Mastering Sales Leadership and Overcoming Challenges in Business Growth

I’m very well. How are you? You okay?

Yeah, sure. Try and cover those three as quickly as I can. My journey is actually a really simple one. Born and bred in the UK, moved to Austria. We’re traveling after university. I moved to Australia or went traveling to Australia, ended up staying for eight years and got a job in sales because I ran out of money really quickly and never intended to go in sales. I don’t think I really knew what I wanted to do in my life at 21, 22 years old. But I found Absolutely found my place in sales and worked in a sales and marketing agency for eight years over in Australia. Then when I reached the grand old age of 30 and started thinking about having children and all those sorts of things, my wife and I moved back to the UK, and that’s when I launched Air Marketing. I would say at heart, I’m a salesperson. I’ve ended up a founder and a CEO, but I think that is a very valuable experience set when you’re trying to build a business. Now Air is eight years old, we’re nearing 100 people. Ultimately, We contribute revenue into other businesses as an agency.

We do that across primarily three different ways, outsource sales development reps or outsource SDR. We’re out talking to your potential customers about your services and trying to book meetings and drive pipeline. Our outsource marketing services, which is us driving marketing campaigns to create demand, so whether that be events or digital marketing or paid ads or content that captures your audience’s attention and gets them talking to you. Also our sales academy, our SDR Academy, which is live trainings, group training sessions for sales development reps from multiple organizations ran live every single week, so people can tap into those training sessions and learn amongst sales development reps or sales executives in other businesses, creating a community of people that are trying to learn and progress about sales all of the time. And through each of those three channels, we help drive revenue opportunities for our clients.

Yeah, I think they make 80% great CEOs. I think it certainly helps to be able to sell. I think without a doubt, it would have been very difficult without being able to sell because, of course, you don’t sell anything, there’s nothing to do. I certainly have always prioritized sales, whether that be existing client sales and retaining existing clients longer or growing an account or new business. What I would say, though, is that salespeople typically Typically, we also have traits that don’t make them a good CEO. We tend to be a bit more short-term-focused, very top-line-focused. We’re not always the best leaders and the best well-rounded commercial people. We’re not always detail-focused. That’s not always true. We can’t categorize one role with traits necessarily. But certainly, from my perspective, it’s been better because I was a reasonably good salesperson and a sales professional. But I could also see weaknesses where around that, it’s not the only skill you need to be successful. So I’d agree on the most part, I’d far rather be a sales lead founder than any other founder.

Yeah, it’s an interesting one Because I’m one of these classic people that went to university because I didn’t know what to do with my life. I was always reasonably intelligent, a bit of a jack of all trades, went to a good school and got reasonably good grades, but never really worked that hard until I got into business and found my passion. But I knew I needed to go to university for no other reason but for the life experience. What I can’t say is I’m so glad I went and studied those things. I studied them because I enjoyed them, not because I had a clear path on where I wanted to go. I blended two things that I enjoyed it, one of which was creative writing and language, and the other is theater, which is a passion of mine and still remains a passion of mine. I don’t think I ever thought that the theater side was going to turn into a career for me. It was more, Hey, I want to at least enjoy what I’m doing when I’m there. The English language piece was me taking it maybe slightly more seriously. But what I would say is by going to university and doing that degree, I learned some incredible life experiences that have helped me where it comes to driving a business, building a team, leadership, ambition, how to commit to a deadline, how to get stuff done, how to manage work-like balance, all those sorts of things.

But then naturally, certainly around the language and the communication skills, in both of those degrees, you’re presenting, you’re doing things that are practical, you’re having to write, dissertations, build effectively a proposal to sell your idea. There’s lots that you can translate into commerce and business after that. But I won’t say that they’re the best degrees for getting into commerce by any means, but the fact that I went through that was very useful for me.

The first 12 months of growing this business was the hardest year of my life, without a doubt. Not helped by the fact that we just had our first child We had the sleepiness nights and the stress of all that stuff added to it. But I massively underestimated what starting your own business meant in terms of the level of commitment that you needed to put in, the amount, the sheer amount of workload that you have to the amount of hours that you have to put into it if you want it to be successful. I always say to people, you can choose not to do those things. You can run a lifestyle business and you can be a founder, call yourself an entrepreneur. But if you want to grow a multi-million-pound business, that first year getting off the ground is critical, and you have to just be so dedicated to its success. I think some of the challenges that I remember most clearly from those days are, one, you are all things to all people. You are the head of client services, you are the head of sales, you’re the head of marketing, you’re the head of admin, you’re the head of IT, you’re the head of office, everything.

The buck stops with you for everywhere. There’s never a break, there’s never a moment to switch off, there’s never a conversation that you’re not involved in. You would flip from being in a sales presentation with a potential client to dealing with a difficult client to dealing with your internet supplier because your internet is not working properly or your phone system supplier into managing the books in Quickbooks or in Xero and you’re suddenly finances. In a day, you’re doing 10 different jobs. The ability to adapt and to move from one task to another, to be organized, to stay on top of it, and to hold a steady mindset and your mental health and your well-being, all that stuff, when you’re working that hard in such a spread way is a real challenge. I think when it comes back to my first 12 months, there’s a lot of operational challenges, there’s a lot of marketing challenges, there’s a lot of specific challenges that I could go into that are fairly granular. But that for me is the one that as a founder is I’ll never forget the weight of that or the impact of that. I certainly didn’t realize it would be as impactful as it was.

I got through it. Got to be resilient, got to be fairly tough, you got to be fairly stubborn, and you got to have enough of a motivator to want to get through that. If your motivation isn’t strong enough, you won’t. But if you do, it gets much, much better every day thereafter. I think probably that’s the thing that I tend to go back to from that first year.

In terms of the traits of the people, you mean?

It’s a really hard one to define, isn’t it? Because I think people’s view on what they need for sales role is very different. For me, I’m always looking for somebody in an interview process who will open up and be real with me. I’m always looking for somebody who will give an opinion, somebody who will get outside of the interview box. I tend to ask questions that people wouldn’t normally get asked in an interview because then you get real them, not prepared them in an interview state. I think I’m always looking to try to identify who they are as a person. But I guess in terms of the traits, I’m looking for somebody who’s pretty driven, pretty stubborn. I said it before, pretty stubborn, somebody who’s got the resilience and the ability to deal with nos and isn’t going to get beat up by that. I’m looking for somebody who’s got something about them in their personality that makes them stand out in a crowd, that makes them be slightly different, that makes them be noticeable because everybody’s trying to sell something nowadays and you’ve got to be able to stand out. I’m looking for somebody who’s genuine, who I can actually get to know in that process.

I’m looking for somebody who will challenge me or who will bring an idea or who will have an an opinion on something, not somebody who’s going to be a passenger on the journey. I think those are just some of the things that I would look for in somebody that I was looking to hire into my sales team.

There’s an interesting thing in growing an agency. We’re about 100 people now. There’s a couple of what I call phases in that growth journey that you go through. One is when you move from somewhere between 10 to 20 people, and what happens is you start to need managers, so you can’t do everything to all of those people. If you get 15, 16 people, you have to choose somebody in your team to banish and to be Then there’s another phase at about 30 to 40, maybe 50 people, depending on the type of agency you are, where you need managers managing managers. All of a sudden, you’ve got two lines of management. I think that was probably the bit of running and growing our business that I got the most wrong, because what happens in that period of time, there’ll be different stages for different people, but your culture changes entirely. The culture of you as the founder, people buying into you, people knowing you as a person, being driven by your motivation, buying into your vision changes and dilutes completely. If you get those people wrong who become the heads of departments or are managing teams or whatever it might be, it can unravel all of the good work you’ve done to that point very quickly.

I went through a period of where I got that wrong, where I either promoted people, what I call for the point of failure. They were really good people at their role, and I assumed, Therefore, they should be able to step up and do the next part, but I wasn’t able to support them and enable them, and maybe they weren’t the right people to be managers as well, and that caused challenges, or I hired the wrong people into the business because it wasn’t clear on what I actually needed and was hiring on the wrong things. That period of growing a business, and I don’t think it matters if it’s an agency or any business, that period where you start to bring in managers that aren’t you as a founder or managers of your managers is a really dangerous period. I would encourage people to get external input and advice at that time. Really stop and think about what you need, what you don’t need, what’s right, not what’s not right. Involve your team in that conversation because we grew really quickly and had to make those decisions on the flight really quickly. I wish we’d done that in a more considered way because we probably lost a year or two of progress just by cultural impact within the business because the business shifted and changes and our processes had to catch up.

Yeah, a really challenging period, one in which I learned a hell of a lot, so I wouldn’t change it. But if I had my time again, I’d certainly do it differently.

I’ll put it back to you. How much rapport have we built talking to each other in the period of time that we’ve had a human conversation today versus our email exchange before meeting each other today. The difference is substantial.

And there’s your answer, right? So the whole time that humans are buying from I’m not saying you’re going to buy anything from me, but if I tried to sell something to you now, I’d argue I’d have a better chance now than I did at the beginning of this conversation. That’s because we connect as humans and we build rapport when we have a conversation. We don’t do that in the same way via email. We don’t do that in the same way via LinkedIn messages. Now, I’m not saying it doesn’t happen at all, but the percentage of impact is so small. The whole time it’s humans buying in B2B, I’m talking rather than e-commerce buying a product or whatever it might be, the whole time we will need humans in in the sales process. The best way a human can engage with somebody else is ideally face-to-face. Let’s face it, it’s face-to-face, so we can physically shake each other’s hand and build rapport and share a cup of coffee in real life. But You’re on a different continent to me right now. This is the second best way of doing it. The third best is the phone.

The good thing about this is we can see each other. But the bad thing is I can’t just pick up the phone. I can’t just pick up Zoom and talk to you and you answer it. It doesn’t work like that. We got to already know each other. The And phone is the only tool that allows me to get to you when I drive it and have a human conversation with you. And that human conversation, for me, is the thing that elevates the connection between a prospect and a salesperson. And it still remains the most powerful tool in your sales tech stack, in my opinion.

For me, AI in the sales process is an enabler, not a solution, not a replacement. I don’t see in my working lifetime, and look, if I’m proved wrong, I’m proved wrong. But I don’t see a time where salespeople will be entirely replaced by AI. I see an opportunity to build huge efficiencies for us to be far more productive, but I also see a negative impact of AI. The volume of LinkedIn messages, the volume of cold email that I’m getting that is at the moment really poor because it becomes so much easier to write a personalized email, it is absolutely ridiculous. What it’s done is it’s walked me away from engaging with email as a channel, with engaging with LinkedIn emails as a channel. When somebody does actually phone me and make the effort to do that and have a human conversation with me, actually, guess why it’s standing out a little bit more because of all the negative noise on digital channels. For me, AI can play a role. What it can’t do for me right now is be a genuine, scalable, outbound solution to win new customers by itself. It can help get your salespeople into more conversations.

It can help them be more prepared for those conversations. I think organizations should absolutely be embracing AI, but using it with caution and care. If you are going to double down or expect it to do all of the work for you, I’m afraid you’re walking towards a hell of a lot of disappointment.

Always on LinkedIn, but just don’t make it via a bot. Make it real. They’re right to me. So, yeah, Owen Richard is on LinkedIn, Air Marketing. Look me up and send me a note. I’m always happy to talk.

Thank you.