It’s the 10th episode of Meaningful Conversations with Revenue Leaders – No fluff. Meaningful conversations only.

We are celebrating the 10th episode of Meaningful Conversations in style - joining us today is none other than Kyle Coleman.

Kyle is a Sales & Marketing leader with a passion for people development, identifying & solving problems, creating & optimizing processes, and unifying departments across the revenue organization.

As our interview host, Jan, said - “If people think about writing LinkedIn messages, they think of Sarah Brazier. If people think of good watches, they think about Switzerland. When people think about cold emails, they think about Kyle.”

Kyle currently leads the Revenue Growth & Enablement initiatives at Clari, and is every SDRs best friend and advisor, regularly sharing reflections and feedback on crafting the perfecting outbound messaging.

Learn what Kyle is passionate about (I bet many of you will not be surprised by what he says!) and hear his advice for SDRs on how to make the most out of their roles and prepare themselves for a successful career ahead. We hope you enjoy this episode as much as we do!

Highlight 1: What are you passionate about?

The main goal for me is people, it’s always about people.

It’s interesting because I feel like a lot of leaders will prize profit over people. But I can’t see how the two are delinked. I really think that if you focus on developing people, giving people growth paths, nurturing them, mentoring them, understanding what’s intrinsically motivating to them - that leads to profit.

And so my intention, always, and my passion always is around people development. Hiring really capable people, making sure that they have roles that are challenging and fulfilling, that are guided enough for them to find success, but autonomous enough for them to kind of evolve it themselves and make it their own.

Over the probably eight or so years I’ve been in this orbit of SDR what I’m most proud of is having hired probably about 140 SDRs. And I have seen over half of them graduate into something else. Now, that’s not always sales, it’s marketing, operations, customer support, engineering, management.

Highlight 2: What are the characteristics of the SDRs that “make it”?

There are three traits that I have found to be commonalities among all the high performers:

1️⃣ People who are endlessly curious.

Curiosity is something that you can’t really teach - you either want to learn or we can’t force you to want to learn. If you’re really curious about your craft - how to write the perfect email, how to nail a cold call, how to do a good video, the personas, the product, the problems that we’re solving, it’s so helpful for your day-to-day.

2️⃣ People who have tenacity.

You fail a lot in this role. If you only fail nine out of 10 times, you’re doing something really right. You have to be tenacious, you have to be able to pick yourself up, you have to really enjoy the process and find the small victories among the losses.

3️⃣ Passion for your work.

The people who are most successful in the SDR role and beyond are people who like the day-to-day work. They like making cold calls. They like doing the work, they like having the conversations, writing the emails. They’re passionate about their work.

In addition, optimism in pursuit of problem-solving is super important. Your attitude controls so much of your results.

Highlight 3: What are the skills that you have learned during your time as an SDR that you use now in your current position?

The SDR role sits right between marketing and sales. SDRs should want to learn as much as they can about both of these functions.

What is the marketing team doing? How are all the things that they are doing coming together to help me do my job better? The messaging that they’ve created and why, why is the product positioning a certain way, why are they communicating to a certain persona in a certain way? If you learn all these things, you’re developing fluency of the marketing language. At the same time, you learn the success criteria for marketers - MQLs, campaigns, pipeline influence.

Simultaneously, you’re doing the same thing on the sales side. You’re learning about sales, qualified opportunities, pipeline, deal velocity, and conversion rates, lifetime value, you’re understanding how to do deep qualification and discovery, all the entry and exit criteria for different sales stages.

So you’re learning the metrics and concepts that matter both to marketing and sales. You develop this fluency of language for both marketing and sales. And you can serve as the translation layer between the two.

What I do now, in my full-time role, is make sure that one hand knows what the other hand is doing. Marketing is doing things that matter to the sales team. And when the sales team has feedback, it makes its way back to marketing. Because I can translate both for them.

My advice to SDRs is to really focus on understanding all of the stakeholders that you work with and that you impact, understand what matters to them and what their success criteria are.

Highlight 4: If you could go back to the first day you started being an SDR what piece of advice would you have like given your younger self?

I was so intimidated to reach out to more senior people at companies. I would look at CTOs and think that I need to know everything, I need to practice every question they could ask, I need to know the details of my product.

But I learned two things.

1️⃣ People are just people.

This work-from-home environment has certainly enabled us to see that the C-level executives you target and talk to are just normal people. As soon as you realize that, that you’re just talking to another person, you don’t have to put a ton of pressure on yourself. There’s just no reason. Of course, you need to speak their language and things like that. But relax.

2️⃣ You don’t have to have the answer to every question.

No one knows how your product works from end to end, from the back-end code to the front-end UI to your go-to-market plans. No one understands that whole spectrum. So why should you?

Do as much as you can to be as firm an expert as you can be. Talk to your sales engineers, listen to demos, get certified, do all those things. But don’t feel like you have to know the answer to every single question that could possibly be asked. It’s just not possible.

Instead, you need to ask the right questions. If somebody asked me a question on the phone that I didn’t know the answer to, the important thing is understanding why they’re asking, what are they trying to know, and why does it matter to them? And then be honest that you don’t know the answer right now, but you know who does.

Highlight 5: The lens of the power line

There’s a spectrum of seniority, if you think about all the folks that you need to reach out to, or that can be influential in a deal. At a certain line - it depends on your company, depends on your segment, depends on what you’re selling, but there’s a certain line where people above that level of seniority can get a deal done, they can sign on the bottom line. And then people below that line probably can’t but are still going to be influential on the deal. And you need to understand the difference between these two above the line and below the line.

For people that are above the line you want to do a bit more personalization because they’re decision-makers. They’re closer to company strategies, they’re signing on the dotted line. So these are the people that you need to focus a little bit more on, do more research on, understanding company strategies, and tailoring your messaging to that.

Meanwhile, you’re also engaging with people that are quote, unquote, below the power line, you’re having conversations with them, you’re learning about their day-to-day processes, you’re using that information to inform your messaging to the people that are above the line.

Want to check the uncut full text? Here's your transcript.

Jan Mundorf 0:04

Kyle, thank you so much for making it. Obviously, you are the man. You’ve written so many good – honestly, I think you could do an onboarding with the content that you did, because that is what I did. And it made me sit here leading an outbound team. I’m not kidding. Like, I started reading your content, and that’s why I started posting. And at the beginning, you know, the guys were already going to the pub, and I was like, I booked this meeting today, I want to share about it and I started posting, and now people are actually following content. So, personal note, we appreciate. I think, I understand a bit what you’re passionate about, but what are you actually passionate about?

Kyle 0:48

That’s a good question Jan, and, first of all, thank you for inviting me on. I’m really excited to share these thoughts, not just with you, but with the whole audience here. So, I’m passionate about - at work, I presume, unless you mean outside of work, it’s a separate conversation. At work, the main goal for me is, is people, it’s always about people. And to me this is… It’s interesting, because I feel like a lot of leaders will prize profit over people. But I can’t see how the two are delinked. I really think that if you focus on developing people, giving people growth paths, nurturing them, mentoring them, understanding what’s intrinsically motivating to them - that leads to profit. And so my intention, always, and my passion always is around people development. Hiring really capable people, making sure that they have roles that are challenging and fulfilling, that are guided enough for them to find success, but autonomous enough for them to kind of evolve it themselves and make it their own. And all in the pursuit of them landing in a career that is exciting to them. And that’s what I love so much about the SDR role - I get to hire people that are either new in their careers, or often new to tech. And I get to help guide and steer and help them explore paths, cancel some paths out, pursue other ones with more vigor and then ultimately decide what they want to do. So, I think that the thing over the probably eight or so years I’ve been in this orbit of SDR land that I’m most proud of is having hired probably about 140 people at this point into SDR roles. And seeing over half of them graduate into something else. Now, that’s not always sales, I would say maybe about a quarter or a third of them moved into sales, it’s marketing, operations, customer support, engineering, even we had somebody make a move into it as well.

Jan 2:38

Cool.

Kyle 2:38

And then of course management. And so that, to me, is the most exciting part about being in an SDR leadership capacity, especially at a startup where the opportunity to sort of chart these various paths is, is just so much greater. And that’s what’s exciting to me. That’s what keeps me in this orbit. What has kept me in this orbit as long as it has, it’s just the constant opportunity to change people’s lives. And that’s what I really like doing.

Jan 3:03

Yeah. And I’m probably sure that you will keep on operating in this orbit for a long time, at least. And unless something else comes. Because you can feel it - like you’re genuinely passionate about it. I think this is so - you did a lot of initiatives with answering these emails, actually helping people. And also, ungating your content, right, it’s free, you know, like you can become a great SDR by just following your advice. It’s all there. But few people are actually working it through, I think and applying the stuff. And I booked one of my greatest deals, I just copy pasted, adapted what you said and it worked.

Kyle 3:40

Do I get commission on that, Jan, how does that work?

Jan 3:45

We can we can think about it, we can think about it. For after that. No, but listen, that, that’s honestly and you could get commission on that, if you like would make a class, people would do it. But you’re not. So I think the entire community loves this about you. And you’ve spoken that you’ve hired about 100 SDRs. And you were able to put them into next position, like more than half of it. What is, a big question from other SDRs was like which are the patterns that you recognize of those SDRs that “make it”?

Kyle 4:20

It’s such a good question. There are three things, three traits that I found to be commonalities among all the high performers. And I dare say, Jan, as much as I know about you, you check all these boxes, and they’re super important - we vet for these three things in our interview process. So it’s really important that as soon as we start evaluating somebody, it’s not so much about their experience or what they’ve done or their accomplishments, that’s important. But the more important thing is the mindset. And again, especially because we’re hiring so many people who don’t have robust experience, and so we’re vetting people that have these three traits. People who are endlessly curious. Curiosity is something that you can’t really teach. You either want to learn or we can’t force you to want to learn. And if you’re really curious about your craft, how to write the perfect email, how to nail a cold call, how to do a good video, if you’re really curious about these things, it’s so helpful for your day to day. But you also need to be curious about the personas, the product, the problems that we’re solving, all these different things that make you go outside what’s prescribed to you in your onboarding plan or your learning plan, and take it upon yourself to learn more, to evolve more, to learn faster, and that curiosity is irreplaceable. So that’s number one. Number two is tenacity. You fail a lot in this role.

Jan 5:41

Most of the times you actually fail.

Kyle 5:44

If you only fail nine out of 10 times, you’re doing something really right, like a 90% failure rate is really good. And so you have to be tenacious, you have to be able to pick yourself up, you have to really enjoy the process and find the small victories among the losses and find a way to dial the phone again, to send the next email, to have the next conversation, to define another pathway to success. And that tenacity is really important, because I mentioned before how much autonomy plays a role in high performing SDRs’ work. And if you have that tenacity, you go and figure things out yourself. And then when you have questions, ask your questions and get them answered. But listen to your gut, trust your instinct to do your own analysis and chart the next course, find out what the next course of action is going to be for you. And that kind of tenacity is super important. And then the third thing is passion, passion for your work. I alluded to this already, you have to enjoy not just the results, you have to enjoy the process of getting those results. The people who are most successful in the SDR role and beyond are people who like the day to day work. They like making cold calls. They like doing the work, they like having the conversations, writing the emails and things that they enjoy. They’re passionate about their work. If you focus so much on results, you’re gonna go on this crazy roller coaster where the highs are super high, and you’re gonna love your job. But the lows are really low. And you’re going to really question your existence. But if you enjoy the work and you’re passionate about and it gets you out of bed in the morning, you’re fired up about it. And you realize that the lessons you’re learning now are in service of whatever you do next in your career. And that’s the fire that’s burning in you, internally. Those are the people that are successful in their SDR role and beyond. So curiosity, tenacity and passion.

Jan 7:28

Mic drop. I think that that’s a lot. An interesting one that Lauren and Matt - you know them both probably from LinkedIn - brought up is optimism. And it’s like constantly being optimistic. But I think it intertwines as well what you said like tenacity, right? Be able to pick yourself up and also be passionate about that. Because if you’re passionate, you have to stay optimistic. Otherwise, it doesn’t make sense to be.

Kyle 7:54

It’s very true. And optimism in pursuit of problem solving is super important. And your attitude controls so much of your results. And I know that sounds kind of crazy, or maybe a little metaphysical, but it really is true. Like if you are positive, if you’re smiling on the phone, like I’m smiling right now, like you made this, it makes other people relax. And if you’re enjoying the work and you have that positivity, you have that optimism, you’re able to will certain things into existence, you can make it happen for yourself. And again, you can’t do this unless you’re enjoying the work. You can’t fake this kind of thing. So I agree with both Lauren and Matt, that’s sound advice.

Jan 8:31

No, that’s that’s fantastic. And I mean, you’ve obviously been an SDR by yourself. I think I calculated, you posted this post, it was like 2.5 or 2.3 meetings per day. Yes, it was another bag of time. Yes, it was. Okay, we get that. It’s fucking insane. Sorry, for swearing. It’s insane. I just thought I’d calculate for everybody else. Otherwise, it’s like, oh, man, how? And I forgot actually to take out the working day. So it’s even more. Anyhow. What are the skills that you have learned during your time as an SDR that you use right now? When you’re not an SDR anymore. And you have even more and more stress and responsibility, and ups and downs actually.

Kyle 8:32

It’s such a good question. And the reason I know how many meetings I booked, by the way, is because I worked for a data analysis company as an SDR and so all of our leaderboards, we used our own product to track it. So it was like part of me was learning how to use the product and part of me was sort of self congratulatory tracking my progress.

Jan 9:37

Constant onboarding, constant onboarding and customer success.

Kyle 9:42

Exactly. The thing, Jan, for me, that is the most enduring lesson and something I didn’t quite realize until maybe a couple years out of seat and I look back I was like, wow, that was really impactful is… This SDR role that you’re in, it sits obviously right between marketing and sales. Now what this means for the people who check all the boxes that we talked about, the people that are curious and tenacious and passionate about the work, is they want to learn as much as they can about both of these functions. What is the marketing team doing? What is the product marketing team, content team, brand team, design… Well, how are all these things coming together to help me do my job better? How can I take the work that they do and magnify it? How can I take the messaging that they’ve created and use that myself? And why have they created this messaging? Why are they positioning this product or this feature in a certain way? Why are they communicating to this persona, in a certain way? And if you learn all these things, you’re developing a fluency of language of marketing. That’s really, really important. And you’re learning the success criteria for marketing. What is an MQL? What is a campaign? And what is pipeline influence? What are all these metrics, that marketing teams, demand gen teams care about? You’re learning all that. Now simultaneously, you’re doing the same thing on the sales side. And I don’t care whether you report into marketing, you report into sales, you work closely with both of these stakeholders. And so on the sales side, you’re learning about sales, qualified opportunities, you’re learning about pipeline, you’re learning about deal velocity, and conversion rates, you’re learning about lifetime value, you’re understanding how to do deep qualification and discovery, all the entry and exit criteria for different sales stages, you’re learning all of these things, or you can learn about all these things that matter to sales teams, pipeline, coverage. The list goes on and on. So you’re learning the metrics, you’re learning concepts that matter both to marketing and sales. And I mentioned this before, but you develop this fluency of language for both marketing and for sales. And so you can serve as the translation layer between the two. And you can make sure and what I have done, and what I do now, in my full time role, is make sure that one hand knows what the other hand is doing. Marketing is doing things that matter to the sales team. And when the sales team has feedback, it makes its way back to marketing. Because I can translate both for them. I don’t mean to say that I’m the only person doing this in my company, but I know that I am serving as as this connective tissue between the two. So my advice to SDRs is really focus on understanding all of the stakeholders that you work with and that you impact, understand what matters to them and what their success criteria are. And those lessons are really enduring. And you’re going to use the fluency, the language that you learn in your role as an SDR in whatever you do next, whether I were to have moved into a marketing role, into a sales role, obviously, I chose a management path. But I could have gone anywhere, because I had such a firm understanding of what matters to the various people on both teams. And I think it’s just a great opportunity - you can’t really get that in many of the roles. So I think it’s a really cool place to be.

Jan 12:40

Yeah, yeah, I love this perspective of things. Because when you speak to my friends that are not in sales, they’re like “I would, I would absolutely despise it. I couldn’t handle the pressure, I couldn’t handle whatsoever”. But on the other hand, like yourself, you learn so much, right? You can literally go wherever you want. And I think that’s encouraging to know. I know, like, I could continue asking like, tons of question, but time is running. So like, if you could go back to the first day you started being an SDR what piece of advice would you have like given your younger self?

Kyle 13:20

Yes, oh man. When I was starting out, I was so intimidated to reach out to more senior people at companies. I would look at like, oh man, a Chief Technology Officer, they are so much more accomplished than me, they are so much more senior to me, I need to know everything, I need to practice every question they could ask, I need to know the details of my product. I need to be completely 100% prepped. And I learned two things. One, people are just people. They’re just, they’re just normal people.

Jan 13:53

Yeah exactly. H2H, or what people like tried to call human to human.

Kyle 13:58

Exactly. That’s exactly what it is. And this work from home environment has certainly magnified that when you know, you’re, you’re on an internal call, say and your chief, your CEO, or your CMO is presenting and one of their kids walks by and like smacks him in the back of the head. You’re like, yeah, that’s they’re just a normal person. And so as soon as they realize that, that you’re just talking to another person, you don’t have to put a ton of pressure on yourself. There’s just no reason. So think about them as being you know, you want to be professional and you don’t want to be you know, too relaxed with them. And you need to speak their language and things like that. But don’t put too much pressure on yourself to like be super formal and super buttoned up. So that’s one lesson - it’s just a person on the other side of the phone. So like, relax. Lesson number two. You don’t have to have the answer to every question. You absolutely don’t. You can’t put that kind of pressure on yourself. No one at your company. No one, not your CEO, not your founder, not whatever. No one knows how your product works from end to end, from the back end code to the front end UI to your go to market plans. No one understands that whole spectrum. So why should you? Now do as much as you can to be as firm an expert as you can be. Talk to your sales engineers, listen to demos, get certified, do all those things. But don’t feel like you have to know the answer to every single question that could possibly be asked. It’s just not possible. Instead, you need to ask the right questions. And this is a refrain that was really important for me. So if somebody asked me a question on the phone that they didn’t know the answer to, the important thing is understand why they’re asking, what are they trying to know? And why does it matter to them? And if I can tell them like, great question, glad you asked. I don’t know the answer right now. But I know who does. So Tuesday at two, we’re going to get them on the phone. Is that a good time for you to meet? And more often than not, they’d be like, “Oh, yeah, that’s fine. It’s like, Oh!”

Jan 15:46

I remember that actually. One of my first calls, I’m just an intern. Same as you. And I got onboarding for a week or two. And then we had to do these qualification calls. And the first thing happens, I prospected in German market, I directly book a meeting with the Head of Demand of this big HR company. And my boss said, “Yeah, great, qualify it, you know, we don’t know anything”. And I prepared my slides. I prepared my challenger sales presentation whatsoever. And he goes, “No, I don’t want to see this. This is BS. I want to see the platform”. I was like, “Okay, I can show you”. But I couldn’t answer any questions. But I could book the next steps. I was like, “Listen, great question. In the next step, if you’re truly interested, I’m going to bring my product specialists into the call”. They were like, “Yeah, sure. Okay. Fair enough”. So I was so surprised. So you know, when the pressure falls down on you, and you just be honest with them, like, “Listen, I don’t want to give you a wrong perception of what our product can do. What I can do is to like do my research, come back to you and book the next step with you.” And he was like “Yeah, sure”.

Kyle 16:59

If that’s the reaction from a German lead, who have the reputation of being you know, pretty cut and dry. Imagine what you can do with some of the folks that are perhaps a little nicer on the phone.

Jan 17:09

Yeah, exactly. Small caveat. They closed today. So it worked out.

Kyle 17:15

That’s amazing. Congratulations. That’s so cool.

Jan 17:18

Thanks. So yeah, it was really funny. It was like, I got the call, like, “Yeah they finally decided to pull the trigger”. So it really works. Like to all those listeners and watchers out there. This works. Cool. Uhm, was there any other piece of advice that you wanted to give before I cut you off in between?

Kyle 17:36

No, that was perfect. I think those two things, if you can keep those two things in mind, you’re going to be in really good shape. And you’re going to skip a lot of pitfalls, that many other people including myself fell into and just accelerate your ramp.

Jan 17:48

Yeah. I would make like small swoop through the emails. And then I have some other questions because time is running again. Of course, like, when people think of emailing, they think about you. And I think if like people think about writing LinkedIn messages, they think of Sarah Brazier, right? People think of good watches, they think about Switzerland. That’s how it works, right? So when people think about a cold email, they think about Kyle. And that’s great, because you answered, like when the LinkedIn hate came up, you started to answer cold emails, which is great, because then we can learn from it. So I know you’ve said this before, but - like we know what you think is the perfect cold email. We know that. That’s nothing I want to repeat. But when and why are you actually answering an email and taking the meeting? That’s what I want to know from you.

Kyle 18:50

Good question. Good question. All right. So I won’t go through the formula that I think is a really useful foundation.

Jan 18:56

You can, you can (muffled speaking). It’s already out there, if they’re not reading it, then it’s their fault.

Kyle 19:04

That is very true. The reasons that I take meetings… So first, I should say, and I love… I am probably more sympathetic to the SDR cause than anybody in the world. However, I don’t just take meetings for the sake of taking meetings because I don’t think that’s the best use of the company’s time, it’s certainly not the best use of my time. So that’s never the reason, I’m never doing it out of pity or anything like that. So some people have that misconception that I just take the meetings because like I just value the role and to a certain extent that’s true, but it’s never the animating reason.

Jan 19:41

You certainly would like to, but you just can’t, man.

Kyle 19:44

I would love to if I didn’t have a day job. But alas, the reasons that I take meetings are when somebody has done - they have to do research. For me, that’s like, you really have to show me that you understand something that matters either to me or to my company. And this is not particularly hard for me because I post a lot of things that I’m passionate about. But for those, like a lot of folks will make the excuse that “Oh, this prospect isn’t active on social media, so what am I supposed to do?” There are companies posting stuff all the time, their CEO, I promise you is doing interviews in some way, go and do the research, go and find out what my CEO has said. And if you use their words back to me in an email, and talk about an initiative that they have that matters to me, and how you can help with that, that’s going to get my attention. So don’t be super close minded about what personalization is, there’s some blend of personalization and resonance, which is really important. So you need to resonate with an initiative that you know, exists for me. So research, a little bit of personalization, show me that the note really is for me. And then importantly, you need to illuminate a problem that I may not know exists. And sometimes I am aware that these problems exist, but sometimes I don’t know, I don’t. If I’m for example, we’re expanding into new geographies, Asia Pacific and the Australian - New Zealand market, I know that it’s different to do SDR work in APAC, but I don’t really know the ins and outs of what makes it different. So if you as a vendor or solution provider, whatever, can show me that you understand what it’s like to take an existing process from the States and translate that into APAC, that’s going to get my attention. And that’s going to be the type of thing that earns the meeting. So do the research, understand an initiative or a strategy that myself or my company is pursuing. And then connect your value prop to that, often by showing or illuminating some problem that exists. Or some challenge that will exist with whatever initiative. And that’s how you get my attention. That’s it, you’re in the meeting.

Jan 21:51

Here you go. To all those - I’ve done it, I did it. I followed that pattern. I just followed your playbook and booked you with that, which was funny. So yeah, thanks for sharing there. There’s another funny one. The craftiest way, you’ve been prospected - we can take this. But I think the really one that I’m getting a lot is scale versus personalization. So when in scenarios, can you have a strict process? And when it’s okay to like, freestyle, let them loose and go - from a close friend of mine. So I want to give them the chance to ask this question.

Kyle 22:34

Yeah, it’s such a good question. And there is… The objection that I get a lot too when I say about personalization is people say, “Oh, well, that doesn’t scale”. And I say - good. It’s not necessarily supposed to scale, like hard things that get results, if they scaled, everybody would be doing them. And then guess what, they wouldn’t get results. So don’t think that “it doesn’t scale” is a reason not to do it. Now, think about the reason that, think about how to squeeze as much juice out of this tactic as you possibly can. That’s a different thing. So saying, “I’m going to send 50 personalized emails this week” is very different than saying “I’m going to send 1000 this week”, like you’re not going to send 1000. But if you send 50 to the right people at the right accounts at the right time, you’re going to be successful. And that is a sufficient amount of scale for most SDRs, or most quotas, for most pipeline needs, like, so don’t necessarily think that scale has to be orders of magnitude difference. It doesn’t. It needs to magnify your impact in a way that allows you to exceed your quota, to hit your pipeline numbers, to do the things that you need to do personally and professionally. Now, that said, the kind of line that we draw between quantity and quality of emailing and LinkedIn messaging and even phone calling for that matter, is we think about things through this lens of the power line. And I’m not sure, Jan, if you’ve heard me talk about this before, but there’s this…

Jan 23:59

Yeah, you posted about this. I shared it with my team.

Kyle 24:03

Perfect!

Jan 24:06

We actually went through it in the stand up. I’m not kidding. You posted it, I think on Wednesday and we went through it on Thursday. Maybe it’s the wrong days. But yeah, tell us about it.

Kyle 24:18

Yeah the concept basically is - there’s a spectrum of seniority, if you think about all the folks that you need to reach out to, or that can be influential in a deal. And at a certain line - and it depends on your company, depends on your segment, depends on what you’re selling, but there’s a certain line where people above that level of seniority can get a deal done, they can sign on the bottom line. And then people below that line probably can’t but are still going to be influential on the deal. And you need to understand the difference between these two above the line and below the line. Now, for people that are above the line, these are people that you because they’re decision makers, because they’re closer to company strategies, and because they’re signing on the dotted line, they are the ones that deserve quote unquote, a bit more personalization from you. So these are the people that you need to focus a little bit more on, do more research on, understanding company strategies, they’re also closer to company strategies. So that will resonate more with them versus the people below the power line, often in individual roles who are more focused on their day to day output than they are on company strategy. And you can do more general outreach to them. And that’s totally fine. So now, on the people that are above the line, the way that I think about this, and I know you’ve heard me say this before, but this methodology of quote unquote, scaling your personalization efforts, is what I call the five by five by five method. So when you’re doing research on somebody, the goal is to spend five minutes to find five key pieces of information about them or their company, and then spend five minutes writing that personalized email. And if you do that, if you spend five minutes and find those five key insights, that’s the only time you have to do research on somebody. And then you have all the ammunition, you need to send five personalized emails. And if you can do this, and it’s hard to do, it’s aspirational, it’ll take you more time to start. But you can time yourself and really try to do this. And if you can do this and do this well, you’ll start to see that, hey, actually writing these personalized emails, does not take as much time as it used to. It used to take me 20 minutes to write one of these things. And now I’m down to five. And then you can start to send 20 a day, and you can send you know, 50 to 100 a week, and then it’s going to start to feel like you’re scaling. And when you’re sending 50 emails a week that get a 10% response rate, that’s pretty damn good. And you’re going to find that your quota is going to start to reflect the efforts that you’re putting in. Now, meanwhile, you’re also engaging with people that are quote, unquote, below the power line, you’re having conversations with them, you’re learning about their day to day processes, you’re using that information to inform your messaging to the people that are above the line. And so there’s this sort of ecosystem that you’re creating for yourself, where you really understand what matters to the companies you’re reaching out to what matters to those people. And you’re canvassing, you’re casting a really wide net, to do fact finding, to build a groundswell of support, and then to write effective messaging. So I know, it’s a lot of advice. But I think it’s a really useful way to think about your outbound efforts as not just being one off things to people or companies, but really existing in this, like I said before, this ecosystem that’s feeding off each other, and your efforts are building off one another.

Jan 27:13

And if you’re then able to also, you know, maybe time this, like, below the line the day before, above the line the day after, sort of like use the SDRs as a way in, what tools they’re using, and blah, blah, blah. Then reply rates will even go up more. You have to run, I feel.

Kyle 27:37

I have a couple more minutes.

Jan 27:39

Okay, couple more minutes. Okay. That’s fantastic. So, um, two more questions. And there’s a really big one. Like, we work in SaaS, people are so busy, we work in startups, it’s so hard to focus on the right things at the right time. Like there’s stuff happening all the time. So one big question that I got is like, how do you find time to focus on the right things?

Kyle 28:08

It depends on what the right things are. It really does. And once you determine what the right things are, and you can do this yourself, with your team, with your manager, whoever, it’s going to be some group of people that helps you understand what your priorities are. The way that I think about this is - there are things that are urgent, you have to do them now. And then there are things that are important that you have to focus on, but perhaps often get crowded out by what’s urgent. So you don’t let the urgent crowd out the important. If there are longer term things, professional development is a perfect example of this. A lot of people will kick professional development down the road, because they’re so focused on their, you know, daily output or their quarterly quota, whatever it is. The way to control this is to be really intentional with your time, really think about what’s important. And then, and I do this to this day, every Monday, when I’m having coffee, I’m looking at my weekly calendar, and I’m saying what of this is important, what of this is super urgent, what of this actually is not important or what of this could be delegated to somebody else, and I’m moving things around and I’m blocking time for the important things. I’m blocking time for the things that I know are going to magnify my impact on the company, or help me with my own professional development or help a team, teammate with their professional development, whatever that kind of thing is. So decide what’s important. And then be really, really ruthless and intentional with your time. Don’t let distractions prevent, as much as you can turn off all the stuff, turn off Slack notifications, put your phone away. But it has to be intentionally on if you’re not intentional about it, then you’re never going to give yourself enough time to focus on the things that really truly matter. And you’re going to end up just kind of going through the motions. So think, be intentional. And of course the predecessor to all this is really deciding what your priorities are. That’s probably the hardest part.

Jan 29:56

Yeah, exactly. No, that, that’s great advice. I remember the first thing I did for my first salary, I bought noise cancelling headphones. I was like, I need calmness. Like, we can speak. We cannot speak, and stuff. So yeah, great advice, I think, I think that you probably would have added like reflection, and you just shared this like “before you go” document that’s really helpful, I find, that you shared, I just did it in a small Excel - my tasks of the day, how did I help, where did I fail, and then the activity and so forth. So that’s, I know, it’s a big thing for you as well.

Kyle 30:34

Huge, yeah, if you’re not… So again, a lot of times, you’ll find what matters to you by reflecting on the work that you’ve done or not done. And I shared a little checklist on the things that I find valuable to reflect on every day or every week. And so I encourage people to go and check that out. But the most important thing there is that you’re actually, again, it’s the intent part of this, you’re actually being introspective, you’re actually thinking about your output, about the things that brought you joy, about the things that are motivating for you. And that allows you to determine what your priorities are. So being retrospective is definitely advisable. I recommend everybody do this in some sort of cadence.

Jan 31:09

Cool. Last questions, because then you have to run to the next one. What are the things that makes you like excited about our space? Like, what are you looking forward to in the next years to come?

Kyle 31:23

I’m excited that it’s getting harder. I really am. And I know people might think that that’s kind of crazy. But the reason it’s exciting to me, Jan, is because five years ago, if you were in an SDR role, you could be successful by just spray-and-pray, by just blasting stuff out there. And to a certain extent, that was kind of cool, because you know, SDRs were hitting quota, and they were getting paid and things were good. However, they weren’t always developing the business acumen, the sales acumen, the skills that they needed to do whatever’s next. But now, because the role is harder, because you can’t be successful spray-and-pray, you have to learn more, you have to learn faster. And so I’m excited that the role is getting more difficult because it’s elevating the profession, it really is. Like, to be successful in this role, you have to think, you have to be strategic, you have to use your head, you have to work with sales, you have to work with marketing, and that is preparing this generation of SDRs to be better, more effective, more sustaining leaders. And that, to me is super exciting. And I know that sounds perhaps a little overly optimistic, but I promise it’s true. I’ve seen it, I see it happen every day. And it’s just exciting to me, because this SDR role that so often is characterized as secretarial, or behind the scenes or low level or entry level or whatever, is not anymore. It definitely isn’t. And because it’s getting more difficult, and because it’s harder, because it takes a certain skill set to be successful now, that’s elevating our profession. And to me, that’s really exciting.

Jan 32:53

Yeah, I love it. Like, I have, like honor graduated, two times, you know, bachelor’s and master’s, and I find it super challenging, you know. I’m happy that I did all the studying, you know, that I know about the frameworks I need to use to structure my time to do proper research five by five by five, you know. So yeah, I had the moment when people were looking down to me like, “You did all of this education, you’re really starting as an intern in sales. Like, are you sure about this?” I’m not kidding. And you go like, “Yeah, like, it’s a good role, like, I like to change people”. So now they maybe think they would have done it, I don’t know. But I’m happy with that role and you certainly are. Kyle, is there anything you would like to add? Anything that was unsaid, untouched before we let you go on to the next call?

Kyle 33:48

I think we hit on everything, Jan. And I’ll just close with something I said before, which is just this remark I want to make to everybody in the role, which is - the skills you’re learning now are enduring. They last, they are the foundation that you’re going to end up building this beautiful house on. So take pride in your work. Take pride in your work, it matters, the skills you’re learning now matter. And if you realize that, you’re going to enjoy the work more, you’re going to be more successful, both now and in the future. So don’t sleep on the value of this role. Don’t try and get out of it as soon as you can, for the sake of movement, savor it. It’s hard. It’s fun, it’s challenging. And if it weren’t hard, if it weren’t challenging, it wouldn’t be rewarding. So enjoy the work. Understand that you’re building the really strong foundation for yourself and for your career. And savour it.

Jan 34:36

Thanks, man. Perfect closing words. Kyle, thank you so much. How did it feel? How was the conversation? You’ve done it a lot of times so you can sort of judge how this was.

Kyle 34:48

It was great, Jan, you have a… You’re brimming with positivity and you care, you care. And you understand, you’re an expert in the role, you’re doing it now. You’re leading a team and a lot of people don’t have that vantage point. And so sometimes when I do these interviews, it’s just like a question and answer, but this was, it felt like much more of a conversation and it helps that we’re on the same page about so many of these things.

Jan 35:10

Cool. Yeah, of course, man. Thank you so much.

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