Wilson Advisory Group

What Wilson Advisory Group does

Wilson Advisory Group is a family-owned, independent insurance brokerage headquartered in Lexington, Massachusetts, founded in 2011 by Warren Wilson and operated as a father-and-son partnership with his son David Wilson. The firm serves Massachusetts residents across the individual and family segments, with particular focus on pre-retirees, retirees, self-employed professionals, and early retirees under 65. Its product portfolio spans five core lines: Medicare advisory (Advantage, Medigap, Part D), individual and family health insurance (including Massachusetts Health Connector marketplace plans), life insurance (term, whole, final expense), long-term care insurance (traditional, hybrid, and asset-based), disability insurance, and annuities (fixed, indexed, and single premium immediate income annuities). As an independent broker, the firm places business across multiple insurance carriers — disclosing representation of 0-8 organizations offering 0-70 products depending on service area — and earns revenue from standard carrier commissions on enrolled policies, with no cost to customers for the brokerage service.

The underlying technology stack is minimal and non-proprietary: a Squarespace-hosted website serves as the digital storefront and content hub, Calendly handles online appointment booking, and customer engagement runs primarily through phone consultations at (781) 357-7573 and a monthly email newsletter. There is no proprietary technology, no AI/ML capability, no mobile app, no API, and no disclosed integration with carrier quoting platforms beyond standard broker channels. The firm's "four decades of combined experience" claim is anchored in the founders' prior careers at Shawmut Bank, Lehman Brothers, and CIBC Oppenheimer rather than in any tech-enabled differentiator.

The go-to-market motion is direct-to-consumer inside sales targeting a narrow geography: phone outreach, free no-pressure consultations, and website/email content marketing. Marketing channels consist of a monthly newsletter, detailed service-page content, free consultation offers, and online appointment scheduling. The firm competes on independent-objectivity positioning (recommending what fits client needs rather than what pays highest commission) rather than scale or technology, and its defensibility rests on personal relationships and switching inertia typical of insurance products.

Name

Wilson Advisory Group

Legal name

Wilson Advisory Group

Website

https://wilsonadvisorygroup.com

Company type

Private

Operating status

Operating

Headcount range

1–10 employees

Short description

Wilson Advisory Group is a family-owned independent insurance brokerage in Lexington, MA, founded in 2011 by Warren and David Wilson, serving Massachusetts individuals and families with Medicare, health, life, long-term care, disability, and annuity products placed across multiple carriers on commission.

Ownership category

akta.pro rank

Product category

Independent Insurance Brokerage

NAICS

Insurance Agencies and Brokerages (52421)

SIC

Insurance Agents, Brokers & Service (6411)

akta.pro primary industry

Annuity & Insurance-Based Retirement Solutions Advisory (FSAEABAH)

akta.pro secondary industry

Risk Management & Insurance Advisory for Families (FSAAADAK)

Keywords

• Medicare insurance brokerage
• Health insurance brokerage
• Life insurance brokerage
• Long-term care insurance
• Annuity retirement planning

Headquarters

HQ city

Lexington

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

Revenue model

1. Insurance Brokerage Commissions: Wilson Advisory Group operates as an independent insurance broker compensated via standard commissions paid by insurance carriers. There is no cost to customers for using their services. Commissions are earned when customers enroll in insurance products through the firm.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels4 records

Core offering

Wilson Advisory Group is an independent insurance brokerage that compares and places Medicare, individual and family health, life, disability, and long-term care insurance policies, along with fixed, indexed, and immediate annuity products, across multiple insurance carriers for Massachusetts residents. Services are delivered through free phone or online consultations with no cost to the customer, with the firm compensated via standard carrier commissions upon enrollment.

Product overview

Wilson Advisory Group is a family-owned insurance brokerage operating as a multi-carrier independent broker in Massachusetts. The company offers a portfolio of insurance and retirement planning products: Medicare advisory services (including Medicare Advantage, Medigap, and Part D plans), health insurance through the Massachusetts Health Connector marketplace, life insurance (term, whole, and final expense), disability insurance, long-term care insurance (traditional, hybrid, and asset-based), and annuities (fixed, fixed indexed, and immediate income). As an independent broker, the company compares products across multiple insurance carriers to recommend options fitting client needs. The services are delivered through personalized consultations and a free review process.

Differentiator

Problem solved

Functional benefit

Products and services

• Medicare Advisory Services Independent Medicare broker services that compare Medicare Advantage, Medigap supplement, and Part D prescription drug plans across multiple carriers and recommend suitable coverage for Massachusetts residents navigating Medicare enrollment.
• Health Insurance Brokerage Individual and family health insurance brokerage services through the Massachusetts Health Connector marketplace and off-exchange plans, spanning Bronze, Silver, Gold, and Platinum tier options for self-employed professionals, small business owners, early retirees under 65, and other Massachusetts residents.
• Life Insurance Brokerage Life insurance brokerage offering term life, whole life, permanent insurance, and final expense policies across multiple carriers serving Massachusetts residents seeking to protect loved ones.
• Disability Insurance Disability insurance coverage that protects income in the event of disability, offered as part of comprehensive financial planning services to Massachusetts individuals and families.
• Long-Term Care Insurance Brokerage Long-term care insurance solutions including traditional LTC policies, hybrid life/LTC policies, and asset-based LTC plans for Massachusetts residents concerned about the high cost of long-term care.
• Annuities and Retirement Income Planning Retirement income planning brokerage evaluating annuity strategies including Fixed Annuities (guaranteed interest for a set period), Fixed Indexed Annuities (interest credited based on market indices such as the S&P 500 with principal protection and optional income riders), and Single Premium Immediate Annuities (lump sums converted into guaranteed monthly income for life or a specified period) for Massachusetts retirees and pre-retirees.

Segments6 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

One partnership is on record.

• Multiple Insurance CarrierscoreOthersWilson Advisory Group works as an independent broker comparing products across multiple insurance carriers. The firm represents 0-8 organizations depending on service area. Specific carrier names are not disclosed on their website.

Scale indicators3 records

Recent moves5 records

Expansion highlights3 records

Direct peers

• The Zebra: Insurance comparison marketplace allowing consumers to compare quotes across multiple carriers. Direct competitor for the price-comparison phase of the customer journey Wilson's prospects run, particularly for personal lines where Wilson-adjacent carriers compete.
• eHealth: Online health insurance marketplace (NASDAQ: EHTH) that helps consumers shop Medicare, ACA, and ancillary coverage. Direct competitor for online Medicare/health plan comparison, especially for the Massachusetts Health Connector shopper segment Wilson also targets.
• SelectQuote: Public, multi-channel insurance broker (NYSE: SLQT) that sells term life, final expense, Medicare Advantage, and other insurance products direct-to-consumer. Directly comparable as an independent consumer-facing brokerage; key difference is SelectQuote's national scale and digital marketing spend versus Wilson's local Massachusetts focus.
• PolicyGenius: Online insurance broker specializing in life, disability, and supplemental coverage, with hybrid digital-plus-advisor experience. Overlaps with Wilson's life insurance and disability practices and competes for the same middle-market consumer via a similar advisor-driven model.
• GoHealth: Medicare-focused health insurance broker (NASDAQ: GOCO) that pairs digital acquisition with licensed agent consultation. Closest comparable on Medicare Advantage distribution model: high-volume, commission-driven, telesales-enabled broker targeting the same 65+ demographic.
• SmartFinancial: Online insurance comparison platform that connects shoppers with multiple carriers across home, auto, life, and health. Comparable as a multi-carrier digital broker intercepting consumers before they engage a local independent advisor like Wilson.
• HealthPlanOne: Medicare and individual health insurance broker operating via telesales and digital channels. Overlaps with Wilson on Medicare advisory, individual/family health, and the same commission-driven revenue model.

Emerging players

• Chapter: Tech-enabled Medicare advisory that digitizes plan comparison with licensed agents. Emerging niche competitor that pairs digital UX with personal advising — illustrating how the advisory model itself is being reinvented by digital-first entrants.

Broad incumbents

• MassMutual: Large Massachusetts-based mutual insurer and financial services firm with captive agent and brokerage distribution serving the same MA retirement, life, and annuity market. Comparable as a broader incumbent with overlapping life/annuity/wealth offerings competing for shared pre-retiree and retiree prospects.

Others

• NerdWallet: Consumer finance and insurance comparison platform that drives traffic into carrier/broker funnels. Acts as an upstream comparator in the same insurance purchase journey — adjacent rather than directly competitive, but a growing channel that can disintermediate small brokers.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat3 records

Key risks6 records

Key highlights6 records

Customer concentration

• Facebookfacebook.com/profile.php

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

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 Wilson Advisory Group