Fleetwood Insurance Group
Independent insurance agency and wholly owned subsidiary of The Peoples Bank, serving Maryland's Eastern Shore with personal, commercial, agriculture, marine, high net worth, and life and health coverage through 30+ carrier partnerships from offices in Chestertown and Easton.
- Company typePrivate
- Founded1968
- HeadquartersChestertown, United States
- Headcount11–50
- GTM typeB2B and B2C
- OfferingServices
What Fleetwood Insurance Group does
Fleetwood Insurance Group is an independent insurance agency operating as a wholly owned subsidiary of The Peoples Bank, a Maryland community bank. The agency traces its operating history to 1946 and was formed in its current corporate identity by the 1968 merger of the Kirby-Fleetwood Agency and the Townshend-Kane Agency, which produced the largest insurance agency in Kent County, Maryland. The company serves individual and business clients across Maryland's Eastern Shore from offices in Chestertown and Easton, with a 25-person staff covering personal lines (home, auto, renters, umbrella, valuable items, motorcycle, RV, flood, classic/antique auto), commercial and SMB coverage, high net worth personal lines, agriculture and farm operations, marine (via the Dockmasters sub-brand), hunting/outdoor recreation, and life and health insurance. Fleetwood represents more than 30 insurance carriers including AIG Private Client Group, Chubb, Pure, Hanover, Nationwide, Progressive, and Travelers, and is compensated through carrier commissions on placed and renewed policies.
The business model is relationship-led and consultative: prospective clients are acquired through community engagement, referrals, and online quote request forms across all major product lines, then routed to licensed agents (several holding CIC, CISR, AFIS, and ACSR designations) for individualized risk assessment and binding. Pricing is quote-based and not publicly disclosed; the agency does not publish rate cards or standard tiers. Distribution relies on the two physical offices, phone-based service, online quote intake with one-business-day agent follow-up, and a structural referral pipeline from The Peoples Bank's customer base. There is no proprietary technology platform; operations run on standard independent-agency software for policy management, CRM, and claims processing, with basic web analytics integrations (Google Analytics) and third-party payment processors (PayPal, Stripe). All customer-facing technology is presented as informational and service-oriented (policy changes, auto ID cards, certificate of insurance) rather than a self-serve underwriting platform.
Fleetwood Insurance Group firmographics
Firmographics- Name
- Fleetwood Insurance Group
- Legal name
- Fleetwood Insurance Group
- Website
- https://fleetwoodinsurancegroup.com
- Company type
- Private
- Founded year
- 1968
- Operating status
- Operating
- Headcount range
- 11–50 employees
- Short description
- Independent insurance agency and wholly owned subsidiary of The Peoples Bank, serving Maryland's Eastern Shore with personal, commercial, agriculture, marine, high net worth, and life and health coverage through 30+ carrier partnerships from offices in Chestertown and Easton.
- Ownership category
- akta.pro rank
Fleetwood Insurance Group industry classification
Industry- Product category
- Insurance Brokerage
- NAICS
- Insurance Agencies and Brokerages (524210)
- SIC
- Insurance Agents, Brokers & Service (6411)
- akta.pro primary industry
- Marine Specialty (Hull/P&I/Cargo) (FSAJAGAJ)
- akta.pro secondary industries
- Personal Umbrella Insurance (FSAJANAA), Inland Marine Insurance (Transit, Equipment & Installation) (FSAJAHAB)
Keywords
Where Fleetwood Insurance Group is headquartered
LocationHeadquarters
- HQ city
- Chestertown
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
Fleetwood Insurance Group business model
Business model- GTM type
- B2B and B2C
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure
Revenue model
- Insurance Agency Commissions: Fleetwood Insurance Group operates as an independent insurance agency (a wholly owned subsidiary of The Peoples Bank since 2007), generating revenue through commissions paid by insurance carriers for policies placed on behalf of clients. The agency represents multiple insurance companies (Accident Fund, Acuity, AIC, AIG Private Client Group, Brethren Mutual, Burns & Wilcox, Chesapeake Employers, Chubb, Cincinnati, Condon Skelly, Cumberland, Donegal, Foremost, Great American, Guard, Hagerty, Hanover, Harford Mutual, ICW, Nationwide, Progressive, Pure Insurance, Selective, Travelers, Utica National, Vault, Westfield, Windsor Mountjoy, Wright Flood, and others) and earns commissions on each policy sold or renewed.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Subscription | Monthly | Quote-based pricing — no standard tiers publicly disclosed |
Go-to-market motion1 record
Distribution channels4 records
Marketing channels4 records
Fleetwood Insurance Group product offering
Product offeringCore offering
Fleetwood Insurance Group is an independent insurance agency that places policies with multiple insurance carriers on behalf of personal and commercial clients. The agency offers personal lines (home, auto, umbrella, marine), commercial lines, agriculture, high net worth, life and health, hunting, and trucking coverages through carrier partnerships with companies including Chubb, AIG, Travelers, Nationwide, Progressive, and Pure Insurance. Revenue is generated through commissions paid by carriers for policies placed and renewed.
Product overview
Fleetwood Insurance Group is an independent insurance agency operating as a subsidiary of The Peoples Bank, offering a comprehensive portfolio of insurance products through multiple carrier partnerships. The company provides personal insurance (home, auto, renters, umbrella, valuable items, motorcycle, RV, flood, and classic/antique auto), business insurance, agriculture insurance, high net worth insurance, life & health insurance, and hunting insurance. Through its Dockmasters sub-brand, the company offers specialized marine insurance covering yachts, pleasure boats, personal watercraft, marinas, boat dealers, marine contractors, and commercial vessels. The company has roots dating back to 1946 and serves clients from offices in Chestertown and Easton, Maryland.
Differentiator
Problem solved
Functional benefit
Brands
- Dockmasters: Marine insurance services specializing in yachts, pleasure boats, marinas, marine contractors, and commercial vessels with over 25 years of expertise.
Products and services
- Personal Insurance Comprehensive personal insurance coverage including home, auto, renters, condo, umbrella, valuable items, motorcycle, RV, flood, and classic/antique auto insurance for individual consumers.
- Homeowners Insurance Homeowners insurance policies that protect against rebuilding costs and replace lost or damaged property with no gaps in coverage, for individual homeowners.
- Auto Insurance Customized car insurance plans covering accidents, theft, liability, collision, and comprehensive coverage with various deductible options for individual vehicle owners.
- Umbrella Insurance Additional layer of liability coverage beyond standard insurance policies, protecting against lawsuits or claims exceeding primary coverage limits.
- Business Insurance Business insurance solutions balancing cost and employee needs, assembling accurate coverage and risk transfer methods to protect companies from loss, for small and mid-size business owners.
- High Net Worth Insurance Insurance coverage for high-net-worth individuals addressing complex risk management including high-end property coverage and personal liability threats.
- Agriculture Insurance Farm insurance coverage for farming operations including farm property, liability, equipment, commercial auto, pollution liability, workers compensation, livestock, and equine liability.
- Life & Health Insurance Health and life insurance products helping individuals sort through different insurance choices to find the right plan at an affordable price.
- Dockmasters Marine Insurance Marine insurance brand under Fleetwood offering comprehensive coverage for watercraft from personal boats to mega yachts, marinas, and commercial vessels with over 25 years of expertise.
- Hunting Insurance Hunting club insurance options including hunting lease protection and guide/outfitter protection coverage for hunting clubs and outfitters.
Companies that use Fleetwood Insurance Group
Customer profileSegments7 records
Ideal customer profiles5 records
Fleetwood Insurance Group technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration3 records
Fleetwood Insurance Group partnerships and signals
Strategic signalScale indicators4 records
Recent moves10 records
Expansion highlights5 records
Fleetwood Insurance Group competitors and assessment
Company assessmentBroad incumbents
- Acrisure: Large US insurance brokerage that has built scale through aggressive M&A roll-up of regional independent agencies. Comparable to Fleetwood in that its target acquisitions are agencies like Fleetwood itself, providing both a competitive threat and a potential exit path for similarly structured independent agencies.
- Brown & Brown: One of the largest independent insurance brokerages in the US, with a multi-line retail segment that includes personal, commercial, and specialty programs. Comparable as a multi-carrier, multi-line independent agency model, though operating at substantially greater scale with national geographic reach.
- Marsh McLennan Agency: Middle-market division of global insurance brokerage Marsh McLennan, focused on commercial and personal lines for mid-sized businesses and affluent individuals. Comparable to Fleetwood as a multi-carrier brokerage serving overlapping customer segments, though operating at enterprise scale with broader geographic reach.
- USI Insurance Services: Large US insurance brokerage serving middle-market and large commercial clients across personal, commercial, and specialty lines. Comparable to Fleetwood in multi-line breadth and specialty practices, though at significantly larger scale and with broader geographic coverage.
Direct peers
- The IMA Group: Mid-market-focused independent insurance brokerage offering commercial, personal, and specialty coverage with multi-carrier representation. Comparable to Fleetwood as a full-service independent agency with similar producer-led, relationship-driven GTM and broad product breadth.
- Hilb Group: Mid-Atlantic and Southeast-focused insurance brokerage that acquires and operates independent agencies. Highly comparable to Fleetwood as a multi-line independent agency with regional concentration, specialty practices, and a roll-up M&A strategy that has acquired numerous small agencies similar in profile to Fleetwood.
- Hylant Group: Regional insurance brokerage with deep specialty practices across personal, commercial, marine, and high-net-worth lines. Comparable to Fleetwood in multi-carrier representation, specialty depth, and mid-market client focus, though operating at a larger regional scale across the Midwest and East Coast.
- NSM Insurance Group: Specialty insurance program manager and broker with expertise in niche verticals. Comparable to Fleetwood's specialty niches (marine, agriculture, hunting clubs) as a focused agency that builds expertise in under-served verticals rather than competing as a generalist.
- RPS (Risk Placement Services): Specialty insurance broker and binding authority with deep expertise in marine, transportation, and surplus lines. Highly comparable to Fleetwood's Dockmasters sub-brand as a marine specialty practitioner placing complex risks through E&S markets and specialty carriers.
- Heffernan Insurance Brokers: Independent insurance brokerage focused on mid-market commercial and personal lines with multi-carrier representation. Comparable to Fleetwood in operating model (independent agency, carrier network, relationship-driven sales) and client base (SMB, high-net-worth individuals).
Market position
Strengths5 records
Weaknesses5 records
Competitive moat5 records
Key risks6 records
Key highlights7 records
Customer concentration
Fleetwood Insurance Group social profiles
Digital presenceFleetwood Insurance Group financial estimates
Financial estimateRevenue estimate
Valuation estimate
Fleetwood Insurance Group leadership team
Management profileNumber of profiles
Profiles3 records
Fleetwood Insurance Group subsidiaries and ownership
Company hierarchySubsidiaries2 records
Fleetwood Insurance Group funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Fleetwood Insurance Group M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Fleetwood Insurance Group
What does Fleetwood Insurance Group do?
Fleetwood Insurance Group is an independent insurance agency that places policies with multiple insurance carriers on behalf of personal and commercial clients. The agency offers personal lines (home, auto, umbrella, marine), commercial lines, agriculture, high net worth, life and health, hunting, and trucking coverages through carrier partnerships with companies including Chubb, AIG, Travelers, Nationwide, Progressive, and Pure Insurance. Revenue is generated through commissions paid by carriers for policies placed and renewed.
Is Fleetwood Insurance Group a public or private company?
Fleetwood Insurance Group is a private company. It is classified as corporate owned and is currently operating.
When was Fleetwood Insurance Group founded?
Fleetwood Insurance Group was founded in 1968. It employs 11 to 50 people.
Where is Fleetwood Insurance Group based?
Fleetwood Insurance Group is headquartered in Chestertown, United States, in the North America region.
How does Fleetwood Insurance Group make money?
One revenue line is on record: insurance Agency Commissions.
Who are Fleetwood Insurance Group's main competitors?
Broad incumbents on record are Acrisure, Brown & Brown, Marsh McLennan Agency and USI Insurance Services. Direct peers are The IMA Group, Hilb Group, Hylant Group, NSM Insurance Group, RPS (Risk Placement Services) and Heffernan Insurance Brokers.
Does Fleetwood Insurance Group have an API?
No public API is recorded for Fleetwood Insurance Group.
What industry is Fleetwood Insurance Group in?
Fleetwood Insurance Group's product category is Insurance Brokerage. Its primary akta.pro industry code is FSAJAGAJ, Marine Specialty (Hull/P&I/Cargo), with a secondary code of FSAJANAA, Personal Umbrella Insurance. Its NAICS code is 524210 and its SIC code is 6411.