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About Eric Boggs: Eric Boggs is the Founder & CEO of RevBoss, an outbound agency on a mission to bring honesty and transparency to the B2B sales process. Using a mix of software automation, creative strategy and messaging, and top-notch client service, RevBoss powers full-service outbound campaigns for 100s of teams across a wide range of industries, including SaaS companies, marketing and creative agencies, video production services, and business services providers. Today, Eric leads the effort to bring happiness to 100s of clients and more than 50 RevBuds worldwide. Eric spent the last 20 years building companies and advising successful CEOs (Device Magic, Kevel, UserVoice, Ignite Social, and many more). He completed his undergraduate studies at UNC Chapel Hill and earned an MBA at UNC’s Kenan-Flagler Business School, where he was a Dean’s Fellow. Check out the latest episode of our Conversational Selling podcast to learn more about Eric.

In this episode, Nancy and Eric discuss the following:

  • The importance of human conversation in sales
  • Eric Boggs’ mission with RevBoss: client and coworker happiness
  • The role of AI in transforming sales and marketing processes
  • Strategies for generating qualified appointments
  • The effectiveness of personalized email subject lines
  • Recommendations for optimizing email cadence and timing.

Key Takeaways: 

  • When you see really long emails, it’s just laziness because it takes a lot of work to be sharp and direct in your communication.
  • My team has probably gotten tired of hearing me say cut it in half, but I think you can cut it in half and usually cut it in half again.
  • Content quality and volume are moving targets, but they are also goals you never achieve.
  • If it can always be shorter, it can always be better.

“AI will not replace human-to-human interaction. However, it is in the process of absolutely transforming the steps in the marketing and selling process that ultimately will lead to human interaction. And it’s doing that with content and decision-making and process enablement. And frankly, it’s going to make the process better in the long run, but it’s making it awful messy right now.” – ERIC

At RevBoss, we do lead generation for hundreds of clients. Most are marketing agencies, PR firms, and business services-type companies. That’s probably 60% of our customers. 30% are SaaS technology companies, and 10% are other. Machine shops and commercial real estate are all kinds of odds and ends. And our strategy and mechanism are generally the same across the board. We’re email first and primarily email. But increasingly, we’re augmenting that with targeted display ads. And sometimes, we’ll layer on a LinkedIn program if it’s targeted and small and makes sense. We’ve never done phone. And I know that’s your expertise. No, it’s more of a personal preference and experience than anything else. We have plenty of clients that have had a lot of success cold calling internally or with partners. And we’ve worked, you know, we’ve told plenty of sales leads in the past, hey, yeah, we don’t do that. But I do think that phone will work for you. We’ve just focused on email because we’re good at it. We can automate it with a lot of technology and increasingly automate it with many AI integrations. And that’s just kind of how we’ve how we built the business.” – ERIC

“As a subject line, I’m rather ambivalent. If it works, it works; if it doesn’t, it doesn’t. We’ve had clients where we’ve dropped emojis and manipulated text. One thing I know works at RevBoss is that subject lines should resemble those you’d send to a coworker. You’d never send an email with a subject line like “Increase your XYZ by some percent,” right? Good subject lines are casual, like “Hey, how’s it going?” or “I have a question about this thing.” You’ll get the desired result as long as you broadly fall into that category. Emojis and text manipulation are great ideas.” – ERIC

“Our general approach is three emails over a week, maybe 10 days. One of the emails is usually like a bump or an inline reply, maybe two; perhaps both are inline replies or forwards. Instead of doing five, eight, or 10 emails or touches over an extended period, we like to do short bursts in seven days. Let that prospect chill out for 60 days 90 days, and then do another short burst over a short period of time. We found that the prospects we retarget—say, I email you today, and then if you don’t reply after two or three emails, I email you again in 60 or 90 days—roughly convert at the same rate as net new prospects. So, a lot of the success we’re able to generate for our clients is based on repetition, process, and ensuring we’re landing in the inbox with enough frequency, the right target prospect, and a tight message to get lucky. And you know, we get lucky to the tune of hundreds of times a day for our clients.” – ERIC

Connect with Eric Boggs:

Try Our Proven, 3-Step System, Guaranteeing Accountability and Transparency that Drives RESULTS by clicking on this link: https://oneofakindsales.com/call-center-in-a-box/

Connect with Nancy Calabrese: 

Voiceover: You’re listening to The Conversational Selling Podcast with Nancy Calabrese.

Nancy Calabrese: Hi, it’s Nancy Calabrese, and it’s time again for Conversational selling – the podcast where sales leaders and business experts share what’s going on in sales and marketing today. And it always starts with the human conversation. Today, we’re speaking with Eric Boggs, the founder and CEO of RevBoss. Eric has spent the last 20 years of his career building and advising successful CEOs. Eric started RevBoss in 2014 with a mission to build a business that made clients and coworkers happy. Today, Eric leads RevBoss’s effort to bring happiness to hundreds of clients and 50 plus RevBuds around the world. You can read about the guiding principles he wrote for RevBoss in the Hat Culture Manifesto. Welcome to the show, or like I said earlier, we have a lot in common.

Eric Boggs: We do. It’s really nice to be here, Nancy. Thank you. [1:12]

Nancy Calabrese: Yeah, I’m really excited. So, what’s a RevBud? I’m going to go.

Eric Boggs: A RevBud is someone that works at RevBoss. Google has Googlers. Lots of companies brand their employees with a fun name, and we call ourselves RevBuds. I did not come up with it. I’m pretty sure Mason, our VP of People and Operations, coined that phrase. It stuck, and it’s really kind of goofy and fun. [1:43]

Nancy Calabrese: Well, I think it certainly caught my attention. So, you know, we again spoke earlier about, you know, the hot button in today’s conversation, which is AI on sales and marketing. What’s your take on it? And can AI replace human conversation?

Eric Boggs: I think my take on it would probably go a lot longer than the 18 minutes you had budgeted for this conversation, but I’ll offer some headlines. And take, certainly, opinion. I would say an informed opinion. I’m not an AI expert in terms of the technology itself but do understand deeply how it works and how it’s being applied in sales. To your question, no, not. AI will not replace human-to-human interaction. But it is in the process of absolutely transforming the steps in the marketing and selling process that ultimately will lead to a human interaction. And it’s doing that with content and decision making and process enablement. And frankly, it’s going to make the process better in the long run, but it’s making it awful messy right now. [3:02]

Nancy Calabrese: Yeah. You know, I read an article today about a gal who boasts that she can have AI do the cold calling and have them sound human. Have you heard of anything like that?

Eric Boggs: I’ve not explicitly heard of that, but I absolutely believe that it exists.

Nancy Calabrese: Yeah. Kind of creepy, isn’t it?

Eric Boggs: It’s a little weird, yeah. And I don’t know that I believe that, believe that exists in a seamless and meaningful way at this moment, but I do believe that it will exist in a seamless and meaningful way in the next, I don’t know, two to three years. [3:55]

Nancy Calabrese: Yeah. So, there are many different or several options nowadays for marketing. Part of it is cold calling, social media, LinkedIn, et cetera. What tools do you use to generate the qualified appointments? What’s your cadence? Do you mix it up with cold calls, emails, and so on?

Eric Boggs: Yeah, so at RevBoss, we do lead generation for hundreds of clients. Most of them are marketing agency, PR firm, business services type companies. That’s probably 60% of our customers. 30% are SaaS technology companies and 10% are other. Machine shops and commercial real estate, all kinds of like odds and ends. And our strategy and mechanism are generally the same across the board. We’re email first and primarily email. But increasingly, we’re augmenting that with targeted display ads. And sometimes we’ll layer on a LinkedIn program if it’s targeted and small and kind of makes sense. We’ve actually never done phone. And I know that’s your expertise. No, no, it’s more like a preference and experience thing for me personally than anything else. We have plenty of clients that have a lot of success cold calling either internally or with partners. And we’ve worked, you know, we’ve told plenty of sales leads in the past, hey, yeah, we don’t do that. But I do think that phone will work for you. We’ve just focused on email because it’s, we’re good at it. We can automate it with a lot of technology and increasingly automate it with a lot of AI integrations. And that’s just kind of how we’ve how we built the business. [5:48]

Nancy Calabrese: Got it. OK. You say email first. Why is that?

Eric Boggs: Why email first? That’s an interesting question. Probably 90% of the leads that we generate for our clients are a direct response to an email or an automated meeting booking that started with an email. So that is our go-to strategy for every client. The other cross-channel things that we do, display ads, maybe 20 to 25% of our clients, although that’s increasing quickly. And LinkedIn, maybe like less than 10%. Just because LinkedIn is kind of unwieldy and awkward and we haven’t had as much success generating outcomes from LinkedIn, which is not to say that you can’t do it. I know lots and lots of people do it and lots of companies do it. It’s just never been something that we’ve been particularly good at. Whereas the email thing, we know it cold. [6:49]

Nancy Calabrese: What about texting? Do you believe in that?

Eric Boggs: We’ve never tried it. Yeah, we’ve never tried it. And it’s never really kind of come up as an idea. And I think that texting for me is a lot more personal. Like I get, you know, business emails and I’ve, and it gets mixed in with lead notifications and Salesforce updates and emails from my team and automated billing, whatever from our own systems. And so, a marketing email isn’t out of place. Text message lands in conversation with my wife and my parents and my 12-year-old son and things like that. And it just feels a lot more off-putting in. And yeah, so we’ve never really done it for those reasons. Again, not to say it doesn’t work well. I would imagine it’s a lot more effective once a prospect is in your funnel and moving forward. I have used text for those types of things a lot. [7:57]

Nancy Calabrese: Yeah, I’m in total agreement with you. I kind of feel like texting is personal. And when I do get some business texts, it’s kind of off putting. No, you don’t know me that well. You don’t know me at all. So why are you texting me? OK.

Eric Boggs: Yeah, I got one today from some guy I don’t know, and I’m not going to call him out or whatever, but it’s like, hey, you might know these people that live in Durham, I don’t know them. Have you got a couple minutes for an intro? He’s like a clothing stylist, which is hilarious because you can see I have on a cap and a Steely Dan T-shirt, and I wear blue jeans and a t-shirt to work literally every day of the week. And there’s nothing I care about less than like my fashion appearance. And so, this guy, you know, the text I got before him was my friend and the text I got after them was my wife and he’s already out of place and he’s trying to pique my interest with something that I have negative interest in. And so, it’s annoying. [9:04]

Nancy Calabrese: All right. Yeah, well, I guess, how did they get your text number? Yeah, I agree. I think it’s intrusive.

Eric Boggs: Oh, I don’t know. It’s probably easy to find my phone number. I’m sure I’m on some list.

Nancy Calabrese: Yeah. Let’s go back to email. It’s interesting you bring that up this week. In one of the sales training classes that I participate in, the whole topic was about email and how to catch the attention of the prospect. And we talked a little bit about the subject line. And it was recommended that if you put an emoji in the subject line or if you bold the text, they tend to stand out and get more attention. Has that been your experience?

Eric Boggs: I am a subject line I would say I’m ambivalent with subject lines. If it works, it works. If it doesn’t, it doesn’t. I’m sure that we have clients where we’ve dropped emojis in places and done things like manipulating the text. The one thing that I know works and that we kind of operate from at RevBoss is that the subject line should look like a subject line that you would send to a coworker. And you would never send an email to a coworker that says, increase your XYZ by some percent, right? You would send a subject line that said, hey, how’s it going? Or, hey, I have a question about this thing. Or then you need to ask, what do you think about this? Those are good subject lines. And I think as long as your kind of broadly fall in that category with what you’re doing, you’re going to get the result that you want. And things like emoji and text manipulation, certainly those are great ideas. [10:58]

Nancy Calabrese: Now, the other thing that really turns me off is when I get an email that is like a book, information dump. What are your thoughts on those types of emails?

Eric Boggs: Yeah, oh geez, I hear you on that. It’s like that Tom Petty saying about songwriting, like get to the chorus before you bore us. And we try to keep the content that we generate for our clients, one, we try to focus on story, a narrative, versus like a transaction or a feature or something like that. Two, we try to use connectors, and connectors are basically things that we know to be true about you, the prospect, that we can incorporate in our messaging. And that can be simple things like where you’re located, or the presence of a certain job title at your company, or the lack of a job title at your company, or some reference to some customers that you have. Something about me that relates to you maybe a shared customer or a shared experience or something to that effect, so that the message that you receive shows that I know you, and which is why I’m sending this to you, and I am also a person and not an AI drone. And then sort of the last piece of that is we try to keep it really short to your point. And when you can do those first two things, a story or a narrative, and surface connectors and keep it really, short, then you’ve got something. You know, when you see really, long emails, it’s just laziness, because it takes a lot of work to be sharp and direct in your communication. [12:49]

Nancy Calabrese: Yeah, that’s interesting. And so how do you know how much is a good amount of information?

Eric Boggs: Um, my team has probably gotten tired of hearing me say cut it in half, but I think you can cut it in half and usually cut it in half again. I had a poetry teacher in undergrad that more than once I would hand in, and I’m not a poet. It was a fun class, but I’m not a poet. More than once I would hand in an assignment and he would like, you know, 16 lines or whatever, and he would circle two lines and draw a big exit through everything else and say, these two lines were by far better than everything else, start over with these two lines as the starting point. And so, I think that, you know, quality and volume of content, it’s a moving target, but it’s also a goal that you never achieve. Like it can always be shorter, it can always be better. [13:55]

Nancy Calabrese: Yeah, interesting. Yeah, so how much time should you put into crafting, say, a researched email? What’s your recommendation?

Eric Boggs: Yeah, well that depends on the context too, right? If you are an important relationship for me to try to develop and you’re a well-qualified prospect or for whatever reason, you know, as long as it takes, as long as it kind of makes sense. Like I wouldn’t spend all day working on an email to a single person, but would I take 10 minutes, 20 minutes? Heck yeah, if it’s worth it. A lot of times it might be easier to find a shared connection. Like if you know Susie, instead of me emailing Susie, I might say, hey, Nancy, will you write an email to Susie and introduce me? Here’s some copy that you can use. That might be a quicker way to end around that process. If it is what we do at RevBoss in its more automated, higher volume outreach, where maybe you want to email 25 people a day or 50 people a day or 100 people a day, then your copy needs to be sharp and direct with the things that we talked about with connectors and narrative, but then you can start to bring in variables into the copy that will adjust the copy based on what we know about you. So, if you have a VP title, the call to action might be a little different than if you have a manager title, or if you have this type of keyword in your company, or that type of keyword in your company, the copy might change. Maybe we highlight a different customer success or a different reference story. And so, when it comes to one-to-one, you can be really deep. When it comes to one-to-many, you gotta be smart about using variables and automation to make the copy relevant. [15:47]

Nancy Calabrese: And what’s your recommended cadence to getting these emails out? How many in total? What’s the spacing in between?

Eric Boggs: So, we actually did a lot of research on this. I mean, it was a while back. It was more than two years ago, and frankly, we should probably revisit it. We found decreasing returns and increasing leave me the heck alone after the third email. And so, yeah, our general approach is three emails over a week, maybe 10 days. One of the emails is usually like a bump or an inline reply, maybe two, maybe both of them are inline replies and forwards. And instead of doing, you know, five or eight or 10 emails or touches over an extended period, we like to do short bursts in like a seven-day timeframe let that prospect chill out for 60 days, 90 days, and then do another short burst over a short period of time. And we found that the prospects that we retarget, say maybe I email you Nancy today and then you don’t reply after two or three emails and I email you again in 60 or 90 days, the prospects that you retarget roughly convert at the same rate as net new prospects. And so, a lot of the success that we’re able to generate for our clients is just based on repetition and process and making sure that we’re landing in the inbox with enough frequency and with the right target prospect and with a really tight message to just get lucky. And you know, we get lucky to the tune of hundreds of times a day for our clients. [17:46]

Nancy Calabrese: Yeah, but let me, you know, a lot of emails wind up in spam. How can you prevent that?

Eric Boggs: Yeah, that’s a tricky one. So there’s the technical aspect of deliverability And a lot of folks on the internet on LinkedIn Make it seem like that piece of it’s really hard like DKIM and DMARC and SPF and authentication and all that That’s that’s actually pretty easy if Once you learn it, it sounds scary, but it’s not there’s some other things that you can do to ensure deliverability with like custom URL redirects for your open pixel or your unsubscribe link and those kinds of things that are a little bit more complicated. But that stuff is kind of meat and potatoes and it’s like a well understood set of steps that you must take and so that’s easy. Where it gets a lot trickier is the content of the email. And when you like, you know, this guy that emailed me about, you know, my fashion needs, like clearly dude I don’t know you, the message was bad, and I’m not interested in that. And so that was a very off-putting message. It would have been a lot different if he had done the work to recognize that I was a better prospect or had reached out to me with something that’s more along the lines of what I need or what I care about. And it’s the same thing with higher volume email too. If the prospecting is on point and the messaging is on point, you’re not going to get a lot of spam complaints or unsubscribed. And those are generally the things that drive you out of the inbox and into the spam folder. [19:31]

Nancy Calabrese: Yeah, well, listen, I told you this was going to fly by. We’re out of time, Eric. We could go on and on. How can my people find you?

Eric Boggs: I told you Nancy, I could keep going. I’m a talker when it comes to email. RevBoss is at RevBoss.com, R-E-V-B-O-S-S.com. I’m on LinkedIn, Eric Boggs, B-O-G-G-S. And I’ve been, one of my sort of goals for the new year was to increase my content production on LinkedIn. And so, I’m sharing a lot of videos and posts about email and the things that I work on and also a lot of personal stories. And so, I’d love to connect there with anyone in your audience that finds this kind of stuff as interesting as I do. [20:21]

Nancy Calabrese: I love it. Yeah, you know, I just learned this today. I had no idea that if you go to, say, I go to your profile and I click on the bell, I’m going to see your post. Did you know that?

Eric Boggs: No. I’m a little bit of a Luddite when it comes to LinkedIn.

Nancy Calabrese: Yeah, see what you learned? Go to people that you want to follow, click on the bell in the upper right corner, and then you’ll see their posts come through. Yeah, I’m going to do that. Eric, you were fantastic. Very easy to speak with, and I suggest everyone to really take advantage of Eric’s expertise especially as it relates to emails, because I’m guessing you’d rather be emailing than cold calling. So, thanks again, Eric, for being on the show and to everyone out there, make it an awesome sales day. [21:18]