Three generations. One operating system.
Heirstead began as a family's insurance career in 1973. What it became for you is a modern, coordinated platform for independent agents — training, mentorship, carrier access, and technology built from decades in the field, not a slide deck.
Independent contractor · Commission-based
Three generations, one continuing standard.
Insurance has been the family business since 1973 — not as a slogan, but as four separate careers that each left behind a working standard the next generation carried forward.
Founding — Charles Ernest Bailey
A 45-year Aflac career as a Regional Director and District Manager, recognized in the Aflac Hall of Fame. His standard, passed to everyone he mentored: “Don’t worry about the money. If you help others get where they want to go and succeed, you will find greatness in yourself.” That belief is why mentorship at Heirstead isn’t a scripted call — it’s the same standard, one generation later.
Second Generation — Kimberly Dyer, Robert Bailey & Camilla Bailey Hughes
Kimberly built more than 25 years in production and training, including District Sales Coordinator and New Associate Trainer roles. Robert, a decorated Navy veteran, built a 20-year career in recruiting and government benefits. Camilla built a 20-year career as a District Manager. Three different specialties, one shared discipline: consistent activity, over decades, is what the business is actually built on.
Current — Joshua Patrick Dyer
For the last 10+ years, Joshua has carried the family legacy forward as an independent broker — building Heirstead as an independent firm that brings together broad carrier access, structured training, and a genuine commitment to agent support. The family's combined careers helped thousands of families and generated over $5 million in premium. Heirstead is that legacy, organized into a system you can join.
What the operating system actually changes
A family history doesn’t train an agent by itself. What it produced, over three generations, is a coordinated system — not six separate vendors, and not a single course you finish and move on from.
- 01
Training becomes mentorship
Product and sales education exists everywhere. What three generations in the field change is who's teaching it — and whether they're still reachable after you're done onboarding.
- 02
Carrier access becomes case design
Access to 40+ life insurance and annuity carriers, including A- and A+ rated companies, so you're rarely forced into a product that doesn't fit your client — and complex cases get real structuring help, not just a rate quote. Carrier and product availability varies by state, appointment, and client need.
- 03
Technology becomes workflow, not paperwork
CRM, quoting, and e-application tools exist to keep a pipeline organized — the goal is fewer hours lost to administration, not a features list.
- 04
Support continues past onboarding
Guidance doesn't end at day 90. It continues for as long as you're an active agent — the same standard Charles described above, still in practice.
Principles, not slogans
None of these are original to Heirstead — they're what four careers in the same family, across 45+ combined years, kept proving out.
Client service comes first
Charles's own words — help the client get where they're trying to go, and the rest follows. Every carrier and product decision starts from what fits the client, not the commission.
Relationships outlast transactions
A book of business isn't a one-time sale. Renewal income exists because a client relationship, not just a policy, was the point.
Preparation before the call
Kimberly's and Robert's careers were built on training and product mastery before production — not learning on a live client.
Consistent activity, not bursts
20–45-year careers don't happen from occasional effort. Activity, tracked and repeated, is what actually compounds.
Continued learning
Product lines, carriers, and underwriting rules change. Training here doesn't stop at onboarding because the industry doesn't either.
Independence with real support
You set your own hours and work from anywhere. You may also build a book of business and earn renewal commissions, subject to carrier contracts, vesting, persistency, and applicable agreements — while never being the only person who's seen your kind of case before.
What you can expect — and what stays yours
Support is provided where applicable. Outcomes depend on your own effort, consistency, and licensing — nothing below is a guarantee.
Candidates can expect
- Structured learning and sales training
- Mentorship, from day one and beyond
- Practical tools — CRM, quoting, e-application
- Case design support for complex clients
- Access to marketing and technology resources
- Continued development past onboarding
Heirstead does not guarantee
- Acceptance into the program
- Passing your licensing exam
- Carrier appointments or contracting
- Leads, referrals, or client volume
- Any specific personal response time
- Production, commissions, income, or success
The agent's side of the relationship
Everything above is provided where applicable. What you're responsible for doesn't change based on how good the system is:
- Obtaining and maintaining your own state licensing and credentials
- Ethical conduct and regulatory compliance
- Consistent activity — the system supports effort, it doesn't replace it
- Actually applying what training and mentorship teach
- Serving your own clients well, on your own follow-through
- Operating as an independent business, not an employee waiting on direction
- Your own personal results
Why this matters whether you're new or already licensed
New to Insurance
- Licensing guidance from application to exam
- Foundational product and sales training
- Structured, staged development — not a sink-or-swim start
- Mentorship from day one
- A clear operating framework instead of guesswork
Already Licensed
- Broader carrier access where your contracting qualifies
- Case design support for more complex clients
- Workflow and technology to run your book efficiently
- Mentorship for situations you haven't seen before
- Expanded client-service capability, without losing your independence
The legacy is real. So is the responsibility.
If the standard above is one you want to work under — and build your own independent business on — the next step is a conversation, not a commitment.
Independent contractor · Commission-based