To know where we are going we need to know where we've been. This is a playbook to download and use as you head into open enrollment to check your strategy.

Don’t Auto-Renew Your Health Plan. Execute a Strategy.

September 24, 2025•3 min read

Open Enrollment isn’t an HR task. It’s an annual strategic review of your company’s second-largest expense.

Yet, most leadership teams treat it as a passive event: a renewal package arrives, costs have increased, and the only question is “how much?” This cedes control to insurance carriers and brokers, leaving you to fund their profits with your bottom line.

It doesn’t have to be this way.

We’ve created a definitive CEO/CFO Open Enrollment Prep Playbook—a 4-phase strategic guide to moving from a passive payer to an active steward of your benefits investment. This is your blueprint for controlling costs, mitigating risk, and ensuring your plan supports your business goals.

Get instant access to the free CEO Playbook for Open Enrollment, helping CEO's, CFO's, and Business Owners get prepared for open enrollment. No pitch, just helping you get your benefits aligned with your strategic goals.

Why a “Playbook”? Because Strategy Beats Reaction

You wouldn’t auto-renew a major software contract without analyzing usage, performance, and market alternatives. Why would you do it with a expense that can easily exceed six or seven figures?

This playbook provides the data-driven framework you need to:

Decode the “Why”: Move beyond “the market is up” to understand the exact drivers behind your renewal increase.
Ask the Right Questions: Equip yourself with the specific, powerful questions to challenge your broker and carriers.
Model Financial Scenarios: Make strategic trade-offs based on your company’s unique financial and cultural needs.
Ensure Fiduciary Compliance: Document your due diligence process, protecting yourself and your company.

What’s Inside the Open Enrollment Playbook?

The guide breaks the process into four actionable phases, complete with the exact questions to ask and metrics to demand.

Phase 1: The Look Back (Data Dive) Begin 90-120 days before OE. Your negotiation starts with data. This phase shows you how to analyze claims loss ratios, identify multi-million dollar driver conditions, audit pharmacy spend, and benchmark your plan against the market. This isn’t just retrospective; it’s your ammunition for the fight ahead.

Phase 2: The Financial Interrogation (Renewal Analysis) Begin 60-90 days before OE. When the renewal hits your desk, you’re ready. Learn how to decode the increase into its component parts (claims vs. profit), model “what-if” scenarios for plan changes, demand full fee transparency, and force competitive bidding. This is where you take control of the conversation.

Phase 3: The Strategic Decision (Plan Design) Begin 30-60 days before OE. With data in hand, you can make confident decisions. Should you stay or switch? Is it time for an HSA/HRA strategy? Are your ancillary benefits priced right? This phase translates analysis into action.

Phase 4: The Rollout (Communication & Execution) OE and beyond. A great plan fails with poor communication. Get a checklist for launching the plan with CEO-led messaging, multi-channel support, and measuring success post-enrollment to set goals for next year.

Stop Funding Their Profits. Start Building Your Strategy.

This playbook is designed for one person: the leader who is tired of writing bigger checks for less value and is ready to demand more.

Your benefits plan should be a strategic asset for recruitment, retention, and culture—not a liability that drags on your P&L.

Download the playbook, and change the way you approach Open Enrollment forever.

[Download the CEO/CFO Open Enrollment Playbook]

Your bottom line will thank you.

Emily Evans

Emily Evans, Founder of Wellth Journey, doesn’t believe in “that’s just how it is.” After a motorcycle accident revealed how broken benefit plans leave families financially vulnerable, she dedicated her career to dismantling the broken benefits playbook—for good. She created a rare blend of razor-sharp Lego-style simplification and a “build-your-people” philosophy to help frustrated business owners escape the status quo. Her clients don’t get another generic quote; they get a custom-built benefits roadmap that contains cost, manages risk, and aligns your benefits package directly with your company’s strategic objectives. When not serving her clients or community, Emily’s off-roading in her Toyota 4Runner—because she’s never been afraid to modify the machine, forge a new path, or build a new vehicle altogether when the old one breaks down. Your benefits should be engineered for exploration, not just built for the paved road.

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