Carolin Berger, Regional Sales Director DACH, Outpost24

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Carolin Berger
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I was fortunate to be referred to Carolin, who has an amazing ability to make complicated sales processes – including interviewing, organizing your pipeline, and selling benefits, not features – seem much simpler through a concise explanation.

I enjoyed Carolin’s direct, practical and customer-focussed advice for aspiring salespeople, and I hope you will too.

You can read Carolin’s full biography here

Jamie: Thank you very much. Just to begin with, Carolin, in your sales career thus far, what have you found most fulfilling?

Carolin: Well, I think sales is the one profession where you get immediate feedback for doing a good job. I think that is what is really fulfilling. Before I joined this sales position, I was actually working as an IT manager; leading IT teams. You implement projects, and there is a certain fulfillment in that as well. Your day-to-day work is not as directly related to results; it is more disconnected.

In sales, I think if you do a good job, if you treat your customers well, if you listen to them well, you have that direct feedback of happy customers and successful sales. That is what I find most rewarding; that there is instant feedback, not a long, delayed process after months and months, and finally, someone says, “Oh that is a nice project that you implemented. Thank you for that.” It is much more direct. 

Jamie: Is that immediacy the best thing about sales for you? 

Carolin: Yes. I would also say that as a manager, I think it is also very, very gratifying that you have that immediate response when it comes to a lack of performance.

Sometimes, in other positions, it is hard to measure if someone is doing a good job or not. People can hide and be vague about their contribution to a team effort. However, in sales, it is very transparent. Either you do a good job, or you do not. You cannot really hide between your colleagues, and I am sure you know organizations, where you feel like twenty percent of the workforce, is just there for decoration, and the rest are carrying them. As a manager, I do not feel like I have to pull other people. I do not have that horrible feeling like, “Ugh, that guy is not pulling his weight, and I have to make up for it.”

Jamie: How do you believe in measuring your team? 

Carolin: I think the most successful companies actually have a short-term and long-term KPIs when it comes to customer success. Of course, the short-term KPI that most salespeople are interested in is commission. There are a hundred varieties; some are percentages, some are kickers and all of that. I also think it is very, very necessary to incentivize and motivate your salespeople to be interested in the customer’s success in the long run. Instead of having those hit-and-run scenarios where people sell something, and then they totally disappear, you have to have a long-term incentive. I truly believe in something like churn rate, or renewal rate, meaning how much does the renewal value increase, should be a measure. I think that the majority of companies are good at recruiting and finding customers but then they are really, really bad at retaining them and growing them.

Jamie: Those companies that do not retain their customers well, what do they tend to do wrong?

Carolin: Well, I would not necessarily say wrong, because it depends on what you want to do as a company. If you are interested in creating a fast growth story and the management might be tasked to sell in let’s say three years, then there is nothing wrong as its about just focusing everything on getting new logos in, and getting new customers in, because that is an amazing growth story and you do not really have to think about the long-term impact.

However, if you really want to have a company for the next ten to twenty-five years, then you have to think about the reputation and the stickiness of your products. If you talk about that, then it is all about, “Can you deliver on your marketing messaging?” So, not only having a really sexy marketing message that everyone buys into, but also can you actually deliver on it? Can you grow with your customers’ needs? It is very easy to find an amazing product at a certain time and meet a certain customer need, but customers evolve, and change and your product has to meet their evolving needs as well. You need really good product management that has a vision and can drive that development. You need to inspire your customers and take inspiration from your customers on where the market is heading.

I think if you want to build a long-term business, it is all about reputation. Very often, the question is, do you maximize your profit today, or do you maximize your profit over the customer’s lifecycle? If your task is to have the biggest company growth in the next year then obviously you are going to maximize the profit today and not give a damn about the future.

If you want to build a long-term success story, then you are probably going to look at the lifetime value of a customer, and really think of it as a partnership and not just see them as a cash cow.

Jamie: Which of those company life stages do you enjoy working with the most? 

Carolin: I personally prefer the long-term vision. First of all, because I truly believe that we also have a professional reputation we need to look after. You have probably come across, and I do not want to say any companies names, but we all know these companies where the company has a reputation, and if you see someone has worked there, you will automatically assume that they are the type of person that feels comfortable in that poor culture and that poor attitude.

On the other hand, I feel it is my professional reputation that I am attaching to the way my company treats my customers. I also think that if you are passionate about what you do, then you cannot accept that your internal core values clash with the company values. I would not feel comfortable taking advantage of my customers. That would not feel good. I would not feel comfortable with that. I tend to be in companies that grow a lot slower, and that more sustainably, where there is a strong focus on building a responsible business instead of growing massively. 

Jamie: What have you found the worst thing about being in sales?

Carolin: There are actually so many.

When I first started out in sales, I think the one thing that I found most stressful is you have to be very, very quick at getting a measure of a person. You cannot take your time to get to know someone and build a relationship. You basically have to develop the ability to build connections with whoever you have in front of you instantly.

Initially, I found that very stressful because you have to be authentic and, at the same time, be accommodating those different needs.

When companies focus more on their financial processes than on their customers’ needs can be a downside. So, for example, that classic, “We have to close a deal this quarter, and we’d rather give you an insane amount of discount to close it this quarter, rather just wait another month.” As much as I respect that, of course, you have planned and you need to hit your revenue target, and all of that, to me it just seems counterintuitive. I would rather have more money in July than less money in June. Not all companies have this luxurious position which allows them to be patient, but I think sometimes we have trained customers to wait until quarter-end and get amazing deals. That is something I really, really dislike.

Jamie: What product characteristics allow for that patience?

Carolin: I would not say it is a product characteristic. I would rather say it is a financing characteristic, in the sense that the company I work in right now is backed by private equity. The people that are investing in this company have invested their own money.Whereas, we can basically look again at our overall performance. We’d much rather have a higher recurring revenue in July than the lower one in June. That is a luxurious situation that is created because our investors are long-term investors.

Jamie:  Would the financial backing of the company be something you’d look at if you were to apply for a job? 

Carolin: I would definitely say yes. Of course, it is very hard because seldomly do you get to actually meet those investors, right? But sometimes if you read up, and there are those notorious venture capital funds, and you read about how long they keep a company and how they treat their staff. Do they IPO them, or do they resell them? What is their interest? Are they taking companies from below a hundred million to one billion? Or are they taking companies from one billion to ten billion? They all have their speciality, and I think it is very important that you feel like this is the type of story you can support.

For example, the investors that we have, they always only buy Nordic software companies, and they make them into global players. They basically look for companies that for some reason, have not become global yet, but have the potential to be global, and then they buy them and globalize them, and then they sell them off. The people I work for are very transparent in saying, “We are not good at running companies that are above a thousand people. That is just not our jam.”

I know I would much rather be in a smaller company where I have a lot of responsibility and can take decisions, instead of being in a big organization where I have a fancy title, but I actually have no authority because there are a thousand different roles.

I think it is very important not necessarily to know them personally but to understand what is their playbook. What are they doing? And do you like that? 

Jamie: How did you go about choosing the industry that you wanted to go into? 

Carolin: Well, I did not really actively choose cybersecurity in the sense that I did not sit down and say, “Oh, I really want to work in cybersecurity.” I made the decision that I am good at selling software. I am still technically selling software. But when the opportunity arose to join this company, I looked into the cybersecurity market, and the one thing I looked at was, basically, do I understand the value, as a non-expert, if I look at the website? And I thought, “Yes, I do. I can see the value. I can see the benefit.” Again, going back to passion, if you truly believe that your product creates value to your customers, then selling is easier, as opposed to selling a product that you do not think is actually useful or sensible yourself. I made a conscious choice to do security because I thought it is a market that makes sense and delivers value. I was not really actively pursuing a cybersecurity career. It is a funny industry, and I can highly recommend it. It is filled with funny people and a lot of bad jokes about penetration testing.

Jamie: A lot of people seek out the industry because it is perceived as being very well compensated. Have you found that to be your case?

Carolin: I come across that a lot when I recruit people. Interestingly enough, yes, cybersecurity has a reputation for having better salaries. I would say it is a mixture. Yes, there is definitely places in the market that pay an obscene amount of money. I worked in the digital experience industry previously, and I would say the same is true in that industry. If you join Adobe, obviously your compensation package is going to be a lot different from if you join a much smaller player, right? I guess you have that everywhere. I think why security has a reputation that the deals tend to be quite big and happen quite fast. If you are in a different industry, you might be stuck with €20-40k deals and security, it easily explodes into million-euro deals. And of course, that is very attractive because there is not a lot of software industries that have these sorts of deals. A lot of them are in the range of an €100k or maybe €500k. A lot of digital experience vendors that have a million-euro deal, so it is just a different sized industry.

Jamie: What are the downsides of a long sales cycle

Carolin: We have the advantage of having a very diverse portfolio. We have products that can be sold for millions plus euros, but we also have much smaller products. I always strive to have my sales reps have a three-to-one ratio in their pipeline. Basically, have three smaller deals that can be closed within one quarter. We talk about one of the penetration testing for like €5k, €6k, €10k. Really small ones. Then two medium ones where we say, “Well, this is probably going to take us three to five months to close but it is in the range of €50K,” and then we have one monstrous deal that is going to take us twelve, eighteen, twenty-four months, but just big one.

I think the key is to get a mixture, so you do not end up tying back to the measurement of performance, because how do you measure someone that is working on three monster deals and he does not deliver anything for months and months? Then you are kind of stuck. You think, “Well, he theoretically has a good pipeline, but in practice, he has not delivered anything.” That is why I always tell them, “I do not care if you are an enterprise account manager or if you are a junior account manager, you have to have a mixture. I want you to close something every quarter, and if it is a small deal, that is perfectly fine. But show me that you can close something and that you have something happening in your pipeline, instead of waiting for that one magical unicorn customer to place an order.” I have to be grateful to product management because I did not create that mixture of products.

Another thing that we tried to do is to push for the “land and expand” strategy. What we have done is that if one of our account executives closes a deal, he owns that account.

He does not need to worry about, “I close it, and then someone else gets to cross-sell.” It is all theirs, and I always tell them to go in for something small, because a lot of the time, companies are overwhelmed if you try to implement something humongous. It is very likely to fail because organizations are not set up to change overnight. Very often, it is a lot easier to change with a smaller project, show success, and then take the next step, and then the next step. Most of our customers that are in the million-plus range did not start as million-plus range customers, but it was abuilding up the trust, building up the confidence in the partnership, building our internal network in that company, getting more stakeholders to buy into us as a partner and then slowly expanding. I think for most companies that have a diverse portfolio, it is a lot better to start something small, get a foot in the door, and then use that to grow the account.

Jamie: The model you use of people owning the accounts that they sell is unusual. Does that change the characteristics you are looking for in a salesperson?

Carolin: Yes, and that ties back to the short-term and long-term. I have worked in companies that had a different style. There was a dedicated account management team. There is the terminology between hunters and farmers, and I think there are certain things to be said about those different mindsets. What I found, and personally thought was a drawback when I worked in a separated organization, is that you end up having hunters that are maximizing the sales the first time, so they tend to sell whatever they can, regardless of whether the customer needs it or not. Then they basically say, “Dear account manager. Good luck.” You actually end up having to fix a lot of the false promises.

I think for me in the long-term, again, it is very good to have the salesperson to be the face that they keep seeing. They’d better think twice what you promise them because you are going to be sitting at that table when that promise falls through, and there is not going to be someone else having that discussion. I find that customers really like that, and they say, “Okay, so you are not going to tell me just a story because you are going to be the guy that is going to sit here the next year as well. I trust you more because of that.”

I do not think there is any right or wrong. It is just about how you want to be seen with your customers. Is it a long-term relationship or not?

Jamie: What are the biggest and most important characteristics you look for when you recruit?

Carolin: I have made a lot of recruitment mistakes and I have changed my recruitment process so many times.I always ask them to walk me through one of their most successful deals from the very beginning to the very end, including any objections that they came across. Why do I do that?

For me, it is very important to actually understand what they did. What was that first interaction? Did they pick up the phone and cold call them and find that person, or was it an inbound lead? Do they actually go out and do presentations or do they have some sort of inside sales team that does all of that for them, and did they just sent out a quote?

They can all have the same title, but different companies work extremely differently, and you cannot just assume that they are going to have the skill set based on the title. I want them to tell me how they work, what they did, who was involved on the side, and who was supporting them.

In a second interview, always ask them to prepare a slide-deck and give me a pitch about my company. I want them to tell me why we are the best cybersecurity vendor. I also want them to give me a success plan for meeting their quota. I basically tell them, “This is going to be your quota. Expect that you get zero accounts to being with. What will you do? What do you need from me? What will you do to make it work?”

The interesting thing is that often people will not show up to the second meeting. They would just basically not do the work. Other people will put in a tremendous effort and actually come up with real plans. They might say, “Oh, you know, this is a target industry and I thought about this and that and this is an angle we could use.” They come up with campaign strategies! Others would just basically do some bullshit Bingo, basically saying, “Oh, yes. I know five people from that company. I just talked to them. I would just give them a call.” The reason why I do that is that I think it is very important to not put someone in a position where they cannot succeed. I do not want anyone to join this company and then be surprised and say, “Oh, I thought I got ten accounts.” So, I ensure that I tell them, “You get zero accounts, tell me what you would do.” And then when they join, of course, I don’t actually give them zero, but I think it is important that they have the mindset that they have to build it from scratch.

Jamie: Best interview you have ever seen? Has someone blown you out of the water and made it, so you have to hire them?

Carolin:  There was someone that did an amazing slide-deck. First of all, what I really admired is that they actually created a slide-deck template with our company colours. A lot of them just basically do them black and white, which is fair enough. He downloaded our imagery from our website and created a company template, and then he really started out with all the campaign. He basically said, “Okay, so I looked at your product. You have cloud security, and you have application security. For this product, I would approach these people. For that product, I would approach these. I have already identified like ten targets accounts for each product area.” That is where I thought, “Okay. This is amazing.”

Then that person continued, saying, “Okay. So, if my target is that, I expect a successful closure rate of forty percent. I need a pipeline of X. I need to make this many calls a day to get these number of opportunities. Just looking at the numbers, I think I should be able to create a pipeline within the next eight weeks,” and I just said, “Wow.” I hired that person, and that is exactly what he did.

I should have said that we are a very, very small company. We do not have the advantage of having a lot of bodies. We are not an IBM, where you basically just wait for someone to tell you, “Oh, I need to buy your product. Could you please send me a quote?” We need to reassess people. We need people that can talk about the customer’s needs, can understand the customer’s pain, promote the value, and really, really sell a product. That is why I want them to create a presentation because very often, you then see people saying, “Oh, I attend trade shows.” And then you are like, “Okay.” That works well if you’re salesforce, because then you already have a company name and you have a reputation, and you probably have twenty trader shows to go to every year. We go to two.

Jamie: Can you talk about how you use the importance of third-party validations?

Carolin: It is very much in our content marketing. We also have the ISO 27001 certification which, if you’re a security company, is really sexy. One of the things we talk about from the very outset is that we say, “Look, it is not just us that says we are great. But there are also these independent resources that tell us we are great.” If you are in the industry, it gives you a warm and fuzzy feeling. We also work a lot with reference customers where we basically set up reference codes because noone ever wants to be named on our website; no-one ever wants to be on a security company’s website. Luckily, we have that relationship that we can actually get them to take calls and that is a big one, when another customer says, “Yes, we have worked with them for two years, and it is great, and we would love to continue.” That builds a lot of confidence and trust.

Jamie:  What advice would you generally give to aspiring salespeople who are starting out?

Carolin: I would say that sales, more than any other job, is about planning and execution.

You know the saying that execution eats strategy for breakfast? I think a lot of the times a lot of salespeople spend time thinking about the perfect target account. I hear these discussions in recruitment talks all the time; “What named accounts do I get?” The truth is that you have to do it. Pick up the phone, write an email, contact people, and then things will happen. It is not about finding the fifty perfect target accounts.

It also needs to be tailored. The worst thing that happens is that sometimes you get these emails where someone completely random is approaching you with a product, and it is not relevant to you at all; they copy and paste it. I think it is a lot better to just approach ten people with a highly relevant message than approach a hundred with something completely random. A lot of salespeople think that its marketing’s problem. It’s great if you have marketing and you can reuse things, but it is your job to actually look at a company and say what is relevant for them. We have so many products. We have many storylines with so many angles. What is the most relevant angle? Why do I approach that guy with this topic now? Make it relevant for them and do not just basically say, “Oh, yeah marketing has created a campaign around X, and now I am just blasting it to everyone without a second thought.” That is terrible. Plan and then execute, and then do it again. 

Jamie: And if you had your career again, what would you do differently?

 Before I joined sales, I was actually an IT manager. That means I was very naive when I got my first sales position, extremely naive. When I joined my first sales position, it was a company where it was not common for people to get shares, but it was also an option, and I stupidly went for a higher base salary instead of the shares. I think if you truly believe in the company, if you think it has a great product, and you truly believe that you can make a difference in making that company a success, go for the shares, not the safer route. But again, it was my first sales position. I came from an IT manager position where you have your salary, full stop. There are no fancy stock options. If you have the chance to really contribute, get that back by having shared. Go for it. Go for the lower base salary. Get the shares.

Jamie: The perception is that salespeople are just disproportionately paid compared to other functions. Is that tied to that willingness to take a risk?


I think, in a way, all salespeople are gamblers to an extent. Otherwise, I would probably go for a different career with less stress and uncertainty. Let us put it this way: if someone is not confident in their own capabilities to take that risk, then they should probably not be in sales.

Jamie: Could you tell me about a time when you or someone in your team did not make a sale, but it taught them or yourself something valuable?

Carolin: Oh, the sad thing is that it is always the same lessons and every single time you are like, “Duh! How could that escape my attention?” We just recently lost a deal simply because of stakeholder management, that situation when you talk to someone and you think they are very influential and they are calling the shots. You have a great relationship, and everything is just picture-perfect and then so when the decision is made, and it turns out that there was a component you were completely unaware of, that is extremely relevant, and you lost because you did not pay any attention to it. Then you feel like, “Yes, I should have been aware of that, and I should have definitely tried to figure out who else is influencing that decision. What is their agenda? What are they looking for? Instead of talking to that one person.”

I think very often in sales, especially when that other person is someone we like, we kind of lay back and say, “Oh, I have this great relationship with this person.

But the truth is there is always someone else. There is always someone that is also influencing the decision, and if you have not met them, then the competitor probably has. So always try to make sure to meet everyone.

Another story about something we lost, and that was actually quite painful; if you have a product like ours, we can actually see if someone is using it or not. We can see, do people look at it? Do people generate reports? We get a good feeling if they are using it or not. But we have not, in our account management, really used these user statistics. When we started to do that, we noticed that some of our customers were not using the product as much as we had always thought. That is always a very, very dangerous sign because someone is going to notice that on the customer side as well. Then they are going to ask the question; why do we spend money on that product? We actually did lose a renewal not because we did not pick up on it early enough to say, “Hey, hang on a moment. You bought that product. You have not really been using it. How can we help you? Do you need training? Do you need us to explain the product?” You have to ensure that your product is relevant. Otherwise, it is going to be on the cut list.

Jamie: Could you tell me a story of a win that you made that someone else might not have without the skill and experience you’ve gained? 

Carolin: One example is a company that has been looking for a product, and they came across us on Google, they Googled, and they found us. We decided to do a POC because they were very, very technical people. They told us, “I have to see the product, a demo is not enough. I have to get my hands on it.” We did a POC and all of a sudden, they started to make that feature comparison, and these scan reports can be humongous. They got us on call and said, “Okay, we have one of your competitors’ reports. We have your scan report, and we have theirs. Can we please compare them for us line item for line item by line item?” I was like, “Oh my goodness, this is going to be hell.” So, thank goodness, partially because I am lazy. I said in my mind, “No, no, we are not going to do that.”

What I actually said out loud was, “Okay, question. The data you see in our report, is it clear? Is it structured? Can you work with it?” And they said, “Yes.” “In the other report, is it clear? Is it structured? Can you work with it?” And they said, “No, it is very confusing.” I said, “Well, you know, we can now go through line item by line item, but the truth is it is just a one-point-in-time situation. This comparison will not be relevant tomorrow or the day after tomorrow or the day after tomorrow because new vulnerabilities show up. Choose a product that enables you to do the job that you need to do. You need to have the information to take action. If our report gives you actionable insights, great. If the other does not, too bad.”

Thank God, they totally bought into that and signed the contract the day after. I was quite impressed with myself. I was quite happy. You have to sell value. Why do they buy a product?

You know the old saying, “No one buys a drill. They want a hole in the wall. They buy a hole in the wall. They do not buy the drill, and if they could get that hole in the wall any other way, they would do that. They are not interested in a drill.”

I think it is very important that you always look at your product like that. Why do they buy the product? Because they want to get security data, so they can take action. Do not look into the details, and do not start comparing buttons and filters. 


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