How to Drive Enrollment with Health Insurance Marketing

Writer: Kerri O’Connor
Date: Jun 26, 2025

Before consumers even ask themselves, “Which insurance policy is right for me?”, health insurance advertisers are already in motion, strategizing how to connect with individuals actively evaluating coverage options. The enrollment period is a critical window, and success hinges on more than just visibility. To truly move the needle, advertisers must harness customizable audience targeting, real-time optimizations, and transparent performance insights. When done right, this approach doesn’t just boost engagement; it drives sign-ups and maximizes impact across every stage of the decision-making journey.

Because when it comes to enrollment season, you don’t just want to show up—you want to be top of mind for every prospect making their critical coverage decision.

TOP TARGETING STRATEGIES FOR HEALTH INSURANCE ADVERTISERS

During open enrollment, your audience isn’t just browsing—they’re making one of the most important decisions of the year. Whether it’s selecting a new provider, comparing benefits, or renewing an existing plan, consumers are actively seeking clarity and confidence. But with so many options and so little time, cutting through the noise takes more than broad awareness. It requires precision, personalization, and timing.

That’s where Simpli.fi delivers. By combining intent-based insights with advanced targeting capabilities, advertisers can meet individuals exactly where they are in the decision-making journey. Here’s how to reach, engage, and convert more of the right prospects at the right moments:

• Location-Based Precision
  Use Simpli.fi’s Geo-Fencing tools to target individuals based on real-world behaviors. Build custom fences around healthcare facilities, pharmacies, community centers, and employer campuses to capture high-intent audiences, then retarget them for up to 30 days post-visit. The Geo-Fence Finder Tool makes it easy to scale by building custom location lists tailored to your audience.
• Hyperlocal, Household-Level Targeting
  Target by address with unmatched precision. Tap into your existing member database to support renewals or promote new offerings or build custom audiences using Simpli.fi’s Addressable Audience Curation Tool—leveraging 3,000+ demographic variables like age, income, and family status. The result? More relevant outreach during key enrollment periods.
• Contextual Relevance That Converts
  Place your message where consumers are already paying attention. Contextual targeting allows you to appear in relevant digital content—like health blogs, insurance guides, or wellness articles—where your plan details and enrollment info feel like a natural fit. It’s a subtle, powerful way to reach individuals when they’re thinking about their health and coverage options.
• Intent-Driven Outreach
  Target individuals based on their search behavior. Whether someone’s looking up “Medicare Advantage benefits” or “how to enroll in a family plan,” intent-based advertising helps you meet them with messaging that answers their questions in real-time.
• Retargeting That Re-Engages
  Not everyone converts on the first visit. Retarget website visitors and guide them toward the next step—whether that’s exploring coverage options, scheduling a call, or requesting more information. Stay top-of-mind throughout their journey to enrollment.

ENGAGE HEALTH INSURANCE SHOPPERS ACROSS EVERY SCREEN

Today’s health insurance journey doesn’t happen in a single moment—or on a single device. Consumers are researching plans during lunch breaks, comparing providers while streaming TV, and checking coverage options on their phones between errands. Their path to enrollment is dynamic and fragmented, but every touchpoint presents an opportunity.

That’s why multichannel engagement is no longer optional—it’s essential. Simpli.fi empowers advertisers to show up consistently and meaningfully across the screens consumers use every day, with creative formats that educate, inform, and drive action.

Reach your audience through a variety of channels:

Whether your goal is brand awareness or enrollment conversions, Simpli.fi ensures your messaging is always relevant—reaching prospects exactly when and where they’re making decisions.

What you gain by meeting consumers across every screen:

• Stronger brand recall: Stay top-of-mind by showing up consistently as consumers research, compare, and decide.
• Higher engagement rates: Deliver personalized creative on the devices and platforms where users are most active.
• Shorter decision cycles: Reinforce key benefits at multiple touchpoints to accelerate the path from interest to action.
• Seamless retargeting: Reconnect with users wherever they are—mobile, desktop, streaming TV, or digital out-of-home displays.
• Better-performing campaigns: Identify which screens and formats deliver results, and fine-tune your media mix for greater impact.

No matter where or how your audience explores their options, Simpli.fi keeps your message front and center—building trust, guiding decisions, and driving enrollment momentum.

MEASURE WHAT MATTERS: ENROLLMENT-FOCUSED ANALYTICS

Great targeting is only half the equation—knowing what’s working (and why) is what turns good campaigns into enrollment powerhouses. Health insurance marketers need more than impressions and clicks. You need comprehensive insights. Simpli.fi’s Reporting and Analytics Center turns campaign data into actionable intelligence, helping you fine-tune every strategy with confidence.

• Website Engagement: Track how ad-exposed users interact with key pages, including content from CTV campaigns.
• Lead Activity: Monitor quote form submissions, email signups, click-to-call actions, and other high-intent signals.
• Enrollment Conversions: Connect the dots between ad exposure and actual plan signups to see what truly drives results.

When timing is everything, real-time visibility helps you move with precision—and lead with confidence.

A SUCCESSFUL STRATEGY REQUIRES A COMPREHENSIVE APPROACH

Open enrollment is crowded, competitive, and critically important. With Simpli.fi, your message doesn’t just reach your audience—it resonates. From precise targeting to enrollment-driven measurement, we help health insurance advertisers cut through the noise and drive meaningful results.

This enrollment season, show up prepared. Lead with personalization. Perform with purpose.

 
Ready to take your enrollment strategy to the next level?
Connect with your Simpli.fi team or email hi@simpli.fi and discover how we help health insurance advertisers stay ahead—one enrollment at a time.

Kerri O’Connor Senior Manager, Content Marketing | Simpli.fi Kerri O’Connor is a strategic product marketer with deep expertise in digital advertising, audience engagement, and campaign performance. As a Senior Manager of Content Marketing at Simpli.fi, she leads go-to-market strategy, messaging development, and product adoption for innovative ad tech solutions. Kerri brings a strong background in programmatic media, digital strategy, and client enablement, translating complex industry trends into clear, actionable marketing. She excels at blending data with storytelling to drive results and help brands connect with the right audiences. A passionate storyteller and data-driven marketer, Kerri is committed to helping brands navigate the evolving digital landscape and maximize their marketing impact.