The Power of Outbound Calling in 2025: How to Book More Sales Meetings with Callum Gregory & Daniel Levy

Speaker A: Dan, welcome to, uh, the first podcast between you and I in 2025. We're here to talk about how to make the most out of outbound calling in 2025. Before we get into it, Happy New Year. How's the year started for you?

Speaker B: Not too bad, Quite exciting. We've got a bigger team than what we had last year. Um, for me it's uh, a case of look, uh, at the successes of last year and uh, grow, rinse even further.

Speaker A: Yeah, absolutely. Uh, you'd agree, a lot to learn from last year, but part of uh, obviously your role. We stepped into a new role. Head of performance, leading RSDR team. Probably a role that you were uh, doing about the title at the back end of last year. What did you. What were some of the key learnings, would you say, in Q4, um, if any? Or was it more about understanding the team a little bit further and seeing how we started the start of 2025.

Speaker B: I think one thing that is very clear is, um, a smaller team can be very reliant on one or two players. Yeah, making a big difference as the team grows. Um, the need for good training, regular touch points and making sure there's a good feedback loop is definitely needed. And that's something that we learned last year, had some really successful training sessions and the results came shortly after.

Speaker A: Yeah. Cool. So if you just. I think we'll stick to begin with, uh, talking a little bit about your role. Uh, we call it Head of performance, um, head of Sales development. Any sort of head of sales role where you're managing, um, an outbound sales team. Um, I think it's somewhere something that a lot of organizations maybe fall short in because they don't value the position or they don't see a need to have someone in that position. Can you just talk me through, um, some of your, I guess, core responsibilities or where you would like to focus, um, your time to make the team better. So you mentioned their training. Um, is that the sort of main responsibility in the role?

Speaker B: I wouldn't say it's the main responsibility. Um, I think being on hand, I, uh, quite quickly is very integral to my role. So one feature that we've got within our tools that we use is being able to live listen to calls. I like to be able to do that. When, let's say for instance, they get past that 2 minute, 3 minute mark, it's quite nice to jump in, uh, listen to how the calls go and maybe send them a quick internal comms message as to good message to say, good statement. Or um, let's transition out, um, or sometimes stop selling, start booking. Right. Because, uh, we can oversell, which uh, we've all been guilty of in this role. Now one thing you mentioned is uh, the perception of the SDR role and being of low importance. Now when I, uh, recruit for this role, I actually position it as the most important part of the sales process and actually the most exciting and can be, uh, one of the biggest rewardings because you uh, get paid very, very well if you do your job well, um, without having the say, headache of quarterly finance targets and all that sort of stuff. So actually a very important role and impacts uh, more than what they get credit for.

Speaker A: Yeah, absolutely. I think obviously why we exist is to fill the top of the funnel and um, book qualified sales meetings. I think you rightly said they're um, I think absolutely critical. It's why obviously organizations come to Sundrama for us to support them, um, in those efforts. We're here to this podcast mainly to talk about the value of outbound calling, the role it's got to play, play in 2025. I know we spoke a little bit beforehand around how we were going to position that and what that looks like. Um, you're a good person to speak to because you, you've done it for a good amount of time. You did the role itself, obviously for a lot of last year you've transitioned into a leadership role where you're now supporting a little bit more the team that are doing it. Um, do you think it's changed? Do you think it's evolved much? Outbound calling, it's obviously got the, you know, I think me and Robbie were speaking on the last podcast, um, around. If anything, it's probably making even more of an impact. Are you seeing that?

Speaker B: I think, um, when I review course that we make and let's say these successful calls where we convert them into that all important sales qualified meeting, actually there's a real big appreciation for the fact that as a human speaking to a prospect and actually wanting to understand their needs, understand their challenges and present a solution that actually fills that gap or at least is exploring that. I, um, think the days of uh, LinkedIn outreach still very critical part of it. You still need that human element. Um, and I think that's one thing that we do very well and the evidence supports that. You're never going to be able to remove how good it is to make that outbound call.

Speaker A: Yeah, absolutely. I think you touched on a very important point which is anything within sales, it is, it's a human to human game. Um, and I think we can talk about, um, making the most of outbound calling and actually transitioning into that. Can you just talk me through what we discuss internally here at Centrama as being, you know, absolutely critical in that, in that outbound call around. Yes, you want to have the product knowledge, the solution knowledge. You want to uncover pain points. You can be very structured in that outbound call. But I know you talk to the team a lot around also focusing on the person having a good conversation. Can you talk a little bit towards that?

Speaker B: Uh, yes. So don't ever want to give away the structure. I spent a lot of time building the central methodology, the methodology of how we structure a pitch. But for me, ah, prime example, uh, I decided to jump on the phones today, lead from the front, so to speak, um, did an outbound call for a cybersec client of ours. Now the difference between that call and any other call, um, that you would normally have is yes, I have elevated pitch, solution led, pain focus, perhaps depending on solution. But I, I lent on that. But actually it was all about the prospect. It was opening them up, building rapport, um, and you know, taking them on a journey together as a hand holding experience where we were, you know, building a relationship throughout that call as opposed to jumping, jumping into it. Pitch slap. This is what I want. Can you satisfy this requirement and is

Speaker A: we're to help the guys out there that are listening. Um, is that something that you learn through experience? I know when we hire and I think we've got a good eye for SDRs. Now you, um, come out of the first stage interview going, good personality, they had a good conversation. We can train them into something. I guess my question is, is that what it is that what's important initially is can they hold a good conversation with you in the interview? Are they personable? Um, without actually having the experience I know a lot of people focus on, they have to have experience in X, Y and Z. What's important to you at that stage?

Speaker B: Uh, experience is the least important thing for me. In reality, it's really nice for them to have some idea of how the business world works. You know that Corporate experience. Yeah, corporate experience. And you know, when you're prospecting B2B, it's good to understand how an IT department works. CIA, CISO, all the different, uh, job titles that live underneath that and the roles and responsibilities. But actually for me it's always, are, ah, you engaging with me? I've asked you a question. Have you answered it?

Speaker A: Yeah.

Speaker B: You know but not from a book, you know, oh, interview prep book, where it's gone. This is the best answer to give. If you're post with this question, it's actually from the heart, you know, they're

Speaker A: listening, that's the answering the question. I think that then as we talk about outbound calling, that's the same. I think some SDRs get over structured probably and they feel like they've got to go in a certain direction as the, the conversation progresses. And actually those that probably see the most success are those that take the structure away ever so slightly and actually answer the question that's being asked. Asked or actually live in the moment of the call.

Speaker B: Yeah, I think you're right to a certain extent. Um, with even when you're prospecting for Centrama or uh, one of our clients, it remains the same. You know, you have to acknowledge what prospect has said then see if you can pivot that into you know, a solution led answer. Uh, that compares to the purpose of the call or what you're looking to pitch. But actually even if it doesn't have a conversation about it, you know, we all live in a world where we're quite knowledgeable. Like just because I'm pitching cyber second someone mentions to me, um, you know, actually one of our pain points is resourcing at the moment. Speak to them about that because the more you go through the conversation, the

Speaker A: more you can unlock, uncover potential other opportunities.

Speaker B: Yeah, absolutely.

Speaker A: Yeah. It's interesting I think um, when we talk about outbound calling then it would be wrong to not reference and speak about the role of tech and how we use it. Um, can you just talk me through? We've covered off human to human, we've covered off the actual conversation. What role does sales enablement technology, um, setting the team up for success have to put play in, uh, the outcome I guess of each call.

Speaker B: I suppose. Um, it's important from a, ah, point of if it's admin related. Right. I like to automate as much as I can. Um, tech is important from a communication perspective. Internally we've got our own internal comms, uh, tools that we use. Getting that information to an SDR fast and efficiently is always important. It can't always wait until a afternoon huddle, end of day meeting. You know, we need to get that information out to an SDR quickly. But actually uh, on top of that, um, the sales enablement tools. So you look at your dialer, is it fit for what you're looking to do, uh, when you're prospecting to certain regions. Does it support localized, uh, number. Now, all these small little tweaks can make a difference, but you need to make sure that you're always looking for the next tool that could make your life a little bit easier. Because at the end of the day, as long as it's getting you quicker to the prospect and actually having a conversation with them, that's all we're ever looking to do.

Speaker A: Yeah, I think that, uh, that builds into just the bigger picture of successful SDR departments are set up for success from the very beginning. So, you know, at Sintrauma, we talk around, we put a lot of emphasis on the briefing. So from when we onboard a client through to the SDR team, equipping them with the right knowledge, understanding of the solution, um, equipping them with a script. I know we've just said not being about too structured, but I think it's important that they've got, um, a good elevator pitch, a good understanding of how they're going to navigate the conversation. Um, this has always played a big role and it will continue to do so in 2025. When it comes to effective outbound calling. Talk to me about data. Data is critical and frustrating and glorious

Speaker B: and everything else 100%. So, um, you and I have spoken about this topic in great lengths over the last 12 months and I'm a firm believer in my abilities as an outbound. So you could call me a CR expert, whatever you want to call me, um, that if you give me the right icp, right from the uh, right say demographic alongside also, um, you know, a really good value proposition. Those three boxes are ticked 30 to 40% of the time I convert them in to an appointment or there would be some kind of follow up.

Speaker A: And is that, is that. Because I'll just refer back to what we touched upon earlier, which is even if the initial need or pain point isn't necessarily aligned to what you were initially looking for, if you do enough uncovering, I guess in natural conversation, you'll find something with the right ICP that the solution can then support with 100%. So you create a need.

Speaker B: Yes.

Speaker A: If you're speaking to the right person.

Speaker B: Yes.

Speaker A: Perfect. Okay, that makes sense. I think we, again, we touched upon it a little bit earlier. I just want to go back to, um, hiring within the SDR team, um, hiring processes. I think this is something that a lot of organizations seem to struggle with, which is they spend a lot of money, a lot of time on hiring the wrong talent potentially. Um, and then, you know, you're back to the drawing board three months down the line. Um, just talk me through how you unearth a good outbound caller, potentially during the interview process. Do you do a task? Do you not? Is there questions that you ask, or is it just experience that then sort of leads you towards the right candidate?

Speaker B: Um, it's never a perfect science. Okay, yeah. Um, previous roles, you know, you always make a snap judgment. You go, I've had a conversation with them. They'd be really good. They might need some support to get them there, but they will get there eventually.

Speaker A: Yeah.

Speaker B: Um, I think it's safe to say it's never been. I've never been right about every single sdr. Some of them certainly think, uh, it was true. You know, they were as good as what I was hoping and all this sort of stuff, and others where I thought they were a sure bet. It took me an extra week or two, and then all of a sudden flying. Uh, we will get there in the end. Um, but I think providing they've got those personable traits where they can hold a conversation and, you know, really, uh, engage with a prospect, I will get them there. It's just a matter of time.

Speaker A: Yeah, agreed. I think from any. I think with the. The experience piece, um, and hiring the right individual, even if they don't have experience, you're hiring people that, as we say, that they're comfortable in a conversation, um, but also that they've got the right attitude and mentality. I think that's a huge thing with outbound calling and making sure that you're effective and efficient on the phone. Um, just talk to me a little bit around activity requirements at Sentraama, what we KPI the team on, because that's potentially something that others can use. Um, but also maybe the importance of activity at the start. I'm a big, big believer in it. I don't hold the sort of technical ability that you do when you're coaching the team. So my go to is always talking about controllables, the will to want to succeed, the activity. To talk me through a little bit about that, what do you expect to see inside the first month when it comes to outbound calling from your SDRs.

Speaker B: Uh, for me, it's, um, it's quite simple. I just want them to be going, yeah, right. Um, we've got. We've got a dialer. You press go, have conversations. Um, I just want to see people committed to the cause. But there is a number. You've got five hours of dedicated time in your day structure that you can use for Calling. I'd like to see half of that active in, in calls or dialing M. So two and a half hours a day, that equates to maybe 250 dials, 150 depending on the dialer that you're using. Um, but within that I'd love to see metrics of 15 to 20 conversations a day with conversion rate from conversation to meeting of 7.5 with a view that we get to 10%. And this is just for a standard SDR. Our Ah, senior SDRs, the expectations a lot higher, uh, because you know, you should do more with the conversations that you're having in theory. Um, but all of those metrics and all of these goals, uh, you know, have many different variables. Data slippage for example and everything else. But really it's just showing will is enough to begin with. And if you show enough will, you're going to get the skill because you don't, don't learn from not doing. I'm not trying.

Speaker A: Yeah, absolutely. I think, couldn't agree more. And I think it's build on that. It's, it's consistent activity over a decent period of time. Um, I think we have been frustrated in the past um, with the team and I'm sure a lot of sales leaders, sales managers out there will be the same that on a Monday they get out 20, you know, an individual might get out 20 conversation, it then dips Tuesday, Wednesday, it's then back up Thursday, maybe dip again Friday. And actually I think if you're an SDR listening to this, it's about consistency and activity. Getting the conversation number, the talk time number, the dial number, whatever you're KPI'd on throughout the week so that your sales manager or leader, ah, can actually support you off the back of a decent data pool. Otherwise it is challenging to support.

Speaker B: Right, yeah, 100%. So, so, um, I know, yes, the RS that are guilty of complaining about data very early on into a process and uh, I'll quickly log up analytics. Okay, great, you've had three conversations, have another 15 for me. So I can really understand whether we're not landing what's going right, what's not and rest assured, two dials later, uh, they're having a successful conversation is resulting in a booking. So we have to allow for slippage. We can't be too quick to moan. Um, we have to really test things out. But uh, the point that you touched on in regards to having a big data pool of um, say calls that you could go back on for training and everything Else it's all very important. And uh, for me as a manager, I'm not there in the moment. I can't speak to absolutely every sdr, um, after a call and analyze it, digest it with them, go to. Well actually you could have tried this, you could have transitioned into say an assumptive close rather than a permission based close. You know, like just going. It's a no brainer. We need to speak again because we've identified X, Y and Z. Um, and that's all um, you know, so having it, um, having everything there for me to be able to go back to a later date is always really good. Listen to calls, you know, read transcripts, um, whatever is the quickest route to try and you know, train and support, develop.

Speaker A: Yeah, I completely agree and I think we've seen, we've also seen success and I think how, where you do your role very well. Um, from what, you know, obviously what we've seen over the last three weeks is actually as a leader and as maybe as an SDR manager, head of performance, again, whatever, head of sales, whatever it's called in your organization is getting that senior person who's comfortable on the phone to go out, have the conversation, then use their own example and get people to listen in. Because it's not just around going out there and just equipping them with bullet points and objections and how you position value is actually them listening to how it's done. Because that's the human element of calling, isn't it? How it's positioned, the tone in which it's positioned, how it's acknowledged to begin with. If it's an objection. Um, is that something that you've, I guess consciously try to do?

Speaker B: Um, latterly, yes, I think with the say recruits we had uh, in Q4, yes, 100% I was still active in the SDR role, it was fair to say, uh, despite you know, kind of taking over a little bit, leading, um, and supporting. But so there was a massive bank of appointments that they could listen to off mine. They could see how I do it and everything else. So that's always really useful I think. Um, uh, but one thing that I, uh, what has been useful is I've picked calls where there hasn't been much structure M. Um and gone through that. Because I think some of the SDRs that I've trained over the years and some latterly as well have been a little bit say, robotic. Right. I need to say my elevator pitch. I need to ask this question, I really need this question. Qualification criteria as well, um, they're comfortable

Speaker A: in the scripts though, aren't they? I think that's the piece.

Speaker B: They are comfortable in the scripts. But actually some of these people, their personality I don't hear in their call as I'm listening to it, whether that's during the call or post call. And I'm like, this person's really fun to speak to and I actually really enjoy interacting with them on a personal level outside, um, of the role. So why can we not have that communicated, uh, in a call? Um, so one thing I've tasked a lot of the STRS on recently is like, let's have Callum come through on that call. You know, Callum, you love cricket, you love football, right? Why not just throw it in when you're having a conversation? You know, Chelsea, God, wish they did better at the weekend.

Speaker A: I do, I really do.

Speaker B: But there you go. And why not, you know, try and resonate with someone on a personal level, but also actually just means you can relax, you're in your comfort, enjoy the call.

Speaker A: Yeah, yeah, agreed. I think that's, um. Again, I think that comes going back to having as many conversations as you can at the beginning, because the quicker that you get over those nerves, the quicker that you have 20 conversations a day consistently, you'll then learn to sort of relax into the opportunity. I think also, again, it's something that's very popular at the moment, something you're a massive fan of, you've always used in your career. I think think I'm right in saying permission based opening. Once you've got the permission to proceed, that is the time to relax and get into the conversation. Because actually they've said, yes, you can proceed. And that's the massive bonus of that approach. Right?

Speaker B: Oh, 100%. But also, you know, you've got the permission. Slow down as well.

Speaker A: Yeah, don't rush it.

Speaker B: Right, don't rush it. Uh, make the most of it, articulate what the value proposition and, you know, emphasize what the prospect needs to listen to. Uh, I've seen so many really great opportunities get thrown away over the years from people not delivering a message in the right way. And I think that's really important to learn as an SDR as well, is how can I position this question or this statement in a way that's going to make them listen and actually take away the key information as well. Uh, I think if we. I won't give any examples because Brand. Um, but, um, but let's, uh. But. But really think about the fact that when you're positioned something To a prospect, it needs to resonate. How can you do that best? Well, they're, they're a ciso, so we deliver cyber security solutions. You know, like, I know that's a bit of a crap example, but for the most part you're emphasizing the words that mean something to them and that they're going to care about.

Speaker A: Yeah, agreed, agreed. We're coming probably slightly towards the end of this, I guess. Um, we've covered off a lot there from the hiring process and why it's important to hire the right talent. Um, setting up for success and then also how you approach it on the phone. Even if you're a new starter someone. Experience, experience focusing on that human to human, um, interaction, um, it would just be good for everyone that's, uh, listening. Dan. I guess just a couple. Even if it's one couple of takeaways. In terms of outbound calling going forward, what do you suggest is going to potentially make people successful? What do they need to focus on? And whether you're a, uh, leader, an SDR leader, uh, as a sales leader, or actually as an individual.

Speaker B: Okay, start with spot. Yeah, fine. Um, so for an sdr, um, if you're deploying the permission based opener, say, uh, tactic, you've been rejected. No, please, by graph, I will not give you 30 seconds. Challenge that, Use that as an opportunity before you let them go, before you risk never speaking to that prospect again. Ask them the question, is it because you've heard, uh, of us before and you don't need our services or solution, or have I simply caught you at the wrong time? Now, by challenging the prospect, you're potentially going to get permission to call them back another time. Actually, it's a really bad time. The kids are, uh, throwing paint on the walls. I need to go or I'm just about to go into a board meeting. You know, great, I'll give you a call at a later date. Better yet, is there a good time of day to normally catch you? Right. Although there is some urgency in what they're saying, you're building some credibility for yourself and you can go again by simply just going, okay, I'm so sorry, and then marking it. And this is one thing my team are very aware of that I absolutely hate. It's marking as not interested. Never speaking to that prospect ever again. That is data that you've purchased. Uh, actually someone who could have been a really great opportunity for your client or for you, um, it's gone. The opportunity's gone forever. And you're never going to try that prospect again, challenge them, find out the root cause. You can go again. That's, that's like it.

Speaker A: Yeah, yeah, yeah. It's good because it's becoming more and more challenging. Actually it's very topical in 2025 because um, technology is advancing even further and actually people are getting warnings on their phones. Potentially spam. Could be a cold call. All the challenges that face, um, outbound calling. And actually you're right, if you get someone on the phone, they're receptive on the phone. If they're not available in that moment, get a follow up in, get a time in which they're potentially going to be more available because you know, that's a good number, a good contact and someone that's willing to speak to you. Great takeaway.

Speaker B: Cool.

Speaker A: I think we'd potentially leave it on that note. I think that's a really, really good spot. It's uh, it's certainly going to be a challenge going forward. Even more of a challenge as tech seems to evolve. And uh, yeah, I think that's a good takeaway for everyone that's listening. Dan, thank you very much mate, as always. I'm sure we'll be on many of these uh, this year. Um, I know uh, there's a previous one with myself and Robbie as well that's uh, well worth a listen. So I encourage you to go and listen to that one. You can also subscribe uh, to our uh, YouTube channel, which I believe is somewhere down here. I always get told a point you

Speaker B: have to like as well.

Speaker A: I don't know, Dan. I'm plugging everything here at this stage, but hopefully you enjoyed it. We wish you the very best of luck on the phone, um, over the next, uh, couple of weeks, months before. I'm sure you'll hear from me and Dan again. But thanks mate.

Speaker B: Cheers Carl.