll reporting setup. Pie's pay-as-you-go model requires ongoing monthly payroll reporting. You'll integrate payroll data (direct entry or through a payroll provider connector) before or at binding.
4. Review the quoted premium — displayed both as per-$100-payroll rate and as estimated monthly/annual premium based on your stated payroll.
5. Add payment and bind; Certificate of Insurance available from the customer portal.

What Pie will ask for: business name, EIN, state, industry class code (they'll help identify from operations description), employee count and payroll, prior WC claims history (including any large individual claims), specific operations, and ownership structure.

If you need a human: Pie has phone and agent-channel support. For non-standard class codes or operations profiles that hit the edges of the AI underwriting model, agent-channel placement may be more efficient than retry-and-fail loops in the direct flow.

Alternatives to Pie Insurance

Different choices for different priorities.

7.9/10

The Hartford

Growing small businesses that need a single-carrier program across five or more commercial lines — especially those needing D&O, EPLI, commercial umbrella, native workers' comp, or commercial auto in the same placement; contractors, trades, and field-services businesses needing GL + WC + commercial auto + umbrella on one carrier; buyers who value 215-year claims-relationship depth over lowest premium.

Better if

Growing small businesses that need a single-carrier program across five or more commercial lines — especially those needing D&O, EPLI, commercial umbrella, native workers' comp, or commercial auto in the same placement; contractors, trades, and field-services businesses needing GL + WC + commercial auto + umbrella on one carrier; buyers who value 215-year claims-relationship depth over lowest premium.

Read full review

7.8/10

NEXT Insurance (ERGO NEXT)

Micro-businesses and freelancers under ~$1M revenue in service classes (cleaning, landscaping, personal training, photography, light contracting, consulting, professional services) that want online quote-to-bind in minutes on admitted paper with strong credit behind it.

Better if

Micro-businesses and freelancers under ~$1M revenue in service classes (cleaning, landscaping, personal training, photography, light contracting, consulting, professional services) that want online quote-to-bind in minutes on admitted paper with strong credit behind it.

Read full review

8.1/10

Travelers Small Business

Small businesses seeking the strongest combination of credit quality, coverage breadth, and at-market pricing on direct-bind paper — especially growing businesses that need D&O, EPLI, or commercial umbrella alongside primary liability; trades, contractors, and field-services businesses needing the full GL + WC + auto + umbrella package on A++ paper.

Better if

Small businesses seeking the strongest combination of credit quality, coverage breadth, and at-market pricing on direct-bind paper — especially growing businesses that need D&O, EPLI, or commercial umbrella alongside primary liability; trades, contractors, and field-services businesses needing the full GL + WC + auto + umbrella package on A++ paper.

Read full review