Starting from his early days of being a Sales Director at IBM to then being the Chief Commercial and Chief Revenue Officer of brands like Railsbank, Fuse Universal, and The Currency Cloud, John has had an impressive career in sales.
Now, he shares his wisdom on sales processes, closing complex deals, and sales leadership as an advisor and a fractional CRO running his own consultancy company JHKL. John also shares his experience and learnings in his blog The NOT so secret CRO.
Or skim through the summary of the conversation along with the key takeaways. 👇
The road to sales leadership
Growing up between London and Hampshire, John went to boarding school there and was into a lot of competitive sports since childhood, which had a huge impact on his professional life later on.
Earlier in his career, he pursued sales management in a way that he pursued sales — was pretty aggressive, very direct, and results-driven. And what he has learned over time is that a more measured, more considered approach can give you not just better results, but significantly better results.
Because often what you're doing is opening up the relationship by making people feel relaxed and calm. You should adopt the position that you are helping them.
"It's too easy to think that I'm selling you something. Actually, where I've got to with all this is I'm a business person, the other person's a business person. I've got something that helps you. We're trying to work out how we do it together. I think if you take that approach rather than this kind of I've got to hit my target, then you kind of get there."
John believes it's really important to remember the impact that you as an individual have on anyone who works in the company you're in. They don't even have to work for you as a senior executive or senior leader.
For example, if you're slacking people late at night, you’re normalizing this behavior, you’re showing that it’s what you expect from everyone. And this will ultimately lead to burnout for people.
There's a great quote by Peter Drucker that John loves: “Management is about getting things done. Leadership is about doing the right things.” For him, that's about behavior, setting the right standards, showing people what good looks like, and making sure it's safe. All those things are really powerful but often hugely underestimated.
"In a really objective business-like way, human beings are the number one resource. But if you flip that model and say, we're a team and we're building a great culture, that, I think, is really what it's about."
Challenges of a first-time leader
Once John got into a leadership position, his main challenge at the time was really about how to get all this stuff that was in his head, that he had been bottling up, out and how to get everyone into it.
John confesses that he’s made so many mistakes he knows roughly what good looks like. But his main mistake at the time was this idea that he made so much sense and everything he thought was so logical.
"I knew what to do. And I was very clear about what needed to happen and the processes. And I was right. But actually, my challenge at the time was helping people understand how it would help them and motivating them into it."
Then, during his time at IBM, John did an 18-month course with 12 weeks off-site and a two-week assessment center. It was a really serious thing. And he developed this incredible set of skills, this infrastructure in his brain of techniques that he could fall back on when times are difficult.
But it’s a lot different for the newer generation of salespeople in tech.
For John, it’s part of the beauty of the tech industry — it's so vibrant because there are so many young people with fresh ideas and fresh technology and all this kind of great stuff, lots of different communities. But the fundamentals remain the same. And if you're not clear about those, then you're going to struggle
"There's no AI that's going to solve the fact that your proposition is rubbish. You know, if you can't qualify well, you're not clear what you're qualifying for, it doesn't matter what tools you've got. If your people can't ask the right questions in the right way, if you can't build rapport, this is where the challenge is."
Building processes and setting targets
When getting started as a first-time leader, all the skills that got you there are totally inadequate for the thing you're about to do. All the things, like being focused and working hard, are not appropriate for leadership in the purest sense. They are of course appropriate for leadership, but actually, it's a whole bunch of other skills that you've got to develop or unravel.
The challenge that you face now is that you know what works because you did it and that's why you got promoted. Now what you’ve got to do is bring a load of people with you. And that's a very difficult thing to do because you’re now putting your future in their hands. You’ve got to teach them how to do it, but they've got to bring their skills to the fore as well.
John suggests finding a way to connect with these other people, so you enhance the pool of knowledge and create that collaborative experience that becomes what drives the next stage.
Yet, in John’s experience, every large company struggles with this because you're nowhere near where the collaboration is to create the process. That is why John chose to work with smaller companies. As the walls are always moving, you have to constantly innovate around processes and ideas and people really buy that because they were empowered to participate in it.
"And I think my advice to [first-time leader] is: Participation is the key because as soon as that participation happens it's not your idea, it's their idea, it's our idea."
If there’s one thing that John knows about targets is that they only go up. So you have to accept that as part of this world. But also your role as a leader is to resource that pursuit — what do we need to hit that target, to be successful? Not just what you need, but also what do you need from other departments? Are you clear about that? Can you ask for it? Could you measure it? Do you understand the investment? What's the return? And all of those things, they all require participation and collaboration.
"The idea that sales are over there and sell, that sort of breaks my heart a little bit because everyone jokes about it. Sales sell something and then hand it over to onboarding and everyone goes: “What the hell did they sell you?” I just think that's just the worst thing. If that is where you're at, something is so horribly wrong that you might as well burn it all down and start again."
John ran a lot of good teams and what was common across those teams was (aside from what we’ve mentioned above) this sense of shared purpose for whatever reason. It was different in each circumstance, but they always had this genuine sense of common purpose which helped John identify the direction he wanted to go in. And people then started to work it all out.
At the same time, John mentioned that the most common mistake he ever made was telling people they had to do something because he needed it. That was actually the number one reason not to do it.
John mentioned a study by Ebsta analyzing the difference between top performers and average performers around things like the use of MEDDIC, updating deals, etc. which is mind-blowing (hundreds of percent). This is the kind of information that he would use to help people understand the value of these things.
"If I can inspire you to connect the thing that you want to achieve with the thing that we're doing at work, it kind of connects like that. And I've given you a method by which you can improve. That's the win. That's how you get processes implemented."
Understanding sales velocity and the “golden period”
Talking about the qualification (or rather disqualification) in sales, John mentions the concept of a “golden period” — the period that the median or the mean period that your deals close. It might be 60 days for some companies, or 180 days, or 360 days, or whatever it is. But there always is a timespan in which your deals close.
If you are one month outside the golden period (according to the Ebsta stats), you have a 60% lower conversion rate. If you're two months outside the golden period, you're at a 90% lower conversion rate. But conversions are 165% better inside the golden period.
John mentions that 68% of deals are closed below the golden period, and 89% are closed at the end of the month. But the high percentage of deals closing at the end of the month raises a concern for him, suggesting a lack of awareness in the sales industry about the pace and rhythm of closing deals.
So rather than hoping a deal would close by the end of the month, John believes in working with people on how they are going to get this deal closed and understanding the average velocity “golden period.”
"So this golden period for me, this kind of velocity pace, is super, super important. I think it's really underestimated in sales because we often think opportunities created x average deal size x conversion rate is the kind of magic formula. For me, there's a little line underneath, it is velocity. Because if I can squeeze the velocity down I give myself more sales cycles in a year that's a really simple way of getting more sales done."
However, John suggests being mindful so you don’t over-compress your deal velocity. Just try to find that magical spot.
If you’re a first-time leader:
Make sure that you build relationships with the people that you're going to lead and understand what they're about. Without that, nothing you do is possible, or nothing you want to do is possible.
Don't assume that you know everything. That is the height of arrogance as far as I'm concerned. Assume you know some stuff, you might know some of the best stuff, but ensure that you're out from everybody else and increasing it.
Assume that you're going to get things wrong, but think of it as experimentation. So if you go into something with this view that says, I'm not sure I know the answer to this, but we've collaborated and we're going to try this and see what happens. And then we're going to measure it. And then we're going to retune based on what we find. You've got a much better chance of success because you're not personally tied to any out.
"I think winning deals is about helping customers. If you have figured out how you're going to improve that customer, you'll win more deals than you lose. Which is all we can hope for as salespeople."