A customer who bought from you two years ago is different from a new prospect, yet many wineries and farms treat them that way. Lapsed customers already know your product, they've paid before, and they're cheaper to win back than to find from scratch. The question is whether you have a system to bring them back.
Segment your inactive customers by purchase history
Not all lapsed customers are equal. Someone who bought one bottle three years ago is a different challenge than a wine club member who canceled last year. Before you run a single campaign, divide your inactive list into meaningful groups. Look at how much they spent, how often they bought, and how long ago they went dormant.
High-value segments, such as wine club members, repeat buyers, and large one-time purchasers, deserve a different approach than casual or one-time buyers. A lapsed wine club member might respond to a personal phone call or a personalized email offering a discount to restart the subscription. A casual past customer might need a broader offer: a discount on their next purchase, an invitation to a tasting event, or new product news.
Use your CRM or sales history to create these segments. If you don't have a CRM yet, a spreadsheet works temporarily, but you'll want to upgrade before running a real campaign. Fracmo's Starter plan includes a self-serve CRM that makes segmentation straightforward. Tag customers by tier, purchase date, and value; then filter your list to target specific groups.
Diagnose why they left, then address it.
Before you offer a discount, ask yourself why the customer went inactive. Did they move? Did they switch to a competitor? Did your prices go up? Did they stop entertaining? Were they unhappy with a purchase? The answer shapes your message. A generic reactivation offer feels tone-deaf if the real problem was a bad experience.
If you have a small list of high-value lapsed customers, say wine club members or regular farmers market shoppers, pick up the phone. A quick conversation often reveals the truth: a move to a different state, a shift in budget, a switch to local producers, or simply that they forgot you exist. That insight lets you tailor your outreach. Someone who moved is not coming back unless you ship to their state. Someone who forgot needs a gentle reminder with new reasons to buy.
For larger lists, you can infer reasons from context. If someone's last purchase was five years ago and they never responded to emails, they may have changed their email address or abandoned their account. If a wine club member canceled six months ago, check whether you raised prices or changed shipping policies around that time. Look for patterns: Did a cohort of customers go inactive after a specific date? That often signals a product, service, or pricing change.
Craft a re-engagement email sequence
Email is your workhorse. It costs almost nothing and you own the relationship. A re-engagement sequence typically runs three to five emails over two to three months. The first email should be friendly and low-pressure: acknowledge that it's been a while and remind them why they liked you. The second and third emails can get more direct, offering a specific incentive. The final email is often a last chance: 'We'd love to have you back, here's 20% off, offer expires in one week.'
Keep each email short and personal. Address them by name. Reference their past purchase if you can ('We remember you loved our Pinot Noir') to show you recognize them as an individual. Include a single clear call to action: 'Restart your wine club,' 'Visit us for a tasting,' 'Shop our new harvest,' or 'Use this code for 15% off your next order.' Avoid overwhelming them with ten different options.
The incentive matters, but it doesn't have to be a steep discount. For wine clubs, offering to skip a month or let them choose their selection might work better than a price cut. For farm CSAs, a free add-on like a dozen eggs or a jar of jam might reactivate someone who paused. For a winery, early access to limited releases or an invitation to a members-only event can feel more exclusive than 20% off. Test different incentives with different segments and track what actually brings people back.
Use retargeting ads to stay top of mind
Email and SMS can end up in spam or get ignored. Retargeting ads, which are display ads that follow a customer around the internet, work as a visual reminder. When a lapsed customer visits your website, they see an ad for your new vintage or product line as they browse other sites. It's not aggressive; it's just a nudge.
Set up a retargeting campaign that targets visitors who haven't made a purchase in the last 12 to 18 months. Use the same imagery and messaging as your email campaign so the touchpoints feel connected. The ad should emphasize what's new, 'We released our 2022 reserve,' or 'New harvest is in,' or the incentive: 'Come back and save 15%.' Keep the ad running for 60 to 90 days alongside your email sequence.
Retargeting is affordable because you're only paying for ads shown to people you already know. The conversion rate is often higher than cold ads because these are warm leads. If you use Fracmo's Growth or Premium plan, your strategist will set up and manage retargeting as part of your overall campaign. If you're running it solo, most platforms (Google, Facebook, Instagram) have built-in retargeting tools and templates.
Make it easy to come back: remove friction.
When a lapsed customer clicks your email or ad, they should land on a page that makes it easy to re-engage. If your goal is to restart a wine club, don't send them to your homepage. Send them to the wine club sign-up page with a pre-filled discount code. If you want them to book a tasting, link directly to your booking system. Every extra click or form field costs you customers.
Check that your online purchase process still works. If you're a winery with an e-commerce site, confirm that checkout is smooth, shipping costs are transparent, and payment options are current. If you sell at farmers markets, make sure your location and hours are clearly posted. If you have a farm stand or tasting room, confirm hours, directions, and any special events are visible. A customer who wants to come back but can't find basic info will just move on.
Consider offering a special welcome back incentive or exclusive product. A free tasting, a bonus bottle, or a limited-edition product available only to returning customers adds a sense of occasion. It signals that you value their return and makes them feel recognized, not like they are just another email on a list.
Track and measure what works
To know whether your re-engagement efforts are working, you need to track basic metrics. How many people opened your email? How many clicked? How many bought? What was the cost of your campaign, and what was the revenue? These numbers tell you whether the effort is worth repeating and where to improve.
Set up tracking before you launch. In most email platforms, you'll see open rates and click rates automatically. Tag purchases made through your re-engagement campaign so you can connect them to revenue. If you run retargeting ads, check the platform's dashboard for clicks and conversions. Compare these results to your normal purchase rate. If re-engaged customers convert at a similar or higher rate than new customers, then you know the campaign is working.
- Email open rate: typical benchmark is 15-30% for promotional emails; your list may perform better or worse depending on subject line and audience quality
- Click-through rate: typical benchmark is 2-5%; better if your subject line is strong and your offer is relevant
- Conversion rate: what percentage of people who clicked bought something? Track this by tagging campaign traffic in your shopping cart or POS system
- Cost per reactivation: divide total campaign spend by number of purchases to see your cost per customer won back
- Lifetime value: once they come back, are they a repeat buyer? Do they stay longer than customers who never lapsed?
Use these metrics to improve the next campaign. If email open rates are low, test new subject lines. If click rates are high but conversions are low, the problem might be the landing page, the offer, or the product itself. If retargeting converts better than email, put more budget into ads. Most campaigns need two or three iterations before they hit their stride.
Set up a system to prevent customers from lapsing again
Winning back a lapsed customer is expensive. Keeping an active customer active is much cheaper. Once you've re-engaged someone, build a system to maintain the relationship. That might be a wine club that auto-ships every quarter, a farmers market presence where they know to find you, or an email list that gets regular updates on new releases or events.
For high-value customers, stay in regular contact. A monthly or quarterly newsletter about new products, farm events, or behind-the-scenes stories keeps you top of mind. For wine clubs or CSA members, consistent shipping and great product keep them renewing. For casual buyers, periodic emails about sales or seasonal releases can prompt repeat orders.
Most importantly, track inactivity from the start. Set a rule in your CRM: flag any customer who hasn't purchased in 12 months. When someone hits that threshold, trigger an automated outreach: a simple email saying 'We miss you' or an offer to lure them back. The longer someone is inactive, the harder they are to win back. Catching them at month 12 instead of month 24 makes a real difference.
See exactly what each Fracmo plan ships. Every deliverable and every price is public: $249, $999 and $2,490 a month, month-to-month, with no discovery call to see a number.
See Fracmo pricing →Keep reading
- What is a fractional CMO?: the plain-English 2026 guide
- Fractional CMO cost in 2026: real numbers, including ours
- AI CMO vs fractional CMO: how the models actually differ
- Compare Fracmo to agencies, in-house hires and DIY tools
- Fracmo's CRM for wineries, vineyards and farms: pre-configured pipeline, booking and KPIs for the vertical
- All Fracmo blog guides