Turn Your CRM Into a Predictable Listing Pipeline

The Problem: Most Agents Are “CRM Owners,” Not CRM Users

Wilson shared something we see constantly: most agents only use their CRM after a deal closes. They dump a client in, let it send a birthday message, and hope the phone rings.

That’s not a system. That’s wishful thinking.

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Wilson’s take was simple:

• A CRM is not just retention
• It can be your most affordable prospecting platform
• If it can send SMS and email, it can create listing conversations at scale

Sean backed it up with a reminder that hits hard:
If you aren’t actually using the data, the data can’t work.

Step One: Start With Data and Know Your Market

Sean opened with a key truth: what works in Seattle might not work in Nebraska or Denver. Before you message anyone, you need to understand your market realities:

• What’s turning over in your target ZIP codes
• What your turnover rate looks like
• What listings are moving right now
• Which segments are most responsive in your area

Your outreach gets a lot easier when you’re confident you’re fishing in the right pond.

The Core Strategy: Reverse-Engineer the CRM

Wilson’s system is built around a mindset shift:

Instead of waiting for your CRM to “retain” business, feed it new homeowner data and let it generate conversations.

His recommendation was straightforward:

• Load in 500 to 1,500 highly qualified homeowners
• Use SMS + email to create consistent touches
• Keep it simple and repeatable so it actually gets done

He’s doing this at scale himself, running multiple campaigns at once, then logging in a few times a day to respond and book meetings.

What Results Should You Expect?

This part was refreshing because Wilson didn’t hype it up like a miracle funnel.

He said to think of this as marketing and exposure first:

• Hundreds or thousands of people see your name, phone number, and brand
• After 2 to 3 touches, they recognize you as a local resource
• If business comes from it, you’re pleasantly surprised

Then he shared real numbers he’s tracked:

Example: 500 homeowners in your CRM

Over ~90 days, you can reasonably see:

• ~10% respond (about 50 people)
• ~50 conversations
• ~10 to 15 appointments
• ~2 to 4 listings (in many markets)

Even if you treat those as “best-case” ranges, the ROI math is hard to ignore.

The Follow-Up System: A Simple Multi-Touch Cadence

Once the contacts are in your CRM, Wilson outlined a cadence that keeps it automated but still personal.

Touch 1: SMS with a graphic

Wilson emphasized that texts with an image get more engagement. His approach:

• Include a simple graphic (photo + contact card style)
• Add a short human message like:

“Hi [Name] - I’ve been updating homeowners on what their equity looks like in today’s market. Want a quick snapshot of what your place might sell for?”

Touch 2: Mail a quick personal note (optional but powerful)

This is where you separate yourself from 99% of agents.

Wilson suggested time-blocking about an hour a day, and doing:

• A short handwritten-style letter (or pre-written Word doc you personalize)
• Include a business card
• Optionally, 2 CMAs per day (keep it small so you stay consistent)

No expensive mailers. No elaborate campaigns. Just simple personal touches.

Touch 3: Email “connects the dots”

A short email goes out 24 to 48 hours later:

• “Just following up on the text I sent”
• Another small nudge for people who check email more than texts

Touch 4: Another light SMS touch

Something casual, human, and not pushy:

• “Just wanted to make sure you saw that market snapshot I sent over”

Wilson’s bigger point:

• The 2nd, 3rd, 4th touches are where conversations start
• Don’t judge the strategy by the first message

Personalization Wins: Don’t Sound Like a Robot

Sean and Wilson both hit this hard.

Sean’s view:

• People can tell when it’s automated
• Relationship wins
• “Neighbor energy” works: local references, personality, value

Wilson’s view was even more blunt:
If it sounds too professional or too polished, it gets ignored.

He encouraged agents to text like a human:

• casual language
• short form spelling if that’s your vibe
• “no pressure” baked in
• acknowledge you’re interrupting their day

This isn’t about being sloppy. It’s about being believable.

Segmentation: Right Message to the Right List

Sean called out two of the highest-performing segments for listing opportunities:

• Absentee owners
• Downsizers

Wilson shared how to “personalize at scale” using list-level details instead of pretending you researched each person.

Downsizer messaging example

Use the filter to personalize:

• “I noticed you’ve been in your home for roughly 15+ years…”

Then ask a simple next-chapter question:

• “Any thoughts on what the next chapter looks like?”

High-equity / likely-to-sell messaging example

Use equity as the anchor:

• “Looks like you’ve built up a lot of equity in the neighborhood. Want me to run a quick value snapshot?”

The point:

• You don’t need creepy personalization
• You just need enough specificity that it feels relevant

CRM Recommendations: Keep It Simple

A question came up about which CRMs to use. Wilson’s answer wasn’t “go buy the biggest system.”

His criteria:

• Must have SMS capability
• Affordable
• Easy CSV upload (bonus if you have a rep who will import lists for you)
• Don’t overpay for features you won’t use

He name-dropped a few options he’s familiar with:

• Lofty
• Follow Up Boss
• HighLevel

But he kept coming back to the real requirement:
If you can’t text from it, it’s not the right tool for this strategy.

The Daily Success Plan: Make It Sustainable

Wilson wrapped with something agents rarely get in trainings: a simple framework for consistency.

Ask yourself:

• What 3 things can you do that you actually enjoy and will stick with?
• Can one of them be checking your CRM for 30 minutes twice a day?

He recommended building a plan around repeatable actions:

• quick CRM check-ins
• message responses
• small daily task like 2 CMAs or 2 letters
• light campaign maintenance

Not what the big-name trainings tell you to do. What you will actually do.

Action Steps: How to Start This Week

If you want the “do this tomorrow” version, here it is:

1. Pick one segment (downsizers or absentee owners are great starts)
2. Upload 500 to 1,500 contacts into your CRM
3. Create a 4-touch cadence (SMS, email, SMS, optional mail)
4. Write one message that sounds like you, not like corporate marketing
5. Commit to 30 to 60 minutes per day to manage replies and keep it moving

Consistency beats complexity every time.

Want the Replay and Next Steps?

Sean shared that The Share Group will send out:

• the webinar recording
• the YouTube replay link
• Wilson’s contact info for anyone who wants help building a plan, choosing a CRM, or tightening up messaging

If you want help putting together your message cadence, segments, or workflow ideas, Wilson offered to do 1-on-1 brainstorming as well.

FAQs

How many contacts should I add to my CRM for this to work?

Wilson recommended starting with 500 minimum, but ideally 1,500 so the numbers work in your favor and you get enough feedback to tweak messaging.

How often should I text or email my list?

It depends on your tone and your audience, but the big takeaway was: don’t judge results by touch #1. Many responses happen on touch 2 to 4.

Should I include images in SMS outreach?

Yes. Wilson said SMS messages with a graphic get significantly more engagement and help you look human, not spammy.

Do I need direct mail for this strategy?

No, but it can be a strong differentiator, especially for audiences that respond better to mail (downsizers came up here). Keep it simple and affordable.

What’s the best CRM for this approach?

The “best” CRM is the one you will actually use and that has:

• SMS capability
• easy CSV import
• simple tracking and conversation management

What should my first message say?

Keep it short, relevant, and human. Lead with value:

• quick equity snapshot
• market update
• neighborhood activity
• And include “no pressure” language so it doesn’t feel salesy.