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In my last post, I shared five tips for structuring and designing effective Medicare marketing emails, covering everything from subject lines to CTAs. This is only one piece of the puzzle, though. In this follow-up, I’ll focus on some additional ways to maximize your conversion efforts.

While the examples focus on Medicare prospects, the following best practices are broadly applicable across health insurance audiences.

1. Tap into behavior-based triggers

I’ve covered this before, and it still holds true. Forget “send emails on Tuesdays at 9 a.m.” as your strategy. If everyone sends emails between Tuesdays and Thursdays, your message is more likely to be lost. Instead, consider setting up event-based automation for the most appropriate timeframe to send messaging.

Here are some examples:

• Did someone just download a Medicare guide? Send a follow-up email with a link to related content like “5 Questions to Ask Before Choosing a Plan.”
• If a prospect missed a webinar, follow up with a recap email that includes an invitation to another event
• Did someone start enrollment but “abandon” the process? Follow up with an email that has a CTA to speak with an advisor.

If you can’t utilize event-based cues, consider using AI-powered send-time optimization to match individual habits, which will increase visibility and clicks.

2. Segmentation and personalization

Personalization goes way beyond “Hi {FirstName}.” Consider segmenting ongoing experiences based on:

• Content the user last downloaded (a guide, checklist, etc.)
• Lead source (Did the lead originate from a paid search ad? Direct mail?)
• Stage of Medicare journey (just turned 65 vs. plan switching vs. renewal)
• Location-specific options (e.g., plan availability by zip code)

Consider developing modular email templates with dynamic content blocks that swap based on profile and behavior. For example, someone who’s viewed content about switching Medicare Advantage plans probably shouldn’t receive information meant for a new-to-Medicare audience. And if someone has already taken an action, don’t prompt them again.

3. Don’t just chase opens, track what matters

Since the release of Apple’s Mail Privacy Protection, open rates are no longer a reliable KPI. Did the audience click the primary CTA? Yes? Great! But now what? Focus on optimizing toward generating a phone call or a web-based action, like visiting your Compare Plans page, downloading an Enrollment Kit, or starting the online enrollment process.

Every email is a new opportunity to connect and convert.

Use Urchin Tracking Module (UTM) tracking parameters in all URLs to tie email behavior to web analytics. Website metrics often give you a truer view of engagement and signal intent far better than email metrics ever could.

4. Test, learn, and optimize

Email marketing is iterative and ever evolving. What worked during last year’s Annual Enrollment Period (let alone last quarter) might not work today.

• A/B test CTAs, layout, subject lines, and variable content blocks
• Use pre-send tools (like Litmus) to check inbox formatting and spam triggers
• Track deeper engagement metrics within a web analytics tool: click-throughs, time-on-site, CTA interaction, and page revisits
• Perform frequent list management to remove hard bounces. Consider also using an email validation tool (e.g., ZeroBounce or BriteVerify).
• Monitor deliverability — work with IT to authenticate your sending domain (Sender Policy Framework [SPF], DomainKeys Identified Mail [DKIM], and Domain-based Message Authentication, Reporting, and Conformance [DMARC]), especially with Gmail and Apple tightening rules
• Consider testing the inclusion of interactive elements like polls or buttons (e.g., “Was this helpful?”) to gather feedback and drive clicks

Partner with DMW to get the most out of every email

Every email is a new opportunity to connect and convert — especially during Medicare’s most competitive seasons. Make sure your messages are timely, targeted, and built to drive action. DMW can help you plan, test, and optimize for stronger results with every send.