Rick Bailey & Company

What Rick Bailey & Company does

Rick Bailey & Company is a privately held insurance brokerage and consulting agency founded in 1984 in Woodstock, Georgia, serving US employers with up to 1,000 employees plus individuals and families seeking coverage outside employer plans. The firm is led by Founder & CEO Rick Bailey alongside a director-level team spanning benefits consulting, mid-market/large group sales, and technology, with average agent tenure exceeding 15 years. Its go-to-market is direct, sales-led consulting distributed through website lead capture, phone sales, and relationship-based account management, with no third-party channel partners. Revenues are generated from traditional insurance brokerage commissions on placed policies and from a fee-for-service consulting model that includes a published $350 individual / $500 family one-time consultation fee; the firm reports a 95% five-year client retention rate and 9.6-year average client relationship length.

The firm's flagship technology is Inrollit, a proprietary Human Resource Information System (HRIS) that functions as a single-point entry system for employee onboarding and offboarding, payroll and tax, benefits administration, ACA compliance, and employee communication. Data entered once in Inrollit is pushed to downstream systems including payroll vendors, insurance carriers, COBRA administrators (via an AdminAmerica partnership), FSA providers, and the IRS for electronic 1094-C/1095-C filing. Surrounding the core HRIS are add-on modules: a Private Benefits Marketplace with a Virtual Plan Coach for guided enrollment, a free iOS/Android employee self-service app, payroll and PTO management, real-time reporting, and freshbenies telehealth/health advocacy. Distribution is domestic, with stated operating geography in the US Southeast and particular depth in Georgia; the firm holds 38 industry awards including a National Distinguished Service Award, NAHU leadership positions, and Healthcare.gov Circle of Champions recognition for 2018–2021.

Name

Rick Bailey & Company

Legal name

Rick Bailey & Company, Inc.

Website

https://rickbaileycompany.com

Company type

Private

Founded year

1984

Operating status

Operating

Headcount range

501–1,000 employees

Short description

Rick Bailey & Company is a privately held, Woodstock, Georgia-based insurance brokerage and consulting firm serving US employers with up to 1,000 employees and individuals, combining traditional brokerage commissions and fee-for-service consulting with its proprietary Inrollit HRIS platform for benefits, payroll, and ACA compliance.

Ownership category

akta.pro rank

Product category

Insurance Brokerage & Employee Benefits Administration

NAICS

Insurance Agencies and Brokerages (52421), Human Resources Consulting Services (541612), Agencies, Brokerages, and Other Insurance Related Activities (5242)

SIC

Insurance Agents, Brokers & Service (6411), Services-Management Consulting Services (8742)

akta.pro primary industry

Employee Benefits Brokerage & Consulting (FSAEADAC)

akta.pro secondary industries

Benefits Administration & Enrollment Support (BPAAAIAB), HRIS Administration & Data Management (BPAAAIAC), HR Compliance & Policy Administration Outsourcing (incl. regulatory reporting) (BPACAKAK)

Keywords

• Insurance brokerage
• Employee benefits administration
• HRIS technology
• ACA compliance services
• Benefits consulting

Headquarters

HQ city

Woodstock

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

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

Revenue model

1. Insurance Brokerage Commissions: Traditional insurance brokerage model where agents earn commissions from insurance carriers on placed policies. The company offers both commission-based and fee-for-service consulting models.
2. Fee-for-Service Consulting: Licensed Insurance Counselors provide fee-for-service consulting instead of collecting policy commissions, allowing clients to pay only for services they need. Available for group benefit plans, technology systems, COBRA cost comparisons, and individual health insurance.
3. Individual Plan Consultation Fees: One-time consultation fee of $350 for individuals or $500 for families, including all services plus year-round policyholder service and support.

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels8 records

Core offering

Rick Bailey & Company is an insurance brokerage and consulting agency that places group and individual insurance products (health, dental, vision, life, disability, supplemental) and operates Inrollit, a proprietary Human Resource Information System (HRIS) for employee onboarding, payroll, benefits administration, and ACA compliance. The firm also provides fee-for-service consulting, ACA compliance automation, COBRA administration, and individual health plan enrollment support to U.S. businesses with up to 1,000 employees and to individuals.

Product overview

Rick Bailey & Company operates as an insurance brokerage and HR technology firm offering a unified platform centered around Inrollit, their proprietary HRIS system. Inrollit serves as the core technology hub connecting employee onboarding and offboarding, payroll, benefits administration, ACA compliance, and employee communication. The platform integrates with multiple downstream systems including payroll vendors, insurance carriers, COBRA administrators, FSA providers, and the IRS for electronic ACA filing. Additional modules include a Private Benefits Marketplace with Virtual Plan Coach for guided enrollment, an Employee Smartphone App for 24/7 self-service access, ACA Compliance Tool, Benefits Administration, Payroll & PTO Portal, and Reports & Analytics. The company also offers freshbenies (telehealth and health advocacy services) and individual insurance products. Services include fee-for-service consulting and HR support, positioned as an alternative to traditional commission-based brokerage models.

Differentiator

Problem solved

Functional benefit

Brands

• Inrollit: Proprietary Human Resource Information System (HRIS) platform for employee onboarding, offboarding, payroll, benefits administration, ACA compliance, and employee communication.

Products and services

• Inrollit HRIS Platform Proprietary Human Resource Information System (HRIS) that serves as a single-point entry system for employee onboarding and offboarding, payroll and tax management, benefits administration, ACA compliance, and employee communication, with data pushed automatically to payroll vendors, insurance companies, and the IRS. Sold to U.S. employers and HR teams.
• Benefits Consulting Fee-for-service advisory engagement delivered by licensed insurance counselors and subject matter experts covering group benefits, ACA compliance, payroll, technology, and HR. Sold to businesses seeking commission-free, transparent advice.
• Benefits Administration Full-service group benefits management including plan selection from multiple carriers, enrollment, life-event management, employer contribution management, and consolidated billing for U.S. employer clients.
• Individual Insurance Products Individual and family insurance placement including health, dental, vision, life, disability, long-term care, critical illness, identity theft, legal, and pet insurance for individuals without employer-sponsored coverage, with one-on-one agent consultation.
• ACA Compliance Service Automated Affordable Care Act compliance service including variable hour employee tracking, FTE calculations, affordability testing, 1094-C/1095-C form generation, and electronic submission to the IRS, for applicable large employers.
• COBRA Administration Offboarding service that manages termination notifications, COBRA eligibility tracking, COBRA notifications, and administration in partnership with AdminAmerica for U.S. employer clients.

Quantifiable outcome

• 95% client retention rate for the past 5 years
• +3 more outcomes

Named customers3 records

Segments3 records

Ideal customer profiles3 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration5 records

Feature6 records

Partnerships

One partnership is on record.

• AdminAmericaminorImplementation/ SI/ Consulting PartnerAdminAmerica provides expert third-party COBRA administration services in partnership with Rick Bailey & Company. RBC partners with AdminAmerica to offer COBRA administration as part of their comprehensive offboarding and compliance services.

Scale indicators7 records

Recent moves5 records

Expansion highlights4 records

Broad incumbents

• Brown & Brown, Inc. Large national insurance brokerage with a dedicated Employee Benefits segment serving mid-market employers; overlaps with RBC's benefits placement, consulting and HRIS-adjacent services but at much greater scale and geographic reach.
• Arthur J. Gallagher & Co. Global insurance brokerage with a substantial mid-market benefits and HR consulting division (including Aspiration HRO/benefits offerings); competes with RBC for the same employer segment but with much broader geographic and product footprint.
• Marsh McLennan (Mercer): Global consulting and brokerage firm whose Mercer benefits and HR advisory practice directly competes for mid-market employer mandates; serves employers of RBC's size and larger with significantly broader product line and global reach.
• USI Insurance Services: National insurance brokerage with strong employee benefits and HR consulting practice serving mid-market clients; comparable business model to RBC's brokerage-plus-consulting approach, with proprietary analytics and integrated HR-adjacent services.
• Hub International: North American insurance brokerage with strong employee benefits practice for mid-market employers; comparable services and customer profile to RBC, but operates at national scale with significantly larger book of business.
• Lockton Companies: Large private, employee-owned insurance broker with deep employee benefits consulting practice; serves many of the same mid-market employer buyers as RBC through dedicated benefits teams and proprietary tools, though at much larger scale.

Others

• BenefitMall: Benefits wholesale and technology provider serving small and mid-market benefits brokers; adjacent rather than directly competing, but operates in the same SMB benefits distribution channel and is a possible platform/partner for brokers like RBC.

Direct peers

• Hilb Group: Mid-market insurance and employee benefits brokerage with proprietary HR/benefits technology and a similar acquisition-led growth model; comparable in target customer size, benefits-heavy mix and technology-enabled service approach to RBC.
• NFP (an Aon company): Mid-market-focused insurance broker and benefits/HR consulting firm with proprietary technology platforms and similar acquisition-driven roll-up history; direct competitor for the same employer benefits and HRIS-adjacent services as Rick Bailey & Company.
• OneDigital: Mid-market-focused employee benefits, HR consulting and HRIS/payroll services firm with proprietary technology stack and similar fee-for-service advisory motion; the closest direct comparable in size, customer segment and service mix to Rick Bailey & Company.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks5 records

Key highlights7 records

Customer concentration

• Facebookfacebook.com/RickBaileyCo
• LinkedInlinkedin.com/company/rick-bailey

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 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 Rick Bailey & Company