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How to Make Your Sales Development Teams Excel in 2023 with Callum Henderson, CRO of EngageTech

In this episode of the Revenue Insights Podcast, host Lee Bierton is joined by Callum Henderson, CRO of EngageTech, a B2B sales development company. They identify the key traits common to all high-performing sales development teams: resilience, determination, and curiosity.  Callum shares his insights on instilling them in your sales development reps in 2023 and the importance of unique and customized messaging for your ideal customer profiles. He also touches on the relevance of personalization in outbound prospecting.

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Time Stamps:

  • 01:01 – 03:34 – Callum’s Story
  • 04:03 – 07:45 – The journey from SDR to Chief Revenue Officer
  • 09:14 – 11:57 – Unique insights from taking multiple businesses to market
  • 12:02 – 14:32 – Common flaws in B2B SaaS go-to-market strategies
  • 15:18 – 16:07 – How to simplify your solution for your target audience
  • 17:15 – 20:19 – 3 key differences between high and low-performing salespeople (please use for the main release – focus on resilience, the first factor he mentions)
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  • 26:14 – 28:02 – How to do more with less and how to pivot your outbound approach to your target audience’s new pains
  • 28:58 – 34:08 – EngageTech’s journey as a bootstrapped business to 150+ employees
  • 34:24 – 35:50 – Callum’s Book Recommendation: Radical Candor by Kim Scott

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Think about if you’re taking a product to market, what would a prospect take from 60 minutes with someone in my team or 30 minutes or whatever it is that you want to do as your first step?

And that I feel is often a part of the process, which is neglected.

Yeah, so I think if there was a couple of things to throw out, it would be the simplicity and the value of the meeting. Welcome to Revenue Insights. Every week, we’ll be joined by revenue leaders from some of the most successful and highest growing companies.

Together, we explore how they built their revenue teams, the journeys that they’ve been on, and the lessons they’ve learned along the way. Revenue Insights is brought to you by Epstor. We’re a revenue intelligence platform designed to help revenue teams to build more pipeline, close more deals, and retain more customers. Hello there, you’re listening to Revenue Insights.

Today, I’m joined by Callum Henderson. He’s the Chief Revenue Officer over at EngageTech.

Callum, thank you so much for joining me. Thanks so much for having me on, Lee. Last meeting before Christmas, so I’ve kept you on too long. We’re literally recording right on Friday the 23rd, a couple of hours before the Christmas break. So I think this is a bit of a fun one to dive into just before Christmas.

I don’t know if we can keep it on a festive mood, but we’ll see how we go.

All right, first question.

So anyone that hasn’t met you before, kind of from our audience, could you let them know a little bit more about who you are, your background, your history, your story, and a bit more about EngageTech as well, and some of the things that you’ve been doing there?

This is a really embarrassing moment. You have to talk about yourself for a little bit, which I’m not historically amazing at. I joined EngageTech as an SDR nine years ago off the back of doing a journalism degree. I typically only really lived in South London my whole life. EngageTech, for people that don’t know us, we help companies with sales development. Let’s talk about some of the problems that we solve.

In a post-COVID world, it is quite tough for people to juggle hybrid work, remote work, and with infinite amounts of lead sources and different systems that reps need to work alongside to be effective. It just kind of makes, particularly for SDR managers and likes of VP sales and marketing leaders, it’s really quite complex to effectively run SDR teams. So there’s a number of different ways that we help businesses with that.

We can build you a team, and provide you the framework and the processes to execute well with them. We have a software which really helps with Data Connect. We also can do the whole problem for you if you want to outsource and essentially rent an SDR from our business.

We do that exclusively with B2B technology companies, which is a niche but a pretty big one that we like working within because technology companies are always looking to grow and always looking to expand and are on the cusp of being innovative, which I think is a good mix in the sales development space.

I’ve been on a nine-year journey with EngageTech, as I said, joined as an SDR, and now fortunate enough to be in a CRO role, which if I’m being honest, I’m just around six months into and very much still finding my feet in the position, but it’s been a challenge and hopefully I’m living up to it. Awesome.

Oh, and I’ve got a seven-month-old daughter, so that’s driven a juggernaut through my personal life and just general life in the last half year, but it’s been an incredible experience. Promoted to Chief Revenue Officer and a newborn. And dad.

Yeah, all in the space of about a month. I suspect that was a heavy 30 days or so. So the bit that I really like and want to delve a bit more into, you’ve been on that journey from SDR all the way to CRO.

So often, speaking to people, they’ve jumped from place to place to place. You’ve actually done it all within the same business. So I’m interested to know how the business has changed as you’ve been moving up the ranks and as well as how your role has changed within that as well to getting where you are now. The business has changed significantly in that time.

If I imagine walking into a company in the region of eight to 10 people as a grad, 28-year-old founder and a group of, what I would say, a group of people who enjoyed socializing with each other, who had some ambition. And if I look at a business now where I went to our Christmas party, there’s 180 people there and we’ve got offices in four global locations.

It is a little bit of a like, not necessarily a pinch yourself, but certainly where we are at now felt like a little bit of a pipe dream at the start of this process. And the iterations that particularly leadership in our business have had to go through has been, I think, a large reason why I’ve stayed here because it continues to represent a new challenge.

And they say that leadership in a business needs to almost operate 12 to 18 months ahead of where the company actually is. You need the leader for 18 months time to get you there. And I think all leadership were dealt a hand where they needed to pivot and change in the COVID period. So that was a given for everyone.

But particularly, if I look at some of the current challenges that we’re facing, how can a group of people who’ve typically managed by knowing everyone and knowing them well and knowing the detail of their professional lives and sometimes what’s happening in their personal lives as well, how do you continue to lead when actually it’s even quite like a task to know who everyone is and remember everyone’s name?

And that’s interesting. And that’s certainly one that we’re going for at the moment. With respect to my personal, the roles that I’ve played, I was an SDR for two years. I enjoyed that super selfish time in my life. You just got your number, you go and hit it and that was fun.

And then I ran a team of, well, started off with about a team of five, but eventually a team of about 40 SDRs for a couple of years after that. And that was the polar opposite. SDRs are at the start of their career. It’s quite a selfless role, I think the SDR manager role. And you learn a lot and make plenty of mistakes in that job.

And I didn’t really move over into a revenue carrying role until about year four or five here.

And yeah, that was, again, quite a challenge. You learn how to sell in a face-to-face environment over the first 12 months of doing that job and teach yourself in a young business how to do it without much outside input. And then next thing you know, you can only sell on team schools and no one’s got any budget because COVID is here and everyone’s a little bit nervous.

So kind of baptism of fire a little bit doing that. And then in more recent years, it’s just been about coaching, guiding people to the outcomes that you maybe faked it a little bit yourself that you could actually do in a business of 30.

And now you’re in a company of 180 trying to impart wisdom, but sometimes looking at people feeling like you’re infinitely better as a specialist than I ever was at this, which is I think what you see in a lot of people in the C level, lots of generalists, helping specialists.

Oh, for sure.

What I actually love is actually almost like your humbleness towards it, you know, having been there, but also so often when you’re, I think you have, when you have reps on the front line, you know, you’re kind of getting given directions from senior leadership and it’s like, it feels like it’s quite disconnected, but actually, I sense from kind of what you’re saying, having been there and done it particularly within the same company, I think it actually gives you correct if I’m wrong, a fairly unique and quite powerful perspective, because you’ve been there, you’ve done that role, and you can really empathize as to what they’re going through and, and kind of their experiences as well.

And I would suspect, yeah, if I was to make a sweeping assumption, I would think that actually helps quite a lot in the way that you approach things now.

Something that I wanted to dig into, and we had a chance to kind of catch up before recording, you mentioned that something that’s kind of unique about your experience that we haven’t quite touched on yet is in that, in that role and, and through the, through the roles that you have done, you’ve been taking different, so different clients to market.

So, rather than just kind of taking Engaged Tech to market instead, you know, you’ve got various different ones. And I wanted to hear a little bit more and kind of in your own words, what you mean by that, and also what that experience was, was like. We’ve got globally about 75 customers at the moment, and we haven’t always had as many of that as the business has grown over the last decade.

But if you take a snapshot at any given, over a six month period, at any given point in the last five to seven years, I have been involved in teams that are taking from an outbound cold calling perspective, technology products to market for a wide range of businesses.

And I think one of the unique things about that, that I explained to you when we, when we spoke last time was, if you look at a typical person who’s nine years into their career, they might have worked at two or three businesses. They might have had an exposure to two or three go to market strategies around a handful of products.

And I think one of the benefits of why I’ve enjoyed working at the business, is that even though a lot of people that join, one of the things they don’t like is the fact that we’re an outsourced function in a business. They want to actually be part of the company they represent.

I kind of see it the other way in that I’ve had a lot of exposure and many other people in our business have had a lot of exposure to lots of different technologies.

And also, I think the learnings that everything in terms of the principles is always the same, but every campaign has nuances and little things that are really important to understand to really be successful.

And one of the things that our founder does with people who are two to three months into the business, he does a little exercise with them where he sits in a room with maybe seven or eight people and ask them their opinion on their campaign.

And the typical responses are always, oh, yeah, they’re a little late to market or they’re a little expensive or there are a couple of really good competitors that it’s difficult to objection handle around. And he always plays a little bit of a trick on them that actually, you’re often graduate SDRs and one of some of these companies have just raised maybe $50 million in funding.

I’m sure the VC fund that invested did a bit more research to know that they’re not late to market.

But after two months of your career, you’ve kind of formed this opinion that it’s tough, right?

And I think what has always been intriguing to me has been that every campaign is difficult if you want it to be difficult, or you can look at it and feel like there’s a puzzle to do here. And once I crack that code, this actually becomes something which is achievable. And I suppose that’s been the, that was what we were talking about last time. That was actually such a nice point.

And actually, the bit that I wanted to pick up on was, I feel like you kind of mentioned one of the things, but you mentioned there that you spotted a number of different things that are important to the successful execution of that go to market strategy.

So having been there and seen it on multiple different occasions, what would you say those important things are to successfully executing on?

Simplicity. Quite often we speak to companies who are of the view that their technology is too complex for a junior rep or someone outside of their business to grasp in a short space of time. And firstly, in most cases, that just isn’t true. But secondly, if it is true, it’s really difficult to impact someone when you don’t know them, you don’t have a relationship.

And when you’re cold prospecting, you have to be able to communicate the challenges that you solve succinctly and present something concise as a solution. And so simplicity is certainly quite high on that list. One of the other elements is in sales development, particularly cold calling, I think focusing on the value of the appointment, which is normally the end goal, is a highly valuable tactic.

Which is that as much as account execs in businesses want the moon on a stick, the job of the SDR is to provide a quality and quantity of leads in the right mix. And their job is to get face time with prospects for a more skilled and knowledgeable salesperson. And so you’re transacting on the value of a meeting. And the value of that meeting is, again, bespoke per business.

But try and think about if you’re taking a product to market, what would a prospect take from 60 minutes with someone in my team or 30 minutes or whatever it is that you want to do as your first step?

And that I feel is often a part of the process, which is neglected. So I think if there was a couple of things to throw out, it would be the simplicity and the value of the meeting. I really love the point on simplicity. It’s very close to my heart in what we do as well.

And I’ve been finding, okay, you know, for Ebster, it’s how do we condense down 10 years worth of software development down into an explainer in 30 seconds and to be able to clearly and succinctly describe what we do. What would your advice be to someone listening that’s like, oh, but you know, but my tech is complicated and they’re really struggling to simplify it down.

What would your advice be to them to actually simplify down what they do and to be able to communicate it in a succinct way?

Start by writing down the problems that you’re solving for your prospects and then probably go a layer down and think about what do those problems do to create painful emotions in those prospects?

And I think once you go through that exercise, it will probably become a little bit simpler to articulate. And also just get the thesaurus out and use it in reverse. And people normally use their thesaurus to make words look complex and make them look more knowledgeable. Let’s do it the other way.

It’s just like, how can you use language that a seven-year-old can understand?

I want to bring us back and touch on the point, something that we mentioned pretty sure as well.

Can you just confirm how many SDRs you’ve managed across your career and how many you’re managing now?

I don’t think I manage any SDRs really now. I am responsible for revenue in a business that owns approximately 130 SDRs at the moment. About 10 of them take our own products and services to market and the rest of them globally represent our customers.

So that’s helpful to know because what I wanted to ask was, over your career up to now, what’s the big difference between a high performer and a low performer?

Perhaps three characteristics, traits, things that really stand out to you that really put some much higher than the rest. So probably the best rep that I ever worked with was actually a friend that I referred into the business. And he’s got like three GCSEs, was stacking shelves and wait rows before he joined.

And I just met him and I was like, you’ve just got a good demeanor about you and I think you can be successful at the company I work at. And two of these things, I think he was a standout performer. The first one was his ability to reset.

And what I mean by that is, I think even the best reps, particularly if you’re willing to prospect at scale, so 80 to 100 outbound attempts a day, even the best reps are failing a lot. And he managed to remove any emotional attachment to a rejection or to a bad day.

And quite often when he was having a bad day, he would pull out something out of the bag quite late, maybe four or 5pm. And by that time in the day, most people that haven’t been successful by that point are in quite a negative headspace. And I really felt like he was incredible at just every dial is a new attempt and what’s happened before is irrelevant.

And then the other thing that he was very good at was two or three days a week, being successful super early in the day. And I think it’s a bit of a myth that calling it like 9am is the point at which it kind of makes sense to start.

If I look at most of the decision makers in our business, and I’m sure you might be able to say the same about yours, they are quite often available for a phone call much earlier in the office, maybe at half seven. They quite often clock up hours, I would say outside of the obvious, like nine to five.

And I think that this individual was really comfortable calling in the kind of 7.30 to 9 o’clock window and would often set up pipeline follow-ups in that period of the day. So if you call someone on a Monday, I’m in a meeting, wicked, I’m going to call you tomorrow at half eight, and just create an environment where you’re constantly starting your day with slightly warmer conversations.

And often, you got off to a pretty quick start in a day and that led to success. Because there’s a nonchalant confidence that comes with that. So those would probably be the main two that I saw in him. Beyond that, I’d probably use a word like curiosity.

I think it’s a role where it really counts to genuinely want to ask good questions and to learn more about the people that you’re speaking to. I think that’s really nice. And actually, just to add to your point of calling outside of, rather than just starting at 9am, talking from personal experience.

I mean, if I think is it during the day, I’m probably in meetings or if you’re identified in my kind of age bracket, perhaps you block out your morning. And it’s like no phone calls to meetings, like I’m getting my head down and that’s when I’m focusing.

Whereas in those hours before in the morning, I think I’m arguably far more likely, and I might regret saying this live and so NSCR actually sees this, but I’m more likely to pick up the phone kind of before that. Really just out of curiosity at who really has the gall to ring me at that time. And also because I’m really not expecting it during the day.

Whereas if it’s like 12 o’clock, you know, on my lunch break, you know, chance of actually connecting is so much lower.

Yeah, I mean, I completely agree. And I think you also, it’s worth mentioning that in the current day and age, if you are calling decision makers, I think you are differentiating yourself from the start. The CEO at our business, he answers a lot of cold calls. Our sales director, he always responds to LinkedIn messages saying, here’s my number, give me a call.

And he gets an embarrassingly low number of people who actually follow up in that way. And I think people don’t like bad cold calls. But they’re normally pretty okay to talk to someone who’s framing the conversation in the right way. I completely agree.

And to the point where it’s interesting because so often because, and a common theme that comes up on this podcast is kind of the difference between like artistry and like science in sales. So for example, in a sales development role, you know, automating your cadences, for example, right, so that you are able to have more, more conversations and more touch points and more activity.

But certainly personalization to me seems to go a hell of a lot further forwards and has a lot more success. I suppose it’s that fine line between spending all the time like trying to personalize an email or to, you know, personalize that first line that you make when they pick up the phone, and actually being able to ultimately get through to them, right.

But it’s, it’s one of those where how can you possibly scale kind of that level of personalization, I think, you know, I’m sure someone will come up with an AI tool for it or something at some point, right?

Seems like the way to go these days. One really interesting part of that, the use of that word, I think personalization is certainly something which I see using a lot, people use a lot on LinkedIn. It’s definitely a phrase I’ve used in our internal chats and in some of the content I’ve posted in the past.

I kind of see personalization as something that creates an environment for someone where they feel like it is only intended for them. Like this bit of communication could only make sense to me. And we were a customer of a business called Refract who were acquired by a company called Lego.

And the chaps that work there are a group of them wrote a book called Problem Prospecting, and I’m big fans of what they do. And they talk about the fact that from their sales team, every first touch email that they send has to be entirely personalized. Exactly as I just said, the person reading it has to feel like it’s only intended for them.

But there’s another way of looking or categorizing this kind of outreach. And I would use the word relevance rather than personalization for it.

And I think relevance is a lot, I think, a lot of the people that are more closely and better aligned to cold calling, which is if I was a rep or a manager with a sales development function, what we’d be trying to look to do is to say, okay, how can I make the messaging today relevant to, for example, an industry?

So I’m going to create a list where it’s only finance businesses that we’re calling today. And this is the relevant messaging for someone in finance. Because I don’t think that the research time versus ROI to results matches on cold prospecting in the same way that it might do other channels.

Okay, if you’re a good cold caller with a relevant message, it actually doesn’t matter if you know that someone supports this football team or went to that university. It’s more about the, can you show someone that you understand them and their business through kind of subtle parts of what you’re saying. And I think differentiating those two things and using them both is valuable.

I think that’s a really important distinction between the two, right?

Where relevance is exactly the right word where it’s, you know, we’re on the same ballpark and or the person that’s reaching out to you is ultimately, you know, we’re speaking the same language.

Okay, now let’s see what you’ve got really at that point. So I’m curious to know, obviously, as you mentioned at the top of the show, we’re at the end of 2022 now, 2023 promises to be an interesting year for sure, certainly for sales teams. And my assumption would be that for certainly sales development teams, it’s going to be a potentially a challenging year.

So are you doing anything differently to prepare and plan for 2023?

Or, or are you kind of, you know, convinced in the way that you’re doing things and you know, we’re going to make this work?

Interesting question. I just want to make sure I understand it.

Do you mean with respect to our approach to prospecting when we are representing our customers or ourselves like in a sales development function?

Or do you mean that at a company level, how are we preparing to make sure that we have a fruitful 23?

So the former actually, so the for your actual sales development team, doing the prospecting?

I think the primary element of the go to market proposition for every company that we represent has to be how can you tweak what you’re communicating to speak to a prospect’s current challenges.

And the adjustment going into 2023 is likely going to be how can you do more with less?

How do you automate parts of your business to mean that you don’t need to hire and bring on headcount, which creates a risk in a slightly tougher economy?

I would be thinking about how to add finance personas to every list that you’re trying to prospect into. Like no matter what happens in 2023, CFOs, finance directors will be on the buying committee. And starting there isn’t actually the worst idea, even if they’re not your direct persona. Because every line I want in terms of spend and future purchases is going to be heavily scrutinized.

I think those are again would be the two things I’d immediately identify as things that other companies can think about that we’ll be doing.

Yeah, I think both extremely, extremely good points. And I particularly like the line of doing more with less. I think that’s a very, very common theme coming up and driving greater efficiencies and so on. And so that actually is quite a nice segue into something that I did want to ask, again, something that you mentioned previously. So you guys have made it to where you are bootstrapped.

So no VC capital coming in at the top.

What have been perhaps some of the lessons that you’ve learned doing it that way?

And actually, I’ll be a bit more specific.

What’s been the biggest challenge as part of that, other than having loads of money to play with?

And what’s been, do you think, the biggest benefit of it as well?

Okay, so challenge wise, and I think we’re about to cross the threshold on leveling up on this. Because of our background as a company that’s comfortable with outbound sales development, we have historically taken quite a functional look at growth, which is build an SDR team, do what we know how to do well, and grow throughout bound acquisition.

And what it has ultimately meant is things like our brand and our marketing and demand generation isn’t really a lever we’ve ever pulled. And if I look at lots of companies that raise funding, it seems to be an area that they normally execute on well, and is a huge part of the revenue growth arm in lots of businesses.

And so I’d say historically, we’ve not done that particularly well, mainly because of funding. The reason why I mentioned potentially crossing that threshold, we’ve made some recent hires, we are actually going for a rebrand at the moment, which has been exciting to watch that play out.

And yeah, so I think those are the main… I wouldn’t call it a downside, but main concession, I suppose, for that. In terms of upside, I think for me, maybe on a personal level, it’s been really interesting to grow within a company who have had to live within their means and be resourceful. I think it’s been very helpful for me to understand how businesses truly operate.

And I think I’ve got a lot of respect for the money that we do spend based on like, I know how hard we need to work to create it in the first place. And I certainly see it like an environment where someone coming up in a different kind of business who’s got lots of access to funding might see that slightly differently.

So yeah, I think those should probably be the headline points. But I don’t mean that in a critical way to businesses that go out and raise funds. I think it’s just a different experience.

And if I look at people that I’d probably consider peers in competitors or other companies, some of them have certainly been on a slightly faster trajectory to what would appear to be like the headline stories of this level of growth or whatever. And I think that a lot of that comes back down to perhaps things like funding.

And so, you know, just it’s just different, different paths that people walk, I suppose.

Yeah, absolutely. And I think, as you mentioned that, I was sensing a very kind of similar kind of thought process almost to when you were describing like the your friends that joined the company in terms of the traits that really helped him to excel, you know, resilience, curiosity, and determination was the other one.

And I think I get the impression that being a bootstrap company myself, it requires a very different type of, not just a different type of individual, but certainly a different type of seller as well to be able to, you know, you don’t have the luxury of all the funds to be able to keep throwing stuff at the wall until it sticks.

It really is a case of, you need to find that way to make it stick first before you’re able to then have the confidence to actually invest more into it. So then be like, okay, we know this is working for us, we know this is driving revenue, let’s focus here, because that’s, you know, it might be an industry where we’re finding success, for example. Absolutely.

And it’s funny, I went to a software event, pre COVID and post COVID. And in the pre COVID event, in, must have been 2018, 2019, one of those two years, felt well out of place, because everyone was talking about funding, we’d not ever really dabbled in that area.

I was a little bit like, do we belong here?

And then in the post COVID event, it was just in the summer gone when a lot of the kind of funding markets had crashed or taken a downturn and funding had started to be pulled and there were lots of redundancies and things being made. And it was like, yeah, go, go team bootstrap. Like this is like, don’t, it’s not all about funding.

I was certainly sat there like, it’s a kind of fickle game, isn’t it really like that, that things kind of pivot like that. I think my light takeaway from that was just, you know, you’ve got to go down the path that fits your business and your leadership team or your personality.

Just be proud of that rather than thinking about like what other businesses are up to and feeling a need to kind of follow them. Yeah.

As always, it’s always a matter of perspective, right?

In terms of how you look at it. And there are some wildly successful businesses that are highly funded and then you’ve got the likes of Mailchimp, for example, we’ve bootstrapped the whole way and they’re a beast.

So yeah, I mean, that’s ultimately how it goes, right?

All right, Callum, final question. And then I’ll let you go and prepare for your Christmas turkey.

If there’s one book that you’d recommend to other revenue leaders, you know, perhaps it sells to relevant leaders or other chief revenue officers now in your new role, which would it be?

I’ve worked in a business that’s historically been quite people first focused. And a book that I think has really helped not just myself, but a lot of people within our company to communicate more effectively is a book called Radical Count Off.

And it’s essentially about an axis of when you communicate to someone, you need to make sure that you show them that you care personally, but when you need to, that you’ll be willing to challenge them directly. And if you can weave both of those elements into your communication, you will get the best out of the team that you work with.

But if you do too much of one comparatively to the other and things are off whack, you might end up shirking away from feedback and just being someone’s friend or being what they call in the book, obnoxiously aggressive and coming across as someone who’s perhaps just a bit rude, obnoxious, not too nice to be around, even if the things that you’re saying are valid.

And yeah, I couldn’t recommend it enough. It’s a very useful tool. That’s a fascinating suggestion. I’m going to check that out because I really like, I think you’re 100% right.

It’s the balance that you ultimately bring to it, right?

And not being too far one end to the other is really interesting. And I’ll be sure to include a link to that in the show notes.

So, so the audience can have a listen as well.

All right, Callum, if you actually alluded to it a little bit there, I know you guys are going through a bit of a rebrand at the minute.

If anyone wants to kind of connect and keep an eye on some of the cool things that you’re doing there and also follow your journey, now that you’re kind of going into the second, second half of your first year as a CRO, where can they find you?

Definitely LinkedIn, Callum Henderson and EngageTech. At the moment, there’s an orange background on my photo, but maybe that will change in the next few months. Elusive. I like it.

Callum, thank you so much again. It’s been great to chat to you today. Thanks for having me, Lee. No problem.

Thank you, Callum. And thank you to the listeners of this episode.