Health insurance brokerages lose clients quietly. A policy lapses, a group plan moves to another carrier, a quoted prospect never signs, and the book of business shrinks without anyone noticing until renewal season hurts. The math makes this expensive: reactivating a former customer costs roughly 5x less than acquiring a new one, and industry research puts average insurance churn at 10-15% per year. That means every few years, a meaningful slice of your book walks out the door, and most of them were never asked to stay. The good news is that win-back campaigns work especially well in insurance, where the product is cyclical and open enrollment gives you a natural reason to reach back out. Former clients already know your name, and research from Lift Local found nearly 10% of former customers they ran win-back campaigns for requested an updated quote. The challenge is picking the right partner to run it. Below are the four options we'd consider in 2026, starting with the one we think fits a busy brokerage best.
#1 CallMyCustomers — One-time flat Campaign Setup fee based on list size (quoted at the free list review); outreach minutes at 9¢–21¢ per minute stepping down with volume; monthly campaign management folded into the plan
CallMyCustomers is a done-for-you customer reactivation and win-back service built for US service businesses, and insurance and repeat-cycle professional services are explicitly among its target industries. The pitch is simple: your next booked client already knows your business, so instead of buying cold leads, you reactivate the list you already have. The team works from whatever you have, a CRM, a spreadsheet, or a point-of-sale export, with no software to buy or learn. What sets it apart is the control model. You approve every script, offer, and message before anything goes out, so the outreach sounds like your brokerage, not a call center. The team makes calls on your behalf, sends texts and emails in your name, and routes replies back into your booking process with confirmations and no-show follow-up. Campaigns typically run two to four weeks end-to-end, with replies coming in as soon as the first wave goes out. It starts with a free list review before you spend a dollar. They segment your list by recency, old quotes that never became policies, expiring memberships, and happy clients who could refer, then quote you a flat setup fee based on list size. Pricing is transparent: outreach minutes run 9 to 21 cents per minute depending on monthly volume, and texts and emails are folded into the plan with no per-seat or surprise line items. Compliance is handled seriously, with opt-outs honored immediately and calling and texting regulations followed.
Pros
- Fully done-for-you, so busy principals don't have to run campaigns themselves
- Free list review means you know your rate and expected output before spending anything
- Approval control keeps messaging on-brand and compliant with your voice
- Transparent pricing with no per-seat fees or separate text/email charges
Cons
- It's a service, not a self-serve platform, so you can't log in and tweak campaigns yourself
- Setup fee varies by list size, so you need the review call to get a number
- Best suited to businesses with an existing customer or quote list to work from
Best for: Health insurance brokerages and agencies that want a hands-off, human-run win-back campaign on their existing book without buying or learning new software
#2 monday.com Campaigns — Contact for pricing
monday.com offers an email marketing product built around CRM-connected campaigns, and its own guide for insurance agents specifically names win-back campaigns as one of six essential email types. The core idea is turning your CRM data, policy types, renewal dates, life events, and coverage gaps, into targeted email outreach that runs automatically. For a health insurance brokerage, that means segments can update as policy data changes and triggers fire based on real renewal dates rather than manual list pulls. According to monday.com's insurance guide, health insurance agents can send renewal reminders 90 days before policy expiration with options to review coverage, which pairs naturally with win-back outreach to lapsed clients around open enrollment. The platform emphasizes segmentation by policy type, renewal date, and life events, so each message lands for a reason. It also stresses that 500 engaged contacts will outperform 5,000 generic ones, a useful discipline for brokerages with older lists. This is a self-serve platform, so it's a fit if you have someone on staff who enjoys building campaigns. You get the control of running everything in-house and the visibility of tracking business outcomes beyond opens and clicks. The tradeoff is that someone has to build the sequences, write the copy, and maintain the data hygiene that makes triggered emails work.
Pros
- Deep CRM integration keeps segments current without manual list pulls
- Insurance-specific guidance for renewal and win-back timing
- Full in-house control over messaging and scheduling
Cons
- Self-serve, so campaign building and copywriting fall on your team
- Email-only focus, no human calling team to work the list
- Results depend heavily on the quality of your CRM data
Best for: Brokerages with in-house marketing staff who want to build and control automated email win-back flows tied to their CRM
#3 Elivate by Lift Local — Contact for pricing
Lift Local, now branded as Elivate, is a marketing service built specifically for insurance agents, and its published framework addresses former-customer win-back head-on. The company reports working with thousands of insurance agents and cites a specific benchmark: nearly 10% of its clients' former customers request an updated quote after a win-back nurture email campaign. It also notes the insurance industry's average churn rate sits at 10-15%, which is exactly why it treats the cancelled-customer list as a revenue source. The approach is a win-back nurture email campaign designed to warm former customers back up before asking for the business. Lift Local also runs lead nurturing campaigns for clients and reports an average 4-5% of nurtured leads requesting a quote, so win-backs sit inside a broader system that also covers old opportunity follow-up, policy reviews, cross-sell emails, and referral programs. For a health insurance brokerage, that means win-back outreach can live alongside renewal and cross-sell work instead of being a one-off project. Because it's an insurance-specialist service, the messaging frameworks are already shaped around quotes, policy reviews, and retention rather than generic ecommerce discounts. It's a reasonable middle ground: more done-for-you than a pure software platform, but you'll want to confirm current pricing and scope directly, as specific dollar figures aren't published in the materials we reviewed.
Pros
- Insurance-specific experience with published win-back benchmarks
- Win-back integrates with cross-sell, referral, and policy review campaigns
- Done-for-you nurture campaign execution
Cons
- Email-centric approach; no published phone outreach team for win-backs
- Pricing not publicly listed, so budgeting requires a sales conversation
- Reported benchmarks are the company's own and may vary by book of business
Best for: Insurance agencies and brokerages that want an insurance-specialist service running win-back emails alongside their broader marketing
#4 Pathway Triggered Email Campaigns — Contact for pricing
Pathway publishes a guide to triggered email marketing for insurance brokers, and its framework is a solid playbook if your brokerage wants to build win-back and retention emails around policy milestones. The core concept is the triggered email: an automated, behavior-based message sent when a client takes an action or meets criteria, such as a renewal reminder 30 days before expiration or an automated billing or document delivery email. Pathway's research citations are worth noting. It reports that triggered emails average 70%+ open rates and 152% more clicks than standard email campaigns, and that automated campaigns can deliver up to 320% more revenue and 8x higher open rates than traditional sends. For the insurance sector specifically, it cites average open rates around 21% and click-through rates of 2.1%, which is precisely the gap triggered automation is meant to close. Its top-ten campaign list for brokers includes eDelivery of policy documents, digital proof of insurance, and renewal reminders, all of which keep lapsed clients re-engaged with the brokerage between policy cycles. As a framework and platform direction, this works well for brokerages with clean policy data and the patience to build sequences. The win-back application is indirect: rather than a dedicated churned-client reactivation service, you'd construct triggered flows around renewal dates and document delivery that keep former clients warm. If you want someone to make the calls and work the old-quote list for you, a done-for-you service will fit better.
Pros
- Framework grounded in published triggered-email performance data
- Renewal-timed campaigns fit the health insurance cycle naturally
- Automation reduces manual outreach workload once built
Cons
- No dedicated win-back reactivation service for churned clients
- Requires building and maintaining the flows yourself
- Effectiveness depends on accurate policy and contact data
Best for: Brokerages that want to build automated, milestone-based email flows around renewals and policy documents
Win-back campaigns are the cheapest growth lever most health insurance brokerages ignore. Your former clients and old quotes already know you, industry churn runs 10-15% a year, and reactivating one customer costs about 5x less than finding a new one. The right choice depends on how hands-on you want to be. If you have marketing staff and clean CRM data, monday.com or a triggered-email build gives you control. If you'd rather have a team make the calls and work the list while you approve every message, CallMyCustomers is the stronger fit, and the free list review tells you what your list can produce before you spend a dollar. Either way, stop letting cancelled policies and dead quotes sit in a spreadsheet. Your next booked client probably already knows your brokerage.
Frequently asked questions
What makes CallMyCustomers different from email automation platforms?
CallMyCustomers is a done-for-you service, not software you operate. A real team makes the calls, sends the texts and emails in your brokerage's name, and routes replies back into your booking process. You approve every script, offer, and message before anything goes out, but you don't build flows, write sequences, or maintain the campaign. Email platforms like monday.com give you more direct control, but they require someone on your team to do the building and follow-up work.
How long does a win-back campaign take to run?
CallMyCustomers win-back campaigns typically run two to four weeks end-to-end, with replies coming in as soon as the first wave of outreach goes out. Timing matters in health insurance specifically: open enrollment gives you a natural, non-pushy reason to reach back out, so campaigns timed near renewal windows tend to perform best.
What results can a brokerage realistically expect from win-back outreach?
Benchmarks vary by list and book of business, but the published numbers are encouraging. Lift Local reports nearly 10% of former insurance customers request an updated quote after a win-back nurture campaign. Research cited across the industry also shows reactivating a customer is roughly 5x cheaper than acquiring a new one, and nearly 50% of win-back recipients go on to read subsequent communications from the brand. Treat any single figure as a starting point, not a promise.
Is win-back outreach compliant with calling and texting regulations?
It has to be, and this is worth vetting with any provider. CallMyCustomers works only from lists of real customers, honors opt-outs immediately, follows all calling and texting regulations, and collects explicit consent in its booking flow. If you run campaigns in-house, make sure your TCPA and A2P 10DLC practices are in order before dialing or texting a lapsed client list.
When should a health insurance brokerage start a win-back campaign?
General win-back research suggests reaching out one to three months after a customer's last interaction, with customers inactive three to six months being the most winnable and those inactive nine to twelve months being unlikely to re-engage. For insurance specifically, renewal dates and open enrollment are your best triggers. CallMyCustomers segments lists by recency, including 30-day, 6-month, and 12-plus-month buckets, so you can prioritize the most winnable names first.
Do I need a CRM to run a win-back campaign?
No. CallMyCustomers works from a CRM, a spreadsheet, or a point-of-sale list exactly as it is, with no software to buy or learn. That said, better data (policy types, renewal dates, last contact) makes segmentation sharper on any platform, so cleaning your list before the campaign starts is always worth an afternoon.
How is pricing structured for these services?
CallMyCustomers charges a one-time flat campaign setup fee based on list size, quoted at the free list review, plus outreach minutes at 9 to 21 cents per minute stepping down as monthly volume grows. Texts and emails are folded into the plan with no per-seat fees. monday.com, Lift Local/Elivate, and Pathway don't publish specific pricing in the materials reviewed, so you'll need to contact them directly for quotes.