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Inbox Conquest: Elevating B2B Outbound with Email Guru Matt McFee

May 05, 2024 Gary, Andy & Tiana Season 2 Episode 1
Inbox Conquest: Elevating B2B Outbound with Email Guru Matt McFee
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Inbox Conquest: Elevating B2B Outbound with Email Guru Matt McFee
May 05, 2024 Season 2 Episode 1
Gary, Andy & Tiana

Happy Friday PROs!

Explore the essentials of outbound B2B communications in this episode with Matt McFee, email marketing expert and co-founder of Inbox Monster. With a rich background at companies like 24/7 Real Media and Yahoo, Matt dives deep into the nuances of email and SMS marketing, highlighting the pivotal roles of data verification and deliverability.

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Matt McFee
Inbox Monster Website

Show Notes Transcript Chapter Markers

Happy Friday PROs!

Explore the essentials of outbound B2B communications in this episode with Matt McFee, email marketing expert and co-founder of Inbox Monster. With a rich background at companies like 24/7 Real Media and Yahoo, Matt dives deep into the nuances of email and SMS marketing, highlighting the pivotal roles of data verification and deliverability.

gtmPRO
Matt McFee
Inbox Monster Website

Andy:

but, I'm a never never, never know with the airsee that, Matt, can you no?

Gary:

Welcome to the GTM Pro Podcast, your essential audio resource for mastering go-to-market discussions in the boardroom. Here we share insights for revenue leaders at B2B software and services companies, especially those with less than $50 million in revenue. Why? Because the challenges faced by companies of this size are unique. They are too big to be small and too small to be big. This dynamic pushes revenue leaders into executive leadership without a lot of help or support. We are here to provide that support.

Gary:

Your journey to boardroom excellence starts now. All right, well, really excited for this series here in May we're going to be covering Outbound and very excited to have our first guest with us, matt McFee, who is managing director, part of the founding team of Inbox Monster, but has a long history in outbound communication. So, just for context, we're kind of setting up really what we need to know about how do we get our messages out into our audience. There's a lot increasingly noise out there about how much more difficult it has become, and so we thought we'd go to an expert and start from the source. So, matt, welcome to GTM Pro.

Matt:

Thank you very much for having me. It's great to be here.

Gary:

We're so excited, All right. So for context, I think what would be really helpful is I will not do nearly as well service providing your background. So can you just walk us through you know where? I guess, starting with Inbox Monster today, give us a little bit of background of that and the genesis for that. But I think there's so much value in going back. You've been in the space now for just before we started recording 23 years now so it'll be really insightful, I think, for the audience to hear some of that background and how one step led to the next.

Matt:

Yeah, that's great, thank you. So yes, inbox Monster appreciate you teeing that up is a company that really we build tools that enable CRM teams to do just a better job of delivering just great creative through both their email channels and their what's becoming much, much more popular in the digital marketing space SMS channels, and so really our entire platform is really designed to be used by kind of enterprise CRM teams to do everything from creative rendering analysis and diagnostics on the creative asset itself all the way down to deliverability monitoring deep into kind of inbox placement rates across their kind of priority global set of ISPs that any sender is trying to communicate with. My experience kind of coming into InboxMonster was really developed over years in the space. I took my first job with a company called 24-7 Real Media back in March of 2000.

Matt:

And this was back in the email space was relatively new. There were some really interesting things being done in email. Video for the first time around that time was being used as an advertising tool in the inbox. So just it was kind of the wild wild west. A lot of companies love the idea of email as a large part of what traditionally was a media network like DoubleClick back in the day, 24-7.

Gary:

Real media Email was the next logical extension of communicating with consumers and connecting that with brands and so this was a time that you may have inadvertently I guess you guys knew and so Andy and Matt went to grad school together, but Andy spent some time at AOL, and so that's the whole. You've got mail period for those that didn't live it Very different than what we deal with today.

Matt:

We all had AOL addresses back in the day, right, we all received that CD in the mail and set up our first email address, as many of us and so, yeah, so then spent time with 24 seven real media, just kind of learning. The email brokerage business back then was the kind of first step into the sales side of email, connecting brands with really list owners 24-7 included, but also external list owners. I moved on in 2001 and started working for Yahoo in a similar capacity on their email team. Yahoo had an internal email product uh, it's called I think it was called yahoo answers that they would, uh they would promote the a lot of their brands messaging alongside their own internal messaging, and so it was almost like a promotional email as opposed to just outright marketing emails. Um, and and then went out on my own in 2004 to try to explore kind of new paths in the email space. So I'd grown to know the email space very, very well, the buyer personas, the value that email as a channel for marketing and for both prospecting and kind of internal retention, marketing and communications, could deliver to brands, and so went off on my own and then somewhere kind of late 2000s started really kind of found a good founding team to build a company called Bright Verify, and so we really wanted to get more into the product side of email technology as opposed to primarily focused on, up to that point was the services side.

Matt:

Spent the next eight years building a business that called BrightVerify that was focused primarily on data verification, with a real sharp focus on email, specifically helping companies identify whether or not, either in the form, experience or within their database, email addresses were real and where we could identify risky and invalid email addresses so marketers could do a better job of removing data quality from the deliverability equation.

Matt:

And so over that time we kind of learned a lot more just about buyer persona, about the deliverability marketplace in general and that kind of leads to. We were fortunate enough to exit that business in 2018. And in 2020, a group of us came together to start Inbox Monster and we saw in this market back in 2020, changes taking place, roll-ups of competitors and suppliers to this marketplace, this deliverability marketplace, and really saw that there was an opportunity to create a really focused and innovative deliverability company. Really was our founding kind of thesis entering market to build great deliverability services to serve the enterprise. There are incumbents in this space, naturally. But we saw an opportunity to come in and be kind of that second or third provider at the enterprise level, and so that's what we've been doing since and the platform has just evolved to still remain within the same buyer group the CRM team but expand our services and what is available to CRM teams at the enterprise level.

Gary:

Yeah, that is awesome. So there's going to be a lot to dig into there, given that experience and for context, for the audience. We hear deliverability and honestly think it's a technical thing that my teams need to take care of, and we would argue that that is something that, more and more, is going to be critically important, that everyone in the organization who touches the customer is going to need to at least to have an understanding of, understanding of Very similar to how we had in the early software days. We had a set of CEOs that knew how to run business but didn't necessarily know under the hood, like how software was developed and products and engineering teams. Well, that doesn't exist today. If you don't know that, you're not in the business.

Gary:

Well, we would argue that if you're in a GTM business, you have to know about this, and the reason being that, if you look at the ways that we can get out to our customer today, we see let's start with SEO. Well, seo is under a massive shift as we move to AI. Even SEO as we know it today, there's so much volume of content on the internet that even your very pithy piece about whatever content it is that you want your buyer to see may not even be indexed by Google, let alone presented to them. And then you've got the pay to play aspects of it as well, which are just increasingly getting more expensive On the social platforms. You have algorithms that are built for the platforms and not for you, and case in point is you can specifically go follow an individual or a company or whatever, so that because you want to see their content, and if the algorithm decides that it's not worthy, you're not going to see it, even though you've expressly said I want to see that content.

Gary:

Um, and then now we're an email where before you could hit send and it would show up in their inbox and it was the up to the reader whether or not they were going to read it or not. Now, as we, as we're going to learn, there's a whole wall of stuff that's happening where your very well-written message may literally be dead on arrival. So, as you're a CEO, you don't need to think about that. So, matt, with that kind of context as background, can you walk us through what you've seen and learned over the evolution of an email? You know, not the email itself, but getting from the sender to the receiver and all the things that have to happen, to make that, you know, make that actually happen.

Matt:

Yeah, no, it's.

Matt:

I love the analogy with social media because, starting today, really probably the last five to 10 years, but the owners of mail platforms, the recipient platforms, mail systems right, like Gmail or Outlook, they've really designed all of their controls to optimize for the recipient, the consumer that uses their products. And that same is true of the security tools like Proofpoint and Barracuda networks that sit over on top of corporate mail systems. They're all designed to, first and foremost, protect the recipient from garbage, from risk, from fraud, but to allow the recipients to receive information that they want, right and they've expressed interest in, either explicitly or through activity, through engagement, through consistent clicks and opens and that sort of thing on a brand. So it is interesting to hear how social media is really optimizing for the platform's benefit, whereas you see a lot of the mail systems optimizing for the recipient's benefit or the user's benefit. Back in gosh, my first years with email, it was so new for not only many of the recipients people receiving messages but also the brands, right. So there was a high open rate, really high click rate and, andy, you remember back in those days, whether it be pop-ups or banner ads, right, they all had meaningfully noticeable click rates and activity rates. But like everything else, right, when the channel gets abused, consumers like all of us, when we put on our consumer hats start to get too much garbage in the inbox that we don't care about. It's hard to filter through and find the stuff we care about. Ignore rates go up, click rates go down, and so over time you know mail systems like Gmail coming in and creating just great controls for the consumer's benefit to keep the stuff they don't necessarily want to see or that would be distracting out of the inbox and either in the promotions or the spam folder for tab users. And so you see, those controls have grown over time.

Matt:

That does not help folks like myself, let's say, in our early growth, when we're trying to communicate using email email with prospects, right. So you put the other hat on business owner or AE or marketing person and you're trying to use email as a channel to communicate with your prospects, you think about it. Typically the sender thinks about it through the lens of I'm sending an email to this person and I think I can get an email to someone at company A or company B or someone with a Gmail address, right. But because of the controls that are in place, because this person doesn't know me necessarily, this is my first outbound email. There is a whole set of controls that make that really really difficult to do, right, yeah, a lot of it is business model related, in my opinion building your brand voice, creating your marketing effort right, creating early followers, early buyers, early word of mouth as you're building that business, and then layering email as a channel in to complement some of these other pieces to generate kind of a new set of interest with the business.

Matt:

Complement some of these other pieces to generate kind of a new set of interests with the business. That I've seen be more successful. Certainly, as we've done it here with Inbox, monster and Bright Verify intentionally layering in as a communication channel in parallel with some of the other things we're doing. We've seen that drive more success long-term. But if a company is just kind of spinning up a URL and a mail at Google Workspace or 365 or Turbify and with a 10,000 row prospect list and just signing up with any of the kind of sales distribution, email distribution platforms, it's going to be really hard to generate any value out of that.

Gary:

Yeah, one thing you mentioned back to the social media analogy is it strikes me as and we had this conversation last week or so is that one of the maddening things about social media platforms, and I'm thinking of LinkedIn in particular is that the algorithm is opaque. I can see one piece of content that looks exactly the same and one gets know tons of exposure, and the next one does not. Um, and it feels like there's more and more of that happening in the email space as well, which is we send out an email and, frankly, the deliverability of that is invisible to us, at least with most of our tools. It's like I don't know whether it got into the inbox or not. I can only gauge that by open rates, and that's a function of a lot of different variables. So, you know, are you seeing that as well? And then, how are? How are maybe a little bit different in a b2b context, but what are some key ways that people can be thinking about? All right, how can I actually?

Gary:

You mentioned great content, which we'll get back to. That's that's, you know, path number one. That's you know, uh, path number one. It's like a monopoly, you know, do not pass, go go straight to jail, um, but even before that is, we think about really setting ourselves up for, um, at least putting ourselves in a better position, assuming we have that great content. What are some things that we can think about? And then are there tools that we can use to help us understand the efficacy of our deliverability?

Matt:

Yeah, great questions. The email service providers. Think about Salesforce Marketing Cloud, think about Braze, think about any of the enterprise ESPs and even kind of the downmarket ESPs that are used by smaller companies like MailChimp and Constant Contact and Klaviyo. Those mail systems are all going to provide a number to the market or the sender that shows sent and delivered, and a lot of times that term delivered is interpreted to mean deliverability. In fact, there are some ESPs that will use the term deliverability in describing that number, and that number is typically 95, 96, 99%. That number really indicates the percentage of emails sent that didn't bounce right, that didn't have a hard bounce, a hard rejection from the mail system. Either it's an invalid email address there's no MX record on the other side, or reached the server and was pushed back for whatever reason. Right, you're a hard block at somebody's mail system, and so that's, I think, the first thing.

Matt:

When we work with customers. We try to help them understand the difference between deliverability, which is you sent 100%, what percent of those emails that were not bounced ultimately reached the inbox, or what percent ultimately were kind of quarantined over into the spam, junk or bulk folder. And if there's a percentage missing, they need to know that too. Right, and that's probably one of the biggest challenges in the business to business email space is understanding because, as you mentioned, everything is opaque. Right, you can monitor click. You can monitor click rates. Certainly that's going to be helpful. Open rates, as you said, have been less. They haven't been this inaccurate, probably ever. That'll just continue. Right, that'll be more of a, I think, a general metric. People keep an eye on long-term trends, but it's not a great indicator of early success, and so having insights into where you deliver by mail system is super important. That's why companies like Inbox Monster exist, right.

Gary:

By mail system. That's really interesting yeah.

Matt:

And that's the tricky thing for the business to business marketer. You may think you're sending an email to someone at Inbox Monster and you're either going to receive you're going to get your messages through and I'm going to receive your message, or you're not. But really what we are is we're backboned off of workspace and so a sender to inbox monster has to be able to communicate effectively to the workspace mail system. Before I can ever see a message that is sent to my inbox, and so that's, I think, one of the trickiest things for B2B marketers.

Matt:

Not only is deliverability information typically opaque, the ultimate owner of the mail system that you're communicating with is also opaque. Some of the big corporate mail systems are protected by proof points, for example, right Great security tools that are intended and designed to keep marketing messages, that are intended and designed to keep marketing messages, sales messages and risky messages from the end recipient at corporation A. So understanding that proof point is blocking all your messages and that has an effect on a lot of big corporations you're trying to communicate with. That's where that information is often lost or really never obtained because the opacity you mentioned.

Gary:

Can you see from the outside, looking in, that an organization has a tool like proof point in the email process, like you would? You know, looking at a website and looking at built with and seeing the tech stack that's there? Is that? Is that something that's visible? To know? That Cause I thought your point about one of the things that most tools don't do is look at open rates by email platform so that you can To your point. The absolute isn't the issue, it's the trend we can see. Are we having an issue with a particular platform? I thought that was interesting. Maybe this is a case where, if we can find that companies are using tools like Proofpoint, that that's an issue. Is that visible?

Matt:

There's a few tools that are good for kind of one-off searches. If you're communicating, a great majority of your outbound emails go to a handful of corporations. You can do some one-off searches and check out which tools those corporations use. We built some tooling that really more enables our user base which, again, as I mentioned up front, is more of the enterprise ICP to do a more kind of higher volume search across their entire data set, right? So we'll provide a tool where a data set can be loaded of domains and we roll them all up to their respective mail system, their mail exchange records, so we can tell you which percentage of your data set or your segment rolls up to each respective mail system. So, proof point maybe 50 or 60% of somebody's data set. Or Gmail maybe 50 or 60% of someone's data set. With B2C it's a little easier because you can sort your domains by Gmail and run account and say, okay, this percent of my data set rolls through the Gmail mail system. With B2B it's much more difficult.

Matt:

You can't look at inboxmonstercom and know where I'm backbone, where our company is backbone. So it's really important to have those insights at volume. That's what tools like ours help enable. And then it's as, depending on who the customer is really, it's as important to tell them which percentage of their data set rolls up to each respective mail system. It's just as important to then list out all the domains that are a part of their segment that are being blocked, right? So if, for example, mail system or security tool A is blocking your messages, what are all the domains in your list that you're not reaching? And those are just some great additional insights for the average B2B sender. So they can really not just say, oh, we're having trouble mailing to corporations protected by security tool A, it's no, here are the hundred domains we're not getting messages to. We need to fix that.

Gary:

Yeah, and that's really interesting for plenty of middle market companies. Lower middle market companies are selling into large organizations, and we have to understand that there's a whole you know fortress of protection of your information getting into that audience, and if you're oblivious to it, then you're spending a lot of time and effort and it's not getting there. I know one of the things that we chatted about is, which was news to me. Would make sense, though, is that, because of the rise of outbound because, frankly, a lot of companies got lazy, they loaded up what we proverbially call the spam cannon which is not necessarily MailChimp, but now more than ever is Outreach, sales, loft, apollo and others and sending those emails that those larger company email systems are actually looking for trackers associated with those things and, you know, potentially literally quarantining or blocking those messages? Is that that's something you've seen, and is that you know what? Along those lines, what else are you seeing the tool providers at larger companies start to do to help again protect the user?

Matt:

Yeah, yeah, it's so to the tracking piece, tracking links, tracking pixels.

Matt:

We all know the logic behind these enablement tools, the logic behind having those in place right, you can create the journeys necessary to intelligently we think anyways intelligently communicate with the end recipient based on what's convenient for them when they last opened, when they last clicked, the security tools.

Matt:

Mail systems have become much smarter now in protecting their users from bulk prospecting emails, and one of the ways we've seen just in our experience the mail systems protect against is messaging with known tracking links that can be linked pretty much one-to-one to outbound prospecting emails.

Matt:

Volume also has some effect on that as well. If you're a marketer who just says I'm going to queue up these 50 leads or prospects and send 50 an hour to eat successive segments, and I am a security tool sitting over a mail system and I've seen 10 or 15 messages come to folks in my company, I'm going to quarantine that and potentially eliminate it altogether, but at least quarantine it. You're not just going to let that stuff through, right. So they're becoming smarter at identifying certain things in content that would indicate they're prospecting in sales emails and have not been opted into most likely and filtering those. But we tend to see that behavior more when there's more than just one email being sent within a corporation. The mail system will quarantine things and hold them before they make a decision whether to deliver or never deliver. And that's where we kind of see those two things correlated pretty well tracking information and then volume.

Gary:

Yeah, yeah, it's interesting in our personal experience. You know, we have the GTM Pro newsletter, and so there's a handful of domains that we literally see that well, there's a handful of people at the same domain and every single time they're opening and clicking the message, every person at that firm which we're like. That's not happening, so chances are, and then we see it because these happen to be financial services firms that you know. That's probably something where the tool I'm going to guess here. But our hypothesis is that the tool is looking at that, opening the email, clicking the link in the background, making sure that there's nothing there, and at that point either deciding, okay, I'm going to let this through or I'm not, and it's just going to sit here in quarantine and wait for the user to actually come in and say, yeah, that looks good, go ahead and let that through, which is like the ultimate promotions tab.

Matt:

Right, it's not just there that you go. Look at it. There's a lot of steps to get to the quarantine. You nailed it, man. Those security tools will just randomly go through emails, click every single link, make sure the landing pages at every single link are safe. There's no risk there. They're smart, you know they're. They're smart, right, these systems are, are really designed really, really intelligently to kind of figure all that stuff out, check content, open it up, click on every single link. And I'm I'm sure, gary, if you got deeper into the click analytics, you'd see those clicks happening pretty much at the same exact time. Yeah, you know, you wouldn't see a click and then another click a few minutes later. It's like boom, boom, boom. If they click on, the systems will click on everything to like to check what's on the other side of that. So you I think you're the behavior you're seeing in that well, I'm sure you want to believe huge open rate and engagement rate. It's likely the security tools yeah, yeah, fair enough.

Gary:

Fortunately it's limited, so at least that's what we're telling ourselves. Um, so I think then I'm going to come back to kind of some specifics that a lower middle market company can be thinking about. But so in this era of AI still very, very early, but you can envision a day where those tools actually get even smarter and more selective and maybe even down to the user specific in terms of what you want to see through, what you don't. Are you seeing any developments that as it relates to kind of email security, or you know firewalls or you know protections, things like that?

Matt:

yeah, I mean the way you mentioned kind of the opacity of some of the analytics I use that same word with how mail systems and security tools are developing some kind of some advanced controls. They don't. They don't publicize it. I think largely because folks that would seek to abuse it or try to bypass those controls are creative, are clever, they are well incented, right If they can find a way around controls. There is real value there for folks that are just blasting a ton of volume and aren't as concerned with best practices.

Matt:

So I think that's a driver of keeping a lot of this information close to vest when you're a security tool or other systems. I mean Gmail does a really nice job of communicating to the sender to say here are the standards you should be concerned with and they're not going to tell you you know what percentage weighting they apply to each of the variables like complaint rates and engagement rates and other types of things that they will control on. But they make it clear and they're also very, very good at controlling, you know, at keeping the high volume uninteresting stuff out right, the spam and the fraud and the phishing. But yeah, I would say largely while we see advancements taking place as we're trying to monitor the effects of certain trends for our customers, it's unclear as to exactly how those new tools are going to affect senders. Most likely they're going to adversely affect senders who are trying to find ways to bypass the controls.

Matt:

They're just going to get smarter and smarter and smarter. I know there's tools on the marketplace that will spin up new IPs and new subdomains for a sender to try to avoid getting bulked or blocked consistently. They'll have a little bit of success. Then they find they get blocked. Then they'll spin up a whole new set of infrastructure and then send through that until they get blocked. Those are the types of things I think that'll be first affected. It's just not trying to bypass best practices in my experience, in my opinion, never a good way to find success in the long run. So I would suspect that those are the folks that are really going to see it become more and more difficult to find any success with that model.

Gary:

Yeah, it is interesting how you reference earlier about how, back at the beginning, when you're talking about pop-ups at AOL and early email marketing, really any tactic falls to the we can beep this, the law of shitty click-throughs right, which is that anything that works will get abused to the point when it doesn't, and that's what we're seeing.

Gary:

And so you just reinforced if you think about really any channel, reinforced if you think about really any channel the bar for uh, the bar for scalability and repeatability has gotten much higher on just raw quality. And raw quality comes through really knowing your customer and not being very broad, so that because quality is defined by the recipient, not the deliverer, and so if we're not really tight on who that recipient is, then, and nine out of 10 messages you know are on the wrong frequency, then you're not going to get those engagement metrics, you're not going to get those signals and you're going to end up not even getting in the inbox. So the bar back to your original point of there's no escaping, just being really good at the quality of the content that you're delivering and then these channels open up to you. But if that's not there, then it's getting harder and harder to do the end around.

Andy:

And you're escaping Google either in general. So, like with Gmail and you mentioned this you mentioned their policies and we saw this with organic right Very same things. They loosely define certain things, but when these new initiatives, like Panda being one and Penguin and so on, coming out, you have no idea what the weights are and how different things affect that. But you do know, wow, this thing that I know in the back of my head, my conscience was telling me wasn't exactly right, just got wet. And you just mentioned something huge which is and I've been saying this on LinkedIn like don't do this, which is spinning up those domains, and you're seeing it. And there's like companies you know that are that's kind of what they do, or at least it's a component of what they're enabling. And I'm like if if somebody's sitting on your shoulder saying, should you really be doing that, you know, does it feel right? And and and that that's my, my point there is they're gonna catch it, it's gonna happen yeah, that it's the old you know would.

Matt:

Would you want what you're doing to be broadcasted on the cover of the Wall Street Journal tomorrow? It's that kind of character threshold. Look, some companies build a model around that and try to find as much success in the near term as they can, and that's where folks like Google are just kind of creating better best practices, better control. So the average marketer who's doing a good job and being responsible and communicating properly, they are likely going to be unaffected.

Matt:

There's a lot of and I'm sure you guys saw this as well there was a lot of anxiety at the enterprise level three, four months prior to these changes going into place, especially once CRM teams got beyond the holidays holidays. Then they all started panicking a little bit, wondering what the effects would be on them. But the the responsible marketer communicating properly, using the channel properly, respecting opt-out requests, um, letting spam, the spam rate trends influence their own marketing initiatives and making changes in response to that, I mean those folks are not effective. It's the ones that are trying to bypass. So great, call out Andy. I'm Google in general, but I think the industry as a whole, they're just doing a better job of protecting consumers from the folks that are trying to bypass the controls and do a poor job and making sure we're getting what we really want.

Gary:

So let's spend a little time on the building blocks and deliverability. So you know, for those that have spent a little time dabbling in the space, we have DKIM and DMARC and things like that. So can you walk us through the terminology and some of the core? Structurally, a typical B2B marketing company excuse me, b2b, lower middle market company is likely sending messages through their application, through SendGrid, through a marketing automation platform like HubSpot, potentially a customer slash product support tool like Intercom, through Outreach, salesloft what have you? Directly through Google or Outlook. So there's a lot of places from which email is originating and all of those have different IP addresses and different structures. So, starting with the fundamental building blocks, where should we be honing in?

Matt:

Great question, and my disclaimer here is I am not a technician or deliverability expert, and so what I'll share is certainly my experience in the space and our experience as an organization as well, but I'll keep it a little bit more broad, and hopefully that's okay.

Gary:

That's great, that's perfect.

Matt:

As you kind of step up to the larger mail systems, you'll get a little bit more better guidance around. You know your authentication records, spm to BKIM. Having DMARC set up properly is now a mandatory component for bulk senders and for Gmail and Yahoo, and those are defined as sending more than 5,000 emails a day from the root domain to that mail system. The respective mail systems.

Gary:

And Matt, just before you go there. So just kind of some of the terminology that you threw out, because I think you know we throw out the terms but generally, what is DMARC, what is DKIM?

Matt:

You know, what are the things that we're just kind of plumbing, setting up the plumbing, yeah, so SPF and DKIM are kind of the standard authentication methods to allow me, as a sender, communicate properly with the recipient mail system and to confirm that I am who I say I am, I own the domain, I'm sending over IPs owned by whichever mail system is powering the send, and that I'm safe to deliver to the inbox. The controls that are set up at the large mail systems now won't even allow messaging to get through if you don't have your authentication records set up properly.

Matt:

Right. So caller ID if I call you, Gary, you recognize my voice, you know that I'm coming up as a potential, as a contact, and you know that it's me calling, kind of similar concept. Right, you send an email, you'll have these records set up properly in your SPF record. You're confirming your IP addresses, that if you're sending off of a dedicated IP, but they're authentication records, they're going to make that.

Gary:

Does that need to happen, then, in each of those? So we mentioned HubSpot, intercom. Does that need to happen in each one of those platforms or is there kind of an overall at the domain level?

Matt:

Yeah, that, usually it's taken care of at those larger platforms. Yeah, it's, depending on the size and structure of your sending infrastructure. If you're spinning up a new instance at Salesforce Marketing Cloud, most likely you're gonna have, for example, someone on the technical team getting those records set up for you because you're now sending off of their IP addresses, the linkage between their IP addresses and your new sending domains, even though you may have used them for years. That's new. So the ISP, the mail systems, need to understand that there's new authentication and you are who you say you are and you have authority to send from the domain and the IPs and so sometimes it's taken care of for you just by the fact that you're sending over another platform. Sometimes, if you're an enterprise, you likely have to make sure that's set up, but in partnership with whichever ESP you're sending through. So those are kind of the fundamentals, right? We've heard it described. That's the driver's license to send email. Without an SPF record or DKIM record functioning properly. You're going to have deliverability issues. It's just you're going to have deliverability issues. It's just you're going to get rejected.

Matt:

The DMARC is, I won't say new, but relative to how long SPF and DKIM have been best practice. Dmarc is relatively new. Dmarc is kind of the way receiving mail systems will confirm that either you are fully authenticated and therefore your messages are being successfully delivered and that you're not spoofing someone else's domain not considered a phishing email, not considered a threat. There are three stages to DMARC. Dmarc is P of none, which means if a mail system sees an email that looks suspicious it's coming from a different IP, even though it's your domain. They don't know that IP on your behalf. They do nothing with that. But you can monitor those failures like a system like ours would monitor those failures. Anyone that provides DMARC monitoring would monitor those failures. There's also quarantine and none. So most enterprise marketers are stepping up to quarantine and stepping up to sorry, not quarantine. And's also quarantine and none. So most enterprise marketers are stepping up to quarantine and stepping up to sorry, not quarantine and none quarantine and reject. So what that does is it gives recipient mail systems permission, like Gmail, to say oh, these guys are saying quarantine any message that's coming from their domain but a different IP. That is unauthorized. So don't even let it get to the consumer inbox, keep it over here in the spam folder, for example, or, if it's, reject anyone who's trying to spoof this domain from an unknown IP block it altogether. So that's where the marketer can get more intelligent about how they're managing risk on behalf of their brand.

Matt:

We've all seen those phishing emails, right, the ones that hit your inbox. You're like that looks weird. It says it's coming from that domain but there's misspellings. If we look on the call to action link, it goes to some URL I've never heard of. It's not associated with the brand. Those phishing emails would fail. They would be rejected completely from your inbox if the sender that had the mask brand has a demark record set up to reject fully. So those are just different sets of controls around risk. The Demark piece specifically, all super important Demark used to be more optional, but now for Gmail and TurboFive well, sorry, not Gmail and TurboFive, gmail and Yahoo now those systems are mandating at least a record of none and that'll evolve over time. We think to then mandate a quarantine and mandate a reject altogether as they kind of walk marketers through best practices for better control risk.

Gary:

Yeah, and how do you get like outside of that? Like once, once you land on the spam folder and once you're, you're categorized as a spam. And how do you get outside of it? Like, how do you change that reality? Like once you're already there?

Matt:

Yeah, great question. If you're an enterprise marketer and you find yourself and you've typically delivered very well and have very successful communication channels using email with your recipients or your prospects and all of a sudden, through one inbox, through one mail system or through a number of mail systems, you find yourself in the spam folder. There's a lot of indicators, leading indicators that that are kind of around the periphery your reputation, your complaint rates, things that could provide leading indications that something may happen here shortly with deliverability. So we may want to address that. Um. And then naturally, once you're there, the panic button gets pressed right. The notifications start going off the alert saying oh, you're bulking a hundred percent now at this mail system and it's an important mail system to you.

Matt:

Digging out of that location is as much about understanding what got you there in the first place as anything you need to understand through the signals you see in a platform like ours. Is it a data quality challenge? Data quality was going down over time, which ultimately is an indicator of we're likely going to hit some risky spam traps, for example, that will lead us to get blocked somewhere, ultimately bulked at a mail system or blocked altogether from the mail system. Other things like your reputation status. If you are looking at your Google Postmaster Tool reputation status and you see your complaint rates rising Eventually, that'll cause you issues. That'll cause you a reputation change.

Matt:

We know, with Gmail's controls now, they eventually will consider you that you should be a part of the spam folder if your complaint rates stay too high for too long. So there's a lot of leading indicators as well as those trailing indicators that would tell you hey, this is why this is likely, why so, if you can fix these things and operate better for a period of time, your messages should start coming back out of the spam folder and back into the inbox. It's not easy and we always talk about kind of the cost of not having access to this data really being that if you have to spend 45 to 60 days to dig out of you know a place like a spam folder at a priority mail system for you as a sender, that has revenue impacts, right.

Matt:

So it's better to have kind of leading indicators access to the data that could tell you something's going to happen and make the changes early, before you ever end up bulked. But once you're there, it does take time to get things right. Right To get back to best practices, to clean up your whatever data quality. If that was an issue, to get back below certain spam complaint thresholds if that was the issue, a quick spike, for example in like Google Postmaster Tools or their complaint trends, a spike from almost zero to 0.5, is not going to get you bulk. It's staying there, right, it's continuing to send stuff that people are going no, this is trash. That's what gets you in trouble. If there's that anomaly and it comes back down to zero, that's an anomaly. It's typically viewed as an anomaly by the algorithms, but it's where you're climbing up to a bad number and then you exceed it. That's when the mail systems say all right, we're going to put you over here and time out for a bit and until you get things right.

Andy:

speaking of anomalies, that was amazing. Um, we actually had our own email show, a spike in postmaster tools against spam complaints. That we're pretty convinced wasn't even real. For one Number two it was based. We think the only main variable that was changed was the was the day of the week that we sent and we saw a huge spike like zero to like seven percent. Have you? And granted, it's on a pretty small base, we don't send to very many people but have you seen that be based purely on something like day of the week where you would see something like that?

Matt:

Not in complaint rates. Yours is probably an anomaly, and that sounds like that's the way you're looking at it, and I'm assuming it came back down. Is that that?

Andy:

case it went back to zero. Yeah, okay.

Matt:

So it could very well have been small base. You never know if a couple of people within that small base clicked the wrong button, uh, and it ended up, you know, spiking the rate a little bit. What I will say is, when we typically see this around the holidays, most large brand enterprise marketers have cadences and volumes that are kind of correlated to days of the week, right? So Mondays and Wednesdays are heavy volume days, whereas Tuesdays, thursdays, fridays are more segmented to the highly engaged or to specific parts of the country. So the mail system algorithms start to learn that this sender sends heavy Monday, wednesday and then lighter Thursday, thursday, friday, and they kind of grow into that familiarity, right? So the algorithms are like yep, we expect that, we expect that.

Matt:

We expect that it's when volume becomes volatile that the mail systems, the algorithms, start to not like what they're seeing and the volume volatility could lead to a bulking. Because all of a sudden the algorithms are like, yeah, this is not what we expect. We wonder if these guys are getting hacked. People are spamming their database from their domains, so we're just going to kind of put them over here until things get right.

Matt:

So our deliverability strategists work with big brands leading into holidays so we can understand what kind of change in volume may take place on a daily basis. You see a lot of brands around the holidays re-engaging the inactives, so bringing a whole bunch of people that haven't purchased or opened or clicked in the last year trying to re-engage them, heading into holiday sales right. And so you have to be very intentional about how you approach holidays and make sure it's as consistent as possible with what you do throughout the year with respect to your high volume days, and if it's not, you really kind of reach out to the isps and the mail systems to let them know things are going to change a little bit for the next two, three months. Haven't seen it on day of the week on complaint rates, but volume certainly can have a negative impact if it's not relatively consistent so interesting.

Gary:

It's like andy says all the time email is not free. Right, we have this idea that, oh, it doesn't cost us anything because we don't have to pay ads or whatever. It is far from free. There's, I mean, that the the opportunity cost of doing it poorly is enormous. Uh, you know, you're mentioned about, you know, ignoring the spam rates and the signals and things like that. At the best, the best, the best. Uh, what is it the uh the best? Um, I'm gonna be the best cure. What is it the? The best I'm going to be your best cure is prevention.

Gary:

All right, that's the thing out of there Kind of reminds me of my workouts. My number one goal in every workout is do not get hurt, because it'll take me a week and a half to recover.

Matt:

We know at our ages how easily that happens.

Gary:

Yes indeed. So, matt, as we kind of wrap this up, so I mean one of the things that we appreciate, a lot of things, but you have bootstrapped and been very pragmatic about how you've grown your both Bright Verify and now Inbox Monster as well. The lower middle market life. You guys are spoiled in that. You're in the industry of email deliverability, so you, for your own company, have that. But what are some things that companies that aren't going to have the luxury of having a real expert in this, what are some things that they can do? You mentioned some of the platforms. Do that? Are there some fundamentals that say a marketer or sales leader or whomever? Just some kind of some? We talked about content being number one and being very thoughtful about that, but just some basic things that we can say hey, make sure to your point, you've got these set up properly. You know, work with your providers so that we can avoid getting into the penalty box.

Matt:

Yep, yeah, I think the old model of you know, like you mentioned the spam cannon, right that old model of I've got a large database and now I'm going to set up a distribution tool and I'm just going to send to it, that model doesn't work right. So, intellectually, getting away from that model and stepping back and thinking about your business and how you're investing in marketing, how you're investing in traditional and intentional outbound on a more selective basis, doing things that I know in the podcast that preceded this one, you guys talked a lot about and I'm going to use this term, I don't know if this is the term you use meeting the prospect where they are right. If they're mid-contract, they're likely have zero time to look at your platform, but being a resource creating value in the relationship, so when they're where they are, becomes now we're being, now we're considering new solutions Perfect, you're the one they think of, right? That's true of email as well, right. Just last I got a whole bunch of volume and hoping it lands where it's supposed to land and someone engages. It's just not not the model that has legs, it's not the model to build a business on top of. So to me, it's as much a business model challenge than anything. You can have very well-constructed content, have all your authentication records set up, have a system like SalesLoft or Outreach and Apollo that is really well built and really well designed, but if all you're going to do is just blast a whole bunch of stuff through it and expect value, that just doesn't really work anymore.

Matt:

So I think being selective in your messaging, also having a healthy mix of messaging to your current customer base in a very intentional way, like don't abuse that. Our approach to messaging our customer base is always at a maximum feature updates and upcoming educational opportunities like webinars. We do not abuse that channel to market stuff, to really do anything other than hey, what you need to know is what we're going to use this channel for, and I think a lot some other organizations get that wrong. You sign up with an organization and then within days you're getting hit with marketing messages right, you just pushed into a database. So even at the most intimate level, someone has said I'm gonna spend some money with you, here's a credit card, or, or you can a LAC ate you from this account. I mean the treatment of a lot of customers by a lot of organizations is just like we're going to kick you like into the prospect funnel. Now we're going to market this other stuff and that's just again.

Matt:

That's a business model challenge. But it is hard to say have great, send great content, do it at high volumes through a mail system and you'll have success. I think it's much more complex than that and I know you're going to get into the SDR model at some point here in the very near future with some experts in the space, and SDRs are the ones traditionally that have been sending a lot of those messages. It's hard, it's hard to reach the inbox. So, say, for having the types of signals that a platform like InboxMonster can provide, which, as I've said, is really kind of focused, pointed more towards the enterprise CRM teams, those kind of lower to mid-market customers and certainly the B2B senders. Just, they're not going to have a great set of insights unless they want to pay up for signals like this because it's not inexpensive.

Matt:

But everything you mentioned, like we've talked about here, I should say having everything set up properly, having good content, being intentional about how you're messaging, not just blasting a bunch of data, but thinking more about one-to-one and less about one. Excuse me, less about one-to-many is probably a great place to start. It's more time consuming, of course, but you know the business leader in that, you know, in that case, has to make the decision. Is it time and value, or do you just want to click, send and hope it works? The latter of the two just haven't seen any value in that.

Gary:

Right, that's great advice and I think it summarizes, you know certainly what we believe and I know you believe which is we're really back to first principles that the days of the easy buttons. We have a an entire generation of people that grew up in you know. Things were new and they worked, and so we spent more time optimizing for the tactic than we did for the fundamentals. And, um, pretty much every channel we can think of has all these guards and controls and all these things up that are there to prevent bad behavior and really focus on quality, and quality is hard.

Matt:

It is, and it's just not about content.

Gary:

Yeah.

Matt:

It's about everything. It's about experience, it's value proposition, it's product quality. It's a lot.

Gary:

Yep Indeed Awesome, all right. Well, matt, where can people find you if they want to learn more?

Matt:

I'm on LinkedIn and certainly inboxmonstercom.

Gary:

There you go, Well we'll put both of those links in the show notes and send them out. I can't thank you enough. This was fantastic. We got a PhD lesson in this and, I think, all very practical advice for everybody, so really appreciate it, matt. Thank you.

Matt:

My pleasure guys.

Gary:

Great to see you all, All right, we'll stick around for a minute, but for now, until next week. Bye. Thank you for tuning in to GTM Pro, where you become the pro. We're here to foster your growth as a revenue leader, offering the insights you need to thrive. For further guidance, visit gtmproco and continue your path to becoming board ready with us. Share this journey, subscribe, engage and elevate your go-to-market skills. Until next time, go, be a pro.

Navigating the Email Deliverability Evolution
Email Marketing Challenges and Solutions
Email Deliverability Insights for B2B Marketers
Email Deliverability and Best Practices
Managing Email Deliverability and Reputation
Strategies for Email Deliverability and Growth