Lauri Kinkar, CEO, Messente Communications

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Lauri is a long-standing successful entrepreneur, with a twist. While many entrepreneurs (including, admittedly, myself) will rush to talk up their achievements and give potentially unwanted advice, Lauri prefers to be thoughtful, tailor his approach, and admit the role of luck and timing in his successes.

Lauri has survived some of the most difficult times at Mobi and then Messente, including losing a global client worth 40% of their revenue at the time (!). His wisdom level is all the higher for it.

You can read Lauri’s full biography here



Jamie: Just to begin with, Lauri, what have you found most fulfilling about your career to this point?
Lauri: I think it is the life of relative freedom in the sense of being in charge of my own time, my own hours; I think is what I value that the most. I think that with some sales jobs or with some sales careers, this freedom is something that you get early on, with the need to have a very good self-managing skill, which I have. Of course, sales jobs differ greatly with their level of freedom, but I think that is what I like the most.

Jamie: What is the worst thing about working in sales?
Lauri: I think the flip side is the self-management; not only the simple things like how to manage your own time but also what makes you get out of bed every morning; the handling of the emotional side. Everybody in sales goes through rough patches with very little or no results. You plateau, and then you have to have that wisdom to look for a second opinion, perhaps from a mentor of some sort.

Raising yourself out of this hole in the terrain is extremely difficult emotionally. I have been certainly through a number of those; it does not matter how far along in your career you are, they still happen.

Jamie: Do you mentor younger salespeople at the moment?
Lauri: Sometimes, in Estonia. I am very involved in the Estonian tech scene and the Estonian start-up scene. It is quite successful, overall, I would say. I try to give talks occasionally at start-up events and offer advice when people ask for it, but it is the Estonian way to not ask for advice very often. Everybody tries to tackle their problem alone. We have been starting a fair number of equity investments, as well. Sometimes, I even have the moral right to push my advice on these companies, although I am very cautious when I do these things because I do not think that sales is a uniform thing. For almost all of my life, I have worked with the type of sales where the sales cycle is at least three to six months long. That is very different than selling books door-to-door in the US, for example. I try to think of myself as a student of the game. For a rookie salesperson, I hope it teaches them so much about being energetic and how to handle emotions, going door-to-door sales; perhaps even more than I can teach them myself.

Jamie: In terms of the emotional resilience that is needed for the longer sales cycle, what advice do you give to salespeople?
Lauri: In terms of how to handle the emotional side of it, I would say that I have a very pragmatic approach to everything; there is a reason why you get the answers you do. If the sales cycle delays and you do not know why then it is best to rather pragmatically ask questions.

What do you think is going on, on the other side right now? Which part do I really understand? Who is making decisions? Do I really understand why they are buying? Why did they get rid of me in the first place? What is the value I failed to deliver? The self-analysis, with as few emotions as possible, is greatly helpful.

That is pretty hard to do. At the end of the day, we are all human. With long sale cycles, it is like that.

For short cycles, it is more like B2C sales, where it is more impulsive decisions. Then you can almost compensate for everything with just having super high energy.

When we hire salespeople, we always look for that enthusiasm. For example, all of those Southwestern people who have made door-to-door sales always get past the first round very easily. But then, once we hire them, there is always a fair amount of adjusting how they do things. When those people have been taught how to handle the long sales cycle, that is a really awesome combination.

Jamie: How did you choose your industry?

For me, a lot of things have happened by accident. I think that being completely in control of all the aspects of your own life is a bit of a myth. The opportunities happen to you. You can probably make more of them happen; depending on how active you are in different fields of life.

I started out studying public administration. I was on track to be a government official, but that didn’t happen because I met a person who had just started a company called Mobi, which has now grown into a group. I joined this company as the first salesperson twenty years ago. I am pretty much still here.

If we are talking about career advice, then the one thing that resonated with me a lot is a certain amount of loyalty. Especially in start-ups, they get excited about an idea, you work and probably have some traction. You have some financing and work with it for eight months. Then you lose the first sparkle in your eye, and then you jump on something else. The world is spinning more this way; this from a guy who has stayed more or less in the same place for the past twenty years. Obviously, I advocate loyalty or at least some persistence. Twenty years is obviously a long time, but at least I stayed in one place for a few years.

Jamie: What are the benefits that aspiring salesperson can see if they persevere and spend a few more years in one place?
Lauri: At least in the companies that I have seen and we built in our group, that means you have a very good understanding of the product.

You have a very good understanding of the value of competition and the customer profile – what this company is doing, why, and for whom? Which means that sales, I think, is the ultimate springboard for any other job in that company.

I have seen a lot of salespeople ending up as head of operations exactly, and advancing the highest management levels. You are very well equipped to do so. If you have the patience to wait this one out, then these things might start to happen. But they might not as well, which is the downside.

Jamie: Is it then more important that you select your company well in the first place?
Lauri: Again, in my experience, it comes in joining companies early on. If you join a well-established company that has very clear career paths, then your future might be steadier. If you join the company early on, as a first or second salesperson, for example, that has its own benefits as well. Once a company grows, and you are also growing in the structure.

If I were to choose a company as a young salesperson, I would look at the product and the value in the market. The best companies are those whose product is in a very good position five years from now, and obviously not in a declining market. If you are selling something for which the demand is already slowly declining, it is a no brainer, just get out. But if you are somewhere where the world has not caught up with the value that this thing might provide; that might be a really good position 5 or 10 years from now.

I think start-ups are great opportunities, and if you are the person who can turn this product into actual cash in the bank account, then you are seen as a very valuable player.

Jamie: To best take advantage of those opportunities, if you find a company with a product you believe in, would it be better to have built up expertise on the industry or expertise on sales?

If it is something very complicated, it is better to know the industry. Someone I know is building a company nearby. They deal with ticketing systems for transportation. This has so many complications that you are better off knowing a lot about the market. If it is a less complex sales cycle, then you are better off knowing more about sales techniques.

I think there is a balance, but you have to understand both sides with the value proposition. Am I selling here? If that is your first sales job, the only thing you could have is your high energy, because you don’t bring much more to the table.

From my own perspective, we have this thing that we do not really hire very experienced salespeople. If I had spent 10 years or 20 years in sales, I would not hire me because then I might have a strong idea of how sales are made. The more experience you have, the less you can change your mind, even if the context is a little bit different. We want, “Let’s try some other things.”

I found that for people in their first sales job, no matter how complicated the products are or however complicated the context is, they can learn and if needed, they can change their mind about few of their sales principles. That is the biggest luxury that I have with my young sales team, rather than just confronting the senior salespeople who are trying to tell my sales manager how to sell, and then there is a lot of friction.

I have been in those situations where this beautiful new salesperson energy is something that I am looking for. I am not at all sure this is the right way for everybody, but I have gotten into a habit of recruiting young salespeople exclusively.


Jamie: One of the biggest differences you mentioned is the energy – is that the difference between successful and unsuccessful salespeople?
Lauri: From a world of long-cycles sales, a huge part of it is work ethic. Never skipping a step; otherwise, your feet can get tangled up. Always going through the same process; the same steps, and phases. It is not about hours, or how long someone stays in the office, but it is about whether they actually want it – or are they just going through the motions? The best salespeople that I have seen are the ones that are meticulous in what they do.

Jamie: What are you looking to for someone to say or do in an interview which proves to them that you are your type of salesperson?
Lauri: I do not really give people the “sell me this pen” tasks. I have written a LinkedIn post about never asking anyone to sell me a pen. What I am looking for is, firstly, their ability to bring clarity into a confusing situation. If they are people who can zoom in and out when necessary. I come from the world of fairly complex products, and the need to explain how these things can benefit your company. Then, showing skill at the right moment is extremely important to convince me. I ask them—”What have they done so far? What was the last product that you showed in your last company? Why was this important? Who did you choose to facilitate? Why?” Then if they can explain it to me so that I would buy; this is something that I am looking for. I always give them a writing task because I believe that clear writing is a sign of a clear mind. I look for people who have a very logical way of expressing content.

Jamie: Could you speak to the importance of having a clear and concise elevator pitch?

Yes, I have flunked so many elevator pitches myself. I think that at the beginning of any conversation, especially if it is a cold conversation, it is super important to understand that you have just a few seconds to make an impact. For the cold approach, as well, I get a lot of emails, and I respond to very few of them.


You obviously write hundreds of emails to people that you interview. Your email was three sentences and I never even for a moment thought that I might ignore this one. It comes from you, a person who has a clear idea of what exactly he wants, and you are very economical with your words.

When you have a clear understanding of what you want, you are more inclined towards a good elevator pitch and developing it over time.

Jamie: What other issues do you see with written approaches that you ignore; and the things you are testing for in the written part of the interview?
Lauri: Written approaches are good, and I always look at the cover letters as well. It is a huge source of information.

Your CV might be somewhat interesting or it might not, but it is just a list of chronological events. I always look at whether the person wants to work for us or just wants a job.

Cover letters are important to me. You have to explain whether you are intrigued by the company or not. I see people writing cover letters that already start to go into their train of thought on what the company should do next. That is great. The amazing amount of cover letters – more than two-thirds of what I get – is a person talking about wanting a job, but they do not tailor it to the company at all. We all want a job, but it doesn’t really explain like why you would want to take them up on it for this particular setting.



Jamie: What elements of sales culture do you think an organisation needs to be successful?

Lauri: A culture of jumping on opportunities. For example, in our company, sometimes, let’s say, a request comes in. It is not about the sales manager needs to funnel into the correct person. If you see an opportunity, jump on it. There is a certain element which is the hunger for commission. A culture of work ethic is important, meaning that you really feel the culture of ownership about what you do. A culture of ownership of your craft, as well. You are a craftsman, and you should take pride in what you are doing and do it every day, and let other people understand that you are proud of what you are doing. When you have that, you can have a culture of relative freedom in sales.

Regarding remote work culture, I believe this immensely, and I think that people, in general, are valuing freedom more. Nobody wants someone to look over his or her shoulder constantly, right? But that comes with the company culture where things are done in a very clear way. It is super easy to say, but it is really hard to do. We are consciously trying in the group in which I work. I think we have done somewhat of a good job.

Jamie: As a salesperson looking for a job, how can they be sure that this is a culture of ownership and they won’t have someone looking over their shoulder – what questions would you ask?
Lauri: There are two sides to it. How can the person applying for a job be sure that the culture in this company is what they expected? I try to ask interviewees what they like and dislike about the management they had at their last job or the challenges they had. I usually ask the few things that make you regret your decision once you were hired are; tell me a few things you seriously disliked. Some feedback is so generic, and some is unique and interesting.

“I would really like to go jogging from 9:30am to 10:30am, and if I have to clock in and out of work, then this annoys me.” You get this free-flowing description of how this person wants to work. You get whether this is authentic or they are just trying to get as many perks as possible. Personally, I try to be very upfront about what we are expecting, and it is quite pointless to ask whether you are a person who fits those standards because everybody goes “yes.” But once people open up and you get those unique preferences, I think that goes a long way.

Jamie: Tech is a competitive sector. What experiences or activities can you do out of work to give yourself a leg up?

I think that what helps is if you see a couple of organisations from the inside, then you have that acquired knowledge over time. If you have seen a couple of companies and then you can bring ideas on the table. At least in our culture, it is such that there is a fair bit of democracy in deciding how we do things. When someone has a genuinely good idea, then it is always appreciated.

So that’s one.

Another is that if you are selling tents, you should be like voyager at heart, right? If you are selling cars, you should be a petrolhead. If you are selling telecommunications, you should be interested in the tech. Just be genuinely interested, because I do not think that you can survive in a place that you know from nine to five, that is my job, but outside of it, I am not absolutely interested. It has to be a way of life. Other than that,

I think that if you want to be in sales, you should read about sales. I know few very good salespeople who absolutely dislike sales books. It is not a requirement to be a good salesperson, but I have rarely seen a no-good salesperson who actively reads, which means that if you do that, then that is a sign that you are interested in your own craft and I think gives you a high floor of success.

Jamie: What is the single biggest piece of advice you would give to an aspiring salesperson?
Lauri: If it were limited to a single piece of advice, then I would have to pick the most important one: how to handle the pressure. Don’t worry about things that you cannot control. They will eventually follow if you are meticulous and controlling the controllables.

Jamie: If you had your sales career again, what would you do differently?
Lauri: I would spend some of the last 20 years working elsewhere and have seen more different companies. I mean for myself, to be very honest, one of the things that I wish is that I had seen a lot of companies from the inside. I have seen them as a person who might invest in them, or as a person who has been building them, or companies that are my clients, but I have not really worked in a bigger structure, like other companies that we have built and sold. I wonder what would it be like to be one of the 15,000 Facebook employees.

Jamie: Could you tell me about a time that you did not make a sale, and it was really painful, but it taught you something valuable?
Lauri: We had a huge client, and when they left, it was super painful because they were about 40 percent of our revenue at the time. We tried to get them back. We tried all sorts of things. We met face-to-face, and then I could not understand; why would they decide to leave? The prices were right, and then one of their founders, whom I knew well, told me,

“I mean no offence, but we are leaving for a global operator. You seem to be a regional one at best.”

 Boy did that hurt! I argued with them, and then went back home and it took me about a week to understand that they were 100% correct. In terms of lessons, this was one of the biggest. Estonia is very small. I am very thankful for the candid opinion. I think we ended up developing into more of a global operator, just because of that sentence, at the upcoming year.

The takeaway that I still remember is that sometimes, it is really important to take super painful advice and try to internalise that truth, because people tend to have a very optimistic view of themselves and how they sell.

Jamie: Could you tell me about a sale you made that another salesperson might not have, that shows off the skills and experience you gained throughout your career?
Lauri: We were about to close a deal, and there was a person on the buyer’s side who quite frankly, I thought was an idiot – at the time I was quite sure of my assessment. That was a long time ago before Gmail had the ‘undo’ button which allows you to call back emails seconds after you’ve sent them out.
I had a call with the buyers about a complication in making this deal, and after the call, I wrote to my business partner, saying, “Look, this guy is clearly an idiot.” I hit send, and I realised that I had sent the email to the person in question. I remember weighing my options, then – understanding there’s no way around it – calling this person and telling him that I had made that mistake. I do not remember what happened five or six years ago, but I remember we started to get along pretty nicely after I owned up. We ended up making the sale, and truth be told, this guy is actually super smart.

What that taught me is that the way we think about people will show in our attitude and in our results, as well. Sometimes, you hear salespeople saying, “I have been trying to sell to those guys, but they don’t get it.” In these cases, I always try to explain that if someone does not get your sales pitch, it’s always your fault, not theirs. If you do happen to screw up, please admit that you made a mistake.


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