I worked with Ryan at Gartner, where I always admired his independence, resilience, and thoughtfulness. Despite coming into sales later in his career, Ryan took and obstacles in his stride, remained level-headed and worked hard inevitably to become a top performer – which I understand was also the hallmark of his career as a chef!

Knowing the thought and diligence with which Ryan puts into his sales career made him an obvious top interviewee.

You can read Ryan’s biography in full here

Jamie: Ryan, to begin with, what have you found that was fulfilling in your career up to this point?

Ryan: I think there is nothing more fulfilling than standing up in front of a new team for the first time and doing the equivalent of whatever ringing the bell is  – here, we have a bell. Basically, being able to signal to your team that I am here. I was hired to make a contribution and being able to actively signal that. There is no better feeling than that.

Jamie: What is the best thing about choosing sales as a career?

Ryan:

The best thing about being in sales is that I have the opportunity to learn something new every day. The diversity of the clients that I work with, and the diversity of the problems they look to solve.

I am fortunate in that I am not selling in an IT silo where I am responsible for procurement software that is part of the ERP system, where what I do is pretty narrow. What I do is a different animal. Every conversation with every client can be very different because, in one instance, it could be a finance team that is looking to be more effective; or move jobs from one location into a shared services centre. On the other end of the spectrum, it can be an HR team that is kind of looking at their own processes and how can they take seven teams at seven businesses and combine them into one and find those types of efficiencies.

I just sold a deal about three weeks ago for an industrials company that, what they do is they work with coal slag. And as coal mining has gotten so much more expensive, the slag products are much more expensive. This company takes up the coal slag and repurposes it for other manufacturing purposes, like shingles and other things like that. Given the changes in fossil fuel economies, coal especially, their cost base for these products has gone up significantly. So, they have to rebuild their entire corporate strategy for the next five years. The diversity of conversations that I get to have across my client base is massive.

Jamie: Do you think that sales as a function allows you to disproportionately better yourself and learn more about the world and more interesting things that other functions do?

Ryan:

Yes, because nobody expects a salesperson to be the expert. There is a product guy for that. One of my talents is being able to get up to speed very quickly on a new subject, where I can get to an intelligent and conversational level with the topic very quickly.

Jamie: What are the other things that candidates must have to want to go sales?
Ryan: I think they have to have a natural way about them, socially, where they can mix with people with ease, and no one shape takes. I am not always the best at walking into a room and finding the right person, finding somebody to say “hello” to, and starting up a conversation. For some people, that is very easy. I have other things that I am good at, socially. One of the associates I work with now, he has the opportunity to be an extraordinarily good salesperson, simply because he can poke around. He knows how to get a group of people all engaged, even when one person is dominating the conversation. He has the instincts to see that happening and to change the dynamic. I think that is a very high level of social skill. It can be one of several types of social skill, though.

Jamie: What is the worst thing about being in sales?
Ryan: Losing streaks.

Jamie: How do you deal with losing streaks?
Ryan: Grind. Just work hard and have faith that the luck will change. Every salesperson has had a bad quarter, and there is just nothing worse.

There is nothing worse than falling just short. You never want to be in a position where you look back and say, “I could have done something more,” or, “If I had worked a little harder; I did not exhaust all of the things I could have done to try to close that deal or get that one more meeting.”

So that, I think, it is a combination of not hitting a goal or a losing streak, and then second-guessing yourself, because that is just something that the competitive nature of people who go into sales, to begin with, can fall into that.

Jamie: And what processes do you put in place to avoid falling just short?
Ryan: I do not. That is one of my weaknesses. I am not as processed-driven as I could be. It, therefore, becomes hard to hold myself accountable to. I do not do one specific thing. I can sense when I am in a place where I need to be doing more, and I just focus on output. I put my headphones on, tell everybody around me that I am going to lock it down for three hours and just crank on something, which I did today. Not because I am falling behind; it was just, today was the day where there is a lot to do. I had to get that done. I have to get that box ticked.

Jamie: What are the biggest differences you see in successful versus unsuccessful salesmen?
Ryan:

I think one of the biggest differences is intellectual curiosity. I think salespeople, the successful ones, do have a natural intellectual curiosity – and it may not take the same shape as my own. It may not be their interest in politics and sports and travel and food, and all kinds of different things. It may be that they have a narrow interest and go a little bit deeper, instead of a mile wide and an inch deep. They might be 20 meters wide and 100 meters deep or some other shape of that, but there is a certain volume that their mind needs to have filled.

I worked with a salesman a few years ago who was the opposite of me. He was a deep fintech guy. He loved banking systems. He liked core banking systems, and he wanted to know everything there was to know about it, and he knew every blog, every book, every product, and everything. I was like, “Wow. That is interesting.” When I cooked professionally, there were chefs that I admired who literally knew everything there was to know about three-Michelin-star cooking, and they had read all the books and tried all the recipes. I knew I was never going to be that person. I was never going to know all of it because I need to show off a range of dishes.

Jamie: What elements of culture make a sales organization successful?
Ryan: Transparency. I think the goals have to be clear, the targets never moving. And I think there has to be consistent feedback applied across the organization so that what is good on one team is good on any team. I think that is one part of it. I think it has to be fun. Nobody wants to be part of a team that is kind of sinking, and when nobody is closing deals in any part of the business. I think there has to be leadership that inspires. Again, that can also take many shapes. You can have an articulate and soft-spoken leader, who is a fantastic communicator with few words; and you can have a passionate, emotional, outspoken leader who inspires differently. But I think there has to be an element of inspiration.

Jamie: Can you give a specific example of a person in an organization, a person with goals, that you found inspiring?
Ryan: Yes, my current MD. She is an inspirational leader because she is honest, and she is a straight shooter. She is very open with us about the business and what the expectations are; much more so than other MDs I’ve worked with in the past, other MDs in the industry, and other business leaders out there more broadly. We will fight for her. My whole team would fight for her. We would go to war for her. She is just one of those people. She is just great. On the flip side of that, I have worked for teams that were the exact opposite of that. Where you look around, nobody wanted to go to work for the boss. Nobody liked the boss. Nobody wanted to be there. We had to develop the culture and the camaraderie ourselves. We developed ourselves, and we knew we would go to war together. We would not want to go to war for the general, but we would do it for each other.

Jamie: When you had great leadership versus not-so-strong leadership, what differences did you see in terms of staff turnover and retention?
Ryan: Well, significant. One business, I was employee number one. We grew the business to fourteen, in about two years. I left to go get experience and kind of see the other side of sales. It had been my first sales job, and I came back to the business, nine months later, and was effectively employee number five the second time around. There were only one other, maybe two other familiar faces,. The business effectively turned-over more than about one hundred per cent in nine months.

Jamie: How do you go on about picking the organizations and products that you sell?
Ryan: It is also something I am not necessarily the best at. In my first sales role, I networked my way in after a move to England. I had been a freelance chef for a couple of years, at dinner parties and stuff. Once my family decided to settle in the UK permanently, I realized I do something different. Through personal networks and former colleagues, I was introduced to my former boss’ lovely wife, who wanted to give me a chance on her sales team. I was ready to get the job offer, then they missed their seed goals and had a hiring freeze. My boss-to-be was like, “You should meet my husband, he is hiring.” I met him. He hired me. That was my first sales job. I was there a couple of years and left and went back. The greener pastures I left for were not necessarily the right fit.

I was in a role for three months after that first sales job. Part of the reason for the short tenure was that the organization was changing, and I didn’t know that in advanced. I had no way of knowing. When I took the job, we were a brand-new team. We were three new hires, really great people on the team. The guy who hired me was super smart, really great. I could have learned a ton from him. But even before I started, before I got my contract, I learned that instead of having an office in Central London, the business was relocating to Slough. My team was going to have hot desks, and I was not going to a permanent environment where I was surrounded by people every day, and I would not have co-workers around every day. It was going to be remote work – ironic if you look at where we are now with COVID. And as soon as that happened, I knew it was not going to be a fit, and that is how I founded myself at Gartner.

Jamie: What advice would you have for aspiring people seeking a good organization and a good product to sell?
Ryan: I think what you need to do, more than anything, is to find the right person you want to work for, that can be different for all people. It can be wanting to learn from somebody with a very different set of skills than you or wanting to learn with somebody who has what you think are very complementary skills to you. I think it is more important to find the person for whom you want to work than the product you want to sell. In any type of sales organization, I could learn the product and try and find things about it that I think is really interesting, and would stimulate me intellectually in a way that I can do the job. What would be more important for me is finding the team I work with, because that is where you spend your time.

Jamie: And what is the single biggest piece of the general advice you would give to an aspiring salesperson?
Ryan:

Just put your head down and crank. It is a grind. It is like running a marathon. I think if you want to have a career in sales, you are not just trying to sprint from deal to deal. It is about establishing a consistent cadence. I aspire to have a sales pipeline that is metronomic; that I am carrying over, with consistency, meetings, and deals, and revenue, because that is when you get into a cadence of predictability, which I think is really important and that is when sales can be even more rewarding.

You have to know you are set up to be consistent this quarter and next quarter. Then those sprints, that 100-meter sprint and that 200-meter sprint; those are the extra deals that you can chase on top. Those would be the icing on the cake. Then you can push and go for a quick sprint here and there because there might be a quarterly accelerator or quarterly bonus. But I think it is more important that you want to run the marathon.

Jamie: If you have your career again, what would you be, differently?
Ryan: I would not have left Gartner and gone back to a previous role, that was a big mistake. It was a risk-reward situation that I knew could play out one way or another, and it played out the other, which is fine. In reality, what that did was bring me to the place that I am now, which is as rewarding a role as I could imagine being in. It’s a company that I know values me. That allows me to express myself and my ideas, and allows me to get involved in many other parts of the business; to influence the direction of my team and the culture of the organization. That is a cool place to be.

Jamie: Could tell me a time that you didn’t make a sale, but learned something valuable?
Ryan: I had a project some years ago in the retail space, and it was a budgeting process transformation project, where the head of finance for a larger retail company that normally operated with a team of three, but had some attrition, needed to do their yearly budgeting cycle and wanted to rework the whole process and bring in a consultant. We found the perfect person and know that they would just hit it off. It seemed like an easy sale. We even kind of got through to the last stage of the contract where it was out for signatures, and things are being reviewed by lawyers, and then the consultant’s father was diagnosed with cancer. The consultant had to turn down the deal the last moment, and it was too late, nobody else could replace him. The client was really upset, and there was really no going back because there were no other people that could do it. The way it played out was that they wanted us to replace the consultant on the same day rate. We were not in a position to do that. It would have cost our business money. There was just no way to make it work, and the relationship ended up blowing up because of it. Because of that deal that I missed the first quarter that I have ever missed, simply because that fell through the cracks.

I learned that there is probably something else I could have done that quarter to get another deal because I was just short of the line, and this deal would have brought me well over. I probably could have found another £25,000 deal over the quarter to get to my number and not fall short, and I realized that is where you need to try to be more steady instead of up and down. Interestingly, I spoke to that client again, just this past Monday.

He brought up in the course of that conversation how sceptical he was of even taking the meeting in the first place because of how things that happened in this first deal some years ago. We were able to bury that hatchet and have a really, really great conversation. I learned two things from that; not every broken relationship needs to stay broken, and you can always go back to people.

Jamie: Can you tell me about a sale you did make that shows off the skills and knowledge you gained throughout your career?
Ryan: One of the first projects I worked on, we were introduced to the client by an intermediary. They were doing a huge business transformation project. And it was pretty clear from the middle of the first phone call that we were late to the party, that they had already been interviewing people and they were probably pretty far along in the process. To me, that is usually a red flag; that we should not waste time with it, but I knew we were going to have a really good opportunity to throw a spanner into their plans if we did react quickly, and we did.

We did not end up winning that deal. They ultimately went with somebody who was already in their pipeline, and subsequently imploded and regretted that, because they should have let it breathe a little bit more.

A month later, the same client was so pleased with the way we served her the first time, even knowing we were pushing and coming from behind. With the acknowledgement of that, she wanted to give us the first chance.

She came to me, he was looking for a very specific type of a person – a Chartered Accountant with different types of skills to fit in and really kind of be the analytical person behind the business transformation, and help build business cases for different investment scenarios. I took that away and went around and was talking to consultants trying to get some proposals together from her, and what I came back with was somebody very different than what she asked for. It was not a Chartered Accountant, but it was somebody who had helped stand up the analytics practice at a big four accounting firm. He knew enough about accounting and was numeric enough to be able to do the job effectively, and he was fundamentally a problem solver.

Instead of coming to her with a proposal of three or four candidates in different price ranges, I gave her a proposal for one candidate and said, “This is your guy, and you need to talk to him. He is great.” They had both worked for the same big four firm, and they spoke the same language. They absolutely hit it off. She called and hired him on the spot for a significant contract. Subsequently, the head of transformation, who hired him, was going on maternity leave – he has just been reviewed and offered another year because he is going to step up to her role in her absence. What we ended up doing was giving them somebody that was so much more than what they initially asked for, and through COVID, what they needed more than anything was not somebody who could just be accountant, building their models and stuff, but somebody who could really help problems solve and help them adapt very quickly to all of the chaotic scenarios that COVID put into place. That has been a great success, for them and for us.

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