Operators Ep 33 Transcript

Delian Asparouh...: Hi everyone. My name is Delian and I'm a principal at Founders Fund, a venture capital firm based in San Francisco. This is operators, where I interview non-VC, non-CEO, non-founder operators that make the startup world go round. Today, I'm interviewing Jaimie Buss, SVP of commercial sales North America at Zendesk. Jamie is a veteran sales leader with experience selling everything from SaaS, to virtualization, storage, and networking. During her first four years at Zendesk, she was VP of North America and led SDR, BDR, SMB, commercial and enterprise sales. During her 20 plus year sales career, she has held sales and leadership positions at Andreessen Horowitz, VMware, Coverity, Meraki, Coraid, and Inktomi. I hope you enjoy the show. Cool. Yeah, Jaimie, super excited to have you on the podcast. Thanks so much for taking the time.

Jaimie Buss: Thanks so much for having me.

Delian Asparouh...: So we always like to first dive back and go to people's sort of early career moves since I think it helps sort of put together the story for how you eventually ended up at Zendesk. And so, rewinding all the way sort of pre the dot-com bubble, your first job out of college was at Deloitte as a systems analyst and then sales engineer at Inktomi.

Jaimie Buss: Inktomi, yes.

Delian Asparouh...: Inktomi. Okay, Inktomi. And so, you got really involved in sales very early on in your career. I'm curious, what was your path from just college? Was it something where you already kind of knew that this was a path or role that you wanted to go down, and how did you end up sort of making your way to sales sort of so quick? I feel like a lot of people don't necessarily realize it that early on in their career.

Jaimie Buss: Yeah, no, I think it's a great question. And I actually didn't realize it right out of the gate because as you mentioned, I do have an engineering degree. And honestly, I would look down my nose a bit at the business students who would party on a Thursday night and I would not be because I would have a 7:00 AM civil engineering class to attend and needed to get as many A's as possible to keep my GPA up. So I always felt like I'm a very competitive person and I always wanted to do something that was hard. And engineering for me was it was not a very natural act. And then the systems analyst piece was like, "Hey, I want..." My parents afforded me a nice life as a kid living with them and I wanted to be able to support myself, and that was a great way to do that.

But I think to your point, that was before the dot-com bubble, it's like people didn't realize companies had to actually make money. I was really young and didn't understand that companies had to make money either. So I got lured by Silicon Valley very quickly. I went and spent about a year at Deloitte where I did learn how to be professional, so how to dress appropriately, how not to overindulge when at a work event, all the basics that I think sometimes we forget to teach our recent college grad sometimes these days, but I think it was a great experience.

And I actually was in IT for six months at Inktomi before I moved into sales engineering. So I had a little bit of a bridge there where I was working with the sales team, helping design a product for them. And then the sales engineering director came up to me and said, "Hey, you're really good at presenting, and you're really selling this product you're building for the team really well, have you ever considered being a sales engineer?" And that's where it dawned on me. It was a much more lucrative option, it kind of wasn't completely sales, but it kind of bridged my prior experience. And I ended up ultimately really enjoying the sales aspect of it.

So what I would say is I can empathize with folks that are maybe more on the product side, who kind of look down their nose, perhaps a little bit at salespeople, "Oh, it's not as difficult as a job and whatnot." But what I learned is that, when you do it well, there's actually a lot of sophistication to it, and it's a very interesting career for the right people. And I just never looked back. Once I got bit by the bug, there was no turning back for me.

Delian Asparouh...: I was going to say, I'd love to hear, it seems like your next move over to VMware sort of combines both your engineering background. Obviously, the product that you're selling too is a very technical product and then I'm sure that buyers are also they, themselves, technical. And then you started off sort of like in inside sales and so people, I see them coming to you with interest in the product and you were sort of helping get them over the line. And so, it feels like, yes, it was technically a sales role, but I'm sure it also had a very technical nature to it as well.

So yeah, I'd love to both understand what attracted you to sort of VMware and especially at a time where I imagine this is during, this seems like sort of in the trough of the dot-com bus, I imagine, it's sort of when this was all happening. And so yeah, how you found it, how you decided to go work for that company in particular since it really just seems like... I don't know. I can imagine in the sort of trough of 2002, tough to make the right call, you very much made the right call there.

Jaimie Buss: Yeah. So I was pretty naive back. That was when the bubble was bursting, in fact. And people around me at Inktomi left and right were being laid off, but being naive and overconfident, and I kept not getting laid off, I thought, "I don't have to worry about this, I'm going to be fine." And it was a good lesson because eventually, I walked in the office one day and my boss said, "Yeah, I'm going to need to see you in my office." My stomach dropped and I went, "Oh no, I'm not going to have a job. Oh my gosh, this is terrible." So I gathered my paperwork and my COBRA paperwork, had to figure out how that works because I needed insurance still. And then I went back to my apartment and I was like, "Holy cow, I have no job." So I didn't even look. That was not best move on my part.

Now, what I had done though is when I was adding to me, I had a mentor there who told me, "What do you want your brands to be? When people think of Jamie Buss, what do you want your brand to be?" And this was pretty early in my career, maybe 24, 25, I'm not going to tell you how many years ago it was, but it was a lot. And so, I really thought about that. And so, I wanted my actions to portray what I wanted my brand to be. And I did that well enough that it was my network that helped me get the interview over at VMware.

Because think about it, I never carried a bag directly. I was a sales engineer and I wanted to get into... What I realized was is I loved the sales aspect of my job; I did not love the engineering aspect of my job. I wanted to be a seller and carry the bag directly, but that meant I had to have someone to take a chance on me. And people that didn't know me from Adam weren't as willing to hire me as a sales rep because I was only a sales engineer and I had never carried a direct quote on myself. I'd had an overlay quote to share with a rep.

So the Inktomi crew, Carl Eschenbach moved over to VMware, Kirk Bowman, Brian Cox, that leadership crew that I'd worked with was over at VMware. And I'd heard through the grapevine that they were hiring account executives, and this was still... they were very early on. I mean, there was maybe 10 reps in North America. I mean there was a very small team. It was 2002, it was a long time ago. And so, I remember talking to Brian and he's like, "Yeah, okay. I think perhaps, but you need to talk to Carl and convince him." So I had to get on the phone with Esch and convince him, "This is why I want to be a seller, take a chance on me. I'm going to do good work for you."

And eventually I had to sit down with Diane Green and convince her as my little 25-year-old self, that I was going to be able to sell her software. That was very intimidating. But fortunately, I made it. And then once I got into that career, we can get into a bit, I think there's some good lessons from that experience, but net net, it's having the brand and maintaining the network that has really helped me flourish really to this day, that Inktomi experience really pay dividends for the next 20 years.

Delian Asparouh...: One of the things that I feel like I always noticed with folks that have both identified sales as a core skill set, but then have chosen to continue to refine is do you feel like they just applied a science to this thing that almost sometimes feels like a dark art in some ways. I think about this when I helped incubate this company, Verda, and we had our first sort of like biz dev person start about two months into the company. And there's a particular deal that I was working on, that we're just like not getting over the line, or it was not really empathizing well with, let's say, my counterparty at the other organization.

And literally, on his like first day, he starts off the call and he's like, "Hey, I looked you up ahead of time, I saw that you're a big..." I don't remember what the fuck who it was, like a malbec enthusiast actually like I have a friend with a vineyard here, blah, blah. And just completely melted the counterparty of the other organization and deal got signed 24 hours later. I remember being that moment where I was like, "Oh my God, this is a perfect example of just like a tactical moment where it's like, I just never did the work, I just kind of kept trying to drive through it."

And there are so many different, I feel, ways to apply that science. I see people take the challenger sales model. They're like relationship-driven and they're like consultative model. And it seems like for each personality type, and each type of company, and each type of product, there's a variety of ways to do that.

And so I'd love to understand maybe even from the sales engineering role, but then also from the first, let's say, six months, a year at VMware, what were the things that you sort of, let's say, tactically discover that you were like, "Hey, I am best suited for doing this or here are the things that I can use to add as skillsets in my toolbox. And like yes, I'm a great presenter, and yes, I can talk to these people, but like here's how to transform this into a science where I can be like a top 10%, top 1%, top 0.1% bag holder or deliverer."

Jaimie Buss: Yeah. I think you hit on a great point, is that I think there's art and science to sales and I think that people make some assumptions about it in that you have to be an extrovert. I'm not an extreme extrovert. I'm usually the first at sales kickoff to sneak out and you'd go to the restroom, but I don't come back because I can't take that many people for that long. I do not like parties with a lot of people that I don't know, I really don't, I find them very exhausting. But I love selling. I love working with my customers. I love being with my team, it's different. So I think that's one assumption to take into consideration is that you can have introverts that are phenomenal at sales.

And I think the point you hit upon is, yes, there's a connection aspect to it where you want to seek to understand first, you want to ask good questions of the client first, you really understand them in their situation. But what I learned that I took from engineering that I applied to the sales is that once you have established that there is a need that the client has, and that you have a potential to meet the need, and that the need is acute enough that they will do nothing, so you have a potential opportunity here. There's a lot of project management that happens between that point and getting the deal signed.

There's a lot of moving parts, there's just from players involved, they're going to make decisions for different reasons. You have to understand along all those points, how things can go wrong, what's the competitor going to say? What's sales strategy is the competitor going to use? Is there a quarter, end of the year or a quarter a month after yours? So are they going to use a delay sales tactic? Are you going to have to use a flank tactic to kind of get next to them to understand? So engineering is a lot of process and getting from point A to point B, but so is sales, it's just a slightly different process.

But I think I didn't realize what I was doing at the time. Now, I've definitely codified because I lead a big team and, of course, I teach this stuff now, but back then, I was always thinking, "What don't I know, how could this go wrong? What don't I know, how could this go wrong?" And I would just ask questions and listen, and then I'd pull on the threads as I'd heard them. And I think that was the key to having enough detail to know how to close the deal and when it would close.

Delian Asparouh...: And so, do you have a particular, let's say, deal of VMware in that sort of first year or two that it was maybe embodies this where you ditch or pull on a thread and that you found something that probably wouldn't have been discovered if not for sort of that inquisitive and like, let's say, curious and sort of paranoid nature that allowed you to actually get the deal over the line?

Jaimie Buss: You're asking me a question that is so long ago, there's no way possible I'm going to be able to give you a story of that. I mean, literally, you're talking like 2003, it's 2021, so I have no idea. And in VMware, it's product led growth and there was a monster amount of inbound. So it was a completely different environment than most companies have. I've been in that kind of environment and then I've been in where it's not product-led growth. And there was a lot of lessons I learned about that, the differences between those motions, but unfortunately, I don't have a specific... I could talk more about recent things, but I don't have a VMware deal story for you.

Delian Asparouh...: No worries. It seems like as a part of VMware, a big part of your role there was sort of hiring team management. And you talked about obviously now a large part of your role is sort of teaching people and bringing them up. I guess, yeah, how did you transition from sort of individual seller to then starting to actually build out these teams and any you feel like sort of mistakes that you made early on that you now sort of caution sort of new sales managers against that have really become codified lessons, and then may have on the flip side, who were people that really helped sort of mentor you and bring you up to speed in terms of how to sort of be a sales manager and sales team builder?

Jaimie Buss: Yeah. So first of all, I think that this concept, and I'm feel very strongly around this topic, and I think it applies to anyone who's an individual contributor role and finds themselves leading people. You could be a founder of a technology and you start building your company. You are now a people manager, you are now a leader and you've found yourself in this role, whether or not you had intended to be there. And I think what's really important is to realize that that job is a distinct discipline. There are different aspects that make you good at that job that's different than being a good developer, or being a good seller, or being good in HR, managing people.

What I look for at least then as of today, I always want to understand when you lead the people, what does that mean? Describe to me, how do you do that? And I'm looking for very specific examples. One book that I read really early on that was recommended to me by one of my early managers was First, Break All the Rules by Marcus Buckingham. And I love that book and I have an entire shelf of leadership and sales books sitting here behind me, but that one has some very practical advice on why people are going to be engaged or disengaged in their work.

And in fact, you can actually take their 12-question engagement survey yourself and you can tell how you're feeling about your job. Has someone given me direction or talked to me about my career in the last six months? Has someone giving me feedback in the last seven days? Do I have someone at work I feel I can confide in? Do I feel that my opinions are heard? There's a whole list of these things and you can actually rate yourself on one to five. And if you find yourself kind of in a red state, you can actually start to isolate. Well, why is that? And then maybe it's something that you can address.

I actually survey my team on this every six months to determine my engagement level, and where I might have pockets of disengagement, and where I might be able to be doing better because I obviously have a lot of frontline managers at this point. So I think the biggest that I learned was, A, it's a different discipline. You have to have some form of thought or methodology on what you think it's going to take to be the boss that people want to work for rather than the boss people leave.

And then the other thing to watch out for is when you go from IC to manager is that I think in my experience, you can kind of come in at one end of a [inaudible] come in as a jerk or you come in as the buddy. And neither one of them are good because if you come in as a jerk, no one wants to follow you and you're going to have a lot of disengagement on the team. If you come in as the buddy, they might like you, but they're not going to be top performers and they're going to complain about other things because you're probably empathizing with them. When they come to complain about things, you're like, "Oh, I know that's terrible." And now suddenly they feel very vindicated in whatever they're complaining about.

So I think that knowing where your personality might lie, and just be aware of that, and the goal should really be to kind of bring yourself to center where you have empathy, and you're candid with them, and you understand them as people, but you also set really clear expectations, and you hold them accountable for that, and you can have those tough conversations. I think it's hard when you first going to management to really nail it right in the middle.

Delian Asparouh...: So after a very obviously solved career at VMware for seven years you ended up deciding to leave and joining two different startups, again, focused on more inside sales, which I assume means they're sort of more product-driven growth versus then joined a company where you're director of corporate sales, which I imagine it was sort of more outbound. I guess, could you walk us through a little bit of sort of what was the decision-making around leaving VMware and then some of the sort of, let's say, differences in sales environment that you noticed given the different types of organizations and sort of where the top of funnel was coming from, whether it was product-driven, or sales, or marketing-driven.

Jaimie Buss: Yeah. So I learned some really great lessons when I left the VMware. So one of the reasons I left, and this is for all the moms or parents out there, I had my first child at the end of my tenure at VMware and I was in a travel job. I was managing a field team. I was on the road every week and I just didn't want to be gone every week when I had an infant. And so, I was looking for a job that I would still travel, but it wouldn't be every week. And so, I followed one of my colleagues from VMware who was leading sales at the next job that I took. And I was brought in to build out a transactional business because that's what we had done really well at VMware.

But here's the thing, it's not a person that builds a transactional business, it's product-led growth. And if you don't have a product that has a freemium or an easy free-trial motion, you're not going to have product-led growth and you're not going to have... it'll have less emotion. It's just full stop, there is no building that. I actually still have conversations today where I'll talk with an entrepreneur and they're like, "Well, we really want to build a transactional business." I'm like, "Well, just tell me how your product is going to help you with that." Because that's where it starts. It's not about hiring someone like me who understands product-led growth to make it happen. The product has to do it.

And I didn't know that at the time because when you come from an environment that's been very successful like a VMware and you really haven't failed, you think that you aren't going to fail, and you feel that you can influence things, and that you have the power to make things the way that you want them to. And I was still young and not as wise as I am now. And I learned that lesson that, okay, this is a product-led growth and I can't really change that, there's not much I can do about that. I did go to some product-led growth companies subsequent to that and learned that.

But here's the other lesson I'd say by being in a startup environment too, is that I learned a great lesson from every single company I was at. Product-led growth is one of them. I think the other one was also that you can't depend on inbound forever, and at some point, you're going to... And it's great, if you're in a position where your reps really don't have to do any cold calling, you're in a great position. And we were like that for VMware a very long time, but eventually, you're going to get to the point where that's not possible anymore.

And so, I think the importance of building an understanding of how to successfully build an outbound motion, I use John Barrows' training to do that. When I didn't know how to do it, I studied Aaron Ross, Predictable Revenue to understand how he did it at Salesforce. So I think that's something to keep in the back of your mind is that eventually, that becomes something that's important as well.

The third thing I'd say, and I look for this in candidates today is that I think a very important lesson I learned is that you can never make an assumption that what worked in one place is going to work in another. And I think that people that have worked at too few of companies, so when you see your resume and someone's been in some type place for 20 years is not necessarily a bad thing, but what you have to be careful of is how much have they seen and tried to realize that every single environment's different? And it's like kids, sure, they have the same parents, but they come out very different. And if you try to raise them the exact same way, that might not turn out so well.

It's kind of the same with products, you can't assume, hey, I'm at Zendesk. If I go work somewhere else someday, am I going to assume that everything that worked here is going to work there? No. I'm going to ask a lot of questions. I'm going to understand what's going on at that company. I'm going to understand the product, understand the customer and then understand where some of the bottlenecks are and address them. I could use my tool belt from the past, but I'm never going to ever make an assumption. And I think you do want to watch for that with candidates that have been in only a handful of environments because they just don't have the breadth of getting a little beaten up.

Delian Asparouh...: Is there a particular exercise or set of interview questions you use to dive into this particular topic or looking for this particular flag of trying to understand whether or not somebody sort of shows that level of mental flexibility or self-awareness to not necessarily just apply exactly the lessons they learned or techniques that they've learned at the prior successful place they were at?

Jaimie Buss: Yes. So I'll ask a candidate, "So tell me the environment you walked into when you joined such and such a company, and what changes did you make and why?" And then I just leave it at that. I mean, I don't really think you need to make it more complicated. What you're looking for is, are they asking questions? Are they looking at data? Are they seeking lots of different perspectives, identifying a problem and then experimenting on how to solve it? That's what I'm looking for. I'm not looking for, "Well, I had this great program that I did at Salesforce, and so I just implemented it there." I'm like, "It's not really what I was looking for." That's a bit concerning.

Delian Asparouh...: Makes a ton of sense. And so yeah, after a couple of sort of stints at various startups, you ended up deciding to go join Andreessen Horowitz as sort of like operating in a partner there on their market development team. I'd love to understand as somebody who had obviously either joined multiple sort of successful startups, what was the decision-making around joining something like Andreessen as an operating partner in terms of career step since obviously they only hire so many people and there's not an infinite number of Andreessen's in the world. And so, there's not that many operators, let's say, or sales leaders that have actually gone through that type of role. I'm curious, what was the decision making around that and what do you feel like the perspective or benefit of that was vis-a-vis colleagues that haven't done that type of role?

Jaimie Buss: So that was a very unique opportunity that initially, I was reluctant, honestly, to respond to. I'd gotten a LinkedIn ping and I'll be... I was six months pregnant. I wasn't planning on going anywhere from my current job, obviously. I was just going to have the baby and see what happened after that. But a friend of mine convinced me, "No, you should respond back to that." I'm like, "Why on earth would a VC company be interested in me? This makes no sense to me at all." But I didn't understand the model. I didn't understand a16z, but a good trusted advisor friend of mine said, "No, just take the call, see what it is."

And so, I did, and it turned out that it was kind of twofold. It was to build a team, to do two things. It was to build out relationships, the Fortune 500 CXOs and invite them to participate in briefings at the briefing center. And then we would then host those briefings with business development reps who would then custom curate agendas and we would, kind of like a sales rep would, host the C-level executive and then we'd bring in the various portfolio companies, we can help them with their pitches and all that kind of stuff.

And then the other component was working with the product-led growth SaaS companies within the portfolio on when they were early-stage, questions like what type of sales reps to hire. Sometimes I'd help with interviewing, I'd help look at their comp plans, think of the pros and cons of what you might want to put in a comp plan or not. And I think what that did is it helped me, A, empathize with how hard it is to be an entrepreneur and you have to hire sales reps who are very difficult to hire. Our sales leaders are very difficult. We can sell really well in an interview, but how do they're actually going to do what you need them to do?

So I definitely got a good perspective on different business models, how to fit different GTM models within those different business models, and a little bit more what it's like to walk in the entrepreneurs' shoes. So I got a very, very good bird's eye view of a lot of different companies and got a lot of ideas from them, too. Different comp plans they tried, different roles that they had implemented. So I got exposure to a lot more than I would've been, had I worked at one company. I had a phenomenal experience there, learned a ton from Mark. He's got a phenomenal enterprise sales approach that I had not really built up at VMware, to be honest, because we were running so hard and so transactional, we didn't have to be as disciplined. But I did take that from him and use that now. But yeah, it was a phenomenal three-and-a-half-year stint. It was an unexpected stint, but I'm very grateful for it.

Delian Asparouh...: I feel like with that type of opportunity, you also get a very good filter for the venture upside in various opportunities because you start to see how venture investors compare the upside of opportunities. And so, I'm curious, how did the increase Andreessen experience venture lead to sort of your next career decision, that they've sort of been the longest stint that you've had obviously since you left VMware, in terms of just analyzing Zendesk, the opportunity, the fit with the founder, the business model, the product-led growth, all these things you've talked about, how did you analyze that potential opportunity with all that, perspective you gained from Andreessen, VMware, and some of those startups that you joined and before Andreessen.

Jaimie Buss: Yeah, I think that's a good question and it's interesting because, when I joined Zendesk, it was post IPO, not pre IPO. So when I was thinking about what's next... Here's one thing you realize when you work at a VC firm, is that most of the startups are not going to have a GitHub level of outcome, or Okta, they had some very successful slack. They had some very, very successful companies, but they had a lot of other ones that didn't have that level of success. And so, when you're a venture capital firm, you can make several investments in a fund and you don't need them all to hit. But when you're one individual making one decision, then it matters a lot more. You don't have the benefit of a portfolio, you are picking one.

And so, it was harder for me to decide, what type of startup I might want to go into, but then from my old Inktomi network and VMware network was at Zendesk. And Brian Cross was CRO at the time, and I happened to meet him for lunch, not looking for a job at Zendesk, but just kind of looking for his advice on thoughts on what to do next. And he said, "I think I might have a job for you." And I'm like, "What, at Zendesk?" He's like, "Yeah, it's product-led growth, it's what you're good at, it's the type of sales motion that I think is right in your wheelhouse. I think you'd really kill it here."

Well, I mean, it was like it was head of Americas at the time, huge portion of their business, I couldn't turn down the opportunity, to at least speak with them about it. It was a very big role of a public company running a huge part of the business. I mean, to me, that was like a golden opportunity, regardless of whatever the money was going to be. I was like, "This is an experience that if I can get the job, will be a phenomenal experience."

So it really wasn't that I sought out that opportunity so much as I got really fortunate that it was available at a time that I was kind of exploring what to do next. And then, fortunately, Zendesk gave me a shot because this was a really big role and I was a little bit of an unknown person at the time, at least not to the CRO, but to everyone else. But they gave me a shot and I'm very grateful that they did.

I think we've done phenomenal work over the last almost five years, built a great team, I love working with my team and all my business partners at the company and I think we've done some pretty amazing things. So I think it goes back to my point of building that brand early. It keeps paying dividends beyond when you think it's going to, and just keep your network going, because you just never know what's going to surface.

Delian Asparouh...: Obviously at Zendesk, either lead some huge teams and I assume they were sort of larger relative to even at the peak VMware, what we're leading. I'm curious at that sort of scale, what were some of the things you had to change about just management style or strategies around recruiting, scaling the team. I'm sure at that scale and also being at a public company it's just slightly different, like at a private company, you don't have to deal with people getting distracted by the stock price, whereas, that happens in the public world. What were some of the things that you sort of noticed pretty early on you had to sort of adjust in terms of that team-building process?

Jaimie Buss: And I was at VMware when it was public as well. So I was familiar, I was there obviously way pre IPO through IPO, so I'd been on both sides of that, I'd been there. I think it was at VMware, to just over a billion dollars as well, so pretty good run. But when I was in the role here at Zendesk, what I realized is that, at a public company, running a team of that size, you have to be very precise. So there is a lot more wiggle room when you're at a startup, with forecasting as an example, or with your hiring process, your performance management process, because you have to be really conscious of the risk you're taking on and in either one of those in any of those circumstances.

So when I first got into Zendesk, I realized one of the first things I had to do was figure out a system for being able to forecast the business because we didn't have a good methodology in place and we were really missing the forecast by a country mile. And I had to figure out, well, why was that? Why was it, what could I change to impact that? And then our hiring process too was slow, we had people present on the Zendesk solution and I just was like, "They don't know Zendesk." We can't hire as many people as we need to and have our process be this fast, so we kind of streamlined our hiring and then really focused it on knowledge, qualities, and skills. And then we had attributes under each of those three segments and then different people would interview for either knowledge, quality, or skills. And then this way, the candidate experience was better. You're not being asked the same question every single time.

And then we also made sure that we covered all of our bases and we didn't have too many people on a panel. We had a good size, I think like four, maybe five people on a panel, so it was enough that we could get a good perspective, but it wasn't so much that it took forever or exhausted the candidate or us to be quite frank. And then we just really organized ourselves around the interview process. So I think that discipline definitely helped us. And then coming up with, and having a qualification methodology and a sales process, which I don't know how much you want to get into, but that was definitely... We went from maybe 20% accuracy to being able to easily forecast within 5% accuracy and I try to be 1% or 2% closest to [crosstalk]-

Delian Asparouh...: Yeah, I'd love to dive further into that in terms of, it sounds like obviously, it was a major challenge on the forecasting side of things, but with either taking that or implementing that in terms of sales qualification, accurately forecasting what an actual deal would look like and what the likelihood of it converting was. What were some of the first steps that you took, especially in an organization of that size? It's not a matter of like, "Let's gather everybody in a room," given that doing that becomes an unproductively large meeting. And so, how did you even start to dive into understanding the problem and then actually, starting to implement some of these fixes, it sounds like one of them around sort of sales qualification.

Jaimie Buss: Yeah, so what I did is, I brought in a firm to come in, that Mark Cranny had introduced me to, that I knew could help us build out a sales process that was based on customer verifiable outcomes, not on actions that we had taken as sales reps. So let me give you an example. So oftentimes if you're in a stage two opportunity, that means that you had a discovery call, that's from the rep perspective. But if you say, "Well, what was the customer verifiable outcome that this was a discovery?" Well, the person who you think could be a champion attended the call, they've identified that they do have an issue that we could solve and the customer agree to next steps. That's much different than saying, "I, as a rep had a discovery call." And so, what we did is we built out these verifiable outcomes at every stage within the process. And one of the most important ones was, I don't let anyone move a deal off of stage three until two things have happened. One, I know, do nothing, is off the table, because I don't care what you're selling. That is always the biggest competitor.

Do nothing is always... that's your biggest threat because it can be perceived as the least risky option, is to just keep doing what they've been doing. So have you demonstrated that the current as is state is hemorrhaging enough, they're either losing money, they're not able to make money, or there's too much risk in the system, for them to stay at as is state.

The other component is that assuming you're competing with someone, that you're the vendor of choice, so I don't want a deal move to stage four if I'm still competing with one of my competitors because that stage four deal is the best case for me, and it's not best case if I haven't won. I want to at least be vendor of choice, now, could I still potentially not close the deal? Yes, maybe we don't come to terms on commercials, maybe we don't come to terms on the MSA. That can happen, but it's less likely. But if I can still lose to a competitor, I don't want it. I don't want things moved over. So how has the client verified to us that they're absolutely going to move forward with something? Have they absolutely made a decision is there's an economic buyer and a champion who say, "We're definitely making a change, we're deciding between you and so, and so?" And then once that decision's made, I'm comfortable moving it on.

Delian Asparouh...: And for example, with a process like this, again, as a part of a larger organization, you were responsible for North Americas, was there a part of sort of partnering with the rest of the organization in terms of the equivalent on, the Euro side or Asia Pacific, to start to sort of implementing similar process so that the forecasting for the company as sort of like a whole got better. What were some of the parts of just being part of such a large organization that were maybe different even from, I'm not sure what the peak headcount was when you're at VMware, but I imagine my intuition would be that Zendesk headcount when you joined was larger. And so, with that just comes, more complexity and coordination, which I'm curious, what things were maybe more difficult than expected in terms of coordination, and complexity, and maybe organizations or structures that you needed to coordinate with that maybe didn't even exist at companies at a smaller scale.

Jaimie Buss: Yeah, I think when you're at a smaller company, the nice thing is that if you want to add something to salesforce, you can, if you want to change your process, you can. And no one's really going to stop you because everyone's just running and gunning and moving really fast and there's just not a lot of bureaucracy in your way. When you get to a larger company, it's harder to do some of those things because you're right, there's more people that might have say or influence over what is done. For an example, when I used my qualification methodology, I really wanted it in its own object where I could score all of my different components of it so I would know the score of my opportunity, to know if I felt that I was in a strong position to win it or not.

So I had to convince the IT team to create it for me, but then what they'd have to do is create in their view, that had that component in it and strip it out of the other views for the other regions. So fortunately at that time, we were still small enough, that I was able to get that done. But the larger company you're at, the more you have to take into consideration, because I was piloting this methodology, this was not corporate sanctioned. This was me finding the money to pay for it, moving money around in my own budget to pay for the training, and then deciding to move forward. And we actually did end up rolling it out globally because we had a very positive impact on conversion rate, average deal size, and our growth of multi-year deals improved. And because the data showed that we were increasing our productivity while some of the others weren't, then it became a global initiative eventually, but we were kind of the guinea pigs to try it out.

Delian Asparouh...: And can you talk about that conversion process of North American Guinea pig to sort of global conversion of was it like collect all the data you need, present it to the executive leadership, and then sort of immediately gets rolled out or sort of how did you build the case to eventually obviously influence people that are in a faraway country, maybe doing their own process or the preexisting one that is perfectly working, and lo and behold, North America comes along, says, "Here's this fancy new thing, that everybody's got to do." I guess I could imagine there being some levels of layers to get that sort of fully rolled out that I'm sure were sort of fascinating to go through.

Jaimie Buss: Yeah, I mean, first, I wasn't trying to force it on anybody, but what I did do is, they would see my quarterly business review that I would present again, and again, and again, quarter after quarter. And I would point out those metrics as well as my productivity, meaning my bookings per rep and I would post it, and then I would mark what I attributed it to. So again, and again, and again, they would see what my stats were versus everywhere else. And then, the other component I would recommend that early-stage startups consider, is that when you're a sales leader, there's two business partners that are super important to me. I mean, there's many, but I need strong sales operations and I need strong enablement, especially if you're going to scale quickly. And so, fortunately, enablement and I have a phenomenal relationship. And when they saw what we did, they loved it, and they themselves got trained on how to train the trainer on this methodology.

So then what they could do, is go introduce it because then the other regions themselves raised their hands. It wasn't me, or anyone else forcing them to do it, they were like, "No, no, we want to implement it as well." And then enablement was the key to binding that all together and creating the materials that allowed us to train the rest of the org. So I know that sometimes it feels painful to invest in overlay sales resources that are not quota carrying, but if you want to maximize the productivity of your team, which is your bookings per rep, then I think enablement and sales operations are two really big keys to helping you do that.

Delian Asparouh...: Interesting, yeah, very much sounds like it was sort of a bottoms-up adoption approach where people just saw it and got excited about it. And I guess in relation to some of these teams, obviously, there's a seed-stage, single AE probably can't afford to have a sales ops team at that point. But I'm curious, when do you think that transition point sort of happens? At sort of what scale of either ARR or sales team do you think it starts to really make sense to start to invest into these secondary functions as institutions, as opposed to just something that's a side project for one person.

Jaimie Buss: Yeah, absolutely. I think what you have to have... I would look for very obvious product-market fit. So not experimental product-market fit because there's no sense in having sales enablement when you're not even sure what you're going to replicate. So if you're kind of like Davy Crockett, trying to forge the path still, that's not a time for enablement. But if you have strong product-market fit, and you have enough investment, and you're capacity constrained, meaning your reps have so much either inbound or opportunities, that they can't even get to them all. They're doing no outbound, everything they're doing is just coming at them, your capacity constrained, you have product-market fit, you're going to have to do some mass hiring. Let's say you're planning on going from like 20 reps to 100 reps, you probably want to look at, do you have enablement that's going to really help with your onboarding process and your continuing ongoing training process if you're going to go to that type of growth?

But between one and 20, and you're still trying to figure things out, I don't think that's the time. The time is product-market fit, capacity constrained, adding a lot of reps, you've got the money to add the reps, then you want to make sure that when your rep is in seat, their time to value is as quick as possible, and the way to do that is through building proper onboarding and ongoing training.

Delian Asparouh...: I feel like this sort of, let's say hot new KPI in the world of SaaS is all-around sort of net negative churn which I feel like either comes down to sort of expanding wallet share versus focusing on new logos. I'm curious how you guys balance that at Zendesk or within your role, focusing on net new prospecting and really trying to sort of capture new logos versus sales still being involved in an ongoing basis to sort of get more divisions, get more wallet share within the sort of preexisting ecosystem.

Jaimie Buss: Yeah, I think this is a very interesting question and I think companies can handle it in different ways. So I'm not one to prescribe a one-size-fits-all here. I know that some people do complete hunter farmer, where you land a new logo and you either hand it off right away, or you keep it for 90 days, or you keep it for six months, or you keep it for a year. There's a lot of different flavors of how to do the hunter farmer motion and for some products, I probably still tend more to believe that where you've sold something is the best place to sell again, is where you've already sold. And so, especially when you're more upmarket, if you have someone who has spent the time to navigate a complex sales cycle and land an opportunity, and it's a sizeable opportunity, why would you pull that account away from them?

They know the economic buyer, they know the politics, they know who's for us. They know who's against us, they know all that. You're going to take all of that knowledge, and what, give it to a farmer rep. I just really feel like you're losing momentum when you do that. I think that the way to balance it is, if you do have a team that handles both new and expansion opportunities, you just have to look at how many install base accounts that are growing. But install base, in general, are assigned per rep. Because if you have too many assigned per rep, A, they're going to get all caught up in account management and they probably can hit their quota on expansion only. And they're not going to spend much time either prospecting or working on their new inbound leads, they should be producing their own, but let's say, from a BDR, or marketing, or something like that.

So I think the trick is to make sure that the account per rep isn't too high and to make sure that the quotas are such that you can't hit your number on expansion alone, because if you can't, you're going to be forced to have to hunt for it. I think I want the growth in hunting mentality in my account executives, because if you have a product installed, but let's say, you sell department by department typically, let's say, like Okta, you're all in, you're going to sell wall to wall, Workday, you're going to sell wall to wall. But a lot of products, it's land and expand where you sell department to department.

You can't tell me that if I've sold to the product group, but now I want to sell to marketing, that's a completely different sale. So do I really want an account manager figuring that out or do I want a hunter who knows, "Okay, I've got to change my messaging, my value prop's got to be different? I need to get an intro from here to here, and I have to make sure that I understand their problems that I'm solving." I still think that's an account executive hunter mentality, even though it's an installed-based account. So I think it depends on what type of growth? What does it look like? How does your product land? How does it expand? What does that sales motion look like? I think that's what kind of feeds into, how do you do hunter-farmer, and then how do you quota and allocate the accounts per rep?

Delian Asparouh...: Makes a ton of sense, I guess, yeah, has that been relatively similar across the very sort of let's say, product-led growth organizations that you've been a part of, or even between sort of VMware or Zendesk, you've actually noticed, differences in terms of how that sort of hunter-farmer split is set up.

Jaimie Buss: In both environments, we pretty much do hybrid, where we're doing both, where we prescribe to the model where don't have too many accounts per head and then make sure that the territories are such that you are blended. And then the other thing that I did at VMware as a manager and then also that we do here, is kind of the concept of, and it's very tactical, but it's time blocking. So are you building expansion, do you have time blocked to build expansion pipeline? Do you have time blocked to be dedicate it to driving new business? Do you have time blocked to do your account management work? I think you have to be disciplined, because if you don't, the easier stuff will be what you end up doing.

So that's the other piece of it. You do have to be organized and disciplined because otherwise... And then measure it. So as a sales leadership team, you have to be really maniacal. If you're a frontline sales manager, how much pipe are your reps building every week? And how much is new business? And how much is expansion? How much is expected of them? And if you start seeing trends where it's not hitting where you should expect, you have to look into that, it's like inspect what you expect. But that pipe gen piece is really important, especially... I would say, even if you're a hunter-farmer, you should be maniacally managing the pipe gen per week, because that's the lifeblood of your future.

Delian Asparouh...: And you also started this program at Zendesk called Rising Stars. Can you tell us sort of a bit about that program and the impact you felt it's had on the organization?

Jaimie Buss: Yeah, absolutely, this is actually one of the points I think earlier, in VMware, one of the reasons why I stayed so long as I did, was because the company was obviously growing very fast, so there was a lot of opportunity, but they believed in me and they saw and thought I had potential. And so, they kept giving me larger and larger spans of control. I was given opportunities to take on new responsibility that I hadn't done before, and that's really what kept me there for as long as I did. And then when I came here to Zendesk, we had some programs for helping people move from one role to another, but not many. And then, my people would leave because they felt like they didn't have a path to get from one role to the next.

So I partnered with enablement, one of my best friends of business partners, and I thought, how can we solve this problem? I want people to be engaged, I want to give them an opportunity and the first Rising Stars that we ended up creating, was for aspiring leaders. And the reason we did that is because I wanted to be able... My team wasn't willing to take a chance on their own reps to move them into management at the time and I was thinking, "Gosh, but if I hadn't been given even that chance, I wouldn't be where I am at today. You got to take a chance on people sometimes." But I also understand that it's a big risk because a manager can really affect a team. So what we did is, we built a six-month program called Rising Stars, and this one's aspiring leaders, where you are exposed to the different aspects of leading the business, leading the team, leading yourself, that are part of being a manager.

The intent of the program is twofold. One is if you know you're interested in management and you want to demonstrate that you're interested and you want to do well in that program so that your top consideration when a manager role opens. But the other one was, "Hey, you might not be sure." Join the program and if you don't like it, great, you know now that you don't want to be a manager, we'll put you in the Rising Stars for enterprise, and then we'll teach you how to be a better enterprise rep.

So I have had people that have come out of it and like, "Oh yeah, no, this is not for me." I'm like, "That's fantastic, then it did its job because you didn't have to waste a year being miserable in the job. You got to try it out for six months while you made money in your current job, perfect, not a bad outcome."

So I try to really sure that there's no shame in deciding that's not for you. The goal is, try it on, like try a pair of shoes on, if they don't fit, don't buy them, it's fine. And I think that, combined with the fact that the people who really did find that they liked it, now that I'm looking at my 2022 plan, I've got manager role openings, and I got a lot of phenomenal candidates that have all raised their hands that do want management opportunity and are now in the interview process to take on roles for next year.

So I feel really good about that because I feel like it gives my top reps an opportunity to take on more responsibility, and also gave more confidence to my direct reports because now they could see how those folks would behave in leading the business, lead themselves, lead the people, lead the team. So it kind of solved a lot of issues for us. And the components are, we have, you observe, you actually do, so you run some forecast calls, you mentor someone, so you actually run through the forecast with them. So you have to do some really hands-on, not only are you learning and joining sessions, but you're actually doing hands-on type of activities as well. So that combination has really worked well.

Delian Asparouh...: Yeah, it seems like a really great program. I'm curious relative to this part of what seems like it is teaching people how to mentor, how to manage, but I'm curious, as somebody who is listening in on this podcast and is maybe a fresh grad or maybe also recently left Deloitte and is excited to join the world of sales and sales engineering, what would be your feedback or advice today, in a world where obviously since you started career tech, and SaaS, and enterprise SaaS, in particular, have become such institutions and so much larger and so much more opportunity there in some ways, what would be your advice to somebody sort of now much younger in their career that wants to eventually get into a role sort of like yours, a very senior in a public company, leading very large teams, having a massive impact?

Jaimie Buss: Are we talking about somebody who's debating if they want to kind of get on the sales path? Is that kind of where [crosstalk]-

Delian Asparouh...: More like if they're already on the sales path, what's the best role in the world of 2021 to get to the place where you're at today and maybe how that's different than the path that you had to take from the dot-com burst onwards.

Jaimie Buss: Honestly, I don't know that it's that dissimilar, because if you think about it, you've got to be really good at the role that you want to lead. So you want to be top of the class for being an account executive. So repeat, strong performance, you want to demonstrate that you are ready and interested in leadership. What does that mean? That means when you have new hires, you're a mentor for them. That means when you see a problem, you don't complain about it, but you come up with a solution and you share it with the team. That means when you find something that works really well, you're proactively engaging with your peers. It's really about helping, it's a we versus a me type of mentality, that I think you want to really demonstrate, and you want to go above and beyond your current role. I always say, "You want to kind of prove you can do the next job, while you're doing the current one."

So what are opportunity is you can take to demonstrate that you're stepping up, you're interested in leading. Oftentimes, you can create those opportunities, you don't have to wait for the company to create it for you. A lot of companies aren't going to have an aspiring leaders' Rising Stars type of program, but there's so much material on leadership and management out there. You can start creating your own thoughts around it, your own playbook. You know what you like, or don't like when you're being managed, ask some of your peers, what are some of the best managers you've had? What have you liked or not liked? You can start kind of putting together your own playbook, but then your actions will demonstrate that you're ready.

And of course, I always tell people this too, we still to this day, have people come up to us and say like, "What's next for me?" And I'm like, "Okay, well, whose job is it to manage your career?" I'm not in your head. I mean, I can tell you what the options are, but I think that there's a personal responsibility to driving your own career that you have to own, you can't expect people to take care of it for you.

You're the product, how are you going to sell it?" If you're a salesperson, you should know how to sell yourself as being a product. And it's not just up to your manager or whoever you report to, it's not really up to them. It's up to them to support you, in what you want to do, or maybe help explore options, but it's not their job to be like, "Here's a silver platter, here's what you should be doing next." It's like, "No, I think you have to be an equal partner in that."

Delian Asparouh...: Makes a ton of sense. Well, Jamie, truly appreciate you taking the time to hop onto the podcast today. A really enjoyable conversation.

Jaimie Buss: Yes, Delian, thank you so much for having me, I appreciate it.

Delian Asparouh...: Thanks for listening everyone. If you'd like to support the podcast, please sign up for a paid Substack subscription which we use to pay for transcripts, mics, and other improvements. If you have any comments or feedback on what kinds of questions I should ask, who should come on the show, or anything else, please do let me know. Have a great rest of your day.