Joining Zoom

Alex Kracov: So I'd love to start today's conversation with when you joined Zoom back in 2016 as an SDR. Can you talk a little bit about kind of what led you to join Zoom at that time?

Chris Michelmore: Absolutely, and I would love to. So it kind of I don't know how - please stop me if I go too far down the rabbit hole. But I guess I'll just preface it high level with, I was looking to get into tech sales. I wasn't in tech sales in any way, shape or form prior to this. And so, really, the short answer is I fell in love with the product, even from an outsider, really, really quickly and really early on. This was 2015, so it was still relatively a newer product. But same thing, we can say now, as we said, that it just works. So it was easy to see that as an outsider. So for me, looking for a company, what I was looking for was the market fit and how well the product worked. In other words, could I answer for myself, well, I'd be really excited to sell this? That's essentially what - I mean, there's a longer story around how I got introduced to the company and why I pursued it, but that's what I was looking for.

Alex Kracov: It is just such a magical product. I think about the earlier iterations of video conferencing software. I think I used probably Webex and BlueJeans and things like that, and it just didn't quite work the same. I think I probably used Zoom, probably the first time, generally, around that time when it's like, oh, wow, this works. The video is just so good. It's just like so simple but so amazing. And so, yeah, I totally see why that's like, okay, I got to go work at that company if I'm going to go try and break into tech sales.

Chris Michelmore: Yeah, absolutely. It's a very fortunate thing. Not everybody can always say that at all points in their career. But it is a very fortunate thing to say I'm selling something that really works and that I really believe in. So I definitely was looking for that first.

Alex Kracov: Yeah, and it's so important as a sales person to tell something you believe in, or else you'll just kind of you don't have the energy to get up every day and face the natural rejection of what is sales. Yeah.

Chris Michelmore: Yeah, absolutely.

Succeeding as an SDR

Alex Kracov: And so you've held seven roles at Zoom, which I think might be a first for a guest on our show. So I'd love to kind of walk through your career progression and those different stages of your journey at Zoom. So you were an SDR for, I think, five-ish months before you got promoted into an AE role. What made you so successful as an SDR at Zoom? What was the SDR role like at Zoom back then?

Chris Michelmore: So personally, I kind of mentioned how I was looking to break into tech sales. So I didn't come from this. So my answer really is it's just like a little bit of a chip on my shoulder, to be frank. So when I moved for this job, I realized that there was going to be a sacrifice involved. I know we didn't get into that too much prior. I actually moved from close to where you are. I moved from the San Francisco Bay area. So I was out in San Jose, California, which is where our headquarters is. My mindset really was, you know, I moved my whole family. I had two kids at the time. I wasn't going to move my family halfway across the country and not give it everything I had. It was kind of like a proving moment, I thought it was. So, I think just mindset of, first day, what was the previous record? How do I go beat that? Second day, what was the record that I just broke? How do I go beat that? I just kind of had that mindset from day one. Again, a little bit of a chip on my shoulder, I wanted to prove that I could make this work. So, yeah, it was more of a mindset. I do think the other element of it, and not everybody might - this isn't a teachable thing. But I came from owning my own business. That's what I did prior to entering as an SDR. So again, I was willing, I just wanted to get in somehow. I didn't care what the role was. No ego about it, by any means. But I had the business. If somebody gave me keys to the door right now and said, "Hey, you own a Zoom building. Good luck. Go after it." That was the mindset that I had. I basically owned my own franchise, and I was going to go figure out a way to make it work.

Alex Kracov: I love that approach. I mean, I think I had the same sort of chip on my shoulder and mindset when I first started my previous role at Lattice where I was hired as this early marketing person. But from my perspective, I was like, I'm going to run this thing forever. I'm going to be the VP of marketing. This is my job. I just kind of came in with that approach. Then that also elevated what I did every day. It wasn't like I just kind of sat in my role. I was like, okay, I'm going to try and bear hug much of this business and work my ass off too to kind of get it done. Because every SDR in history wants to go be an AE. They want to do exactly what you did. What advice do you have for them? Is it really just it comes down to mindset and hard work? Is that kind of what you would say to them?

Chris Michelmore: I think that, yeah. Well, so as you go up in different roles, what I've learned is, a lot less of it is in your control. When you go from that, when you make that switch from IC to manage a leader, things start leaving your control on a day-to-day basis. The beauty, the benefit of an SDR and an AE, the earlier on the roles, really, you can outwork your job. I really do think that's true. Again, as things start becoming out of your control, you have to change your mindset. You have to adapt to that. I think that's the best part about that role, is you really, truly can outwork the number out that. So mindset and hard work, I truly do believe that. But again, I think the common theme is just going to be treating it like it's your business too. The other, from a mindset standpoint, thing I think that was most helpful in the same context of owning a business was that nobody was going to - it's very easy, probably maybe more so as an AE. It's like, "Oh, I don't have that tool, so that's why I didn't have a number." Or, "I didn't give in this level of support, that's why I didn't have my number." But if you go back to the owning your business mindset, nobody is going to say, hey, your bathroom is really dirty, and you'd go, well, somebody else will go clean that. No, you have to go find a way to go make it work and maybe live outside, stop thinking of it. You have to live within the confines of just kind of what was given to you. So I don't know if that's kind of a little bit longer of an answer. But yeah, mindset and hard work.

Alex Kracov: No, I think it's a super important lesson. Because I think too many SDRs, especially in SDR world, it's like there's too many cool tools. Everyone wants to use this thing and that thing. They're going to try and automate it and use AI SDRs and whatever. It's kind of just a grind. You kind of just got to push forward and reach out to people and be a person and have that mindset. That's like what ultimately works. I think it's honestly a very important lesson that I think gets lost on the new generation of outbound and how we talk about that role, which is funny.

Chris Michelmore: Yeah.

Transitioning to an AE Role

Alex Kracov: Okay. So after SDR, you moved to an AE role, which I assume you're starting to close business and really run the full sales process. What was that transition like for you? How did your skill set change? I assume you kind of carried forward that same mindset and ownership mentality. But what was that journey like of sort of shifting your skill set to just attracting business to, okay, now I got to actually run the full funnel and close the business too?

Chris Michelmore: I think for me, and I'm sure everybody is different in this answer. I'm not telling you how to think by any means. But the hardest part is in transitioning to asking people for their money. I think, again, it's a benefit that I ran my own business. I was very comfortable doing that. I had to. You have to. Wasn't at first, definitely. I think that's the same answer. I start asking people for money, and you got to kind of change your mindset around them. Being better as an AE meant understanding their business better. Like as an SDR, it's very much about you. You're trying to get your number. You're trying to make your calls. It's all about you and your role. The transition to AE is, I had to make it all about them and about the customer. I had to do that in order to earn the right to start asking people for their money. You never had to do that as an SDR prior to that. So that would be the biggest mindset shift.

Alex Kracov: And you were selling, I think it's like the mid-market. What does a mid-market customer look like for Zoom, and how would you kind of describe that sales process? Was it fairly transactional and quicker? Was it a longer, it felt maybe more enterprise, a lot of stakeholder sort of sales process? How did you sort of think about the customer and matching it to the sales process?

Chris Michelmore: So I would imagine it's very similar to most companies that I talk to, as far as what a mid-market space is. But in general, that time, we were little more inbound. We're trying to get to market. So there was a good balance between inbound and outbound efforts. We were both, just to be clear. We weren't like separated, or segregated, or separated by only inbound or only outbound. We're both. So you had to get good at both those skills, which is another key point, right? So balancing the inbound and outbound.

In general, what my takeaway on mid-market space though is: the size of the company that you're selling to really determines their buying process. Most mid-market companies, really, are trying to figure out what they want to do when they grow up too. They probably don't have a full, built out internal IT team. They're usually using outsourced programs, MSPs, partners. They might have one person in internal from an IT perspective, but they probably don't have like a CIO yet or a CTO. So understanding where they are in their life cycle is a huge part of selling into the mid-market space. Because you're understanding how much they have to take on. A lot of those conversations are around how you make the IT, the software, the people who manage the software, how do you make their life easier? How do you make it simpler on them? Because most oftentimes, when you are selling to a mid-market company that is in that lower life cycle, if someone be burdened, it's not that your product is or isn't a great fit for them or that's the right thing. And so we just don't have the bandwidth. This is going to add more complexity. So that's a big hurdle overcoming that space.

Alex Kracov: Did you think of your sales cycle as more like bottoms up or tops down? Because I assume you're working with this IT buyer. Then I imagine you eventually want to go wall-to-wall within the company, and you're going to sell - every single person at the company should have a Zoom license. That makes sense, right, if you're using this type of technology. But I imagine some people are like, "Oh, let's try it with these people first, and then we kind of go from there." Or, "If I were you, I'd be like, well, this is the demo. This is the proof of concept. We're on the Zoom call right now, right? We're doing it right now, right?" And so I'm curious how you thought about that proving value in the sales cycle. Because it's a big decision for a mid-market company to say, hey, we're going to overhaul all of our video conferencing software. So how did you sort of prove the value in that process and think about it?

Chris Michelmore: I love that question. It really is a perfect mix between the two. Ideally, well, the benefit of a mid-market space is that you have easier access to a top-down sell. That's for sure a statement, right? Usually, they wear many hats, the decision makers. They're also accessible, and they're also trying to figure out how to make it work. So that's great. The outbound motion makes it very, very, very solid approach. But what you have to get good at when you are balancing the inbound element? Why is there an inbound element? Well, somebody at that company said, "Hey, you know what? I have a need, and we're kind of too small of a company. It's not really getting served." Or, "Maybe I have the ability to kind of go off on my own and figure out what's right for my role, what's going to make me successful." A lot of mid-market-sized companies do provide that autonomy for their employees. So that's building the champion motion and selling and creating groundswell. Basically, making the product a need within departments and teams so that the above the line, the buyer, is like, "We don't have a choice now." If you have a really good product fit, I think you're doing both at the same time, especially in the mid-market space. Probably not so much so in different segmentations but definitely in the mid-market space.

Alex Kracov: Yeah, because I imagine the sale is so much easier once you kind of like seed Zoom links to each little department, and they start using it for their calls and things like that. Then you can go to the CSO or whoever the main buyer is and say, "Hey, look. All these teams are using it." It's really easy, find the security features or whatever the things that they need.

Chris Michelmore: Absolutely. Especially when you have, it depends on the company too. If you have a freemium type product, that bottoms-up entry point becomes a lot easier. It allows you to treat those users as leads and really dig in to understand the intricacies of the business. They're a little bit more willing to share the day to day, which helps you build a great case when you do finally get access.

Managing and Coaching AEs

Alex Kracov: Then after like a year or so, I think you shifted into more of a manager role. So you're climbing through the ranks really quickly here at Zoom. What was that transition like for you, going from, okay, closing the business and figuring out this customer to, okay, now, actually, you're coaching AEs and helping them close the business? What was that transition like for you? Because I don't think you had done that before. Maybe as a business owner, you had some management experience. But yeah.

Chris Michelmore: Well, I think there's two of them. One is a very traditional answer. The probably more straightforward answer is, like I mentioned a little bit earlier, giving up a little bit of control of the day-to-day success. That's definitely a big challenge. I think the other biggest challenge, that at least I try to talk to as many leaders as I can, is getting the pitfall of caring more about their success. They as in your direct reports, your reps, your team, caring more about their success than they do. And so it's a difficulty of meeting them where they are. Meeting them where they are as far as what their drive is, what their passion is, and meeting that energy level but then also, at the same time, understanding that at a certain point, there's an element where you're giving up control of your day-to-day success. That's a very difficult challenge. Anybody has to learn that, myself included, by all means. The more enjoyable part of the transition for me, though, was again a little bit from owning the business prior. But also, coaching is what I love to do. And so if that's what you love to do, it very quickly outweighs the fact that you give up some of that control. Because you're getting fulfilled much more. Your cup is being filled up much quicker by a number of people that you're helping versus just yourself and what you are going to accomplishing. So for me, it filled my cup a whole lot faster being a manager or a coach.

Alex Kracov: It's so great to see people succeed. I mean, that's the funniest part about managing people. There's nothing better. Yeah, it's such a fun part. And the flip side, it's terrible when they're not succeeding. You got to be kind of the firm leader and hold people accountable. That's not fun. But on the coaching side of things, how would you tactically go about kind of coaching a sales rep? Are you listening to call recordings and sharing feedback? Are you helping them write emails? How do you sort of go about, like, what device do you have for sort of coaching sales teams?

Chris Michelmore: I mean, all of the above. I think, from a coaching standpoint, there's a couple key foundational items. So, first of all, just understanding their why. It's a lot easier to keep somebody motivated when you know what they're working for, and you understand what's important to them. That's what I meant. You can always come back to meeting them where they are, as far as their drive and what their passions are. So definitely understanding that, understanding why. This is hard. You're going to get shut down so much, so quickly, so often. Why are you doing this? Why do we keep doing this? And so that's a big part of it.

And then asking, right? What is it? How do they like to be coached? How do they want to be coached? That is such a broad spectrum, individually understanding that but reviewing as much as they'll allow you to. I think the better answer is just through questions, through questions and curiosity. Just like you would talk to a customer, you don't want to tell the customer what's right. You want to help them self discover it. So I think from a coaching standpoint, best thing, just like with a customer, you know a customer understands what your value is when they can explain it back to you. The same thing is true. You know that a rep has learned something, grown, when it's their idea, when it's their idea and then they go and get it. Because one of the other challenges from transitioning to a manager is keeping people accountable. Well, keeping people accountable when it's only your ideas as the manager and you're saying, "This is what we have to go do," without aligning that to their why or realizing that they are not going to do it because of their motivation factors. If it's their idea, it's so much easier to keep them accountable to it. "This is what you said you wanted to do. How do I help you go do that?" I think that's a big part of it.

Alex Kracov: I think anchoring it to their why and their goals is so important. I've always tried to do that as a manager. Because I think depending on what their goals are, the way you work with them is so different. Like if one sales rep is like, "I want to go be a CRO one day at a big company," then you're going to maybe ride them a little harder or give them more leadership opportunities and things like that.

Chris Michelmore: Totally.

Alex Kracov: If they have that super sort of aggressive career goal. Then there are some sales reps who are maybe like, "I just want to support my family and make a lot of money and then close my laptop at the end of the day and not worry about that, because I have family and stuff." And so very different ways, I think, you would go about coaching those people. If you try and coach the CRO-type candidate, as the family man, make a lot of money, it's going to conflict. I think it's so important aligning it to the why. That's why it's always something you can go back to, too, in those tough conversations where it's like, "Hey, I'm trying to hold you accountable to being a better manager, because you told me you want to go be a CRO eventually. This is the skill. This is what you're going to have to have to do eventually." So I don't know. That's something I think I learned when I was at Lattice. It's just really stuck with me as the way to approach management. That way, it makes it about them. Not about you.

Chris Michelmore: Absolutely. Exactly. I think it's this element of humanness. Like I said, the same principle is true when you're talking to a customer. I mean, at that point, the reps are your customers theoretically, at least thinking of them that way.

Managing a Remote Team of Managers

Alex Kracov: Then as you've progressed in Zoom, you sort of moved, I think, beyond just a frontline sales manager. I want to learn more about your roles. But you went into like SMB segment leader, then senior, then head of SMB acquisition, head of mid-market acquisition. So I imagine you're a manager manager now. Can you talk a little bit about kind of, what are you doing today at Zoom?

Chris Michelmore: So you're right. The next iteration of that was manager of managers. We're going a lot. Now you're starting to manage - this is an interesting key piece of it. You're starting to manage not just people in your local office. Obviously, back then, we're all in person. We're anchored in offices and things. But now the teams grew internationally, and so you're managing people remote, which is another element of it. You're remote to them even though - before everybody was remote, you're still remote to somebody if you have a dispersed workforce, right? So that was managing managers all over the country. Then after that was, along with line size changes going from SMB to mid-market and changing some of that segmentation, then I was managing directors or leading directors. So second-line leadership role. So, yeah, that's the kind of the current state, if you will.

Alex Kracov: What changes when you're managing a director versus an AE or a manager? Is it kind of the same principles just now you're, I don't know, just at a higher level? How do you think about kind of that challenge?

Chris Michelmore: Great question. It's a difficult one because the balance gets harder and harder. The things that you loved about the frontline leadership role: you're in deals all the time, they need help, and you get to be the fixer. Although there's a balance there and you want to be really cautious to not just come in and fix everything, right, you're teaching. You're coaching and not just fixing. But you do get to be involved in that. You get to see much quicker the outcomes of those conversations. So you do start getting a little bit further and further away from the day to day. That's one of the challenges. It's to how do you prevent that from happening? How do you still keep your ear to the ground? How do you still keep yourself front and center in front of the reps? I think the answer there is to break down barriers.

One of the things that at least I try to, I can't say that I always do a great job. It's always work in progress. But break down the barriers and not let the, "Oh, I can't go talk to Chris because he's too busy. I can't go talk to Chris because the deal isn't big enough, or it's not vetted all the way through and really hard to try to make sure that those barriers aren't there." The same things that I love to do as a frontline manager, I still love to do it. While at the same time, you have to be more strategic. Instead of the reps are being your customers, now your managers, your directors are your customers in this example. So that creates a lot more forward thinking. So it's a lot more strategic. You're always working 6, 12 months in advance. Because things move slower, right? You can't make an immediate change like as a rep can and see an immediate difference. So it's a comfortability level. We just kind of, okay, we can put something into place. It's going to take a lot longer to get to the adoption level that we want, at the rep level. Then once that does become adopted, how are we going to track it? How are we going to then coach to it so that the levers get bigger and they move a little bit slower? Then the last piece to it is, yeah, you start introducing a lot more of those kind of HR positions, HR conversations. You're dealing with things that you didn't necessarily get into the role for. But it's a reality, and you have to learn that very quickly.

Alex Kracov: Are you also managing more by numbers in this role, too, where it's like I assume each director owns a quota, and then whoever is missing their quota, that's where you kind of laser in on? Is that kind of a little bit more about how you think about the team? Because I think that's where I ended up when I was the VP at Lattice. It's a little harder in marketing the numbers. But I tried to build this numbers infrastructure where I could kind of laser in the eye of star on and be like, okay, there's the problem. Because it's a little harder when you're so many levels above the frontline people where the actual challenge is.

Chris Michelmore: Dead on. You're dead on. You don't necessarily want to. You don't want to come across as you're only - you're trying to keep the individual contributors in mind at all times. Because you want to lose them in numbers. The numbers are for you. But yeah, the things that start becoming your senses of pride in that role are the ability to foresee risk in the number and really, really have forecasting bottom down. So, yes, you get really, really ingrained in the numbers. You can start managing to those instead of leading through those. They're very, very different. Different things, right? Here is what I need you to do. Here's what you have to go do. Versus if you do this, this is what will happen. This is what it'll lead to. That's a much different conversation and lands a lot better.

Alex Kracov: Yeah, super interesting. I want to go back to one thing you mentioned a couple of minutes ago around managing remote teams and international teams. That must have been a really crazy transition, an interesting transition. I mean, the good news is you already had the technology to support the transition, so you didn't have to think about that part of the challenge. But what's that like? I mean, what's it like managing a global sales team in different time zones? How do you think about managing the team and maintaining the team culture, and also holding people accountable, all the things we've been talking about? How does that change?

Chris Michelmore: Well, you touched on the most keyword in all of that, and that's culture. That's a challenge, for sure. But I think if you keep culture as your North Star, that guiding light, it definitely makes it easier and better. I think also allowing subcultures to foster. Our office, our group, our team, what do you want to be known for? I think fostering the mindset of, what do you want to be known for? What are we going to be known for as an entire SMB mid-market department? But again, these are ideally all of their words, all of everybody else's collective words. Not me or anybody else sitting there saying, "This is what we're going to be known for whether you like it or not." Once you've established that culture, you're making sure everybody's on board with that but also being okay with the subcultures, great. Okay. We're collectively, we're going to be the hardest workers. We're going to be the most strategic whatever it is that you're going to hold a sense of pride around. But then, okay, office A, great. What are you going to be known for? Office B, what do you want to be known for? Then it creates this really fun, really fun environment. You get the mini competitions, a little bit of bragging rights. We'd sent trophies to different teams and things. What doing that allows you to do is celebrate success in kind of those tribe levels, while knowing that it's all raising everybody up at the same time.

Alex Kracov: I imagine each of those offices and the leaders have a lot of pride for each of the subcultures and their teams and a good, friendly competition. I started my career basically as an SDR at Yelp, and we would have teams. Whoever closed the deal would go up and ring the gong and things like that. It was kind of silly, but you did get excited when people on your team were doing it. I tried to kind of foster that culture. But, yeah, too much cold calling for me, though.

Chris Michelmore: I'm still a big fan of cold calling.

Alex Kracov: It works, yeah. Actually, while we're just talking about cold calling, is that a big part of your outbound process today, cold calling?

Chris Michelmore: Yeah, absolutely. You need to be very intentional about it. There's cold calling for the sake of cold calling, and that's not what works. That's not what I'm talking about. You got to start with the who, identifying who do you want to talk to, and why, understanding why that is and getting really good at that. Then it's intentional cold calling, and that's super, super effective still.

Growing with Zoom

Alex Kracov: Yeah, you can catch someone in the right moment and have that impactful conversation or convince them a little bit to pay attention. It really, really works. I'd love to shift gears a little bit. Obviously, Zoom is a generational company and has gone through quite a transformation over the last decade. You were a sales leader throughout all this hypergrowth. I'm curious, what was that like for you personally just keeping up with, I assume, so much change at the company, new initiatives? How did you sort of personally keep up with the company growth, and not only just keep up with it but thrive throughout all of it?

Chris Michelmore: That's an interesting question. I don't really know if it's truly how I kept up with it. I don't really know if I have a concrete answer. I think, just personally, I love change. Not always is this true, for sure. But there's a general statement of: if it ain't broke, break it. This feeling of being stagnant, especially in tech and in sales, I think the better way to describe that would be a Kaizen mentality, if you're familiar with the mentality. But it's kind of like always trying to find, always trying to be better. And so when things are changing, actually, thrive in that situation when things are constantly changing. Because it's very easy to get stagnant when they're not and not try to always try to either self improve, or try to improve your surroundings, or try to improve your team, try to improve the technology. I just love that environment. So I don't know if it's a good answer around just like a way to go do it or advice to how to be good in it. I just think it's a general love for always trying to figure out how we avoid being stagnant. And so if it's being created for you naturally - because things are always changing, whether it's in the world, macroeconomics or your own company - I think you have to love being in that environment.

Alex Kracov: And is that why you've been able to stay at Zoom for so long? I think most people today are progressing their careers by job hopping and switching every year or two to something. Especially in sales, I mean it's crazy, the amount of turnover. But you've worked there seven plus years. And so I guess, what has made you so committed to Zoom and also just be able to thrive there for so long?

Chris Michelmore: Believe it or not, I hardly believe it myself. I'm about coming up on nine years, which is great

Alex Kracov: Wow.

Chris Michelmore: I think part of the answer goes back to the very first thing I said around why I found Zoom in the first place. It's gratitude for a company, for a product, that is always trying to get better. And so when you're in an environment where innovation is constant, you don't have to go look inside, oh, I need to go find the next innovative thing, if you're always being innovative, you're always trying to figure out ways to make things around you better. So I just think that constant change really does make - I would argue that my experience has been multiple different companies within the same company, right? Whether it's my role has been different and it's more of a different role than I would have gotten in a different company, or just the company itself, the market that it's serving, I'm kind of getting that change through innovation and through market growth that you would probably try to go look for elsewhere. So that's one answer.

Another important answer is personally. Personally, it goes, again, back to a little bit of loyalty of, why did I try to get into tech in the first place? I tried to get into tech in the first place to find a product that really, really worked and to continuously be learning about how to progress in that industry. All of those needs have been met every step of the way. So personally, I'm just grateful for the opportunities that I've been given. I think having that gratitude goes a long way.

Alex Kracov: There needs to be more people like you in tech, honestly. I think it's such a fantastic answer and such a good approach to career and life. I think that's probably a great place to end the podcast. Chris, thank you so much for coming on. It was a really fun conversation to kind of hear your mindset as you think about, as you've gone through this amazing sales journey at Zoom. So I really appreciate the time today.

Chris Michelmore: Absolutely. My pleasure. I absolutely had a great time. Thank you.