Articles·Strategy and support

Four ways to get AI into a benefits agency, and where each one wins

Chris Cordon · 4 min read
A woman at a trailhead with signs for Do it yourself up a cliff, Big firm down a toll road, and Built for you along a lit path.

Doing it yourself with ChatGPT or Claude wins when one person wants a better writing partner, a big AI implementation firm wins when you’re large enough to fund a long project, and a fractional CTO wins when you need a senior technology leader part time. A benefits specialist like DoBetter (dobetter.plus) wins when a small benefits agency wants its retyping mapped, connected, and taught to the team by someone who has worked a renewal season.

How do the options compare?

Do it yourself with ChatGPT or ClaudeA big AI implementation firmA fractional CTOA benefits specialist builder (DoBetter)
CostA subscription per personVaries by firm, usually a large projectA monthly arrangementFixed fee after a $1,500 discovery
Time to startTodayWeeks of scopingDepends on availabilityAn intro call, then discovery
What it handlesDrafts, summaries, questionsLarge systems across many teamsTechnology strategy, vendors, developersMapping, connecting tools, training, a written AI policy, support
What it knowsWhat you type inAI, across many industriesTechnology, across many industriesBenefits agencies: census files, carrier portals, renewals
Who maintains itYouThe firmThe CTO, while they’re retainedSomeone on your team, taught to fix it with their agent

When is doing it yourself the better choice?

Doing it yourself with ChatGPT or Claude is the better choice when you’re curious, your team is small, and the goal is better first drafts. A subscription and an afternoon of practice will get you somewhere.

The tradeoff is how most people use it. They “still look at it as a glorified Google search, questions and answers.” They upload documents into the chat, copy the answer, paste it into another system, and edit it there. That’s the biggest learning curve I see. Telling an agent to go work on the computer is a different skill, and it rarely gets picked up alone.

When is a big AI implementation firm the better choice?

A big AI implementation firm is the better choice when you have many teams, many systems, and the budget for a long project with a project manager. Big firms bring specialists and process.

The tradeoff is fit. A small benefits agency’s problem is usually one census that gets retyped three times, which is a small job for a large firm. Big firms also work across every industry, so someone on your side ends up explaining what a renewal is.

When is a fractional CTO the better choice?

A fractional CTO is the better choice when you’re hiring developers, choosing between large platforms, or need someone to own technology decisions at the leadership table part time. That’s a senior role, and it’s the right hire for an agency with a technology roadmap.

The tradeoff is that a fractional CTO leads technology. What most small agencies need is the retyping gone and a team that uses the AI they already pay for.

When is a benefits specialist the better choice?

A benefits specialist is the better choice when the problem lives in benefits work: census files, carrier portals, quotes rekeyed into proposals, renewal follow up. I’m Chris Cordon, a 17 year benefits producer. I built and run my own CRM, notetaker, and proposal generator with AI.

I start with a 2 to 3 hour discovery that looks at who’s on staff, how the data flows, who touches the information, what you do to bring business in, and how that’s structured. Then I tell you where and if I can help. “I’m the wrong guy to ask” about build versus buy, “because I build everything.” When an off the shelf product is the right answer, I’ll set it up anyway.

Support works the same way. I’m available to fix anything that breaks while I’m retained, and it rarely happens. I’d rather teach someone at your agency to have their agent fix it.

Quick answers

Can I mix these?
Yes. Keep your ChatGPT or Claude seats and add training and connections around them.
Do you replace a fractional CTO?
For most small agencies, you won’t need one. If you’re hiring developers, you might.
Do you work outside benefits?
Benefits and insurance agencies are who I build for.
Do you write an AI use policy?
Yes. 55% of independent agencies have none.