Mailchimp Playbook

Grow The Greenhouse
through email

Action plan + ready-to-send copy templates — everything in one place.

5Steps
10Action items
10Email templates
💡

Each action card below includes the why, how, and which Mailchimp report to check. Click "View email template" on any card to expand the ready-to-send copy — fill in the bracketed fields and paste straight into Mailchimp.

1
Account Setup

Connect Your Tools & Build Your Audience

Connect Squarespace + Square to Mailchimp

Setup

Sync your existing customer data so you can email people who've already bought from you — without starting from zero.

Segment
Full audience
Do this
Week 1

Why it matters

The Greenhouse already has customers in Square and Squarespace. Connecting these pipes your existing customer emails into Mailchimp instantly. Every future purchase or signup is captured automatically.

How to do it

  • Mailchimp → Integrations → search Square → authorize. Past customer emails import automatically.
  • Squarespace → Marketing → Email Campaigns → connect Mailchimp → add signup block to homepage + /wine-club.
  • Add a paper signup at the register; enter manually under Audience → Add Contacts.
  • QR code at the RAM Saturday market booth linking to your Mailchimp hosted signup form.

Mailchimp report to track

Audience → Overview → Audience Growth chart. Target: +5% list growth per month.

Create 4 Core Audience Segments

Setup

Tag every subscriber by what they care about so emails always feel relevant — not like mass blasts.

Segment
Full audience
Do this
Week 1

Why it matters

A plant buyer doesn't need the same email as a Wine Club member. Segmentation increases open rates, reduces unsubscribes, and drives more foot traffic per send.

The 4 segments to create

  • Coffee Regulars — tagged via homepage form or Square sync
  • Wine Club Members — auto-tagged on join ($68/mo, highest value)
  • Event Attendees — anyone who clicked an event link
  • Plant Buyers — Square customers who purchased a plant

Mailchimp report to track

Audience → Segments → View Report. Compare open rates across segments monthly. Under 30% = wrong content for that group.

2
Automated Welcome Flows

Greet Every New Subscriber Automatically

New Subscriber Welcome Series (3 Emails)

Automation

An automated 3-part sequence that introduces The Greenhouse to every new subscriber — without you lifting a finger.

Trigger
Subscriber joins audience
Sends
Day 0 · Day 3 · Day 7
Goal
First visit or Wine Club click

Why it matters

New subscribers are most engaged in the first 7 days. Without a welcome series, new signups sit dormant and forget they subscribed. A 3-email sequence converts curious visitors into regulars.

How to build it

  • Automations → Customer Journeys → Start Building.
  • Trigger: "Subscriber joins audience."
  • Email 1 (Day 0): Who you are, hours, happy hour, parking.
  • Email 2 (Day 3): Wine Club intro + plant drop dates.
  • Email 3 (Day 7): This month's events with links.

Mailchimp report to track

Automations → [Welcome Series] → View Report. Target 50%+ open rate on Email 1. Set a Goal on the Wine Club page to track conversions.

SubjectWelcome to The Greenhouse 🌿 here's everything you need to know
PreviewCoffee, plants, cocktails — and a seat with your name on it.

Alternative subject lines to A/B test

You just found your new favourite spot in Jacksonville
Plants, coffee, cocktails — welcome to The Greenhouse
SubjectTwo things we think you'll love (based on your vibe)
PreviewA zodiac-themed wine subscription and fresh plants every month.

Alternative subject lines

Your horoscope, but make it wine
New plants on the 1st + a wine club worth joining
SubjectWhat's happening at The Greenhouse this month
PreviewTrivia, Bingo, a silent book club, and more.

Wine Club Member Onboarding Email

Automation

Fires the moment someone joins the Wine Club — sets expectations, builds excitement, and reduces early cancellations.

Trigger
Added to Wine Club segment
Sends
Immediately + Day 3 follow-up
Goal
Reduce churn, build loyalty

Why it matters

Wine Club members pay $68/month. A strong onboarding email reduces cancellations by setting clear expectations and reminding them of the 20% retail discount before they forget they have it.

How to build it

  • Create a Journey triggered by "Subscriber is added to segment" → Wine Club Members.
  • Send immediately: confirm membership, list all 4 perks, link to /wine-club page.
  • Day 3: "Your first box ships soon — here's what to expect" with zodiac theme.

Mailchimp report to track

Automations → [Wine Club Onboarding] → CTOR. Below 10% means the email body doesn't match the subject line promise.

SubjectYou're in — welcome to the GH Wine Club ✨
PreviewYour first zodiac-paired box is on its way.

Alternative subject lines

Welcome to the club — your first box is almost here
The stars (and your bottles) are aligned
3
Recurring Monthly Campaigns

Stay Top-of-Mind Every Month

"What's Growing This Month" Newsletter

Campaign

One monthly email covering all events, the plant drop, and seasonal specials — sent on the 1st to the full list.

Send to
Full list
When
1st of month, 9 AM
Goal
Event clicks + Wine Club signups

Why it matters

Your audience has diverse interests. One well-crafted monthly roundup gives every segment a reason to visit and keeps The Greenhouse in their inbox during quiet weeks.

How to build it

  • Campaigns → Create → Regular Email. Schedule for 1st of month, 9 AM.
  • Subject formula: "[Month] at The Greenhouse: [Event], Plant Drop + [Seasonal hook]"
  • Structure: intro → events list → plant drop → featured drink → Wine Club CTA.
  • Use merge tag "Hi *|FNAME|*" in the greeting.

Mailchimp report to track

Reports → Campaign Reports → click map. See which section (events vs. plants vs. Wine Club) drove most engagement — double down on that content.

SubjectApril at The Greenhouse: Trivia, Plant Drop + Spring Cocktails
PreviewEverything worth showing up for this month.

Monthly Plant Drop Announcement

Campaign

A short, urgent email to Plant Buyers the evening before the 1st — creating anticipation and driving early visits.

Send to
Plant Buyers segment
When
Last day of month, 6 PM
Goal
In-store visit on the 1st

Why it matters

Plant drops are a key traffic driver. Without a heads-up email, subscribers miss new inventory entirely. An evening-before send creates urgency and gets plant parents to plan their morning.

How to build it

  • Create as a separate campaign from the monthly newsletter.
  • Send to Plant Buyers segment only, last day of month, 6 PM.
  • Keep it short: 3–4 sentences + a reminder that it's in-store only.

Mailchimp report to track

Reports → Campaign Reports → Plant Drop. A spike in website visits the next day confirms the email drove foot traffic.

SubjectNew plants arrive tomorrow — don't miss them
PreviewIn-store only. They go fast.

Alternative subject lines

Plant drop tomorrow — first come, first served
Fresh plants hit the floor tomorrow at 8 AM
Your plant collection is about to get an upgrade

Wine Club Zodiac Drop Email

Campaign

A monthly editorial email to Wine Club members revealing that month's bottles, zodiac pairing story, and Spotify playlist.

Send to
Wine Club Members segment
When
25th of each month
Goal
Retention + referrals

Why it matters

This email is what separates a transactional subscription from a community membership people brag about. High-touch, editorial quality makes $68/month feel like a steal.

How to build it

  • Send to Wine Club segment only, 25th of month.
  • Include: zodiac intro, bottle descriptions, compatible sign pairing, Spotify link, 20% discount reminder.
  • End with a referral nudge: "Forward this — memberships are open."

Mailchimp report to track

Forward rate = your referral signal. Open rate should stay 55%+. Below 40% means the zodiac content or subject line needs refreshing.

SubjectYour [Zodiac Sign] box is on its way — plus your perfect pairing
PreviewThis month's bottles, your compatible sign, and a playlist to drink to.
4
Promotional & Re-Engagement Sends

Drive Foot Traffic & Win Back Lapsed Subscribers

Spritz Hour Weekend Reminder

Promo

A short, breezy email every Thursday at noon reminding subscribers that spritzes drop to $7 Fri–Sun from 1–3 PM.

Send to
Full list
When
Every Thursday, 12 PM
Goal
Weekend foot traffic

Why it matters

Spritz Hour is an undermarketed revenue driver. A weekly Thursday reminder turns a passive offer into an active reason to visit — and keeps The Greenhouse in the inbox consistently without requiring new content each week.

How to build it

  • Campaigns → Create → Regular Email → Schedule as repeating weekly.
  • 3 sentences max. No images required — plain and warm.
  • Rotate the 5 subject lines below to keep open rates from declining.

Mailchimp report to track

Filter Campaign Reports by "Spritz." If open rate declines after 4 sends, rotate the subject line or add a seasonal twist.

SubjectSpritz season starts tomorrow 🍊
Preview$7 spritzes all weekend. Just saying.

Rotate these weekly to keep open rates up

$7 spritzes all weekend — see you there?
Your weekend just got a little bubblier
Tomorrow: $7 spritzes + good company
This weekend's plan: spritzes at The Greenhouse
We saved you a seat (and a $7 spritz)

Seasonal Menu Launch Campaign

Promo

Three times a year, a dedicated email announces new cocktails and coffee specials — making subscribers feel like VIP early adopters.

Send to
Full list
When
Late Feb · Late May · Late Aug
Goal
First visit for new menu items

Why it matters

Menu seasonality is one of The Greenhouse's strongest storytelling assets. Drinks like Bourbon Peach Pie and Cherry Blossom are inherently Instagram-worthy — announcing them by email gives subscribers a timely, exclusive reason to visit.

How to build it

  • Feature 1–2 new cocktails + 1–2 new coffees with short flavor descriptions.
  • CTA: "Be the first to try it this weekend."
  • Always include a Wine Club CTA at the bottom for non-members.

Mailchimp report to track

Target 4%+ click rate on the menu link. Screenshot the click map — it shows which new drink generated the most interest.

SubjectOur spring menu is here — meet the Cherry Blossom Latte
PreviewNew cocktails, new coffees, same lush vibes.

Adapt subject line by season

Summer menu is here — sip something new
Fall is here. So is the Bourbon Peach Pie Latte.
New season, new menu — come see what we made

90-Day Lapsed Subscriber Win-Back

Re-engage

Fires automatically after 90 days of inactivity — re-engages lapsed subscribers or cleanly removes them to protect deliverability.

Trigger
No opens in 90 days
Sends
Day 0 · Day 7 last chance
After
Archive if still no open

Why it matters

Disengaged subscribers hurt deliverability — Gmail starts routing your emails to spam when too many inactive addresses are on your list. A win-back either re-activates them or cleanly removes them. Either outcome improves performance.

How to build it

  • Automations → Customer Journeys. Trigger: "Contact has not opened email in 90 days."
  • Email 1: friendly check-in with a low-friction offer ($7 spritzes this weekend).
  • Email 2 (Day 7 for non-openers): "Last chance to stay in the loop."
  • After no open on Email 2: archive the contact automatically.

Mailchimp report to track

Automations → [Win-Back] → re-engagement rate. 10–15% re-engagement is a strong result. Suppress the rest to protect deliverability.

SubjectWe miss you — here's what's new at The Greenhouse
PreviewA lot has changed. Come see for yourself.
SubjectLast chance to stay in the loop
PreviewWe'll stop emailing if you'd prefer — no hard feelings.

Alternative subject lines

Still want to hear from us? (quick check-in)
We're about to stop emailing — unless you want us to keep going
5
Measure & Optimize

Track These 5 KPIs Every Month

KPITargetWhere in MailchimpAction if below target
Open rate≥ 40%Reports → Campaign Reports → Open Rate columnTest new subject lines; segment more narrowly
Click rate≥ 3%Reports → Campaign Reports → Click Rate columnAdd a single clear CTA; reduce links per email
Unsubscribe rate≤ 0.2%Reports → Campaign Reports → Unsubscribed columnCheck if wrong segment received the email
List growth rate≥ 5%/moAudience → Overview → Audience Growth chartPromote signup at RAM Saturday market and Square checkout
Wine Club signupsTrack monthlyReports → E-commerce → Revenue (requires Squarespace + Mailchimp integration)Add Wine Club CTA to every campaign footer; run a dedicated Wine Club email

Where to start

Begin with Steps 1 and 2 — get your account connected and your welcome series live within the first two weeks. Everything else builds on top of a healthy, well-segmented list. The Wine Club email program is already your strongest asset; Mailchimp lets you extend that same editorial quality to every subscriber, not just members.