Dairyland Cycle Insurance

What Dairyland Cycle Insurance does

Dairyland Insurance Company is a US specialty vehicle insurance provider operating as a brand underwritten by members of the Sentry Insurance Group, headquartered at 1800 North Point Drive, Stevens Point, Wisconsin. Founded in 1955 and operating for over 70 years, Dairyland focuses on motorcycle, nonstandard auto, and recreational vehicle insurance, serving high-risk auto drivers and specialty vehicle owners who face difficulty obtaining coverage from standard carriers. Its product portfolio includes auto, motorcycle, ATV/UTV, snowmobile, dirt bike, and scooter/moped coverage, supplemented by SR-22 and FR-44 certificates for high-risk drivers and partner-distributed Mexico auto (IIGNS), RV, and renters insurance (MyLifeProtected). Customer segments are horizontally distributed across motorcycle riders, nonstandard auto drivers, off-road vehicle owners, and scooter/moped riders.

Dairyland operates a multi-channel insurance technology platform supporting online self-service quoting, policy management, claims submission and tracking, and a mobile application available on iOS and Android for bill payment, ID card access, and account management. Underlying technology is described as an insurance technology platform with 24/7 claims service availability. Distribution combines a network of local insurance agents, dedicated phone sales lines for auto and motorcycle quotes, online self-service, and a mobile app. Customer acquisition is supported by organic social media presence across Facebook, X, Instagram, and YouTube, plus a content marketing resource center covering auto, motorcycle, and off-road insurance topics.

Revenue is generated through recurring insurance premium payments on annual policies, typically billed monthly or as a single payment. Pricing is quote-based and varies by vehicle type, driver history, coverage levels, and location. Dairyland's stated differentiators include 70 years of brand history, domain specialization in nonstandard auto and motorcycle coverage, 24/7 customer support, and a 4.5/5 customer service rating. The company is privately held within Sentry Insurance Group with no external venture capital investment or public shareholders, and its most recent strategic move is an April 2025 partnership with digital insurance platform Roamly to distribute products across recreational vehicle, marine, and motorcycle lines in Florida.

Name

Dairyland Cycle Insurance

Legal name

Dairyland Insurance Company

Website

https://dairylandinsurance.com

Company type

Private

Founded year

1955

Operating status

Operating

Headcount range

5,001–10,000 employees

Short description

Dairyland Insurance Company is a US specialty vehicle insurer operating under Sentry Insurance Group, providing motorcycle, nonstandard auto, ATV/UTV, snowmobile, dirt bike, and scooter/moped coverage to high-risk drivers and recreational vehicle owners across the United States.

Ownership category

akta.pro rank

Product category

Specialty Vehicle Insurance

SIC

Fire, Marine & Casualty Insurance (6331)

akta.pro primary industry

Fleet & Commercial Auto Liability (FSAJABAA)

Keywords

• Motorcycle insurance
• Nonstandard auto insurance
• Recreational vehicle insurance
• High-risk driver insurance
• Specialty vehicle coverage

Headquarters

HQ city

Stevens Point

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure

Revenue model

1. Insurance Premiums: Recurring insurance premium payments from policyholders for auto, motorcycle, ATV/UTV, snowmobile, dirt bike, scooter/moped, Mexico auto, RV, and renters coverage. Policies are typically annual with monthly or single payment options.

Pricing tiers

Go-to-market motion1 record

Distribution channels4 records

Marketing channels3 records

Core offering

Dairyland Cycle Insurance is a specialty vehicle insurance provider offering motorcycle, auto (including nonstandard/high-risk), and recreational vehicle coverage (ATV/UTV, snowmobile, dirt bike, scooter/moped). Policies are sold directly to consumers via local agents, phone, online quotes, and a mobile app. The company also distributes partner-branded Mexico auto, RV, and renters coverage through trusted providers.

Product overview

Dairyland Cycle Insurance is a direct-to-consumer insurance provider specializing in vehicle and recreational insurance products. The company offers a unified portfolio of core insurance products centered on motorcycles and off-road vehicles (ATV/UTV, snowmobile, dirt bike), supplemented by standard auto insurance including nonstandard/high-risk coverage. Additional products include Mexico auto coverage, RV insurance, and renters insurance. The product architecture is a single-brand platform with co-branded partner products for supplementary coverage types. Dairyland also provides a mobile application for policy management and account access.

Differentiator

Problem solved

Functional benefit

Products and services

• Auto Insurance Standard auto insurance coverage for personal vehicles, including liability, collision, and comprehensive coverage options, designed for drivers including those with nonstandard risk profiles.
• Motorcycle Insurance Specialized insurance coverage for motorcycles including cruisers, sport bikes, and touring bikes, offering liability, collision, comprehensive, and roadside assistance options.
• ATV/UTV Insurance Insurance coverage for all-terrain vehicles and utility task vehicles used for off-road recreation.
• Snowmobile Insurance Insurance coverage for snowmobiles used during winter months.
• Dirt Bike Insurance Insurance coverage for off-road dirt bikes used on trails and motocross tracks.
• Scooter/Moped Insurance Insurance coverage for scooters and mopeds, including mobility scooters.
• SR-22 Insurance High-risk auto insurance for drivers requiring SR-22 certificates, commonly needed after DUI/OWI offenses.
• FR-44 Insurance Insurance coverage for drivers in Virginia and Florida requiring FR-44 certificates following DUI or other offenses.
• Mexico Auto Insurance Specialized coverage for driving in Mexico, offered through trusted partner IIGNS.
• RV Insurance Recreational vehicle insurance coverage offered through trusted partner MyLifeProtected.
• Renters Insurance Renters insurance coverage offered through trusted partner MyLifeProtected.

Quantifiable outcome

• 4.5/5 customer service rating
• +1 more outcomes

Segments4 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration1 record

Feature3 records

Partnerships

One partnership is on record.

• RoamlycoreGTM or Marketing Partner · 22 April 2025Roamly, a digital insurance platform expanding into Florida, has partnered with Dairyland as one of eight national carrier partners to offer digital-first insurance products across recreational vehicle, marine, and motorcycle lines. This partnership enables Dairyland products to be distributed through Roamly's digital platform to Florida customers.

Scale indicators3 records

Recent moves5 records

Expansion highlights4 records

Direct peers

• Progressive: Progressive is the largest U.S. writer of personal auto and motorcycle insurance, including nonstandard drivers. It is the closest direct competitor to Dairyland across motorcycle, ATV, and nonstandard auto lines.
• Markel Insurance: Markel is a specialty insurer with a strong motorcycle, powersports, and recreational vehicle book, serving enthusiasts with tailored coverage. Directly comparable to Dairyland's motorcycle, ATV, and snowmobile offerings.
• Foremost Insurance Group: Foremost (a Farmers Insurance subsidiary) specializes in insurance for mobile homes, motorhomes, motorcycles, ATVs, and other specialty vehicles. Highly comparable product mix to Dairyland's recreational vehicle and powersports portfolio.
• National General Insurance: National General, now an Allstate company, is a leading writer of nonstandard and specialty personal auto insurance including motorcycle coverage. Direct overlap with Dairyland's nonstandard auto and SR-22/FR-44 lines.
• Kemper Corporation: Kemper is a specialty insurer focused on nonstandard personal auto and high-risk drivers, including SR-22 filings. Closely comparable to Dairyland's nonstandard auto segment for high-risk customers.

Broad incumbents

• GEICO: GEICO is one of the largest U.S. personal auto insurers and offers motorcycle and powersports coverage as part of its broader portfolio. Competes with Dairyland across motorcycle and personal auto lines.
• Allstate: Allstate is a major U.S. personal lines insurer with motorcycle and nonstandard offerings (including through National General). Overlaps with Dairyland across most product lines but as part of a much broader portfolio.
• State Farm: State Farm is the largest U.S. personal lines insurer, with motorcycle coverage distributed through its captive agent network. Competes with Dairyland for motorcycle and personal auto customers through a different distribution model.

Emerging players

• Hagerty: Hagerty specializes in collector car and classic vehicle insurance, with growing enthusiast motorcycle offerings. Comparable niche specialization in vehicle hobbyist insurance, though focused on collectibles rather than daily riders.

Others

• Roamly: Roamly is a digital insurance platform for recreational vehicles, marine, and motorcycles that distributes products from Dairyland and other carriers. It is both a Dairyland distribution partner (announced April 2025) and an emerging digital-first competitor to traditional specialty underwriters.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks7 records

Key highlights7 records

Customer concentration

• Xx.com/dairylandcycle
• YouTubeyoutube.com/@DairylandIns
• Facebookfacebook.com/info
• Instagraminstagram.com/dairylandins
• LinkedInlinkedin.com/company/sentry-insurance

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Dairyland Cycle Insurance