Society 88 · Pilot Plan
A Plan for Society88

Selling what you
already do — to the
customers who
already trust you.

A small email pilot to your warmest existing clients, introducing the in‑home service. A template for marketing this and future offers.
Prepared by Jeff For Mark · May 2026
02 · The Opportunity 02 / 12
The Opportunity

You're already doing this.
Most of your book has no idea.

A handful of your customers already book in‑home stays. To you, it's the biggest opportunity in the business — the high‑end version of everything you already do.
The rest of your book has no idea you offer it. And they're the best people you could ever offer this to: they've already paid you, they already trust you with their dogs. You couldn't buy a better list of potential customers if you tried.
Your service ladder
In‑home
Top spenders
Club members
Repeat customers
All customers
Society 88 · Pilot Plan Opportunity
03 · Who Buys This 03 / 12
Who Buys This

Who's the ideal customer for this?

Three I can see from the outside. Who else beyond that?
i.
The Hard‑to‑Board

The owner whose dog struggles with boarding.

Anxious, senior, reactive, or rescue. Boarding is hard on them and on the owner. In‑home is the version that actually works.

ii.
The Lived‑In House

The traveler who doesn't want the house empty.

Pets, plants, mail, routine. The house staying lived‑in is part of what they're paying for.

iii.
The Outgrown Boarder

The repeat boarder who's outgrown boarding.

Already trusts you. Would pay more for something built around their household.

iv.
Or someone else?

Probably a profile only you'd see from inside.

Who am I missing?

Society 88 · Pilot Plan Audience
04 · Where The List Lives 04 / 12
Where The List Lives

The list already exists.
We just have to use it.

Every customer, every booking, every dog you've cared for is already in your systems. We don't have to build the list, buy it, or guess at it.
We pull it out, analyze what's there, then enrich it with even more information.
Already in your system
Kennel Booker
Name · email · phone · address · booking history · dog count · last visit · lifetime spend · anything else?
Gap-fill
Stripe
Only if Kennel Booker is incomplete.
Analyze + enrich
From what's there, plus what isn't
First a hard look at what's already there — neighborhoods, booking patterns, lifetime spend. Then we enrich it — homeowner vs. renter, married vs. single, anything else useful for targeting and messaging.
Society 88 · Pilot Plan Data
05 · Segmentation 05 / 12
Segmentation

Choose the right audience.

We pick the customers you most want to serve — the ones most likely to say yes.
Most active, top spenders, club members, specific neighborhoods, something else — gets decided once we see the data.
i.
Active customers
Last‑visit recency, by your call.
ii.
Boarding frequency
Multiple times a year vs. one‑and‑done.
iii.
Spending tier
Lifetime spend — your top of book.
iv.
Club membership
Club vs. non‑club, pulled from the export.
v.
Neighborhood
Bethany, Lake Oswego, anywhere else you want to grow.
vi.
Homeowner vs. renter
From address enrichment.
vii.
Dog profile
Reactive, rescue, anxious, senior — from your booking notes.
viii.
Household
Married vs. single, household composition — from enrichment.
Society 88 · Pilot Plan Targeting
06 · The Offer 06 / 12
The Offer

A Society88 caretaker,
in their home, while they're away.

You're already running it for a handful of customers — still being dialed in. We turn it into something the rest of your book can buy.
Plus a hook that lets us count whether it worked.
The Offer
Boarding-grade care, and beyond, at home. Your team stays with the dogs, keeps their routine, and looks after the house. Plants watered, mail in, the place clean and ready when they're back.
The Hook
Something like: "First night free — if we watch your house at least three nights."
When a customer claims it, we can count them — and that's how we'll know if this is working. Final wording is yours.
Society 88 · Pilot Plan Product
07 · Mechanics 07 / 12
Mechanics

Calibrated to how you actually deliver this.

Two ways your team runs an in‑home job — overnight stays at the house, or a few drop‑ins through the day. Additional services beyond that as the booking calls for.
The 24/7 stays load the team very differently from the drop‑ins. The pacing math depends on which mix is selling — we figure that out together, then size the pilot.
Pace the campaign to the team.
— The questions
The questions still open — pricing, capacity, the daily pace (slide 11).
Society 88 · Pilot Plan Mechanics
08 · Setup 08 / 12
Setup

A separate sending lane —
so your real inbox stays your real inbox.

Kennel Booker can mass‑email — true. But it segments only by booking activity, not by neighborhood, club, lifetime spend, or dog profile. No separate domain, no real editor, no automation hook. For this one we want our own lane.
Not from your Google Workspace either — that's your day‑to‑day inbox, keep deliverability there clean. We send from a subdomain (mail.society88.com). The customer sees an email from Mark at Society88; replies land in your real inbox.
Sending subdomain
mail.society88.com
Keeps your everyday email separate from campaign sends.
ESP [email service provider]
MailerLite
Drag‑and‑drop builder, real segmentation, set up so the emails actually land. ~$10/month at your list size.
Replies
Routed to your real inbox
Customers reply to a Mark@society88 address you already read.
Society 88 · Pilot Plan Infrastructure
09 · The Sequence 09 / 12
The Sequence

Two emails. Written like you wrote them.

Sent to a small, hand‑picked list of people you already know. Personal, warm, signed by you. Written together — your voice, my pen.
01
"Hey [name] — first time I've ever sent something like this. Wanted to tell you about something we've been quietly doing for a handful of our customers..."
— A friendly note. Introduces the in‑home service. The offer lives here.
02
"Just a quick note — in case you missed the one I sent a few days back..."
— A quiet check‑in. Only to people who didn't read the first.
We send, watch what lands, and adjust — the next round goes out smarter.
— The loop
Society 88 · Pilot Plan Sequence
10 · Success Criteria 10 / 12
Success Criteria

What does this look like, when it works?

A question to you, not a number from me. We should have a sense of what "worked" looks like before we send — and the answers shape the next campaign as much as this one. Here's how I'd think about it from the outside; what comes to mind for you?
i.
They read us

Opens, replies, raised hands.

The earliest signal — the message landed. Someone answered, asked a question, mentioned it at pickup.

ii.
They booked

In‑home stays on the calendar.

Imagine 50 emails out, five new bookings in two weeks. Real revenue, in your dollars.

iii.
The unlock

A customer who couldn't board with you — now using your in‑home service.

Net‑new revenue. No cannibalization. Probably the biggest story in this whole campaign.

iv.
Or something only you'd see?

A signal from inside the business I'd never spot from out here.

The bar is yours to set. What would land as a real win for you?

Society 88 · Pilot Plan Measurement
11 · What I'd Need From You 11 / 12
What I'd Need From You

Here's the part only you can answer.

Most of these are worth knowing whether we run the pilot or not — they're how you read your own business. Phase 1 sharpens the draft; Phase 2 only matters once we've decided to run.
Phase 1 — small asks (helpful, not blocking)
  1. Sample customer records
    A handful to see what fields exist. (slide 4)
  2. Total customer count
    Overall, and how many are in the membership club.
  3. Active-customer definition
    The last three months? Six? Or more? (slide 5)
  4. Repeat-customer rate
    Of your book, what % repeat — under whatever cadence you'd call "repeat"? Pairs with the active definition above; tells us how much of your book is true repeat business vs. one-and-dones.
  5. Target neighborhoods
    Bethany and Lake Oswego — is that right? (slide 5)
  1. Today's pricing + what's included
    Per night, per weekend, per week. So the offer math uses your real numbers.
  2. Club mechanics
    Fee, discount, member count, renewal cadence. We may segment by it or message differently to members. (slide 5)
  3. In-home capacity
    Concurrent max per day, and how you'd measure it. (Likely differs for 24/7 stays vs. drop-ins.) Paces the pilot to your team. (slide 7)
  4. Type of dog mix
    % reactive / rescue / high-energy vs. typical. Sharpens segmentation and messaging. (slide 3)
Phase 2 — bigger asks (when we segment + enrich)
  1. Full Kennel Booker customer export
    Or a filtered subset. (slide 4)
  1. Stripe export
    Only if Kennel Booker is incomplete. (slide 4)
Worth thinking about
"
What's a typical customer worth — and which segments are worth most?
Average LTV across your book, then by segment — club vs. non-club, top spenders, longer-stay buyers. Tells us what a customer's worth, and who to chase first.
"
How does a customer book today — self-serve, or always through a person? And how would you catch someone claiming the offer?
Code, phone mention, reply, however — needs to leave a trail. We need it accurate so the offer + hook are both grounded. See slide 6.
"
What would you want to know about your customers — if you could just ask?
The export keeps working past the pilot. Top spenders by neighborhood, who books in winter, dogs that come back — pick a question, the data answers it.
Society 88 · Pilot Plan Inputs
12 · What's Next 12 / 12
What's Next

Yours to own. Let's run it together.

Here's what I want out of this. To see it run. New bookings on the calendar. A campaign that actually works for you. Built so it's yours — templates, list, sequence, the whole shape — and we run it together.
The shape is what travels — different offer, different channel, different test, same playbook.
— The playbook
A four‑six week shape
Week 1–2
Pull the list.
From Kennel Booker. Enrich for homeowners and neighborhoods. Finalize the pilot segment.
Week 2–3
Draft together.
Write the two emails. Set up the sending subdomain and the ESP.
Week 3–5
Send the sequence.
Watch opens and replies. Any call, booking, or mention tied to the offer.
Week 5–6
Review and decide.
Against the success criteria. Decide what's next together.
Prepared by Jeff End · Society 88 Pilot Plan · v3