SDRealness Podcast Episode 14 Graphic Horizontal - Creating & Managing Sales Cadences with Rory Caulfield from PagerDuty

Episode 14 Transcript

Alex: Hello and welcome to The SDRealness Podcast brought to you by Sales Development Revolution where we’re talking with practitioners in the space about important topics for them. I’m Alex Ellison. Here as always with my co host, Greyson Fullbright. 

Greyson: Hello, and good morning or evening, everybody. 

Alex: So, this season’s theme for the podcast is see action, take action. Our goal is to dive into a specific topic about sales, development and learn, you know, those specific tactics from experts who do it every day. Today’s topic is on creating and managing sales cadences. Joining to discuss this with us is Rory Caulfield. He’s currently a commercial account executive at Data Dog. But, more importantly, Rory, you’re really one of my first mentors when I started as an SDR over at demandDrive. So, I’m so glad you could hop on with us today. 

Rory: Yeah, thanks for that introduction. I my ego is definitely doubled. 

Greyson: Awesome. So, to kick things off, Rory, I really wanted to go into the the very beginning of this conversation about sales cadences, what they are, why they’re important, and how you actually get started and prepared to use them. So, one, I wanted to just get like a quick vibe from you on, you know, why should reps and why should SDR specifically be seeing their activities and their week to week workflow more as a journey in a cadence rather than just individual touches? And then from that, could you give us like a quick walkthrough of how you or your team members, both prep, and then also create those cadences.

Rory: Yeah, so I think with cadences, I like to think of it as like kind of the backbone of like organizing your day to day, like how you go about your account list or whatever. So, that can really kind of come into a couple of buckets. The way that I like to think about it is, and this has been really helpful for me as like a rep is really kind of bucketing down like your accounts, your different like different kinds of priorities.

So, whether that’s like you have top 10 strategic accounts that are a little bit more on like the customized outreach. But, then you also want to keep in mind that there’s those smaller, more transactional accounts that you want to cycle through and have those sprints.

So, just making sure that like, you’re, you’re like, I put my calendar to have all of my like outbound activity to be aligned to whatever sprint who might be working or anything like that. So, it really just keeps, you know, reps accountable. And especially just like throughout the process, because you obviously want to make sure that you’re cycling through as many contacts and so forth with that cadence.

And it gives you a kind of a good pulse on like, where the where they are in the buying process, especially as you start to kind of like highlight the rest of that cadence. So, do you want me to just kind of dive into like, I don’t know, first touch and all that? Or is there specific examples that you’d want to cover on that side of it? 

Greyson: Yeah, I think so I think we’ll get into kind of the first touch versus follow up touch soon. But, I’m really interested in what you mentioned about the fact that, you know, you have these accounts, and not all of them are the same. And what that implicitly means is, I mean, unless necessary, they shouldn’t have the same cadence either. It should be customized to that specific buying group. So, I wanted to kind of follow up and just ask, what do you do to actually look at your accounts, kind of organize and map them out and then decide kind of how you should play a case? So, what’s the difference between like a, like a VIP account versus a more transactional deal? How would those cadences differ? 

Rory: Of course, I mean, obviously, it depends on like the tech vertical you’re in and like the personas you’re reaching out to like that cadence can kind of be different, right? Because there’s certain tech verticals like information security, where it’s high touch points, and just like low Connect rates, whereas you’re reaching out to someone like HR tech, obviously, the connect rates are going to be a little bit higher.

So, I mean, since I’m reaching out to typically like IT, DevOps engineers, I mean, obviously, like, we’ve, we’ve seen more on the side of like, they don’t you probably you can get them on the phone, for sure. But, there’s definitely a lot of tailored messaging that comes with it. So, for me, it could be like someone’s GitHub profile, or if you’re going on crunchbase to look at their accounts, right. So, I’m really like looking at revenue, like fast growth or anything like that, and just using sales [inaudible 04:37] so I mean, I think company to company like, you know, depending on where you’re representing the sales for it, it really kind of just there’s ways to kind of like, allocate like resources and how you want to go about the cadence to really make sure that it’s really in line with like the vertical that you’re reaching out to and the people that you’re eventually going to put into the purchasing process. 

Alex: Yeah, and I mean, that makes a lot of sense really, when you think about it, you don’t want to spend too much time reaching out to even if it’s like, right, you have a great conversation, the guy seems like an awesome dude on the other side or something like that, at the end of the day is this sale, if it’s gonna be smaller, you just, you can’t really spend that much time on it because that’s not how you’re gonna, you know, grow the company and you know, and make the commission that you probably want on top of that. So, yeah, I think it goes back into that sort of bucketing that we’ve talked about in past episodes and things like that. But, I think that’s a good point.

If you really look at you know, Crunch Base, and really take the time to do the research that’s so important, you’ll be able to, to figure out which bucket it goes into and reach out that way. So, great advice there. I do now sort of want to get into that, that first touch you were talking about. Because it is such an important part of the cadence and just of the SDR role as a whole, you know, a bad first touch bad email, you’re screwed. There’s nothing you can do to overcome from that sometimes.

But, on the flip side, if you send a good first touch, a lot of prospects will notice it and go, Okay, I see what you’re doing there, and then wait for the next touch, which is, you know, another thing we can get into in a bit, but I just want to dive into sort of your thought process on first touches, what you do for them, do you have any good advice, or good examples of successful first touches that you’ve used in the past or tend to use a lot?

Rory: Yeah, actually, it’s a funny story, because lately, I’ve been using this template and I call it the Nicolas Cage template. And ironically, I’m not even a fan of Nicolas Cage movies at all. So, this is just to give you a breakdown, one of the companies that was reaching out to I couldn’t really find any good trigger events to kind of reference even with the person’s profile, because I mean, even if like they had like a certain like alma mater, or hobby, I tried to reference that just so that, like, they know that I’m reaching out to them as a person. But, this time, I couldn’t find anything.

And so I went on the company’s blog, and it looks like, okay, so they had some funny about story about ordering the same Nicolas Cage pillow in their office or something. It was it was weird, because but like, the way that I like broke down that email was like, like, okay, so noticed, blank, right? Just make any, like anything very specific to that person. And then you have that tailored that aside, like I’m reaching out because of these XYZ initiatives. Here’s what we do. Want to have a conversation to see if this is somewhat similar. What do you think?

Very simple, but I think that kind of gives you like that idea of like, yes, you can tailor the message within that first outreach, but then you don’t have to do it, like, first touch template to first touch template, you can make it more operationalized. So, that, like, you’re still hitting your metrics, and then you’re increasing the, you know, conversion rates, with your outreach and everything like that as well.

Alex: Yeah, and I like that, because you just you the the part that’s not personalized, you still make sure is relevant, right? It’s not just like, hey, Nicolas Cage pillow, can I take a call, right? You’re not just doing the personalization, you’re also taking the time to like the template below, it is really what you want to get across, you’re just making that that warm intro to them sort of segue into what you think is going to be relevant for them and actually pique their interest in a business sense, right?

Rory: Absolutely. And I think the one thing that I like to use too, is that like, I know we talked about this before, but like having I I don’t like use, like, I use really weird names for my email templates. Like I don’t do like first touch this first touch this, it’s like Alex Ellison 2020 email or something, like anytime I get like a [inaudible 08:25] with like, like a certain body or certain hook of an email, like I just like, have that in my mind. So, like, I’ll pull in, like maybe a call to action, like from someone else’s email, but then a body of like the product pitch or whatever from another.

So, I think like, once you especially like, as you get more comfortable in the seat and everything like that, you start to kind of like piece together. So, whether like, depending on like how you kind of learn. I mean, I’m just I have a very odd process of how I go about templates, clearly if I’m making them up for [inaudible 08:52] But, but I mean that it just goes to show that like you have like, there’s different ways of being creative, where you could automate the, the outreach process, especially with email and not make it such a, you know, time suck out of your day. Because I know, I mean, I see that myself sometimes, too, where it’s like I spend an hour and it’s not having that operationalized like, way of going about your templates, or how you will collaborate with them can really kind of just take time away from other value added activities for sure. 

Greyson: Yeah, yeah, I definitely agree. I think you touched on two really important things here. One, like the first touch is not only the first impression, but it really sets the stage for the rest of your cadence. You know, as Alex mentioned, you know, one bad touch can really kill that relationship and make it hard to repair later on. And so it makes sense. And it’s, it’s valuable for SDRs to spend a little bit of more time on that initial touch so you can have some clout and look like you did your research.

But, on the same side, another really good point that you made is it still needs to be repeatable, and it still needs to be operationalized so that it’s not just overbearing, I think I personally use this type of format for outreach often where it’s like, you know, it doesn’t make sense to personalize every line of an email or a script. So, just personalize the first bit, so they know instantly that you’re, you’re human, and then you can move on to start engaging them on something more relevant. And so I think that’s something that I think people need to understand when it comes to managing cadences is, you need to put enough personalization and enough research into it so that it’s relevant. But, it still needs to be designed in a way that you’re allowed to hit metrics, because Rory made a good point that, you know, personalization is great.

But, it can definitely impact the amount of volume you can put out, sometimes in such a way that even the higher conversion rates don’t offset and you still don’t hit quota. And so it’s something that I think people need to be careful about as they kind of go into building out a cadence.

Rory: Absolutely. I was just gonna add I mean, I mean, if you do mess up with like, maybe like a little first touch template, like, I’ve gotten me once, where it was like, I had the wrong name of the the CTO, and then I literally bumped the email right there, put a star and I was like, Oh, sorry, Stuart, please, if this is the reason why we part ways then I understand, but got a meeting out of it. I’m not… So, I mean, I’m not saying do that all the time. But, like, you do mess up the person you like, see it right after you send it like, What do I do? Bump it and see. 

Alex: Yeah.

Greyson: Yeah, I think that emphasizes the importance of journey too, because I mean, like, even if they are mistakes, mistakes can humanize you. And that can be part of the story that you construct for them. I know of a strategy for a follow up email, like a second touch email that I believe worked last year, but it’s already kind of fizzled out and become too popular. But, it was essentially sending an email. And then within like the first hour or two, immediately following up, basically forgetting to mention something. So, it kind of brings about that, like, oops, I’m a human, oops, I’m making a mistake. But, it’s still really engaging and at the time that we got a ton of responses, just from that second follow up email.

But, I want to kind of go beyond the first touch and really talk about the kind of follow up and additional journey from your perspective Rory, you know, what, what does a second touch look like versus a third touch? And really, how do you think the cadence needs to change as you gather more information? So, whether someone is more or less engaged, just they kind of go through the cadence? 

Rory: Absolutely. So, first off, as long as the email doesn’t bounce from the first touch, right, like, we’re good to go. And then we got that going. So, with the with the bump said, and it’s funny, because I’ve definitely taken more of a different approach and I did I look at demandDrive or prior companies going into Data Dog, because I noticed that there’s been a lot of success doing like bumping the same email and same thread sometimes. But I, I’m trying to get better about like, making sure that okay, if like, if they haven’t read this thread for five emails straight, maybe, like, change that up a little bit, right.

So, with the bump that I always think of them as bumps, follow ups, whatever. But, if you can find like, a quick two-minute overview of what your company does in a video, that’s great, like, being like, hey, I’ve got this simplifying this would help help you determine if we’re a fit. Here’s what we do, let me know what you think. Or if you have like online sessions that are coming up, hey, here’s an online session we’re hosting each week, like, I mean, depending on the you know, like how, like the, you know, marketing events kind of go about with like, the the prospects I’m selling from, but in terms of that, I think there’s a lot of different content you can leverage.

One thing I actually do like to do a lot is kind of keep bump emails specific to the day of the week. So, like, if it’s a Friday email, or if it’s like one right before, like a three-day weekend, just kind of making it tailored in that like, hey, like, I know we’re out of the office this weekend, just want to finalize my calendar, I think there’s a good way about that. My personal favorite is no, I’m going to be out of vacation, I’ll pretend like I’m some sort of celebrity and I’m like, Well, I’m out of the office. But, if you want to get back to me I’m finalizing calendars. I mean, people it works, I think that there’s ways to be creative about it, ensuring that like, it’s still keeping yourself accountable to the fact that if they’re not opening up the emails, and you want to change it up, and I think one thing that I I’m always trying to get better at is like checking the open rates with some of these emails, because whether you’re using like a [inaudible 14:14] or Yesware or whatever, like, I mean, if you’re like, wasting all this time, and not really noticing that this email doesn’t even like has not been opened whatsoever, they have maybe have a second email that they use for the company, like there’s so many different variables that can happen.

So, I think just keeping an eye on like, the traction you’re getting with the cadence and then understanding like, okay, maybe at that point, do you want to like want to nurture it for three weeks and then send a breakup email or is the account even worth going after at that point, right. So, I think right, there’s, I think towards like that bump up my goal with the bump of the cadence is that like, I want to make sure that like I’m at least getting getting an answer like connecting with anyone from the company, right? Whether it’s we’re not interested, not right person, whatever. Like if I can get some pieces of information or some initiative that might be valuable to one of our value drivers are, then I think that that’s really kind of how I like to think about the goal of like what you want to achieve out of [inaudible 15:10] other than getting a meeting.

Greyson: Yeah. 

Alex: Yeah. I think that’s I think that’s a really good call out. I love that you mentioned kind of like proactively looking at engagement metrics as the cadence goes along. Because I’ve always seen sales cadences as something that’s dynamic, where you kind of have this layer at the bottom that’s automated. And and it’s assuming that they literally go through it, go through the whole thing and don’t respond. But, then on top of that, you should have reps or marketing teams, looking at when people open emails, when people connect with the brand page, when people visit their website, and then start customizing the activities that an SDR does based on that. And that’s kind of the whole thing behind lead scoring. You know that’s the intention anyway, is to kind of get an a sky view understanding of where an SDR should be focusing their time as people go through the journey. Because even if you’re not using a sales cadence, there are people in companies that are qualified, that have found you via inbound or found you via social or maybe, like, unsubscribed to you two years ago. But, now they’re back on the map and looking you up. And there’s so many journeys that go on between a buyer and a seller from beginning to end. And really all a sales cadence is trying to give an SDR and the sales team a little bit more control over kind of A, discovering where they’re at, and B, influencing the direction of where they’re going. And so I think this advice is really beautiful. And one thing I wanted to kind of touch on is like, what in your mind is the difference between, like a cadence to try to actually generate a conversation and catch their attention, versus maybe some later steps that’s more for like, kind of nurturing, and just relationship building, because I’m sure you know, as you get the step 10, 11, 12, you probably change your stance a little bit and kind of like focus on different goals. So So what does that look like? 

Rory: Yeah, I mean, I always create a folder called circling back breakup or kind of nurture emails, right. And that like, could really, I think there’s like an overlap with like, what you can put in, like under a nurture template, and like one that’s like, a bump for like a first kind of in that first around the cadence where there’s like, just content driven stuff. So, like, if you have launched a new integration, that you didn’t have you didn’t have before, something like that. Like, that’s something to leverage in the circling back kind of bucket as well.

But, also just like, We’re in Q4, so like, I love like sending in those end of Q4 like, or like going into Q4, like, typically we see organizations try to cut costs, streamline efficiencies, whatever it is, right, reduced risk, whatever. Like is, like having like that kind of be part of the journey, because I see a lot of success more so on the circling back side have knowing that the person’s like, looked at the email or what have you, and then trying to translate that into kind of like, you know, gauging where they’re at now, right?

I think and also, I think with–the cool thing about if you were to kind of like, do like a second sprint of this account, and you’re kind of like, running like out of contacts, if you find a new hire, like, I always like to just like, map out, like, here’s how I’m thinking of this organization, like this person oversees this, can you help me out here? Because circling back emails doesn’t necessarily have to be the goal of like let’s get a meeting. Because if you can, depending on like, how complicated the sales cycle is for the relative product you’re probably selling into, it could really just kind of depend on, you know, just getting like those open ended questions answered to get your foot in the door. Right? Whereas maybe if you’re more on the transactional side, then yeah, like, obviously, it’s just kind of like getting like, yes or no, and then kind of like, do I want to spend more time like circling back on this? Or do I want to kind of backfill that account and put another one in there and to build that contact out for future outreach? 

Alex: Yeah, yeah. And that makes a lot of sense as far as, excuse me, as far as really just understanding, right, a lot of what he’s talking about, you really need to understand the prospect. And I think you do a great job of that of knowing sort of what what you think their goals are, right? If it’s transactional, sort of by doing all your research, and then tailoring the cadence to that. But, then on top of that, being able to do that at scale in a way that you can do this, and still hit sort of the volume numbers that you want to do. So, yeah, it’s been great talking to you about that.

There’s one thing before, before we wrap up here, I know we just have a couple minutes. I want to point out that you said and sort of what it does, and I really liked when you said you know if if you’re going on vacation, you act like a celebrity, right. And I think that’s that’s something that I think you’ve always done a really good job of is you know, your own importance as an SDR. I think this isn’t really related to cadences, but it’s an important point. I think, a lot of SDRs especially if you’re new in the role, you’re like, Oh, I’m just like the entry level sales guy, I just like pass leads. I don’t really know anything. It’s a lot of SDRs don’t really have that, I guess, self confidence to be able to say like, hey, it’s my job to get this meeting with you. I know it’s important and I think it can help you, let’s, let’s have a conversation about it.

So, and one story I just have to share from from our days together just comes to mind, you were always great that you would call someone at like 9:57, or like right before the top of the hour. And if they pick up the, they’ll go, I’m sorry, I’m just running to a meeting, or I thought this was me dialing into the meeting, and you say you, and they’re lying and your response was always, Oh, me, too. I just wanted to get one last call in before I hop into a meeting, and it totally just like, I guess, destabilize their [inaudible 20:34], they were like, oh, what do I do? And then that gives you the open to sort of have sort of take control of the conversation with that confidence that you’re bringing into the call. So–

Rory: 100%. Because you can translate that into your cadences. I mean, I think that there’s an alignment there because I think that like there’s one way to like have that bravado over the phone for sure. And like, you know, to be empowered as like an SDR and then also just like putting that in your messaging sometimes like, Look, Mr. CTO or whatever, like, you’re probably getting bombarded a lot. Because if it’s like a company that just got funding, like I’m sure every SDR in the world is like hitting them up, right? So it’s like, just calling out like, hey, like, yeah, I didn’t hit because like, you’re, you got to think of it. Like, how many reps are reaching out to the same account? Right? Like across a bunch of different vendors, right? Not just like one vertical you’re supporting. So, like, you got to stand out. Right? So I think that that like that, that’s something a way to kind of like leverage, leverage that into your like, day to day on the on the email side.

Alex: Yeah. 100%. Yeah, definitely something that I learned from you like back in the day. Rory, thank you so much for joining us today. Always good catching up. And I really love this conversation we had about outreach cadences and really about SDR work as a whole. And if people want to find out even more about you or more about Data Dog, where can where can they go to do that?

Rory: My Instagrams is @RoryEats, you can follow me on LinkedIn. I have a Twitter, but it’s usually it’s not that exciting. I just, I just post about tech stuff like very [inaudible 21:58] so it’s not, there’s nothing juicy out there. But, yeah, you can follow me there. 

Alex: Awesome. Awesome. Thanks so much. This has been Alex and Greyson for the SDRealness podcast. Until next time, SDRs, keep it real.

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