Win is Turning a Potential Customer into a Lifelong One.

Most people don't say yes the first time. Follow-up keeps the conversation going until they do.

An open hand, waitingA lead, caught

What is Our Win Automation System?

Win is the next thirty days — the stretch between "we're interested" and "we're booked." It's where the most money leaks and where owners feel it least, because nothing looks broken. The quote went out. The conversation just stopped, and nobody chased it. It's the second of three. Catch is the first five minutes, Win Jobs is the next thirty days, Keep Clients is the next three years. This one is usually the fastest to feel.

The difference

Who is Win Jobs For?

You need this if:
✓Quotes go out and you're not sure what happened to any of them
✓Your follow-up is one email, and if they don't answer it, that's the end
✓You can't say how many open estimates you have right now
✓Leads reply once, then go quiet
✓No-shows and reschedules are a normal week
You probably don't if:
✕Every quote already gets a scheduled follow-up and someone owns it
✕Nobody answers in the first place. Start with Catch, not here.
✕You close in one conversation and there's no gap to fill

A couple of platforms we specialize in

We are flexible and like to use already existing infrastructure if possible! 

What we build to win more jobs

Automation that keeps the conversation going until they decide.

Quote and estimate follow-up

The highest-value gap in the business. Estimates get a real cadence over weeks instead of dying in an inbox — and it stops the moment they reply.

See quote follow-up

Email marketing

A welcome series, follow-up emails, and a monthly newsletter, written in your voice and sent to the right group.

See email marketing

Reminders and no-show recovery

Confirmations and reminders that go out on their own. Missed appointments get rebooked instead of quietly becoming lost work.

See appointment reminders
Book a call with Automation Experts

How working together goes

The Blueprint

Sixty minutes on a call, after we've done our homework. Before we talk, and with your OK, we contact your business the way a customer would. You leave with a written plan, the order we'd build it in, and a fixed price. Free for the first five.

The build

We build it in the software you already pay for, in your accounts, under your business name. Every business is different, so nothing comes from a template. You approve every message before a customer sees one.

Switch-on

We turn it on a little at a time, not all at once. We watch the first weeks closely and fix what breaks.

We watch it

Nothing we build is left running unwatched. Skip monitors it and alerts us, not you.

The difference

Most automation agencies sell you hours back. We help businesses build longterm client retention.  

Pebble Digital
✓Built around trust and retention, not hours saved
✓Your accounts, billed to you at cost, never marked up
✓Ground rules published on the site, not buried in a contract
✓We tell you if your follow-up is already fine
✓A number you can call right now and judge for yourself
✓Fire us tomorrow and everything keeps running
Other agencies
✕Sold on time saved and headcount cut
✕Usage bundled, and they hold the logins
✕Terms you find out about later
✕Always another service to add on
✕Testimonials you have to take on faith
✕Leave, and the systems leave with you

I've sat across from a lot of businesses with this exact problem.

I came at automation from the customer side — retention, follow-up, why people stay and why they quietly don't.

Most people building automation came the other direction. They can connect your CRM to your calendar. That's a real skill. But they can't tell you which follow-up wins the second job, what a good response actually says, or why someone referred you.

That's the part we care about. The systems are how it gets done.

Cade Bagley
The reality of many busy Business owners

You vs. the customer's experience

Your Side

  • Messages in six places
  • Nothing tracked
  • Nobody sure whose job it is

Their Side

  • One form, submitted
  • Two days of nothing
  • They went somewhere else

"My CRM Already Does This"

It might. ServiceTitan, Jobber, Housecall Pro, and Workiz all ship follow-up sequences, quote reminders, and drip campaigns. Most contractors use very little of it.

The software was never the hard part. Every one of those tools hands you an empty sequence builder. Somebody still has to write the seven messages, decide what goes out on day three versus day twelve, make it sound like you instead of a template, and rewrite the ones that stop working when your pricing changes. If you're already paying for it, our first job is switching it on.

The quiet cost of waiting

Most churn is silent. People don't complain, they just don't come back — and the businesses losing customers this way usually think they're growing.

Leads you already paid for go cold without anyone noticing

Customers leave quietly, and the numbers show it months later

Whoever answers first usually wins — often within hours

Find out what's leaking

Sixty minutes on a call, after we've done our homework. You leave with a written plan, the order we'd build it in, and a fixed price.

FAQs

Everything owners usually ask before automating. Still have a question? Book your free Blueprint and we'll answer it.

What do AI automation services actually cost?

Every build is different, because it depends mostly on what you already run. Some platforms are easy to work with. Some fight you the whole way. The One More Job System is $6,000, and our first five founding clients pay $3,000. Every project starts with a free 60-minute Blueprint.

Will this make my business feel impersonal?

Most first automations go live within one to two weeks of your audit. Larger, multi-step systems take longer, and we give you a clear timeline before any work starts.

What tools do you work in?

Whatever you already pay for, where possible. If you're on ServiceTitan, we build around ServiceTitan.

Where we're choosing, it's usually GoHighLevel or Keap for the platform layer, and n8n, Make, or Zapier for the connective work.

How long until we see results?

First working system is usually inside two weeks.The honest variable is you. If we're waiting on logins, access, or answers to questions, that's where time goes — build time is rarely the bottleneck.

What happens if something breaks?

We monitor your automations and fix issues before they reach you. Ongoing support is part of the deal — you're not left maintaining it alone.

What happens if we stop working together?

You keep everything. The systems are built in your accounts and documented so someone else can run them! We just want to see your business thrive!

Do you work with businesses in my industry?

Most of the work so far has been ecommerce and trades — contractors, field service, the businesses where a missed call is a lost job. The systems aren't industry-specific though. What changes is where the leaks are, and we find those in the audit.

Tagline

Our team

A small team that builds automation for a living — and runs our own shop on it. Two founders and one very tireless AI teammate.

Cade Bagley
Founder

Cade maps where your business leaks time and designs the systems that plug the gaps — the same automations we run in-house every day.

Brielle Bagley
Client Success

Brielle keeps the business and its clients running smoothly, making sure every build fits how your team actually works — not just how the software wants it to.

Skip
Manager of Automation Quality

Skip is our AI teammate — yes, really. Built on the same automation we sell, Skip sends updates, answers questions, and keeps your project moving 24/7. Living proof this stuff works.