Case study · Insurance operations
Past engagementPaper intake became a searchable, trackable Medicare lead operation
Capstone Health is an independent Medicare agency in Tampa. Every inbound call started life on a paper lead sheet, and everything after it depended on somebody remembering. We rebuilt intake, timing, consent, and follow-up into one operating system, and audited 61 workflows and 116 tags on the way through.
Ran live for months / engagement ended when the agency changed CRMs
This system was live and in daily use at Capstone Health for months. The agency has since moved to a different CRM, so we write about it in the past tense: what was built, and what it produced while it ran. The domain knowledge on our insurance page came out of this work and it did not leave when the engagement did. No client data, Medicare numbers, or names appear here or anywhere else.
4,742
Contacts flagged do-not-contact
61 / 116
Workflows and tags audited and rebuilt
Same day
Paper leads entered and routed
Will Smith / Capstone Health Insurance / client testimonial
About the company
Capstone Health is an independent Medicare agency in Tampa, Florida. The owner is a licensed broker who is good at the part of the job that is actually hard: sitting with a beneficiary, understanding what they need, and getting them onto the right plan.
Medicare is a business governed by a calendar. T65 means turning 65, which is when a person first becomes eligible. The annual enrollment period runs October 15 to December 7 and it is the busiest stretch of the year. A scope of appointment has to be agreed 48 hours before a sales appointment. The annual notice of change lands September 30 and tells every member what is changing on their plan. Miss a window and you did not lose a sale. You left a beneficiary on the wrong plan for a year.
The problem
Every inbound call started on a paper lead sheet. That works perfectly well for the conversation, and it is where a lot of good brokers still live. The drag comes after: every next step depended on somebody re-entering the lead, classifying it against the right enrollment window, and triggering the right follow-up. Lead status lived across paper, memory, and scattered notes.
The follow-up timing depended entirely on the operator remembering who needed a call back and when. In a business where timing is the product, that is the whole exposure. It works right up until volume arrives, and in Medicare the volume arrives on a date you can see on a calendar a year in advance.
There was a second problem, and it is the one that keeps most brokers from automating anything at all. The owner was genuinely afraid that dispositioning a test lead would fire a real thanks-for-enrolling email to a live client, so he entered fake email addresses on his test records. He was right to be careful. He also flagged the compliance gap around pushing Social Security and Medicare numbers through generic automation before we did, which told us we were working with somebody who understood his own risk better than most vendors would have assumed.
He entered fake emails on his test records, because he did not trust software not to send a real client a real message by accident. That fear was correct.
The solution
We rebuilt the intake-to-enrollment workflow. Every inbound call moved from paper capture to a structured record the same day, with automatic classification that mapped each lead to its real enrollment timeline and started the correct follow-up path immediately.
The compliance rules became build constraints rather than a disclaimer. Dispositioning a lead can never fire an automated message, which was the owner's specific fear and became a specific guarantee. Kill switches pause every sequence the instant an appointment books, so nobody gets chased for something they already did. Sensitive identifiers stay out of the automation path entirely.
Then there was the book itself. We audited 61 workflows and 116 tags, and rebuilt the tag architecture so the pipeline meant something. Deduplication ran on a rule we now use everywhere: search first, never blind-write. Find the contact before you touch it. On that book, 4,742 purchased contacts carried a do-not-contact flag, and a careless merge that silently dropped one of those would have been a far bigger problem than the duplicates ever were. So the system proposes merges and a person approves them.
One more thing we got right by listening rather than designing. The owner told us that once the appointment is booked, the CRM's job is finished. He trusts his own close rate, and he wanted the record pushed to his enrollment system the instant it booked, with the real outcome recorded after. He was right. The bottleneck was never his selling. It was everything that had to happen to get a qualified person on his calendar on the correct day.
The impact
While it ran, every inbound lead was captured, classified, and routed digitally, with an automated nurture engine running from first contact through enrollment and wake-up sequences that re-engaged the whole book ahead of enrollment season. Booking sent its own confirmations, reminders, and compliance documentation without anybody driving it.
The human work stayed human, which was the design. Live calls, benefit conversations, and every compliance-sensitive judgment stayed with the licensed broker. The system handled the repetitive state changes, the follow-up timing, and the pipeline visibility that used to eat hours a week.
The agency has since moved to a different CRM, and this engagement ended with it. We are telling you that because the alternative is a case study that quietly implies a client we do not have. What the work produced is still real: a broker went into his biggest enrollment season with an operating system instead of a stack of paper, and the compliance vocabulary that runs through our insurance page came out of this build.
Close rates improved and the admin side got quieter. Appointment setting became consistent, and everything ran through one place.
Under the hood
How the system actually runs.
Every inbound lead becomes a structured record the day it arrives, classified against its real enrollment window, and moved by the calendar rather than by memory. The gates are the interesting part: this is a regulated business, and the system is built so that the things that would embarrass you are the things it cannot do.
What goes in
- Inbound calls, web forms, referrals, and purchased lists, each carrying a different compliance posture
- Part A and Part B effective dates, which are what everything downstream is timed against
- The compliance calendar: T65, the annual enrollment period, the open enrollment period, the annual notice of change
What the system does
01
Capture same day
The paper lead sheet becomes a structured record the day the call happens. Paper can still exist. It stops being the only place the lead lives.
02
Search first, never blind-write
Find the contact before touching it. A purchased-list import that overwrites a do-not-contact flag is a compliance problem, not a data problem.
03
Classify against the calendar
Turning 65, annual enrollment, open enrollment, dual-eligible status. The lead goes on its real timeline, not into a generic funnel stage.
04
Nurture with kill switches
Sequences that pause the instant an appointment books. Dispositioning a lead never fires an automated message. That was a hard requirement, and it was the right one.
Human checkpoint
Every plan recommendation and every enrollment is the licensed agent's, in the agent's own system. The automation never recommends, never enrolls, and never touches a Social Security or Medicare number.
What comes out
A qualified appointment on a licensed agent's calendar, on the correct day of a window that closes, with the consent trail already in place.
Results
The numbers, plainly.
- 4,742 purchased contacts flagged do-not-contact, with a deduplication rule built to protect that flag above everything else.
- 61 workflows and 116 tags audited and rebuilt, so the pipeline stages meant something.
- 100% of inbound leads captured, classified, and routed digitally, same day, instead of living on paper and in memory.
- 0 automated messages fire from a lead disposition. That was the owner's specific fear and it became a specific guarantee.
- 0 Social Security or Medicare numbers pass through the automation path, a gap the owner named himself before we did.
- 1 rule came out of this build that we now use on every CRM system: search first, never blind-write.
In his own words
“He translates what you need into a system that works, and that's genuinely hard to find.”
More work
Other systems we built.
Read next
The thinking behind the work.
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