Mine your past customer list
Scan your CRM for customers due for their next visit.
Wingman Welcome-Back Pilot
Charlotte
Customer Retention
Brings past customers back. Seasonal reactivation, loyalty thank-yous, and recurring-service reminders, each one written from the customer's actual history.
What Charlotte does
Charlotte owns the past-customer database that most service businesses forget about. Every quarter she reaches out to your eligible past customers with a personal reactivation message that references their actual last service, not a template. She also runs loyalty thank-yous for your repeat regulars and natural-recurrence reminders for trades with built-in cadence (HVAC tune-ups, dental cleanings, pest control). Charlotte never spams. She has a built-in cooldown lock so the same customer never hears from her twice in 80 days, and a max-nudges lifetime cap so loyal customers don't get burned out.
Capabilities
Built to do this every day.
01
Reads each customer's history before writing
Before Charlotte drafts a single message, she pulls the contact's last service, last conversation, and tags. The result: 'Hey Tom, it's been about a year since we replaced your dishwasher. Want me to send a tech to give the kitchen a quick check before winter?' Not 'Hi {first_name}.'
02
Quarterly seasonal campaigns
Spring tune-ups, summer maintenance, fall prep, winter check-ins. Charlotte fires one well-timed message per quarter, customized to your trade and your customer's history. 4 campaigns a year, never more.
03
Loyalty thank-yous at the right milestones
When a customer hits 3, 5, or 10 jobs with you, Charlotte sends a personal thank-you with an optional reward (discount, priority slot, branded gift). The message references your actual relationship, not a generic 'Thanks for being a customer.'
04
Natural-recurrence reminders
For trades with built-in cadence (HVAC annual tune-up, dental 6-month cleaning, pest control quarterly), Charlotte tracks when the next service is due and sends the reminder at the right moment. She suggests a calendar slot, not just 'time for your tune-up.'
05
Built-in 80-day cooldown
The same customer never hears from Charlotte twice in 80 days. She tracks last_nudged_at in a custom field. If a campaign would violate the cooldown, she skips that contact silently.
06
Lifetime cap so loyal customers aren't spammed
Charlotte caps at 8 lifetime nudges per contact (configurable). Once a contact's been nudged 8 times, she stops reaching out unless they opt back in. Your best customers don't get burned out.
On the job
Just a glimpse of what Charlotte handles.
Charlotte turns your dusty past-customer list into a steady source of returning work.
Instead of letting past customers forget you exist, every contact gets a timely nudge when the next service makes sense for their home or business.
Your team focuses on the jobs in front of them. Charlotte handles the database, the follow-ups, and the seasonal touchpoints.
Track service anniversaries
Note when each customer is due for recurring service.
Send seasonal SMS nudges
Text reminders aligned to the right season for each service.
Send seasonal emails
Email longer reminders when the timing calls for it.
Offer a real booking slot
Include a real open time the customer can lock in.
Greet past customers by name
Open every message with their name and last service.
Reference their last job
Mention the work you did last time so the message feels personal.
Segment by service type
Group customers by what they had done last time.
Tag dormant contacts
Flag anyone who hasn't booked in twelve months.
Alert you on re-engagements
Ping you when a dormant customer responds to a nudge.
Celebrate win-backs
Send you a quick note when a re-engaged contact books.
Re-engage stalled estimates
Follow up on quotes that went cold a month ago.
Send spring tune-up reminders
Text about spring maintenance windows when the weather turns.
Send winter prep reminders
Nudge customers before the first freeze each year.
Send fall service reminders
Time fall outreach to the seasonal calendar you set.
Send storm-prep reminders
Push storm-prep messages when forecasts call for it.
Send anniversary touches
Mark the anniversary of their last big job with a check-in.
Thank long-time customers
Send personal thank-yous to your most loyal clients.
Offer loyalty pricing
Quote a return-customer discount where it makes sense.
Announce new services
Tell past customers when you've added a service they'd want.
Ask for a referral
Request a referral after a positive interaction.
Run quarterly check-ins
Touch base every quarter on a soft, helpful note.
Build re-engagement lists
Pull lists of customers ready for a specific campaign.
Drip win-back sequences
Run a three-touch sequence over fourteen days for deep sleepers.
Personalize each message
Pull in the customer's name, last service, and address.
Mark re-bookings
Note every win-back booking against the campaign that drove it.
Suppress recent customers
Skip anyone who's already had service in the last ninety days.
Find your best wins to repeat
Identify what worked last quarter and run it again.
Sound caring, not pushy
Use warm language that doesn't read like junk mail.
Drive to the booking link
Make booking one tap away in every message.
Suggest a call when it fits
Offer a quick call for higher-ticket re-engagements.
Pitch annual service plans
Introduce maintenance plans to one-off customers.
Sign off in brand voice
End every nudge with your shop's tone, not a template.
Honor opt-outs
Honor unsubscribe requests instantly across all channels.
Group by ZIP for batch days
Bundle re-engagements by route to make truck days efficient.
Recap campaign results
Show how many dormant contacts replied, booked, or paid.
Restore archived contacts
Re-add archived customers when a re-engagement lands.
Time nudges for open windows
Send at the hours your customers actually read messages.
Schedule overnight sends
Queue overnight drops so they land first thing in the morning.
Send small thank-you touches
Drop the occasional appreciation note with no ask attached.
In the field
Real scenarios.
March 1 spring campaign for past plumbing customers
It's March 1. Charlotte's Q1 campaign trigger fires. She's looking at 247 contacts tagged past-customer who haven't been nudged in 80 days.
Charlotte reads each contact's last job, drafts a personal SMS or email referencing it, and sends in batches over 3 days to avoid delivery flagging. 41 customers reply. Of those, 22 book a spring tune-up. Charlotte tags each booked customer 'charlotte-resurrected' and SMS's you the wins.
"Hey Sarah, it's been about 14 months since we put in your tankless heater. Spring's a smart time to flush it and check the connectors. Want me to send Mike out for a 30-min tune-up next week? $89 covers it."
5th-job loyalty thank-you
Tom just had his 5th job done with you (a sump pump replacement). The opportunity moves to Won.
Charlotte detects the milestone via opportunity-count, drafts a personal thank-you referencing the 5 jobs across the years, and offers a $50 credit toward his next service. The credit is a custom field on his contact so you can honor it next time he books.
"Tom — sump pump is job #5 we've done together since 2022. That's a real thank-you. We just dropped a $50 credit on your account, no expiration. We appreciate you sticking with us."
HVAC annual reminder
Linda had her HVAC tune-up on April 12 last year. It's now April 1 this year.
Charlotte sees the natural-recurrence cadence (annual), pulls Linda's last appointment notes, and drafts a reminder offering 3 specific dates from your calendar. Linda picks one. Charlotte books it on your calendar and creates the opportunity.
What you'll connect
Integrations
Required connections need to be wired before Charlotte can fly. We'll guide you through every one during onboarding.
- ✓
Phone line for SMS
Same line Mia/Sophia use
- ✓
Gmail or our platform native email
For longer-form seasonal messages
- ✓
Past customer database
Tagged past-customer with last_service_date + last_service_type
- ✓
Seasonal calendar config
What's a Q1 service for you? Q2? Q3? Q4?
- +
Your calendar Optional
So Charlotte can offer real slots in recurrence reminders
- +
Owner phone for win alerts Optional
For 'Charlotte resurrected Sarah' notifications
What gets deployed
Inside the build
When your estimate is accepted, our system automatically deploys these artifacts to your Wingman dashboard. No copy-paste, no manual setup.
- 4 quarterly seasonal campaign workflows (Q1/Q2/Q3/Q4) with native our platform waits + branches
- Eligibility tagger workflow (daily 2 AM cron) that maintains the charlotte-active audience
- Four automation handlers (reactivation_draft, classify_reply, loyalty_offer_draft, recurring_reminder_draft)
- Cool-down lock workflow (anti-spam guard on 80-day window)
- Opt-out enforcement workflow (STOP → do-not-contact + remove charlotte-active)
- Resurrected tagger workflow (on customer tag added post-Charlotte → tag + SMS owner)
- Loyalty milestone trigger workflow (3rd, 5th, 10th job thresholds configurable)
- Natural-recurrence reminder workflow for trades with cadence
- Custom fields: charlotte_last_nudged_at, charlotte_total_nudges, charlotte_resurrected
- Tags: past-customer, charlotte-active, charlotte-resurrected, do-not-contact
Ideal for
Any service business with a database of past customers gathering dust. Especially trades with natural recurrence (HVAC, plumbing maintenance, pest control, dental) or seasonal cadence (landscaping, gutters, pool service).
FAQ
Common questions.
How is Charlotte different from a normal email blast? +
An email blast sends the same templated message to everyone. Charlotte writes a fresh message per contact referencing their actual last service, your actual relationship, and the actual season. The reply rates are usually 5x to 10x higher because the message reads like a real text from a real person.
Will Charlotte spam my customers? +
No, by design. There's an 80-day cooldown so the same contact never gets two messages inside that window, and a lifetime cap (default 8 nudges) so even your most-engaged customers aren't worn out. You can tighten either knob.
What if a customer replies STOP? +
Charlotte adds the do-not-contact tag, removes the charlotte-active tag, and exits silently. No further messages will go out from Charlotte or any other Wingman. The opt-out is honored permanently and across channels.
Does Charlotte work for trades without natural recurrence? +
Yes. For one-off trades (remodelers, roofers, fence installers), Charlotte runs the quarterly seasonal campaigns instead. The reactivation language shifts from 'time for your annual' to 'spring's a good time to think about that deck repair we talked about.'
How do I see what Charlotte's about to send? +
Every campaign has a preview window in your Hangar dashboard. You can approve the whole batch, edit individual drafts, or kill the campaign. After the first quarter most owners trust the preview and let it run on autopilot.
Pairs well with
Build a crew.
Harper
Sales Strategist
Texts every missed-call lead within 5 minutes. Runs a 5-step personalized chase that stops the second they book. Pings you the second a lead goes hot.
Learn about Harper →
Sloane
Email Marketer
Runs your email channel end-to-end. 5-step welcome series for every new lead, a monthly newsletter tuned to your trade, and win-back sequences for subscribers gone quiet.
Learn about Sloane →
Stella
Reputation Manager
Fires the review-request SMS at the perfect moment after every job, auto-replies to positives, and pings you in 5 minutes when a negative one lands.
Learn about Stella →
Ready to hire Charlotte?
Tell us about your business and we'll send a tailored proposal with Charlotte configured for your industry — within one business day.