A business broker's playbook to build an outbound sales engine

Lumping all of your seller contacts into a single campaign is costing you listings.

Now, more than ever, your targeting matters. Your prospects’ inboxes are full of irrelevant mail. To succeed in standing out, you have to do three things very well:

• Segment your leads
• Provide value
• Follow up

Skip to How to outbound if you don’t care to learn why outbound is difficult.

What is happening

Contact data is a commodity. In the past, it was difficult to generate a list of relevant contacts to reach out to. Companies hired entry-level staff solely to do prospecting and paid tens of thousands of dollars for tools like ZoomInfo to amass lists. Now, there are hundreds of platforms that do what ZoomInfo does for a fraction of the cost, and you can build your own prospecting tools using AI relatively easily.

With data so easy to acquire, it’s safe to assume your contact list is not unique. Other sales teams have access to the same prospects and they’re reaching out, too. You’re competing for attention in an increasingly crowded inbox. Daily global email traffic has grown by about 4–5% a year and is on track to roughly triple between 2012 and 2028.

Source: The Radicati Group, Email Statistics Report (2012–2016, 2015–2019, 2018–2022, 2020–2024, 2024–2028 editions). 2026 and 2028 are forecasts.

What this all means: It’s hard to stand out in someone’s inbox, and it’s not going to get easier.

How email providers filter spam and junk

To combat irrelevant emails and protect inboxes, email clients like Outlook and Google use several layers of protection.

1. Identity: Are you who you say you are? Before reading a word of the message, Gmail and Outlook check whether the sending domain is authenticated; that means three DNS records: SPF, DKIM, and DMARC. The rules have gotten much stricter:

• Gmail: Anyone sending 5,000+ emails a day to personal Gmail accounts must have SPF, DKIM, and DMARC, offer one-click unsubscribe, and keep spam complaints below 0.1% (never reaching 0.3%). Non-compliant mail now gets slowed down or rejected.
• Outlook: Senders of 5,000+ emails a day to Outlook, Hotmail, and Live addresses face the same three requirements. Microsoft first sent non-compliant mail to junk, but has now changed course and rejects it outright.

2. Reputation: Has your domain behaved well before? Filters score the sending domain and IP address based on history. A new domain that suddenly sends hundreds of emails looks suspicious. A domain that racks up bounces from bad addresses, or spam reports, gets penalized on every future send, including to people who actually wanted to hear from you.

3. Recipient behavior: How do people react? Google says its filters learn from user input, such as marking mail as spam or indicating they want a sender’s mail in their inbox. Every “Report spam” click counts against you. Replies, moving a message out of spam, and adding you to contacts count in your favor. Mail that people routinely delete unread signals low value. Inbox placement is a running popularity vote: the more liked you are, the less likely you’ll land in spam or junk.

4. Content and patterns: Does it look like spam? Machine learning models scan the message itself and compare it to patterns across billions of emails. Templated blasts with identical wording, link-heavy messages, misleading subject lines, and spammy formatting all raise flags.

Even mail that passes all four layers may get sorted away. Gmail’s "Promotions" tab and Outlook’s “Other” tab mean a message can be technically delivered but remain unseen.

How to do outbound

This is a step by step playbook you can use to dramatically increase your deliverability and provide value.

Step 1: create a list of prospects

This can be done using the contents inside your CRM, or you can build your list from scratch.

Inside your CRM

Filter the companies inside your CRM by a specific industry and, ideally, location.

This should generate a CSV with the company’s name, industry, owner’s name, and contact information.

Build from Scratch

Use a service like OpenMart or Clay to build a lead list of businesses in a specific industry and location.

If you’re a Tupelo customer, use Unlock Leads to get access to leads in specific industries and locations.

Step 2: double check your prospect list

After sourcing your lead list, run it through an AI prompt to make sure your targeted list is accurate. I recommend scraping the company’s website to double-check the target is in the right industry, and then trying to validate the authenticity of the owner’s contact information.

Here’s a prompt you can load into Claude to create a skill.

Bonus Recommendation: Build your own prompt for each industry, specifying exactly which keywords you’re looking for on your target’s website.

Why this is important: Most brokers send well under 5,000 emails a day, so the formal bulk-sender rules may not apply to them. But the reputation and behavior layers apply to everyone. A blast to an unsegmented list generates ignored messages and spam reports, which damages your domain and hurts deliverability. Segmenting and sending relevant content is what keeps you out of the junk folder.

Step 3: build your campaign

Now that you have a highly targeted list of prospects, it is time to begin drafting your outreach. You spent time and money curating this list so your messaging can be specific and resonate with your intended receiver.

I recommend revisiting your campaigns every one to two months, depending on the messaging you're providing. AND you’re always going to want to track your metrics.

Because your targets are now segmented by industry and location, you’re equipped to deliver highly tailored content. Providing value means keeping targets apprised of industry updates, recently sold and similar companies, current on-the-market listings, case studies, interviews with active buyers, interviews with owners who recently sold a similar business, SBA updates, etc.

Key note: If you are planning on sending thousands of emails a week, you’ll need secondary domains.

Step 4: Deliver value

Before ever launching a campaign, review your messaging and ask yourself: If I were the receiver, would I open this email? Would I find value in it?

If the answer is yes, hit send. If the answer is no, fix it.

You do not need to sell your service in every email you send. Instead, make it clear that you are the expert in their industry. The best campaigns are often educational.

Step 5: follow up…please please please

You will get engagement, you will get phone calls, and you will get prospects but where so many brokers drop the ball is the follow-up. Call, email, text; do whatever you need to do to keep pushing the deal forward.

Data consistently shows that it takes an average of five to eight touches to generate a meeting. If you aren't following up, you are doing all the hard work of building and verifying a list just to abandon it at the finish line.

Yes, people will drop off. But be diligent about re-enrolling them into your campaigns. That way, when they are finally ready to engage your services, you will be the one who is present and top of mind.

Let us do the work

If you're tired of manually scrubbing lists and worrying about spam filters, let us do the heavy lifting. Tupelo’s Unlock Leads feature helps you find, segment, and verify high-quality prospects. Grab time to see how we source thousands of leads for our users.

George Wellmer