The 3 Stages of Denial When Graduating Beyond Founder Led Sales with Mixmax (Video + Transcript)

Typically founders are the first salespeople. After all, it’s likely they know the product the best, and they can use customer feedback to measure market fit. However, at some point, a founder needs to hire a sales team. Learn how to recognize the signs of ‘founder denial’ and accept that the growth of your company is dependent on the recognition that limited sales skills may actually be hindering your company’s early success.

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Olof Mathe | CEO @ Mixmax

Katie Helton | Account Executive @ Mixmax

FULL TRANSCRIPT BELOW

Olof Mathe: Hey.

Katie Helton: Good afternoon, everyone. I hope you all have been having an amazing time. There’s already been so many rich conversations occurring and I’m sure only more to come over the next day or so. I’m Katie Helton, an account executive at Mixmax and with me today is Olof Mathe, CEO of Mixmax. We’re here to share a few personal stories of the three stages of denial you go through as a founder doing sales, like Olof, and ultimately to building out a sales team and hiring people like myself on this journey from zero to $10 million in ARR.

Olof Mathe: The hope for this talk is that it’ll be very hands-on and potentially a little bit self-deprecating and that you’ll all hopefully, either recognize yourself in some of the stages of denial that I/we went through as a company. You might even be in other stages of denial, so you might even be able to elaborate on this preliminary list of the three.

Katie Helton: Yeah, and from a rep’s perspective and being at previous earlier stage startups, I’ve seen CEOs grapple with this transition from founder to first salesperson, because after all they likely know the product best and are able to use customer feedback to measure product-market fit in real time. However, at some point, you do need to hire a sales team as a founder or else I’d be out of a job. Olof, tell us about the three stages of denial you went through as founder and CEO of Mixmax.

Olof Mathe: Yeah, I’d love to. We can actually bring them up on a slide here as well. These just reflecting on our own journey at Mixmax in terms of the evolution we had as a company. Here are a couple of the stages of denial that I think I went through as founder CEO from doing sales completely on my own, to building out a sales team and finding actual leaders for the go-to market team. The very first stage of denial that I went through, and I’m sure some of you in the audience have gone through, is this notion that as CEO, I can be a great sales rep for my company.

Olof Mathe: A lot of people will tell you, as CEO, you’re an amazing rep, you have to be an amazing rep. As we’ll go into, there couple of reasons why that actually might not be the case. The impact of this stage of denial is you’re too late in terms of bringing on the first couple of reps to your team. That leads into the second stage of denial, which is when you bring on your first reps. That’s typically really hard because you’re building out a function from scratch, so you don’t have the detailed domain expertise in sales. You find a set of candidates and you feel they’re just right, so you tell yourself, “These people will grow into the role.” Of course, in a lot of cases, it’s just too hard and they might not.

Olof Mathe: That’s the second stage of denial. Then the third stage here is once you have a first couple of ICs you tell yourself for a variety of reasons we’ll go into that, “I as CEO can double down or double up and actually be head of sales and we don’t need a functional leader here,” so you’re too late to actually build out senior leadership in sales. As you notice on these, these are various stages that you go through. It’s a little bit of a funnel. Once you hit the first stage of denial, you’re fresh onto the second one. You don’t realize it yet and you graduate through these stages. Right now, there’s probably a fourth stage of denial that, I mean, that will be a great topic for Saastr 2020.

Katie Helton: Yes, when we briefly spoke about doing this discussion a week or so back and you floated these three stages to me, they definitely even resonated on a rep level as well. As a teammate, I’ve seen COG sales and that, of course, has some benefits, but a few drawbacks as well. It’s always exciting to see new ICs brought onto the team that have a lot of projected growth. Of course, the risk then becomes too much growth in them actually filling into that role. Then, finally, CEOs actually letting go and handing over the reigns to seasoned sales professionals. Why do you think founders struggle with these three stages of denial?

Olof Mathe: Yeah. What I’ve extracted from just my own introspection on this is, there’s just a huge difference in the skill set you have to have to be a successful entrepreneur, pre-product market fit versus post-product market fit. What really distinguishes a lot of entrepreneurs is we’re typically pretty multi-functional, we have this can-do attitude, pre-product market fit, we might be juggling 10 or more functions on our own, and we’re so used to diving into the nitty gritty and details of all functions that we often forget that there are people who are literally 10 times better in all of these functions than we are.

Olof Mathe: And so the interesting transition once you feel you have product market fit and the post-product market fit world is, it’s no longer about your own can-do attitude, it’s about finding seasoned professionals who can execute on particular functions and who are great operators. I’d even go so far as to say as I think founders are perhaps overall in the discourse in the world of startups, founders are probably a little bit overrated and operators might be a little bit underrated as the unsung heroes of the startup world. I just think that difference between pre and post and how you have to completely shift your mindset as an entrepreneur is a big contributing factor to going through these three stages.

Katie Helton: Sure. Just going ahead in tackling this first stage head on, this idea that you as CEO will be the best rep actually seems to make a lot of sense. Most founders, CEOs, they build the product themselves or at least are heavily involved. I know you especially are a big product guy, have a lot of background in that and have had a heavy hand in how Mixmax has grown, and you know it better than anybody else. Do you secretly at first think that you would never need to hire a sales team and would be able to do it all on your own?

Olof Mathe: Yeah, a great, great question, and good point to clarify, because I think the short answer to that is, no. Everyone knows they need a sales team, and what’s interesting about these stages of denial is well, everyone knows they’ll need a head of sales. The question is just, when do you? And what you tell yourself as a founder typically on this is, “We don’t need to do this thing quite yet. I can still be closing most of the deals myself,” or, “I can be head of sales for yet another couple of months,” and that’s not how it shakes itself out. A couple of reasons why I think that’s the case and it’s probably particularly the case for businesses that start out as self-serve businesses or have a really strong self-serve component. Mixmax, of course, being a self-serve business, what did we tell ourselves?

Olof Mathe: Well, “Hey self-serve business seems to be booming.” There are all these companies we admire like a Stripe or a Slack or a Dropbox or an Atlassian and they seem to have built these unicorn companies seemingly barely without sales, so you tell yourself, “Well, that seems really awesome. More people, more problems, if I can avoid or postpone building up this other function that’s going to cost a ton of money, the longer the better.” That’s one reason. The other reason I think is if you have a self-serve business initially, the type of sales inquiries that you get are just so artificial and weird, so if you have a self-serve business, what types of inquiries do you get from people? Well, typically, you have people writing in, they’re already pretty bought into the product.

Olof Mathe: And so the types of sales inquiries you get are people asking like, “Hey, can you explain more about team functionality?” Or, “Can we get a discount for 10 and more people?” Or, “Can you provide a slightly longer trial, because we want to see how it integrates with this other product?” Or, “Tell us more about your security certifications.” What you notice about all these questions, these are not really the typical kind of sales questions you get in a real sales environment, they’re much closer to product customer discovery questions and so what you end up doing as founder CEO who grew up in a product area be it design engineering a product is, you end up approaching these with sales conversations more as customer discovery or user feedback. So you end up with like a 75% close rate, which is completely crazy and indicative of part of the problem in a way.

Katie Helton: Yeah, sure. I would love a 75% close rate. But, on that note, were you running, what did a typical sales cycle look like for you? I mean, were you doing discovery calls and really trying to understand the value that Mixmax can potentially bring to this organization?

Olof Mathe: Yeah, I mean, frankly to me I think it was much more of, what even is a discovery call? That’s some thing I think you discover as a product-centric CEO, when you at first bring on sales.

Katie Helton: Sure.

Olof Mathe: So, by virtue of the type of questions you get and also just because you don’t have a clue of what a great sales cycle looks like, you end up treating these conversations again much more as customer or product discovery sessions than an actual sales call. One of the drawbacks of this is sales quickly gets really boring for you as a founder, because you end up treating it more as like, “Hey, I’m going to show you all the great features of what this product does,” rather than doing great discovery, which is what amazing reps do. It just means that you get very quickly diminishing returns on these calls. You do like 10, 15 of them, you stop to get new learnings from it. Part of the reason is you just didn’t do good enough discovery initially, so you haven’t understood what the unique pain points are or what’s unique about the particular organization you’re talking to.

Katie Helton: Yeah, it’s definitely interesting hearing how you approach sales, definitely differently than how my peers and myself would approach it. Thinking about really doing an intense drawn-out discovery call with thinking about all the different sales methodologies, whether that’s Challenger or using MEDDIC to really hone in on what’s the potential value we can bring to the entire organization and not just maybe a subset of that group, because, of course, we would never want to leave any money on the table.

Olof Mathe: Sure, sure thing. Yeah, it’s funny actually just where you mentioned about discovery calls. I think the first time I sat on the discovery call I was like, “Wait, you spent 30 minutes and you didn’t show off the product once?” Like, what are you doing, kind of thing. That was definitely …

Katie Helton: It’s a process.

Olof Mathe: Definitely eyeopening. I mean, I can think of a couple of other reasons why I think founders who grew up in a broader product or have a product background are a little bit disadvantaged when it comes to sales. A couple of great litmus test, just to ask yourself, for how long should you as the founder CEO be doing sales? One thing you can ask yourself is, what do you really enjoy doing? Do you enjoy building relationships with people or do you enjoy building product? If you’re on the product side of the house, it’s clearly the latter and not necessarily building relationships.

Olof Mathe: Another great litmus test for this can be something like, if you have an hour left, suddenly you have an hour to spare, where does your mind wander and what do you spend time working on? For me, that was immediately I’d dive into aspects of the product or test out new flows or whatever it is, or think about the roadmap or right specs, et cetera. Whereas I think folks like you who are actual reps, you’re excited to do research on your accounts and understand that. Yeah, we’re a little bit disadvantage in that regard.

Katie Helton: Yeah. Actually, I remember early when I joined Mixmax we were talking about the differences between two different types of people, this dichotomy of a monk versus a potential stockbroker and how that plays into sales versus product-focused people. Care to elaborate more on that analogy you love?

Olof Mathe: Oh yeah. Well, it was actually a growth hacker, a growth “marketer” who had showed this to me and it resonated with me. This person was basically, in terms of illustrating the dichotomy between the maker and the closer parts of any organization, so it was very stereotypical but a little bit useful. Broadly in terms of extroversion, willingness to take crazy risks and perhaps how forward or aggressive someone might be.

Olof Mathe: On the one end of the spectrum, you have stockbrokers. They’re used to just haggling, being super forward, and on the other end of the spectrum, you have monks. Monks, obviously, very introverted, about internal peace, so product people tend to be perhaps a little bit closer to monks and salespeople and growth people tend to be a little bit closer to the stockbrokers. Incidentally, you actually started your career as a stockbroker.

Katie Helton: Yes, indeed. Adds up.

Olof Mathe: That’s well. I think the interesting thing too with this analogy is monks being more introverted or internally focused, where stockbrokers is dealing more with externalities and external constraints. There’s a big difference when you’re a kind of the types of constraints you’re used to working with if you are a product-focused CEO, that are very different from the types of constraints you face in sales. On the product side, typically the type of constraints you have are purely internal, you want to execute on some particular part of the roadmap and the constraints you have are typically internal.

Olof Mathe: It’s like, how many people do we have on the team? How many hours will this thing take to build? Do we have the right infrastructure set up? Do we have the right knowledge on the team to execute on this roadmap? All very internal focused. As soon as you deal with sales, suddenly you’re dealing with a ton of external constraints, many of which you try to make under your control but are fundamentally just so different in nature. Some of those being what does the customer org look like, who are the stakeholders? Is this an important initiative internally for them or not?

Katie Helton: Yeah. And timeline, I know something is, you struggled with early on having reps on the team, to potentially pushing things to the next month.

Olof Mathe: Yeah, I mean that was super frustrating for me. I would do sales calls and part because I felt they were a little bit repetitive, I was all about closing as fast as possible and just moving on to the next thing. It was funny, I think there was some point in our early interactions, I was-

Katie Helton: Yeah, I remember it.

Olof Mathe: … like, “Is this deal going to close this month?” And you were just like, “Oh no, they’re not ready yet. It’s going to be a couple of more days.” And I was like, “What?”

Katie Helton: Yeah, it’s interesting. I think, well, you certainly have a point that their timing does kill deals or time does kill deals over time, you also want to be cognizant about making sure an opportunity has the appropriate amount of time to grow into its full potential. That was definitely a little bit back and forth we had on that one, I do remember. Given this background, Olof, do you think CEOs should be doing sales at all?

Olof Mathe: Yeah. Well, well for sure. I think it’s useful in terms of getting a first sense for just how customers react. I think the point here is again, when a timeline is graduating that very quickly to a professional. Yeah, I think there might be a couple of structural reasons to why CEOs ultimately aren’t great reps. One thing about something that characterizes a great rep goes back to discovery, right?

Katie Helton: Right.

Olof Mathe: Understanding customer needs, asking really great open-ended questions, being a great listener and it’s just interesting reflecting on the first part of my own CEO journey, which was so much about evangelizing and you end up doing more talking. It’s just interesting, some of the people I consider the very best reps are coaches and coaches are fascinating, because they spend 2% of the time talking and you as a customer do 98% of the time talking and they charge you a ton of money and still, after a coaching session, you’re like, “Wow,” you’re worth way more than this. It’s just a very different mentality what you get trained into.

Katie Helton: Yeah, I’m curious, as CEO, I would imagine, I know for me it’s always nice having a little bit of a lifeline, but how is that, having no lifeline when you were running your own sales cycles?

Olof Mathe: Yes. So stressful, as the CEO salesperson. Very often in sales cycles, you have the customer, they go like, “Okay, well, we’ll buy if we get this for …,” whatever it is, “4.99 per user per month,” or something like that, “can you do this deal?” And then the CEO on the call, you’re like, who do you call? It’s not like, Who Wants To Be A Millionaire and you just have a lifeline. You can’t go like, “Yeah, let me check this price with my board.” You’re forced to give an answer then and there, whereas you can escalate.

Katie Helton: Yes, and I do. It’s definitely very helpful to have a part of, and it’s typically a part of a lot of sales conversations, but whether it’s you or my head of sales, it’s always someone does have to have that final say, so it’s nice to have that lifeline unlike you having it. It’s a nice segue into the second stage of denial, the idea that, okay, maybe you’re not the best suited person to be the first rep in that you’re going to hire an IC and that you’re going to hire one that has a lot of room to grow into the role, because after all you naturally grew into the role or at least for a good bit of time coming from that founder CEO role. Tell us about some of the first sales hires you made at Mixmax.

Olof Mathe: Yes. Yeah, great points. We’re at the second stage of denial. We’ve realized though as founder, CEO, I need to find someone who’s like 10 times better at sales than I am. It’s just an interesting general question because we all face this in our companies, we’re building out a function for the first time and so we’re having a first hire in a particular function, which of course is really, really hard because we know very little about this function on face value. So, what do we typically do as founders? Well, as founders or entrepreneurs we’re impressed by the prenicorns or unicorns who are ahead of us, so we go, “Hey, those companies are really successful, so we should bring someone on from those companies,” right?

Katie Helton: Makes sense.

Olof Mathe: It makes sense at face value. What you missed there is the person who joined as employee 700 at unicorn company Alpha, was an employee number 17, and so the types of support systems and training that they got was just so wildly different. They might’ve been incredibly successful as employee 350 or 500 and just the constraints they’ll be under at your company are just so different at a series A stage company. So what we ended up doing was we found someone who we were super excited about, really excelled, a real sales pro from a Silicon Valley unicorn company, brought them on. Mixmax being very much an SMB mid-market focused company, this person was an enterprise rep and we were like, “You know what, it’s going to be fine. This person will grow into the role, because it won’t be that different.”

Katie Helton: What happened next?

Olof Mathe: Well, Of course, it didn’t turn out that way, because it turns out that growth trajectory is just too crazy. It was like, we thought that the season sales pro from the unicorn company would be great for us, and that wasn’t really right.

Katie Helton: Sure. What was your thought process thinking about, “All right, well, now I’ve made this, which is a big leap, this first sales hire and they haven’t necessarily worked out,” what did you do on the second hire?

Olof Mathe: Yeah, it’s funny, I think very often in these hiring situations you end up swinging almost between two extremes. We’ve gone this first hire who was super seasoned, amazing rep, just not the right fit given the type of org we were. And so we were like, “Okay, what are the learnings? The learnings are we need someone who’s way more startupy and way more scrappy.” And so you go to the entire opposite end of the spectrum and you hire someone who’s this startup generalist who totally knows how startups work, who can take on any type of function, and you tell yourself, “Well, you want this person to build a sales team over time,” and you tell yourself, “this person will grow into the role over time, even though they might not even have any type of formal sales training.” That becomes really rough too and that’s where we ended up. That person ended up adding a ton of value to the company, but, ultimately, wasn’t able to actually build out a sales team just because they didn’t have that expertise or experience.

Katie Helton: Sure. That definitely is a story of two extremes and obviously unfortunately those not working out as the first two hires. Talk us through what you would do differently if you could go back and make that first sales hire again and what type of personality that might be.

Olof Mathe: Yeah, yeah. Great question. I’m not sure I have anything prescriptive to say. I’ll just share an observation from a couple of other companies that have had, I would say probably just a more mature approach to placing their first sales hire, and then I’ll share what we did that ultimately worked out. What I’ve seen some other companies do, which is really interesting, and this just goes back to this notion of how hard it is to build out a function from scratch.

Olof Mathe: What I’ve seen other companies do successfully is, they hire someone who in sales, has excelled as a rep in a similar type company, and what’s different about this person is, while they have multiple years of sales experience, they don’t want to be VP sales next year. They in fact might think, hey, perhaps they want to go into another function over time. They want to go into BizOps, they want to become a GM.

Olof Mathe: Perhaps they want to do product or own a success org or something like that. They’re intrinsically just having their mind that they might not be in sales two, three years from now, which just makes them way more adept at taking on different functions in the company and, of course, eventually having a head of sales versus what’s otherwise common. You hire a first sales rep who wants to be VP sales within a year and that can create all kinds of tensions. I’ve seen that workout well.

Katie Helton: Nice.

Olof Mathe: Yeah. Then perhaps since you asked too about how we ended up solving this. For us, what we did, and we’ve done this in a couple of functions and it’s worked pretty well for us is, you actually bring on someone who has been a head of sales or VP sales on it like consultant basis. They come in like a couple of hours per week or something like that and they help you build out the team. A great advantage of that is, you have someone seasoned who can help you hire in the function that you don’t have a ton of expertise in, or bleed in a little bit to the third stage of denial here soon. It’ll also help you as entrepreneur iron out any rough edges you have around what it’s like working with the head of sales.

Katie Helton: Yeah, can you elaborate a bit more on what it was like handing over the reins, when you brought on, whether it was a consultant at the time or when we eventually did make a more senior sales hire, what it was like before that trying to be actually head of sales and CEO at the same time?

Olof Mathe: Yeah, yeah. I think this goes to the third stage of denial, Which is as CEO, you think you can be head of sales for way longer than you should be. Let’s dive into why I think that’s a really common stage of denial. By the way, I’ve seen this in so many founder friends as well and I think it goes for almost any executive level hiring and there are almost multiple stages of denial just within this last step. A couple of things you tell yourself is like, “Hey, we don’t need this hire right now. We have one or two reps.” Hey, with one or two reps, the management burden isn’t that great. It’s not like it’s a 10-person team and suddenly you have so much else you have to deal with.

Olof Mathe: You’re happy to postpone it. You’re also really nervous about bringing in a senior year hire, because senior hires cost a ton of money. You know that the failure rate intrinsically from what you’ve read is just higher than in other functions. You’re nervous that you haven’t figured it out. You’re nervous that, hey, we don’t exactly know what our funnel looks like. Perhaps we’re going to change our commercial model a year from now. There’s so many uncertainties. Hey, the thing you have to realize is the reason you’re bringing on a senior hire is that they answer those questions. You don’t have to have all those answers for yourself. That goes back to the little bit this can-do attitude that becomes your worst Achilles heel. You’re now bringing on people to solve those problems for yourself in a way.

Katie Helton: Yeah, sure. Can you elaborate more on this idea of sales just being a funnel and the mindset you had where, “It can’t be that hard, it’s just a numbers game, clearly with my 75% close rate, I’m crushing it and so surely I can help a few reps pick themselves up and do a great job”?

Olof Mathe: Yeah. Yeah. It probably goes back to this, CEOs who haven’t necessarily come of age in sales but come in a product function, because you’re typically analytical and numerical yourself. You have a couple of reps, they seem to be doing great, so you’re like, “There aren’t enough of them that they need a ton of management. I don’t need a formal career ladder or anything like that yet.”

Olof Mathe: It’s about funnels and numbers. Awesome. I can do this. And so what ends up happening with this is, you end up being six months too late in terms of building out a sales organization, and this is actually what happened in our case. At one point my two co-founders set me down and they were like, “Hey, weren’t we supposed to actually have a sales team by now?”

Olof Mathe: I felt really defensive about it, and then later on that evening I was like, “Damn, they’re totally right.” In theory, as CEO, you can do all these things, but what takes you three days to do, takes a head of sales, like three minutes or 30 minutes to do, so you’re just wasting company time.

Katie Helton: Yeah, I’m curious, outside of the co-founder sitting you down and thinking like, “Hey, Olof is the sales team,” are there any events that stick out to you of like, “Wow, maybe I’m in over my head trying to manage being two jobs at one time”?

Olof Mathe: I think it was probably just this realization that whenever I would spend time on something sales related, it would just take exponentially more time than I felt it should be for someone who’s really senior, so bringing on that consultant was a big watershed moment for us and helped us a lot.

Katie Helton: Yeah. Well, wow. What a journey. Definitely through these three stages, it’s clear that you’ve come to the realization, in some capacity, that you do need to hire a seasoned sales professional at each level as well. Switching gears a little bit, let’s dive into more tactical sessions. Interviewing candidates after going through these three stages of denial, how this prior experience of being a rep yourself, miss hiring the first few couple of reps and then trying to be CEO and head of sales at the same time, impact how you went about hiring the sales team as it stands today?

Olof Mathe: Yeah, well, I think our role was just a very humbling experience overall and one I think just give it a little bit more humility in the overall interview process, so definitely a long learning journey. Okay.

Katie Helton: Yeah. What are some of the questions that you started to ask that you felt like were leading to some of these successful hires?

Olof Mathe: Yeah. Well, actually, I wanted perhaps just to flip it around to you too, it would be interesting to hear your view as an AE and candidate perspective on what you feel some of the best questions are that you’ve been asked in your career when you’ve interviewed at companies?

Katie Helton: Definitely, yeah. I think it’s a very rich topic and one that’s important, because at the end of the day you’re also interviewing this company as well, so what they ask you is really important. For me, three things stick out and the first is some type of exercise, because at the end of the day, I want to make sure they know how I’m going to do my job, talking about my past experience a bit, and then whether I’m a good culture fit and, ultimately, it’s a small startup, that culture aspects become super important, because you never want to join the wrong team when there’s so few of you.

Olof Mathe: Got it. Got it. It’s interesting that for you as a candidate, the three big areas you mentioned are what I feel is entrepreneurs, CEO are really important too. Having some skill-based exercise in sale, understanding past experience and then culture. On the notion of a skill-based exercise, it’s interesting that you bring that up because I would imagine as a candidate you’d be like, “It’s great if I don’t have to do a skill-based exercise.” Why is that important to you?

Katie Helton: Yeah, I think, I mean, in theory everything would be easier, but things that are easy are not as satisfying. It’s almost a more of a red flag if someone’s not asking me to do some type of exercise because, how are they going to have an accurate idea of how I’m going to perform on the job? I think it’s perfectly fine to have some type of mock or role play of a discovery or demo call, that way the head of sales or CEO, whoever’s interviewing you, really gets to take a sneak peek into how you would be selling their product.

Katie Helton: I tend to believe that you should just demo the product that you’re currently selling, because you should be an expert and it’ll be very clear when the other side of the table starts to ask questions that you’ve probably never heard before, because likely they’re not familiar with the product and you either do or don’t know how to address them really clearly. I do think that exercise component is important in the interview process.

Olof Mathe: Got it, got it. Got it. To me, there’s this age-old question of when you have a rep do some demo or discovery in an interview, what do you ask them to demo? You’re saying ask the rep to demo, they’re the candidate, the current product they’re selling, not your product, not some other super well known SAS product, like a Dropbox or something like that, but the product they should know.

Katie Helton: Yeah, I mean, I think it’s preference, of course, but why not put someone on the spot with something they should be an expert at, because then it’ll become really clear if they’re not currently an expert at the current product they’re demoing.

Olof Mathe: Got it. Got it. What about past experiences? What are some of the richest questions and most motivating questions you’ve gotten on past experience?

Katie Helton: Yeah, I love the question like, “Tell me about your worst month,” or, “What did you learn from your worst month?” Of course, as a sales rep, I never want to have a worst month and I never have, Olof, don’t worry. No, but sales is generally just so many no’s sprinkled in with yes’s. I think understanding how a rep responds to no’s and potentially a bad month or a down quarter is really relevant in terms of who you’re bringing onto your team, and how they respond when it becomes tough. Deals always can go south, and so I think numbers will tell a certain story and those are really great to see and understand about a rep’s past performance, but understanding the nuances of how they respond to adversity is really important for me when being interviewed by a head of sales or CEO.

Olof Mathe: Got it. So the question of like, “Tell me about your worst month,” or potentially, “Tell me about a deal you were certain was going to go through that you then completely lost”?

Katie Helton: Yes, exactly.

Olof Mathe: Interesting. A lot of these, they tend a lot to the topic of adversity or learning, which are just so important for early sales hires. Right?

Katie Helton: Yeah, yeah, and I think especially even at startups. I think through these questions of understanding how a rep responds to adversity and knows, really bleeds into a culture fit and whether this rep is someone who will go above and beyond. I think if a CEO or a sales leader is not asking, alluding to how I go above and beyond as a rep myself, that’s a little of alarming, because I want to be inspired by you every day and know that you’re going above and beyond, so I think that just indicates how a day would be on the sales floor if you’re not even caring about how I’ll pull myself up by my bootstraps when things get a little rocky. On that note, because culture is so important, especially at early stage startups, I’m curious how you approach assessing and interviewing candidates and feeling out whether they really would be a good culture fit.

Olof Mathe: Yeah, great question. I think, on the topic of adversity, one is getting a sense for their learning mentality. Actually, also, I would like to ask a couple of questions on ethics, just to gauge a little bit what level of emotional maturity they have. On learning, I think it’s really interesting, do they actively take part in their own learning trajectory? A question I might ask there is, “Tell me about the most inspiring sales rep on your team today and what’s unique about this person and what have you learned from that person?” Just to gauge a little bit their competitive nature and also like, do they learn from other people and are they looking at how other people are successful as well?

Katie Helton: Yeah. On that ethics topic, curious, can you elaborate a bit more on what you mean by that?

Olof Mathe: Yes, it might be a question, “Tell me about the least ethical thing you saw someone on the sales team do.” Hopefully, they share an example where it’s not, someone did something blatantly bad or purely criminal, but it’s a little bit more like, might be a little bit more subtle in a gray zone. Perhaps they got into an argument about a lead or a shared commission or some nuances about whether a customer had gotten an oversold or not and their ability to talk through that in great detail and richness I think tells a lot about both learning and integrity.

Katie Helton: Sure. Thinking about the questions that I find are super important, culture, past experience, some type of exercise, are these the same type of questions you asked when we eventually brought on our current head of sales?

Olof Mathe: Yeah. Very similar. I think there might be just a couple of differences and nuances to it. Even for someone in a leadership capacity, I think it’s super helpful to ask them to do some kind of skill-based assessment, in part because they’ll be lead-by-example and role model to your team, so it’s awesome if they can do great discovery as well. Of course, the skill-based assessment might be a little bit different because for a head of sales you might ask him to do a full-on sales modeling and how you think about building out the org. What you might not ask of an IC.

Olof Mathe: When it comes to leaders otherwise and sales leaders, perhaps a couple of things that come to mind on the culture aspect. One being, a really wonderful thing you can do is, since there are a lot of products now to record sales calls, you can share a sales call with them that wasn’t great. Then you can ask them like, “Hey, give me feedback as if I were the rep and tell me how to improve this call.” That’s something they’ll be doing daily, so you get a sense for A, what do they actually know of Sandler and Challenger sales or whatever it be and how-

Katie Helton: So you do know these sales methodologies.

Olof Mathe: Long journey, but you get a sense for how they give feedback, right?

Katie Helton: Yes.

Olof Mathe: Related to the topic of feedback, I think overall as leaders it’s really easy to be leaders who recognize who the low performers on the team and manage them out are. It’s much harder to find leaders who are also able to turn low performers around. And so since you go to ask the question like, “Tell us about a low performer on the team,” who you actually managed to turn around and made very successful and there you’re looking for real depths on what the performance issue was and what specifically they did to turn it around.

Katie Helton: Interesting. Before we wrap things up, one question I have is, I know you’ve mentioned before that a question you love to ask during interviews is potentially what would make someone stay at a company, which I think is super interesting, because it puts them on the spot and forces them to think about that a little bit differently. Can you walk us through, what do you ask people on the spot?

Olof Mathe: Oh, well, won’t be so much an on-the-spot question, I just think it’s a helpful thing for, I guess, anyone to think through in general in their career, in the current job they have. If I’m talking to a candidate, I love to understand what would make them call off their job search and stay at their current job. Or if their CEO called them right now and they could ask whatever they wanted of their current CEO, what would they ask and how would that change their current job search? What that tells you is, do they actively think about shaping their careers and shaping the environment around them, do they take ownership for their own situation or not? Of course, taking ownership for your own situation is what characterizes great sales, sales hires in early stage companies.

Katie Helton: Sure, that also ensures you’re bringing on someone who would be an amazing culture fit.

Olof Mathe: Yeah.

Katie Helton: Otherwise, well, I think that about wraps up the time for us. Thank you Olof so much for sharing-

Olof Mathe: Thank you, Katie.

Katie Helton: … these three stages of denial that you’ve gone through, building out the Mixmax sales team and thank you all for joining us.

Olof Mathe: Thank you. Cheers.

Published on October 8, 2019

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