Revenue Rehab: It's like therapy, but for marketers
May 8, 2024

Crafting the Click: Mastering Email for Meeting Success

This week our host Brandi Starr is joined by Jeff Winters, CRO of Abstrakt Marketing Group. While at a previous sales position, Sapper founder Jeff Winters implemented a unique email strategy that consistently landed him in Fortune 100 boardrooms....

This week our host Brandi Starr is joined by Jeff Winters, CRO of Abstrakt Marketing Group.

While at a previous sales position, Sapper founder Jeff Winters implemented a unique email strategy that consistently landed him in Fortune 100 boardrooms. But every time he finished his pitch, these companies would grill him on his strategy: “Great product, but how the heck did you get this meeting?" In 2013, after hearing this a dozen-too-many times, he started Sapper Consulting. Since then, Jeff has led the business to become one of the fastest growing companies in St. Louis and was most recently featured in St. Louis Business Journal’s list of 40 under 40. He is a candid, thoughtful, and dynamic leader. Once Sapper was acquired by Abstrakt Marketing Group in 2021, Jeff took over as Chief Revenue Officer, leading the sales and sales enablement teams tasked with getting the company to reach their $70M yearly sales goal.

In this episode of Revenue Rehab, Brandi and Jeff address the challenge of ineffective BDR/SDR emails that often get overlooked and demonstrate how a refined email strategy can significantly increase meeting acquisition rates.  

Bullet Points of Key Topics + Chapter Markers:

Topic #1 Evolving Email Strategy in Sales [09:28] “There's no such thing as a good list, you have to verify everything," Jeff states, underscoring the necessity of due diligence in sales prospecting. "A lot of people skip these steps and then wonder why their email campaigns aren't effective. It’s about the discipline in verification, and then actually getting out there and confirming email addresses.” Jeff continues, emphasizing, "This is what separates the successful outreach from the noise in your inbox."

Topic #2 The Art of Writing Sales Emails [17:45] Jeff explains the nuanced craft of engaging potential clients via email. “Avoid traditional greetings and close with something unexpected. Use an ampersand, keep it short, and stay away from jargon that makes your email cringey,” he advises. Brandi adds, “It’s about connecting with the person on the other end, understanding their problem, and presenting your email as a conversation starter, not just a pitch.”

Topic #3 Integrating Technology and Email Sequences [31:09] “Technology now plays a bigger role in making sure our emails get noticed,” Jeff remarks, discussing the evolution of email tools. “We’ve moved from just crafting content to focusing on how to get our emails into the eyes of decision-makers.” He shares, “A successful email sequence involves multiple touchpoints over weeks, combining emailing with calling, respecting the cool-off periods, and constantly testing our strategies to optimize for response rates.” This approach, he notes, is crucial for maintaining domain health and avoiding being blacklisted.

So, What's the One Thing You Can Do Today?

Jeff advises revenue leaders to base their sales planning and budgeting on the number of meetings rather than traditional sales quotas. He suggests assessing how many meetings are held, which channels are used, and the closure rates of each channel. By focusing on these metrics, leaders can create more accurate and reliable forecasts, transitioning from quota-based forecasting to a model that emphasizes the effectiveness of meetings in generating sales.

Buzzword Banishment:

Jeff Winters’ Buzzword to Banish is the term "value add." He expresses his disdain for the phrase by explaining, “It’s just so overused and nebulous. Everyone throws it around without really understanding what actual value they’re adding.” Jeff wants to rid the business world of this term to encourage clearer, more meaningful communications. 

Links:

Get in touch with Jeff Winters:       

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Transcript

Outro VO  00:06

Welcome to revenue rehab, your one stop destination for collective solutions to the biggest challenges faced by marketing leaders today. Now head on over to the couch, make yourself comfortable and get ready to change the way you approach revenue. Leading your recovery is modern marketer, author, speaker and Chief Operating Officer at Tegrita Brandi Starr

Brandi Starr  00:34

Hello Hello and welcome to another episode of revenue rehab. I am your host Brandi Starr and we have another amazing episode for you today. I am joined by Jeff winters, while at a previous sales position. sapper founder Jeff winters implemented a unique email strategy that consistently landed him in Fortune 100 boardrooms. But every time he finished his pitch his pitch these companies would grill him on his strategy, great product, but how the heck did you get this meeting in 2013 After hearing this a dozen too many times he started sapper consulting. Since then, Jeff has led the business to become one of the fastest growing companies in this in St. Louis, and has most recently been featured in the St. Louis Business Journal's List of 40. Under 40. He is a candid, thoughtful and dynamic leader. One sapper was acquired by abstract marketing group in 2021. Jeff took over as Chief Revenue Officer leading the sales and sales enablement teams tasked with getting the company to reach their 70 million yearly sales goal. Jeff, welcome to revenue rehab, your session begins now.

Jeff Winters  01:54

Brandi, thanks for having me. I appreciate it. Excited to chat with you.

Brandi Starr  01:57

Yes, I'm excited to have you here. Your background is really impressive. And we'll get into that in just a bit. But before we do, I like to break the ice was a little woosah moment that I call buzzword. banishment. So tell me what buzzword would you like to get rid of forever?

Jeff Winters  02:19

Total Woosah moment, um, I would like to get rid of the buzzword. Value Add might be two words, maybe a hyphen, value,

Brandi Starr  02:28

I can take a phrase. So why do you want to get rid of that one?

Jeff Winters  02:34

I think because, in almost all cases, when people say value add it is not value add to the customer. Like Like, for example, okay, here's, here's what I like as, as a value add, we're gonna do an audit of your Amazon traffic. And we're gonna give that to you. So that you can have it but really, that's not a value add that's a tool to sell somebody something that is selfish, like on your part, or, you know, as a as a value add, we're gonna give you x along with our product, but like that thing doesn't cost anything and it would have come with the product anyways. And so I by and large think when people say value add it is code for something that helps us or is cheap enough, that looks like it could be a value but actually isn't. So we'd give it away for free. So that's what I want to banish the phrase the compound word or the word value add.

Brandi Starr  03:32

I will take it Yeah, I do agree that there are so many things that get sort of thrown in as the value add that I definitely would agree are not really valuable to the end customer or is something that it's like I would have been in there anyway.

Jeff Winters  03:49

Right? Has anybody said value add before? Am I Am I unique? I really know

Brandi Starr  03:52

that one is unique we do get we do get some that you know come up over and over and over and back in March we had our March Madness for buzzword banishment and bra ended up being the word that was like officially banished across so not a marketing word, but definitely one that I'm happy to get rid of. All right. Okay.

Jeff Winters  04:15

All right, good. Well, I didn't want I didn't want to be somebody saying the same thing. Everybody else I got a synergy. I bet 9000 People said synergy. lovable.

Brandi Starr  04:23

I think the most common one is attribution. Like that is the one that I think has been banished probably 10 times in you know, all 100 Plus episodes. So yeah, value add is a new one. And we'll see how it does next year in March Madness. See if see if people agree at how bad that one is. Okay,

Jeff Winters  04:45

well, I think it's going to age well, so I'm looking forward to seeing how it performs. Awesome.

Brandi Starr  04:50

So now that we've gotten that off our chest tell me what brings you to revenue rehab today.

Jeff Winters  04:55

Oh, just excited for any opportunity to to chat with the revenue leaders of the world. I think that we all need to talk as much as possible all the time. But definitely now things are changing so quickly. And to the extent that I can lend any value or insights to people that are going through what we're all going through and fighting the same struggles, like that's a, that's a great opportunity for me. So I'm so excited. You got such a tremendous audience. And following that. It's, it's amazing to be able to connect with that group.

Brandi Starr  05:33

Awesome. Well, yeah, I know, we're gonna jump in and tackle the problem around leveraging email for sales in how we how you've been successful at using email, the meeting, in a way, that's been so impressive. And so before we actually jump into that topic, I believe in setting intentions, it gives us focus, it gives us purpose, and most importantly, it gives our audience an understanding of what they should expect expect from our discussion. And so, you know, related to the success that you've had with email, what would you like people to take away from our discussion?

Jeff Winters  06:10

Okay, so my intention doesn't have to do with the content as much as it has to do with like, I hope that people think I'm, like, provocative, that's what I want. That is my intention. It's very selfish. It's got a, it's got a tinge of narcissism to it. But like, I feel like if I can be provocative and interesting, then people will listen to my nerdy email takeaways, because I gotta tell you, it's I hate to I hate to spoiler, but they're, they're really helpful. But they're a little in the weeds. And I don't want to bore anybody. So I'm going to try to be provocative with my technical, boring takeaways. Is that good?

Brandi Starr  06:44

Yes, I will take it and I like a little provocativeness. And, you know, it is one of those things that I'm glad you said what you said in terms of it being in the weeds, because that is one challenge, sometimes where revenue leaders don't necessarily think about email, they don't, you know, put a lot of emphasis on it, because it it, it is a tactic, it is very in the weeds. But one of the things that we believe is that it is such a you know, it is like the primary way that we communicate with each other. And so getting that right ties to so many of those other things that are not in the weeds. And so, you know, as leaders, sometimes we got to dip down, we can't spend all our time in the weeds, but sometimes we got to dip down and really understand some of those fundamentals. And email for sales is one of those things that I see so many people getting wrong. Um, I you know, and so would love to, like, let's start with tell us your story, and how you have been able to leverage email effectively, to actually drive meetings and drive revenue.

Jeff Winters  07:59

Yeah, so I'm gonna give you the the origin story, you alluded to it in the intro, and I'll truncate it, and then I'll get to where we are today, because I think it's valuable. So I, I was I was hired at this at this startup, to be the chief revenue officer, like 26 years old. And I had as much business being the Chief Revenue Officer of this company as as like no one like there was there was no reason I was I was under experienced, I had in the industry I was my most recent job was like a sales manager. Like, there's no reason for this guy to hire me at this job. And I got there on the first day, and he's kind of like, hey, you know, the product doesn't exactly work. And we haven't really sold it to anybody. And the only people you can sell it to is Chief Human Resources, officers of fortune 500 companies go. And I very quickly realized why I was hired with having no business or resume or experience or credentials to be hired is because like, nobody else would take that job was impossible. So I, I failed miserably for six months, I'm dusting my resume off. And finally, I started waking up at three in the morning writing funny emails and getting tons of meetings like 180 meetings in a year. And I ended up in boardrooms all over the country. And the one that comes to mind most vividly was Morgan Stanley, I get up there, there's six people in this room. And none of them wanted to talk about the software, they just want to talk about my email and how I how I had written this email at three in the morning, what was I doing and so I'm flying home like okay, well maybe I could do this for other people. So that was that wasn't as smart as a lot of these entrepreneurs out there who were like I see a problem and I'm willing to solve this problem I just I just knew I was good at very few things and this happened to be one of them and I was just gonna kind of run with it and and I I go to school at night and I was like if this thing fails Forget it. I'll go back and do this full time. So started started a business basically sending emails to get sales meetings, and it worked you know we got lots and lots of customers but But over time, I just want to talk briefly about and we can we can go deeper if we want to the evolution of email for sales prospecting because You know, in 2013 2014 2015, it was it was it was basically easy. I mean, if you had the right technology, defined as the sales, engagement tools, things like outreach, or sales loft, or things that we're all pretty familiar with, you were just way ahead of the game, and you could send emails, and it was all about the subject line and the content. Okay, great. And it was, it was great. You get sales meetings all day. And then as those tools proliferate in the market, you got a response from the Googles, and the Microsoft's of the world, and their recipient saying, Hey, we don't really want this, especially for the bad actors. And so those responses made it more challenging 2018 2019 2017 2020. Like in that period, Google and Microsoft, were going through a lot of changes in terms of how they were going to handle different types of cold email, or probably more importantly, like nefarious email, that spoofing emails, or what have you, that sort of all got lumped together. And so that it became about making sure you were authentic in terms of not only your messaging, but also making sure that the system is tied together. And like you were who you said you were. And obviously, with AI now things have changed dramatically. And a lot of people have given up on email on LinkedIn, where, you know, oftentimes, it's people repeating people who are repeating people. So you get sort of this, you know, sort of this echo chamber type feel. Now, people are given up on email, because it's way harder today than it even was six months ago, because now the way you have to orchestrate your technology and layer things together, it's gotten difficult people are like, Screw it, I've given up. So that's what's happening now. And that's my, that's my story on email. And, and the good news, I suppose, as, as I wind up this little intro segment is, it's doable, you can do it, my sales team is getting 200 held email meetings every single month, resulting in $75,000, in monthly recurring revenue every single month, just through email. So it's doable, you just got to be able to do it right. And hopefully, I can help people get on that path.

Brandi Starr  12:08

Yeah, and let's talk about the doing it right, I'm in I'm in several cmo communities. And one of my favorite channels in one of those communities is the rants channel. And a lot of what appears in the rants channel is copy paste are screenshots of sales emails that people are receiving, and they're just horrible. Like they, they say nothing, you know, it's always the I hope this email finds you well, or they try and be you talks about using humor, they try and use some like quirky humor or analogy, and most of it just comes across so cringy that it's like, there's no way I'd ever respond to this. And every blue moon, there's like, you know, somebody will share a win of like, Hey, I, you know, wasn't necessarily interested in this solution. But this was a win. Who knows? Maybe that was from your team.

Jeff Winters  13:10

Bed bugs? Yeah.

Brandi Starr  13:11

You know, it is one of those things that more people are failing than winning at this end. So you know, while we're getting real tactical, and in the weeds, I would love to hear like when you are talking to a client, you know, onboarding a new person on your team, like, what are you communicating to them, that is helping them to write the things that are landing the meetings, and not the things that land up in rents channels in various, you know, executive communities. All

Jeff Winters  13:45

right, so I have some bad news here. You're gonna end up at a ranch channel. And so, if you're sending enough, you're gonna, because they're there, it's inevitable, whether you're making and by the way, you can expand this out of email, cold call LinkedIn messaging, Google ads, Facebook, you're always you're always at risk of somebody going, Oh, this is cringe. And you beyond that, you have to be okay with that. You have to completely accept because I talked to business owners on the other side of it, they got my from my brandings perspective, I don't want anybody getting an email that that they wouldn't want. It's like, well, then you can't do this kind of marketing. And by the way, you also can't cold call, you probably shouldn't do Facebook ads. You know, you're sort of set with content and referrals, I suppose. So first thing is acceptance. Accept the fact that you're going to annoy someone, if you do any kind of outbound marketing email, including and especially and you're probably going to end up in somebody's rants channel. Now, can you avoid the more flagrant issues that end up in Iran's channel? Sure. And here are some easy tips. First, keep your emails under 90 words. A, you're more likely to get people to read it and be it's harder to say something really stupid or cringy and 90 words you just have less you have less paper there. Celeste page. So that's that's tip number one. Tip number two, nothing upfront in your email other than Hi name and the problem you're seeking to solve. No hope it finds you. Well, no, it's been a long time. Don't Don't don't I don't want any of that. None of that all of that is gone has been gone. Sounds silly like cut it out. Third, you want to use some weird punctuation, as much of it as you can ampersands dashes, slashes, unusual punctuation is a a tip I hear underutilized that I love. Because it draws the eye in a way a like generally reduces word count, but B it draws the eye. I just don't see a lot of ampersands anymore, right? Or you see a lot of ampersands in life like that's like other than like book covers. It's kind of rare. Yeah,

Brandi Starr  15:57

it is. I know I am a person that overuses the ampersand. And I always feel weird about it, because everyone spells out and now and it's almost like an unofficial thing that people do. It's sort of like me and my side part like they tell me it's out. But I still do it anyway.

Jeff Winters  16:20

That's so funny. We should we could do a whole other thing. Like I am told routinely. I have like horrible style. And like, no. I just be personally I just bought it. And I don't know what's in or you know, what's in though? ampersands. That's what's in? And then And then lastly is how do I keep it as casual as possible? I want real casual, I want to say hi Brandi. lowercase t so it looks kind of like awkward. This Jeff winters at abstract marketing group. We see a lot of people who are struggling to generate true sales pipeline. Like that. That's the problem. You solve this generating pipeline. And then And then last is zero jargon. You think you're not saying jargon, you're saying jargon. Every company has their own words they use it no one else uses, don't use those words. So those are just a few tips that I would incorporate into my content to make it less crunchy. It's not 100% failsafe, but less crunchy.

Brandi Starr  17:17

I would have to agree with all of those things. And it is interesting to me how, you know, it's like the under nine new words, I see most people embracing that like people, holistically marketers and salespeople have gotten that short is better. And that, you know, you're trying to elicit a response. And you can give them more of the meat, you know of it with the next thing. Let's talk about the problem you solve, because this is one of those things that I think some people get it and some people don't. So, you know, the majority of our listeners, I would say are heads of marketing. And so they are definitely acutely aware of what is the problem that they are trying to solve. Because that is the foundations of you know, all the marketing messaging. When I think about it related to the sales function, a lot of time, especially those that are doing the cold emails, the BDR is the SDR is the ones that are just trying to get a pulse tend to be less, less close, not as close to the messaging around. What is the real problem that solver, you know, that needs to be solved. And so for those that, you know, are kind of thinking about it, and they're like, Yeah, I know, our SDR is like what they're sending out is not you know, it's not really what we're getting at. Do you have any advice for those leaders on how you make sure that those people that are sending the emails, really actually fully absorb? What is the problem that's being solved?

Jeff Winters  18:57

I feel like you're gonna get me in trouble here. So I kind of think the opposite. So yeah, sorry. To all of my marketing friends who I love dearly, and all of those watching at home.

Brandi Starr  19:13

Hey, we said we wanted to be provocative.

Jeff Winters  19:16

So I think General, I think often the salespeople have a way better idea of what the problem that is solved in the right way to say it, the marketing people often like our example, the problem our company solves is we like if you don't have enough sales pipeline sustainably, we solve that problem. Like that's very easy to understand. Like if you're a company, you don't have enough sales pipeline. We help you fill that sales pipeline forever. That's easy. That's very easy to understand. I think that not always, but often. Marketing is coming up with a message that sounds really good in a room full of executives or a boardroom with or to like their peers, but doesn't truly resonate in a cold outbound email. And I think that the salespeople often do, like, it's got to be short, it's got to be tight. And it's got to be very meaty you. And I think that that marketing, by the way, to their credit, we're gonna be dancing, really dancing around here to their credit because I get it on the website or on the social ads, I understand, but this is a totally different game. And so when I hear marketing is getting involved, am I like, Oh, awesome, great marketing is gonna get involved, like, often what I'm thinking is, we're gonna get, you know, we're gonna get told, or we're gonna have to put in words that I don't think are right like this, they get it should be dressed down, not dressed up. And I think sometimes marketing wants to dress it up a little bit.

Brandi Starr  20:54

Okay, so I think what I'm hearing here is there is a key opportunity. And I mean, it wasn't, you know, wasn't intending to go down the alignment conversation. But I know there there needs to mean it. We know there needs to be some some serious alignment between marketing and sales, like that part is self explanatory. But what I'm hearing is the enablement of those salespeople, and messaging and things coming from marketing, your desire is not messaging related to the outbound of what you're saying to drive customers, but more the air cover is that, like I'm reading between the lines, in terms of what you would want to see from the marketing team that you do feel is valuable.

Jeff Winters  21:48

I don't think that sales development or sales emails should ever touch marketing, ever. I think it should be completely separate. And so what I want to see from the marketing team is a great deal of support on all of the other amazing marketing functions that have to go on inside a business, but I don't want them anywhere near my sales team or my sales emails, personally. Okay, I

Brandi Starr  22:14

went down a little bit of a rabbit hole just because my interests but I'm gonna pull it back and get back.

Jeff Winters  22:20

Oh, I feel I feel like, Yeah, I'm gonna get I'm gonna get destroyed. But But

Brandi Starr  22:24

no, no, no, I always love to hear different perspectives. So I want to bring it back to email. So we talked about some of the key things in you know, kind of your four points, the weird punctuation. I love that hopefully, people don't start overusing it. But there are definitely, you know, ways that we can use sort of markup language and things to draw the attention. And then of course, the keeping it casual. Let's talk about a bit about sequencing when it comes to email. I think that is the other place where a lot of revenue leaders struggle, because when I talk to, you know, especially larger companies, there are usually playbooks, and you know, the different technologies, they have the built out sequences, where it's like, you know, send this email, then here's the next one. And I'm all for the automation, like that's at the heart of what we do. But I feel like, sometimes there is, in sales emails, it's almost like they're a bit tone deaf, like, I'm sending this next thing, because this is the next thing in the sequence, not necessarily that it actually made sense for the scenario. And so when thinking about like cadence of communications, and you know, how you tell people to consistently engage when they're not getting the meeting on the first email, I would love your thoughts there when it comes to sequencing. So

Jeff Winters  23:54

here's, here's like, the original four part email sequence, and it still goes on all the time. Here's what we do. Email one, don't have a meeting. Email, too. Did you? Did you see email one? Email three. As a reminder, here's what we do. Email for? Why aren't you responding? In some way, though, that's like the theme of the Forever email sequence. And that's what everyone gets some version of. And so you have to be you have to try to be pattern interruptive to a certain extent. But I have good news, if you're sending bad emails, most of the world's not seeing them. You're not, you're not getting into the inbox like it doesn't, it doesn't matter. And even if you are most of the world's not reading it. So, you know, I guess the more interesting thing here to me, and the slightly less exciting from a content perspective is we used to be in a day and age where content mattered so much where what you wrote mattered so much, and it still matters some but it matters in such matters, some much less than it used to. Because so What matters now is how is your technology set up to make sure you get an eyeball on it in the first place. That's That's what truly matters now. And to people that are listening where their email program is struggling, they know I'm right. Like, they know that they went from getting an enormous amount of email responses a year ago, and now they're getting none. Or they're I talked to a friend the other day, so we sent out 150,000 emails, we got zero meetings. But yeah, that is a thing that is happening. So But back to your question really quick. What would I do sequencing wise, five emails, 40 day period, let them cool off, 90 days later. I know that it is best practice in today's day and age to email and then three days later call and then four days later email like that, that to me is that to me is very indicative of the fact that email alone often won't work, because it's not being done very well. And you have to have calling in your process. And so I fully support that, especially if you have a smaller total addressable market. So if you have a smaller tool, if you have 1000, prospects you can sell to, you gotta treat them all like gold, I'm not sending a ton of emails getting unsubscribes, etc. So my cadence. And my frequency often will depend on how many prospects I have in my market versus any other variable upfront because you just have to be so cautious if you have 1000 prospects or 5000 prospects. But in general, what's table stakes four to five emails, 40 day period, sporadically sprinkling through calls and trying to avoid the sequence I described earlier of? Here's what we do. Do you want a meeting? Did you see my last email? As a reminder, here's what we do. Do you want a meeting? Why didn't you look at my last email?

Brandi Starr  26:50

Yeah, the Why didn't you look at my last email are usually the ones that get the crunchiest. And so I want to so we talked a lot about, you know, the, in the weeds part, I want to elevate the discussion a bit to talk about the impact here. So we know just from your intro, and what you said at the beginning of, you know, what the real impact is, you get the meetings that yields revenue, that part is pretty obvious. But let's talk about this, you know, more holistically in terms of when you fail at this. What does that mean? You know, what is the impact of that on the company, and beyond the obvious direct type meetings, turn into opportunities, which turn into revenue? What are some of the key benefits when you get this right? And so I'd like to hear, you know, both sides of, you know, heads of revenue, heads of marketing heads of sales, like when they are thinking about why they should spend a little time in the weeds, making sure their teams are getting this right, like, what's your benefit? And what's your cost of not getting it right?

Jeff Winters  28:01

So let's talk benefit first. So benefits number one, it's always and forever been your lowest cost channel period. Email is your lowest cost or should be your lowest cost acquisition channel of all the outbound channels I'm not talking about refer I get it people go we get referrals, it cost us nothing fine. That's not what I mean, I'm talking of all your, between digital or or call or LinkedIn, this is going to be forever and always the lowest cost channel and when it get when it's right. That's, that's awesome. The second thing is it is it ought to be a pretty high converting channel. So aside from referrals, and inbound email ought to convert at the third highest closing rate of, of your general channel mix. And reason for that's pretty obvious. I mean, in order to get a meeting through email, think about this. I mean, it's got to get to somebody's inbox. by some miracle, they have to read it by an even greater miracle, they have to respond. And then they have to accept a calendar invite, like you got to jump over four bars to get an email meeting. So those ought to be you know, better than other channels where you know, for example, cold call if I'm if I'm calling you and you're picking up and maybe you're in a meeting, you're distracted. Like sometimes people take a meeting just to take a meeting as opposed to actually having a clear couple bars. So the biggest benefit number one, cost, number two, close rate number three is predictability. If I know like clockwork, I can get 1% half a percent a third of a percent of all prospects. I emailed schedule a meeting, you can set your clock to and those are three really big benefits if you get it right. Where it goes wrong. type people like this better. Where it goes wrong could be pretty bad. So for example, if you're sending emails, marketing emails from your corporate domain and And one of those emails gets a really nasty or you have some pattern of people marking in a spam, then your corporate domain could get blacklisted. And the emails you send to your kids don't go through, I mean that that's a that is the worst negative impact you can have from email prospecting. Let's see seriously, but still business impacting. And it all depends on how much you are leveraged to email as a channel. But Google changes its algorithm. If you're highly leveraged email as a prospecting channel, it could go to zero in a day. Let me know what you're doing. And you're prepared for that. Those are, you're always tied to the whims of Google and Microsoft. And that's tough, I don't care what you're doing, if you're if what you're doing the success of what you're doing, in large part depends on the whim of another platform, where you have zero visibility and zero control. You know, that's, that makes, it makes life pretty tricky. And so that's, that's where it can go bad. And then third, you know, for for whatever reason, you're highly leveraged email, and you have a new product, or you have a new offering, or you have a new something, and you think email is gonna work the same way in product B, as it did in product day. Never happens like that. So. So those are some examples.

Brandi Starr  31:20

I love it. And those are all like, I we talked so much about, like, I almost feel like I, you know, should slip you a little tip on the spam and changes because this is something that we are preaching. And I could not have said it better myself, it's like you have to, you have to spend some effort in making sure the technical setup for both marketing emails and your sales emails through your various you know, through your sales loft, or your you know, your Marketo, or whatever it is, however, emails are going out, everything's got to be set up and monitored in a way that we have the highest chances of getting in the inboxes and not in spam. So to get at least the maximum number of eyeballs on it to have a chance to convert that message.

Jeff Winters  32:16

Can I tell people how to do that? Yes, go right ahead. All right. So so here's what I'm doing. If I'm you, if you're out there, and you're going, my email stinks, we're gonna give up on it we gave up on it doesn't work. Here are some must haves that the best in class folks who, who I'm fortunate enough to be able to talk to all the time are doing. The first is they're using multiple domains, never their corporate domain. So they're setting up multiple domains. And they're using a variety of different senders in those different domains. So like that is, that is table stakes. Anybody who knows, this game knows to do that for sales emails. The second thing is, we are the days of having a pretty good list or over of buying a list from a list source and putting it through a cleansing service and ripping it out of your sales platform would never do it. The best that I've seen are calling and verifying, calling and verifying emails that so think of that extreme of I'm not I trust no one other than somebody who is a full time employee to call and confirm. That's the gold standard. I want to start with the everybody says, oh, start with a good list. Nobody knows how to get a good list. Because you can't, you can't get a good list. There is no good list, the good the good list fallacy is over, I don't care how many platforms come out how many cleansing services don't work, we have some of the biggest companies in the world literally hire us to call and confirm data. Period. That is what they pay us for. They're not dumb. We know what we're doing. You have a gold standard call confirm the email addresses. Is it expensive? Sure. Is it worth it? Yes. And then last, they're sticking to a lot of the best practices and, and also a bonus, if often the tool that you're using is part of the problem. And it is very hard to determine if the tool you're using is part of the problem. Because it's like you ever have like the internet modem, router issue, like people come to your house, you go by Internet doesn't work, they go to your modem, and you bring out the modem, people in the golf match your router. Everybody says the router, the modem, so the provider using the send of the emails has no incentive to go, Yeah, that one's on us. They have every incentive to go. It's your list. It's your content, it's your subject line, we're going to put you in touch with somebody who knows how to do that. And then you're like six months later, like maybe it is the provider. And so I would be very, very cautious of not believing that the provider you're using isn't the issue like maybe it's the modem, maybe it's the router, everybody's gonna tell you a different thing. So like, sometimes you got to change them both.

Brandi Starr  34:45

I would definitely agree. And then the last question that I have is around testing. So you know, you talked a lot about how what works at one point, you know, gets to a point where it no longer works. What work for product A may not work for product B, what do you recommend? Or what are you doing with your clients and teams around being able to test messaging tactics? You know, do you have an ongoing testing strategy? What What are your thoughts around testing?

Jeff Winters  35:18

I think the most important thing people get wrong around testing is using anything other than meetings as an output measure. Meetings are the only output meet metric that measure metric that matters. In Email, prospecting, replies, do not matter. Opens do not matter. They can matter. But they most often don't. I could send a horrible email and get a ton of replies, doesn't mean they're good. And so what am I optimizing for it, you're have to optimize for meetings on the calendar, and then ultimately, from there, close deals related to emails like that as to specific emails. So I think the number one thing people get wrong is, let's because everybody's so conditioned, what are the leading indicators? What are the leading indicators of meetings? It's replies, No, it's not. It's not right. It's open? No, it's not. Those are both wrong. The leading indicator of success is often domain health, like it's the health of your domain, how likely are you to get it to an inbox? That's the leading indicator I would use in terms of testing? Sure. We're always testing, reviewing results weekly, in a great deal of depth campaign by campaign email by email and domain by domain, how healthy are each of those domains?

Brandi Starr  36:38

I love that. And that is a really good like, I do see, you know, I think the one place I would disagree is that I do see some value in the other metrics. I do agree that at the end of the day, like the the thing that leads to revenue, in this case, meetings is the key indicator. But I would say like when it comes to testing, there are ways to test and validate if certain things help you get into the inbox, help you get to the opens, you know, reply, I could take it or leave it on that one. But at least understanding what helps get eyeballs on the content, to then be able to say which content converts? I do think you have to look at both and not just it's like because if you don't get anybody to see it or open it, then there's zero chance of there being a meeting because they never knew it existed. So to me, you have to look at both. Why is your perspective only on the meeting.

Jeff Winters  37:45

So a couple points, that's a great, I completely hear where you're coming from. And also, like, gotta just to me got to distinguish here from like marketing, nurture email, from sales email. So I'm making that distinction. Here's why open rates don't matter to me. I am of the mind that open rate tracking is one of the many variables that will increase the rate at which you go into the spam folder. And so I've turned off open rate tracking on all sales emails. So maybe it is more indicative. But like, Apple, there are certain tools that are like auto open emails, like they open the email, and they're giving you these false rates. So like the open rate to me a, we don't use it. And B when we did I got false rates. And I was doing things based on false rates because Bill, get an auto open of an email through Microsoft. And you're like, I thought I got a 40% open rate, but I didn't it just auto open the email and tracked it. So that's my, that's my gripe with open rates. Although I'm sure like directionally if you get an 80% open rate on a Marketo email versus a 15%. Open rate over time, I'm sure you can try that stuff out just for me. It's not helpful on sales development emails, next on replies. I think replies are very important in that in the context of telling a story. So what we're always trying to do is, what's the story is the story that we got a lot of replies and very few meetings, okay, then we can change and tweak is the story that we got no replies and a couple meetings. Okay, then we can change the tweet to get more replies. My point is, I think a lot of people use replies as sort of a very important metric in their testing to say, okay, replies are great. This worked as opposed to like, who cares? Doesn't matter if the replies are bad, it doesn't work. So I guess maybe if I were to sharpen that statement a little bit, I'm still anti open rate, but I hear your point. And maybe I would just be more cautious around replies and more on sentiment, like email reply sentiment, than I would be on just replies in general. Okay,

Brandi Starr  39:49

I can I can definitely support that. And I, you know, it's more so, not that I would lean heavily into those metrics. It is more so I wouldn't and ignore them. And so it's one of those things that I think, you know, where I think certain metrics kind of get a bad rap is we talk about vanity metrics and things that are not truly leading indicators. And I agree completely. It's just they do also have a place in what we're looking at. So I'm always, I'm very always hesitant or very always, to go all or nothing. I focus on the thing that is actually, you know, the measure of actual results, while giving at least some incremental attention to some of the others. To as your point. See, is there a story that this data is telling us so I wouldn't necessarily be reporting out to anyone on open rates? But looking at the trends of open rates? Okay. Is this telling me something? Because it could be telling me that, you know, my sales development emails went from 50% to 10%. That might tell me somebody st changed something, and I got to figure out, is it the modem or the router? So like, there is, you know, there's some things that I feel we can learn by actually looking at that data, not necessarily just testing for content.

Jeff Winters  41:12

I think that's right. Well, first of all, thank you for latching on to that modem or the router. I feel like that really, were I just, I love a good analogy. Oh, plus, that's like, so if everybody knows that one, everybody's like, who are the modem and the router? Yeah. I'm with you incremental attention. That is my, that I agree with you. Incremental attention. That's, that's what you should pay to any of those metrics agree? Well, awesome.

Brandi Starr  41:36

I was gonna say I love when we can find a middle ground. But talking about our challenges is just the first step and nothing changes if nothing changes. And so in traditional therapy, the therapists gives the client some homework, but here at revenue rehab, we like to flip that on its head and ask you to give us some homework, it very much is a when you know better you do better. And so I would say for those revenue leaders who recognize like listening to you and your success, that they are not seeing that same success with their sales, development emails, what would you suggest as the first step? All

Jeff Winters  42:18

right, so I'm gonna I'm gonna go even back a little further. So I'm gonna say, my, my, my homework for revenue leaders, is to make the cornerstone of your sales planning, the cornerstone of your budgeting, meetings, meetings, like take budgeting all the way back to meetings, often what we see is sales teams that budget based on quota or forecast based on total quota times 85%, total quota times like that is so common, it's like, okay, well, hey, in general, we're gonna hit about 90%, of quota, our total quota is a million bucks, we're gonna hit 900,000. That's what I'm gonna forecast. And the last couple years, we've seen, that's not very true, because then you can hit 400,000, or 500,000. What you can forecasts using so much better is how many meetings, which channels at what rates, do those close in each channel, and then forecasts that way, that is the best advice that I can give.

Brandi Starr  43:19

I love it. And, you know, I that connection that you are making between some of those higher level strategic thinking things that the revenue leaders have to focus on, kept making that connection to the very in the weeds tactical thing of tapping into email and other channels to yield that meeting is a great way to have a little bit of a mindset shift around how we're doing that. So I love that as a takeaway. Nice. All right. I enjoyed our discussion, Jeff. But that is our time for today. But before we can go or before we go, tell us how we can connect with you. And for those watching us live, they can see the gross show light behind us. So make sure to also tell us about your podcast.

Jeff Winters  44:13

So thanks for that. So the growth show is a podcast, sort of got a radio show feel to it. Three of us sitting here we have different segments. And there's a lot of really, really tactical nuggets on on how to grow a business from sales to leads to leadership. Check it out. We'd love to love to have you listen, love to get your feedback. Next, a couple ways to get in touch with me first if if you are a company and you're looking to jumpstart your pipeline or anything I said resonated with you like you know what I need to scratch that itch. Abstract ABS Tra Que te mg.com abstract mg.com or you can always find me on LinkedIn Jeff winters there's only like one of the few there not that many of me.

Brandi Starr  44:58

Well, we will make sure to link to your LinkedIn to abstract as well as to the gross show. So wherever you are listening or watching this podcast, check the show notes so that you can connect with Jeff. Well, Jeff, so I so appreciate you joining me. And thank you for our discussion. I always love when I can learn something from my guests as well. That's

Jeff Winters  45:21

awesome. Well, I appreciate it. I'm glad I was unique in my upfront answer, and I hope all I care about now, make sure people listen and enjoy, but I really hope that it wins the bracket. That's very important to

Brandi Starr  45:33

Yes, as I say, we got it. We got quite a few months before we have another March Madness. But I think you got a good shots. Thank you. So awesome. Thank you. I hope everyone has enjoyed my conversation with Jeff. I can't believe we're at the end. Until next time.

Outro VO  45:53

You've been listening to revenue rehab with your host Brandi Starr. Your session is now over but the learning has just begun. join our mailing list and catch up on all our shows at revenue rehab dot live. We're also on Twitter and Instagram at revenue rehab. This concludes this week's session. We'll see you next week.

Jeff WintersProfile Photo

Jeff Winters

CRO

While at a previous sales position, Sapper founder Jeff Winters implemented a unique email strategy that consistently landed him in Fortune 100 boardrooms. But every time he finished his pitch, these companies would grill him on his strategy: “Great product, but how the heck did you get this meeting?" In 2013, after hearing this a dozen-too-many times, he started Sapper Consulting. Since then, Jeff has led the business to become one of the fastest growing companies in St. Louis and was most recently featured in St. Louis Business Journal’s list of 40 under 40. He is a candid, thoughtful, and dynamic leader. Once Sapper was acquired by Abstrakt Marketing Group in 2021, Jeff took over as Chief Revenue Officer, leading the sales and sales enablement teams tasked with getting the company to reach their $70M yearly sales goal.