Don’t Get Flagged As A Spammer – What To Know About E-mail Marketing

At a recent marketing implementation workshop I was delivering to a room of about 50 MSPs, they asked me repeatedly about e-mail marketing to prospects who have not opted in to your list or given explicit permission to e-mail them (cold outreach prospecting).

The question is always, “Can I e-mail a list of people I’ve bought or otherwise acquired if they have not given me permission to e-mail them? And what exactly is permission?” This is a common question I get that I want to provide some clarity around.

But before I do, let me issue a very stern warning:

E-mail permission, and other digital marketing communications, are legal matters. Therefore, you must find out what the legal guidelines are for your specific situation, target audience, state, and country so you can abide by them.

In Canada, they hang you upside down naked and strip the flesh from your bones while slinging insults if you dare to send a commercial e-mail to someone who has not signed an authorization agreement in their own blood on a full moon giving you permission to e-mail them. (OK, I’m exaggerating, slightly.) I’m not an attorney and I’m not providing legal advice here, folks. Your subscription to MSP Success does not come with bail money. You’re a big boy or girl now, running your own business. Figure it out.

OK, now that I’ve scared the bejesus out of y’all, let’s talk about building that list of e-mails.

How To Get Prospects To Respond To Your E-mail Messages

First, the definition of “opt in” is “to choose to do or be involved in something.” This is the basis of everything I’ve taught my clients about prospecting for new clients for the past 22 years. You want to attract right-fit prospects by designing offers that entice them to request information from youa process called direct response (or lead generation) marketing.

That request may be to register for a webinar you’re hosting or to fill out an online form to download a piece of content such as an e-book, a free report, industry research, etc. They can also request to hear from you (i.e., subscribe) by walking up to you at your trade show booth and handing you a business card or calling your office for more information. Clients who buy from you are also giving you permission to e-mail them (at least here in the United States).

When running prospecting campaigns of any kind, be it a trade show or an SEO campaign for your website, you should be collecting contact information as part of the process, such as the prospect’s name, company, e-mail address, and phone number. In some cases, like when they are registering for an event or consultation, it’s appropriate to request they give you their full mailing address and even cell phone to text-message them.

When a prospect gives you this information, they are giving you permission to communicate with them. Keep in mind, they might opt out after the first e-mail you send, so that permission is tentative. You must earn it by providing value in your content and engagement on an ongoing basis.

This is how great list-building is done. You are running various lead generation marketing campaigns with offers designed to get prospects to opt in to your communications. That’s how we’ve built our list of over 45,000+ MSP CEOs. Further, we only e-mail people who have opted in to our list, and we fully respect the wishes of those who opt out of e-mail communications by either telling us to remove them from e-mail communications or using the opt-out link at the bottom of all e-mail broadcasts we send. This includes clients. If a paying client opts out of e-mail, we can no longer e-mail them marketing of any kind. And yes, this will happen, and yes, you need to respect their wishes.

The problem arises when an MSP wakes up one day with a burning desire to get more clients but has no permission-based list of prospects to send e-mails to because they’ve neglected marketing for years. At that point, they don’t want to invest the time and money involved in running ads and implementing offline marketing campaigns (like direct mail, telemarketing, trade shows, networking events, etc.) to build that permission-based e-mail list.

What they want to do is go on Seamless.AI or ZoomInfo, buy a bunch of e-mails of potential prospects, and spam out a campaign. However, this is not recommended for two reasons.

First, any e-mail service provider will shut you down if they see you spamming a list of people who have not given you permission. All ESPs will not tolerate this—Keap, HubSpot, MailChimp, Constant Contact, etc. That’s because your spamming on their platform and servers will hurt their ability to get legitimate e-mails delivered.

I had a client who sent an e-mail broadcast out of ConnectWise to over 2,000 e-mail addresses she had, only to have them shut her down from sending all e-mails—and ConnectWise was right to do it. She was spamming because none of these people had opted in.

Second, spamming people from your domain will hurt your sender score and reputation to the point where all of your e-mails end up in a spam filter or blocked altogether. Again, the “gold standard” is to run various direct response marketing campaigns to get prospects to opt in and give you permission to e-mail them.

If You Must Use E-Mails In Cold Outreach, Here’s The Best Approach

If you insist on doing cold outreach via e-mail to people who have not opted in to your list, let me give you a slightly less shady option that reduces your chances of being shut down as a spammer.

To be clear, with this approach, you’re still spamming people because they haven’t opted in. That said, here’s what you can attempt at your own risk:

1. Use your personal Outlook to send the e-mail, not your CRM, and . . .

2. Precede the first e-mail with a direct mail piece and a phone call immediately before you send the e-mail (or at least within an hour of calling), and . . .

3. Work in small batches of 25 to 100 a week (not thousands), and . . .

4. Make sure the e-mail aligns with what you said in the letter and in the call, and . . .

5. Do not add them to your CRM for future broadcasts. You can store them there, but put them into a non-broadcast or non-opt-in status so you don’t accidentally spam them.

If you use the above approach, you are less likely to be flagged as a spammer and to significantly hurt your sender score.

Sending the e-mail from your personal Outlook will also make it more likely to get through because inbox-to-inbox delivery is higher than through a broadcasting software and will have a lower chance of getting flagged as spam. Once they opt in, you can use your CRM to send e-mails to them in broadcasts.

[Side Note to TMT Clients: If you are a member of ours using our MAP (marketing automation platform), WE WILL NOT ALLOW YOU TO IMPORT E-MAIL LISTS YOU’VE PURCHASED, SCRAPED, OR OTHERWISE OBTAINED THAT HAVE NOT GIVEN YOU PERMISSION TO E-MAIL THEM. I won’t assist you in hurting your business in that manner. Sorry, not sorry.]

If you want to spam people, you’ll have to find someone else to help you commit suicide on your domain and sender score.

Remember, using this approach, or any type of e-mail marketing, requires that you honor a prospect’s request to opt out if they ask to be removed. Also, all e-mail campaigns must have clear instructions for how to opt out. You should also remove any e-mails that bounce, as they will continue to hurt your sender score if you keep attempting to send e-mails to them.

Opting In Is Only Step One

Getting someone to opt in (i.e., subscribe) to your e-mail list is only step one and is a very difficult and expensive step at that. It’s common for MSPs to spend $100+ to get an e-mail opt-in, even more if you are looking for a very qualified lead that wants to book an appointment to talk to you about IT services.

The goal of lead generation marketing is not to just produce “buyers in heat” but a pipeline of “getting ready to buy” prospects who will, with proper communication and follow-up, turn into “ready to buy” prospects at some point in the future.

From there, you need to cultivate these leads into SQLs, or “sales qualified leads,” that 1) meet your qualifications for a qualified lead, and 2) want to meet with you. You do this with a strategic follow-up process and designing your campaigns so that this delivers the maximum number of appointments, not just leads and subscribers.

If you’re casting a wide net to get the maximum number of subscribers and leads, you will also get a lot of people opting in who are not ready to move forward in meeting with you and are not responsive to additional e-mails. Sometimes they just want to get the offer you made. Sometimes it’s an impulse action birthed from curiosity, not a signal they’re a buyer in heat. This brings me to a very important point: The goal of lead generation marketing is not to just produce “buyers in heat” but a pipeline of “getting ready to buy” prospects who will, with proper communication and follow-up, turn into “ready to buy” prospects at some point in the future.

Therefore, opting in is only step one. From there, you want to continue to e-mail your list no less than four times a month, roughly once a week, with additional content they’ll find useful, interesting, or entertaining. That is the only way to keep prospects engaged and responsive, and it’s extremely difficult to get right. Over time, leads will become unresponsive, either opting out altogether (most common) or simply not opening and clicking on e-mails. When a prospect becomes unresponsive for a period of more than three months, you should send them a “reactivate” e-mail to attempt to get them to open, click, and/or respond in some manner. Here’s an example of one we’ve used successfully:

Subject line: I think we should part ways . . .

<<First Name>>,

My e-mail delivery system shows that you’re not opening, reading, or clicking on the e-mails I’m sending, which is a sign you no longer have interest in getting them.

Therefore, I’m going to unsubscribe you and stop sending you e-mails so I don’t add to your already overblown, spam-filled inbox.

HOWEVER . . . if this is a mistake and you still want to stay subscribed to get my e-mails offering videos, articles, and blog posts, then click on one of these links below to let us know you want to stay on our list:

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Of course, if you want to unsubscribe, then do nothing and this will be the last e-mail you get from me-or you can expedite this and click here to remove yourself.

I’m not trying to be hurtful, but I only want to e-mail people who really want to get them so I don’t add to the already ridiculous amount of spam in the world today.

No matter what you decide, I’m dedicated to providing you value in advance . . . and STILL dedicated to YOUR success,


Don’t Shoot The Messenger

If they don’t respond to something like this, remove them from your e-mail broadcasts (even if they didn’t opt out) because having a lot of unresponsive e-mails will hurt your overall sender score, suppressing the deliverability of e-mail to everyone on the list.

This is a hard pill to swallow, because getting someone to opt in is so difficult. The hope is that they actually are opening and reading your e-mails, but the spam filters and cybersecurity tools are blocking the signal back to your CRM indicating that the person opened (and read) your e-mail even if they didn’t click. While that might be the case, the simple reality is that your ESP will “see” that as unresponsive, and over time, it will hurt your sender score.

Please don’t shoot the messenger (me). I’m confident you can find some “guru” out there who will have a sneaky way of sending out 100,000 spam e-mails from a domain that is not your primary one. You might even get a few leads and appointments.

But it’s my personal and professional responsibility to make sure you know the gold standard of e-mail marketing and the risks associated if you back off of that standard in any way. It’s up to you to choose your adventure. From a purely personal philosophy, I don’t want to spam people who truly don’t want to get my e-mails. I want to focus on providing so much value in the content we create that people want to hear from me and look forward to my e-mails.

This is a very difficult line to walk because some people feel multiple e-mails a week is perfectly OK (if they find the content relevant) and some feel once a month is too much. You can’t make everyone happy. But what you should be striving for is to send e-mails that engage people and keep them wanting more. Do that and you’ll have a hyper-responsive list that consistently feeds you.

There’s no doubt about it: Robin Robins has helped more MSPs and IT services companies to grow and prosper, liberating them from stagnation, frustration, drudgery and low incomes. For over 20 years, Robin has been showing MSPs and IT services firms how to implement marketing plans that attract higher-quality clients, lock in recurring revenue streams and secure high-profit contracts. Her methods have been used by over 10,000 IT services firms around the world, from start-ups to multimillion-dollar MSPs. For more information and a FREE copy of The MSP’s Ultimate Guide To IT Services Marketing And Lead Generation, go to



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