Katrin is an experienced hand in the consulting world, especially in helping start-ups to improve their sales and marketing process, hire, and scale. Her principles come from her book selling days, combined with sales technology and travel, and make for a compelling consultant career.
Katrin’s communication was intense but lighthearted, and fun but direct; as are her stories and anecdotes in this interview.
You can read Katrin’s full biography here
Jamie:. Katrin, in your sales career, what have you found most fulfilling so far?
Katrin: There are a couple of things.
Number one is freedom, like when somebody cracks how a successful sale is made, they will also understand that the whole world is now open to them. By the whole world, I really mean the whole world. Not only can you choose a career on your terms but also can move to any country at any point in time. You can find a job anywhere.
It is like having your own business. It does not matter where you work. Another thing that I love about sales is the constant need for personal growth; you have to keep on learning all the time. You cannot sit in the same corner and be a very good salesperson because the world is changing so fast, and companies are also adapting to these changes really fast. You just have to keep up and be on track.
Jamie: What is going to happen to the salespeople who do not keep growing?
Katrin: I think they are just going to be pushed aside.
It is almost like the train is moving all the time. If you step off the train, then the train will move past you. You cannot be a very successful salesperson unless you are constantly growing and learning.
It’s like you rest somewhere at a point of time, and you stay still, and somebody passes you by; for big egos, that is very hard.
Jamie: Do you feel like you can have too big an ego to be good at sales?
Katrin: I think that for somebody with a big ego, it is hard to accept that the world could move past them and push them aside. Some people are looking for balance, and some are not. For some people, balance is always being number one, at the top of the game. They simply cannot stand when somebody else may become, at some point in time, more successful than them.
Jamie: Would that person then usually be a good salesperson if they are driven to be number one?
Katrin: I think from what I have seen so far, it is typically temporary. I have seen a lot of burnout in this sector. That is, where you just want to be so good so badly and that you are just so used to being in the limelight of being this number-one salesperson. When somebody is actually moving faster, I think that should also be fine because younger salespeople are coming up the boards, who are excellent and more energetic.
Being in the stage of life where I’m having children and building my family, I can still be successful, but I do not need to be number one, at the top of the game, all the time. I am really happy and grateful when I see junior people succeeding. They take all the knowledge they are able from me, and then they move to the next level, and then they become number one. That makes me proud.
What I have sometimes seen is that when people get into the stage of having children and creating a family, it is very difficult to figure out how you can be the number-one dad and number-one salesperson? I have a feeling that you have to choose.
Jamie: Do you feel like you did the pace of change that you are talking about, the risk of being left behind, is higher in sales than in other more technical professions?
Katrin: That is my experience. It can be good. It can be bad. There is the pressure of self-development all the time. The reason why I am saying this, too, is because I am in sales consultancy. Listening to some other consultants, sometimes, I am just surprised because some of the techniques that they teach are 10+ years old. I see that those techniques work in older organisations, where people know nothing about sales, and they just need a motivational boost.
Working with start-ups, I cannot be teaching them some outdated tactics that were common even five years back. Luckily, I feel that I would get bored if I were teaching the same tactics year after year.
Jamie: What are some of the biggest trends you have seen?
Katrin: I would say the most interesting thing for me has been to figure out how sales and marketing should work together. Us older salespeople, we still have this arrogance of, “Come on, marketing does not really sell. You still need to pick up the phone and really sell stuff.”
But now I see that social media and marketing is becoming a more and more important part of the sales cycle, especially for a start-up. Some start-ups that I work with, they really do have disrupting ideas and amazing technologies, but the experienced people in older corporations with money, they know that start-ups can come and go. They do not want to invest their time into dealing with a start-up that will disappear in six months after they don’t get the next rounds of investment. I feel like good marketing can build a lot of higher trust for the brand, for the people, and for the longevity of the technology itself.
Jamie: Given that there are a limited number of people in a start-up, is it true that the sales and marketing personnel are often the same person?
Katrin: No, with my clients, these positions have been filled by different people. Often, the founders or even the companies themselves do not have a clear understanding of what the marketing person should do and what a salesperson should do, and the roles often seem to criss-cross. So, they want the salesperson to do the marketing and the marketing person to make the sales.
Another thing that happens is that when they recruit, they don’t put the functions together and make them communicate, which is sometimes funny because the marketing person works on lead generation, and the marketing message is completely different from the message that the salesperson is trying to close on.
That is what I am doing with quite a few of my clients. I bring the salespeople and the marketing people in the same room, so we speak the same language. They are often super grateful because they typically have amazing ideas for each other, but somehow they never have that opportunity to actually talk to each other.
Jamie: I look at the sales side specifically, what are the biggest skills you advocate hiring for in start-up sales?
Katrin: Sometimes, I participate in the process of hiring salespeople because of my background as a sales leader. Typically, I can spot within one or two interviews if they could be good. With start-ups, basically, teachability is number one; openness to learning. Sometimes, I give them random assignments to test that.
For example, I had an interview with a potential market sales leader for another country. The first interview went OK; I had my doubts. Then I gave him a sales script to practice, and by the 2nd interview, he could not even get past the second sentence. He was like, “OK, I need to start over. I need to talk to start over.” Then, he muttered, “I need to put a salesperson-mask on, so let me do this again.” After four trials, he completely broke down. He was like, “OK, I cannot do this. I was planning on hiring some other people to make the sales for me so I could be a market leader.” To be a sales leader, you need to be willing to go out and get your hands dirty when you need to.
Jamie: Have you ever interviewed someone so amazing that you were like “I have to hire this person”?
Katrin: Yes. Great sales rep candidates for my clients can stand out already in 10 minutes. I believe that even the “10-minute-hire” needs to go through a hiring process, so they feel that they have earnt the position.
What I love about potential candidates is when they come in prepared. When a person comes in, and they have not even checked the website because we reached out to them, that really is a big let-down.
I love those candidates who ask smart questions because they are interested, not because they are trying to teach the start-up or me how “things really need to be done”. Some candidates think that they know better than the company founders, who probably have already tried and validated a ton of ways. Having your own ideas is great, but there is a right time and a way to present them.
Jamie: What is the biggest difference you see between successful and unsuccessful salespeople?
Katrin: The willingness to work with a longer-term potential in mind. People who come in with the “How much I can make today?” mindset typically do not last very long. The ones who come in with the view, “How can I be a part of this amazing journey? And maybe, earn quite good money on the side, and learn something really good for my future.” Those work out.
I have seen so many mis-hires. What happens quite often is that the start-up gets some funding, and they need to get a new salesperson fast. A lot of start-ups – which is one of the mistakes – the first salesperson that they want is somebody who is really experienced in their field. They come in, and they are like, “I know exactly how it should be sold.” But disruptive ideas might need a completely different mindset and even some naïve beliefs about the industry in question.
So, when the experienced salesperson can’t produce results because they fall back to the “old ideas” – it hurts in two ways; the start-up is unhappy because they don’t understand why their idea is not selling, and the salesperson is unhappy because they think that the product sucks, because they are being sold on the “no’s” from the market. It can cause a lot of confusion and pain.
Teachability and openness to adjust and learn on-the-go are huge. Also, real expectations need to be set before day one. I helped to conduct an interview with a 40 plus-year-old person sho was being interviewed to be the COO for an organisation. The organisation was led by the founder, who was under 30. I asked the candidate lots of questions like, “Are you really sure that you can put in the work, and you will enjoy working here?” He was coming from an old corporation and a different style of working. I was quite direct with my questions; “Are you sure you want to do this? All the people here are younger than you. They think that they are smarter than you. They won’t be paying you much money as you were on previously, and there will be no stability in your work and no set schedule.” I was also preparing him for every possible scenario for his first few months and wanted to prepare him for the contrast between “the old and the new”. If he hadn’t agreed to all that, that would have been OK. That hire went very well, but I have seen many older, more experienced salespeople fail because of the wrong expectations.
Jamie: Would you talk a little bit about the importance of having effective salespeople in a start-up?
Katrin: When there is an effective salesperson in a start-up, then the whole organisation can actually work. There are definitely times when everybody loses some confidence in their idea; when it seems it will not work and when there is only negative feedback from the market. I mean it can go both ways. On the one hand, “Does the market really need this product?” But on the other hand, “Do you actually know what you are doing in terms of sales?”
For example, one of the start-ups for whom I’ve consulted refused my help at first, “You know what, we just hired a salesperson, he really loves sales, and he will be helping us out, so no need.” I met that same salesperson at an event about two months later, and when I asked him, “Hey, how is it going with this company?” He was like, “I have no fucking idea what I am doing.” I said, “They told me that you are an experienced salesperson.” He said, “No, I read a couple of books, and I just came back from Australia, and I wanted to learn sales.” He was the only salesperson for this whole organisation. So, we reached out again and closed them.
The funniest part is when we actually started working with this person. So, first of all, we would not have hired this salesperson because
the first salesperson in any start-up should not be a “thinker”-type of person, if you know what I mean. They should be a “doer”. Sometimes they just need to go out and find a way.
That person, when we just started to work out some of the lead generation tactics and emails templates, he called us after every single email, “Hey, what should I do now?”
There was one week we agreed that he would work through a list of about 100 leads to get some market feedback. In two or three days, we asked him, “So, how has it gone?” He said, “Yesterday, I spent four hours crafting this one email.” Obviously, there weren’t one hundred leads which had been contacted.
Jamie: How many of the founders you’ve worked with are actually salespeople themselves?
Katrin: By now, because I get to choose my own clients, I would say most. I qualify my clients because I have worked with some organisations where the founder is not willing to participate in working out sales strategies, and that just does not make sense for me. It does not make sense because there is nobody there to implement anything. I feel that the founder needs to be highly involved in designing and implementing sales strategies.
Jamie: What elements of sales culture make a sales-oriented organisation successful?
Katrin: Accountability, and good communication. A salesperson is a very emotional creature. They need to communicate. They need to share their feedback and feelings. They are hearing a lot of ‘no’s, right? If they are good salespeople, then they will hear a lot of ‘no’s.
They need to share them with someone within the organisation – somebody that will lift them up or at least listen to them – because if they do not do that inside the organisation, they are going to go outside the organisation. Obviously, their friends are going to take their side and tell them, “Yes, it does not make sense, what a terrible product.”
I often bring together management and salespeople, so they can discuss things. It is funny when the management is quite open-minded, they can learn so much from their sales team, and the sales team respects them for just being there and listening.
Some sales organisations are now using completely different tactics for selling than previously. They use automation for lead generation, which sales organisations have never done previously. You need to be listening to young salespeople and be surprised about how smart they really are.
Jamie: What is the single biggest piece of advice you would give to an aspiring salesperson?
Katrin: I would ask them, are they really willing to work really hard, with no short-term certainty, or even no initial results?
For an aspiring salesperson; yes, you can potentially make a lot of money when you become good, but you do not know how long it is going to take for you to become good.
So, are you really willing to work this hard?
Jamie: If you had your sales career again, what would you do differently?
Katrin: What I would have wanted to learn earlier is to have more confidence in my own strengths and abilities, and close bigger deals.
I have always been quite a good salesperson, but I have been good at selling small package. For example, in bookselling, we had small packages and then large packages. During my last summer, I sold books in Alaska, and it was only after the summer that I realised my potential was maybe three or four times higher. If I could have only gotten over the fear of showing more expensive packages.
Jamie: Would you be willing to tell me about the moment that the switch flipped, and you realised that selling bigger deals was preferable?
Katrin: I sold for seven summers, so there were seven whole years of teaching and practising of closing the full bag of books, but when I was actually in front of the customer, I’d close them on whatever felt safe for me. Then, at the end of my career, a classic “pony” story happened, where the family started asking, “But how much is all of it?” I was like, “What do you mean by all of it?” They were like, “All of it on the picture.” I did not even know; I had to take the calculator out and calculate how much it would be. They were like, “OK, do you take checks?” That was completely mind-blowing.
Even when I met a rich family, though, I still would not show them the full bag because somehow it still felt a huge amount of money to me. That was just a very visual memory of somebody simply buying the “full bag”. And after that, I think I started showing larger packages.
Jamie: Would you be willing to tell me about a time that you remember because you did not make a sale, but you learned something really valuable?
Katrin: When I was just starting my sales consultancy here in Estonia, it was myself and a friend of mine. We started this together. We went to the companies, and we provided a free overview using a presentation. It gave them some idea about what was going to happen next, but one of those presentations just went so badly, for so many different reasons.
First of all, the founder himself had investors coming in from Argentina. They were supposed to stay there for one day, but they ended up staying for five, and we were still invited to run the workshop. We were like, “OK, let’s just try to run the workshop anyway.” He sent his only salesperson to listen to the workshop. That was already a bad setting because the decision-maker himself was not there. He came in and out, just saying, “Yes. Hello. Yes, I agree or disagree.” Then he had to leave and go back. It now feels so stupid the way that we did it, but we were just starting and not confident yet.
Another thing that happened is that I continuously got the salesperson’s name wrong. Nobody corrected me for the whole time. I kept on asking him and calling him the wrong name. When I ended the presentation, he was like, “Wait, by the way, this is not my name. That is my name.” I cannot express how embarrassing that was, but I knew that I was going to do better the next time and now, two years later, a co-founder from the same company reached out to me with a different project, and we just started working with them last week.
Jamie: Can you tell me about an amazing sale you did make that another salesperson might not have made, and it shows off the skills and experience you gained throughout your career?
Katrin: That same deal, when we went back to that co-founder, I did not know at first that they were co-founders. It was just a different person reaching out from a different company from my perspective. But when we went to do the presentation or to have the first conversation, then the founder of the first company was in the same building, and we had a chat over coffee and had a good laugh
The second co-founder asked me later, “So how do you guys know each other?” Then I just started laughing, and I said, “He was my first really bad presentation.” I did not try to get away from that, and I think that makes a difference with an experienced salesperson.
We are not afraid of admitting our mistakes and looking back and really laughing at some of the bad stories. That’s what makes people like me inspirational, more than anything. People love hearing me talking about my failures a lot more than they like hearing about my successes.
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