Nobody Told Me That: The New Benefits Admin’s 90-Day Playbook
$47.00
Somebody handed you the benefits program with no manual and no training. This is the roadmap that should have come with it.
Nobody Told Me That: The 90-Day Playbook — $47 value
Five CLEAR stages that take you from your first plan document to running open enrollment like you’ve done it before. Checklists, a 19-term glossary, and the compliance filings you personally own.
BONUS — The Broker & Carrier Conversation Code — $17 value
The exact questions to ask your broker and every carrier in your first 30 days — including how your broker is actually paid.
$64 of tools for $47.
Two PDFs · instant download · yours permanently · 30-day guarantee
Description
This job doesn’t come with training
Somebody walked over, handed you the benefits portfolio, said “you’ve got this,” and walked away.
Now you’re reading plan documents you don’t fully understand. Employees are asking questions you can’t answer yet. And there are deadlines running right now that nobody has mentioned to you — you won’t find out about them until one is missed.
That feeling is normal. Almost everyone in this job started exactly here.
It just doesn’t have to last ninety days.
The roadmap I wish someone had handed me
Nearly twenty years in benefits administration, learned one mistake at a time. This playbook is that experience condensed into a stage-by-stage plan for your first ninety days — what to do, who to ask, and what nobody tells you until it’s already late.
It’s built on the CLEAR Method: five stages that take you from collecting your first plan document to running open enrollment like you’ve done it before.
The five stages
C — Contacts & Coverage Days 1–30
Find your broker, collect every plan document, build your contact sheet, and get system access with every carrier.
L — Learn Your People Days 31–60
Build the relationships that save you when things go sideways — broker, carriers, payroll, AP, and your HRIS.
E — Establish Your Systems Days 61–90
Your 12-month calendar, vendor tracker, invoice process, and the compliance filings you personally own.
A — Act on the Moments Ongoing
Enrollments, life events, terminations, leaves, COBRA, and evidence of insurability — handled correctly, every time.
R — Run With Clarity Day 90+
Open enrollment, communicating benefits in plain language, and showing up in leadership conversations as someone who knows the program.
What’s inside
- Five stages, laid out day by day — with a checklist at the end of each one so you always know whether you’re actually done.
- Your 90-day map on page three, so you can see the whole arc before you start.
- A 19-term glossary — HRIS, QLE, EOI, arrearage, level-funded, creditable coverage, Section 125. The words everyone uses around you and nobody defines.
- The compliance filings you own — Form 5500, PCORI, ACA reporting, Medicare Part D, the gag clause attestation — each with the timing rule behind it, not just a date that expires.
- The rules nobody explains — why elections lock for the plan year, why a life event has two different deadlines, and why “fully insured or self-insured” is the wrong question.
Included Bonus
The Broker & Carrier Conversation Code — $17 value
The exact questions to ask your broker and every carrier in your first 30 days, why each one matters, and what to do with the answer you get.
Including the question almost nobody asks: how is your broker actually compensated? Under the Consolidated Appropriations Act, a broker expecting $1,000 or more from your health plan has to disclose their direct and indirect compensation in writing. Most new admins have never seen that disclosure and don’t know they can ask for it.
$64 of tools for $47. Two PDFs, instant download, yours permanently.
Every number carries its source
Revenue Procedure numbers. CFR sections. DOL fact sheets. When your broker asks where a figure came from, you can tell them. Most benefits guides are unsourced — this one was written to be handed to a professional.
This is for you if
- You inherited a benefits program with zero training
- You’re Googling every question and never fully trusting the answer
- You’re not sure whether your broker is doing enough — and not sure how you’d tell
- You want the roadmap first, and you’ll build your own trackers
This is not for you if you were expecting spreadsheets. This product is the roadmap and the questions — two PDFs, no workbook. If you want the trackers already built, the kit below is what you want instead.
Want the trackers built for you too? The Day One Ready Starter Kit adds the 11-tab Carrier Command Center — with your compliance calendar, COBRA deadlines, and current 2027 and 2026 IRS limits already filled in — plus the CLEAR Method desk card. $103 of tools for $67.
The “You’ll Know More on Day 2” Guarantee
Read Stage 1. That’s it.
If you don’t finish it feeling more oriented, more confident, and clearer about what to do first — reply to your confirmation email within 30 days and I’ll refund you in full. No form, no questions, no explaining yourself.
I’d rather you have the money than a file you’re not using.
Questions people ask
I’ve been doing this a few months already. Is it too late?
No. Most readers aren’t on day one — they’re three months in and realizing nobody ever gave them the foundation. It works as a gap-check just as well as a roadmap.
What’s the difference between this and the Starter Kit?
This is the Playbook and the Broker & Carrier Conversation Code — the thinking. The Starter Kit adds the 11-tab Carrier Command Center workbook and the CLEAR desk card — the tools. If you want the roadmap, start here. If you want the roadmap and the trackers already built, get the kit.
Will it go out of date?
The compliance section is written rule-first — it tells you the timing rule that sets each deadline rather than printing a date that expires. Specific dollar figures carry the Revenue Procedure they came from, so you can check them yourself in a minute.
Is this legal advice?
No, and it says so plainly inside. I’m a benefits administration practitioner, not an attorney. This is the practical operating knowledge of the job. Compliance decisions still go through your broker or ERISA counsel — the Playbook just makes sure you know which questions to bring them.
What format is it?
Two PDFs you can read on anything and print if you want. Downloadable the moment you buy, and yours permanently — no subscription, nothing expires.
Nobody should have to figure this out alone
You can spend the next ninety days piecing it together from search results and hoping you didn’t miss anything.
Or you can start Monday knowing what to ask, who to call, and what’s coming.
One time. Permanent access. 30-day guarantee.
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