Lessons Learned from Enterprise Leaders on Growing and Evolving $1M to $100M ARR (Video + Transcript)

In this panel from Annual 2018, successful enterprise CEOs and Presidents Yvonne Wassenaar, CEO of Airwave, Godard Abel, Co-Founder & Executive Chairman of G2, and Marc Diouane (one of our most anticipated Europa speakers!), President of Zuora share the real-world stories of how their companies overcame the challenges of growing from early-revenue to global leadership.

And if you haven’t heard, we’re building a completely immersive experience for SaaStr Annual 2019! With 3 full days of content sessions, featuring over 300 speakers from the best SaaS companies around the world, SaaStr Annual is filled with actionable thought leadership to help grow your business from $0 to $100M ARR. Use this link to get your tickets to the SaaS show everyone will be talking about.

[TRANSCRIPT]

Lessons Learned from Enterprise Leaders on Growing and Evolving $1M to $100M ARR

Announcer: Please welcome our panel. Craig Hanson, general partner at NextWorld Capital, Godard Abel, co-founder and executive chairman at G2, Yvonne Wassenaar, CEO of Airware, and Marc Diouane, president of Zuora.

[music]

Craig Hanson: Hello everybody. Thank you so much for joining us. I am super excited about the panel we have here setup today. In a minute I’ll turn it over to them to give the brief introduction of themselves. We have Yvonne Wassenaar from Airware, Marc Diouane from Zuora, and Godard Abel from G2 Crowd.

The goal of this is really to walk through and discuss real-world lessons, hard-fought insights and frankly, admitting and talking about all the things that don’t go well on the path from $1 million to $100 million in ARR.

It all seems great in hindsight, everything looks great when the companies are off to a brilliant exit or going public, but the truth of it is as we all know and there’s a lot of the execs and CEOs and founders in the room know, it’s really hard in the meantime and a lot of stuff doesn’t go well.

We can learn a tremendous amount by the things that don’t go well and how we adapt, pivot, learn and grow out of that. That’s what this is about. Let’s get into it. We’ll get into some real-world truth, honesty, talking about the real stories and what’s going on.

With that, let me turn it over. Yvonne, would you maybe give the quick introduction of yourself and give us a sense for the companies you’ve been involved with so we know their stories?

Yvonne Wassenaar: Happy to do that and I love how you frame this. Here’s everybody who failed, but we succeeded in our failures. I’ve spent a little over 25 years working in technology scaling companies, some larger ones. I worked at VMware as an executive from two billion to six, going from server virtualization to the software-defined data center.

Moved over to New Relic, helped take New Relic public. Currently, I’m CEO of a start-up that’s on the lower end of the one to a hundred. I’ve learned a lot and looking forward to sharing what has worked and what hasn’t.

Craig: Great.

Marc Diouane: Marc Diouane, President of Zuora. 25 years experience in management. At Zuora, this is my fifth year. Before Zuora, I worked almost 19 years for a company called PTC based in East Coast.

That company, I’ve been part of company from when the company was 600 people, 150 to 200 million dollars and we built up our business in eight years $1.3 billion dollars.

I failed a lot. I will say I all-time succeeded, but we have to fail to be able to succeed. I’m hoping that we’ll be able to share with you some good stories and help you to learn.

Godard Abel: Hi, I’m Godard Abel and I’ve been building SaaS enterprise companies about 20 years. We’re now building our third company. My first company I started it at tail end of the dot-com era, which a lot of you may not remember but…

[laughter]

Godard: That was in 2000. My first company was all about struggle. We almost died in 2003 but eventually, the company did well and was bought by Oracle. I think that company maybe took 14 years to get to 100 million. Our second company we started was G2 Crowd, which I’m still working on today.

Also, in between, we built another company called SteelBrick, which is now part of Salesforce. I think that company got from one to 100 in more like 4 years. We learned a lot the first time, but still learning a lot the third time. Look forward to sharing.

Craig: Great. All right. My name is Craig Hanson. I’m a General Partner at NextWorld Capital. We’re an enterprise tech-focused VC headquartered here in San Francisco. Also have offices in London and Paris.

We’ll typically lead rounds and then we also accelerate the growth of our companies through a global enterprise platform where we partner with over 100 of the largest global corporates that connect with our startups as customers and partners.

All right, let’s kick it off. I’ll start with Yvonne and then we’ll go through everyone. Give us a sense for…As you’ve seen on that path from one to 100 and beyond, what are the biggest challenges or the hardest parts that you have to get through on that path?

Yvonne: It’s a great question. I don’t want to burst anybody’s bubble, but it’s always hard. It’s hard at a million, it’s hard at 10, it’s hard at 100, it’s hard at a billion. To me, when I reflect back on what are the biggest challenges, I believe it’s when you have to let go of something that you love and you’re good at.

The examples I’ll use…At Airwave, we’re a commercial drone analytics company. We started off manufacturing hardware and doing software analytics. The founder was an aerospace engineer at MIT. Many of the companies were aerospace engineers.

When it became clear that we needed to exit hardware and really focus on the software analytics and the machine learning and all of that, it was just really hard to make that pivot. It was hard because it was personal. It’s where they grew up and it’s what they knew.

The company made that pivot. That’s part of how I ended up being CEO, but that was really, really hard. Similarly at New Relic, Lew Cirne, the founder and CEO, he’s a developer. He’s a developer at heart. We sold to developers, developers loved us.

When we realized we wanted to take the company public one day, we realized we had to sell to enterprise. Enterprise buyers are different. It wasn’t just download the software, fall in love, get a t-shirt, buy a subscription.

[laughter]

Yvonne: You guys think that’s funny. That’s really what it was. Then, Lew actually wrote a blog. He said, “We’ll never sell a…We’ll never do a steak dinner! Never have an enterprise Salesforce!”

[laughter]

Yvonne: It became company history. He’s like, “We need enterprise Salesforce,” and he hired Hilarie, who had been President of Sales at Salesforce. It was her charter to build that.

The biggest challenge was even though Lew got over it and said, “Hey, that’s the right thing for the company,” at that point, the company was 400 people. To go through the shift of from marketing budget to sales budget and then the engineers had to think about scalability and reliability and security versus just new feature functionality, it was a huge shift.

It took the whole company from something they loved in something they knew to a new space. It was the right thing, but it was hard.

Craig: Yeah, great. Marc, how about you? What do you think are the biggest setbacks or hurdles you have to get through on that path?

Marc: Oh, gosh. Trust me, I can spend all day talking about…Not particularly about Zuora, but for my entire career. I would like to focus really on Zuora. Zuora, it’s close to 1,000 people now. This is my fifth year.

I have the tendency to say that every day, you have to think about reinventing yourself and do an iteration around some of your processes of the organization. I’d like to quote, “There is no smooth ride.” That means guys, success, it’s never happened overnight. This is the reality.

All-time, in 25 years, this is my third company only. I liked complex back-end solutions and complex problem that we have to solve. They are hard to solve, but when you solve them, I believe you can build up real community molds.

At Zuora, in five years, we had multiple what I will call plateaus or pivot moments where you have to rethink about entirely the entire company organization. Probably the most interesting one is I joined the company back to early 2014, worked at two jobs from October ’13 to almost January.

First year, my goal was really to give the level of confidence to the people of the company that we can win and this company can be a really good success. I had to roll up the sleeve. I moved from managing almost 2,000 people to manage a team of 50 people and rolling up the sleeve, go in there, and win.

After the first year, very successful. It was actually too easy. I said, “Wow, we can we can really grow and sustain a 50-100 percent growth year over year.”

Then, we hit a wall a year later because we moved up markets where small, medium-sized companies, mainly SaaS in the cloud for the subscription revenue management and we wanted to move up markets.

Moving up markets, it’s coming with lots of different challenges, all set of different challenges there. It’s the buyers are different, complexity around the MSA, product fix, so you have to rethink about the entire company processes.

What I like is you have absolutely every time you do something, think about how you can push the envelope of the company. The company is with the product organization, the engine organization, the managing organization, marketing organization.

This is how you can evolve. Every plateau come…Basically if it’s successful, if you really focus on the right problem and solve it, it will come with another, I will say, years of fast scale and growth.

I had almost sometime two plateaus a year. That mean two times a year, I have to work days and nights, weekend, bring the team, look through all the deals, what’s worked, what didn’t work, where the product has some gaps.

This is constant iterations. Even now, 1,000 people, we keep doing that almost every quarter. Every quarter. The takeaway here for you guys is nothing is granted. What is working today, it’s working until it’s going to break.

Leadership is to be capable to see when it is going to break and start to anticipate that kind of problem there and fix them before, I would say you would just get stalled. When it’s breaking, you have that doubt that you have to overcome. The people, they are doubting. The employees, they don’t know exactly what to do.

You have to be extremely hands-on into the detail until you reach a certain level of scale from the organization, to be able to have leaders that can do what you could do, to be able to overcome those challenges.

Craig: Godard, how about you — from that early product market fit to global scale it was just completely easy, right? No challenges, nothing hard to do? Or did you have to work through some stuff?

Godard: I haven’t figured that out yet.

Craig: [laughs]

Godard: I think for me, a lot of the struggle was emotional. I remember my first company big machine, as I mentioned, we started selling in the dot com era, raised a bunch of money.

Frankly, we burned over $20 million and we were almost bankrupt. I remember 2004 was probably the bottom for me. This was Big Machines. I kind of realized we had to sell because we couldn’t raise any more money. From $20 million we’d only grown $1 million in revenue, and it was in 2003. Nobody was buying anything.

I moved to Chicago at the time because we were almost out of money, and decided it would be cheaper and better. He was from there. I remember in 2004 we really needed this. Our biggest customer was SPX and they were about an hour north of Chicago, in Wisconsin, kind of by Lake Geneva.

I remember we drove up there and we were going to see their president, Don Ken Turner, to get a big add-on order. It was about $300,000 which would kind of fund our business for 3 months.

We showed up in the lobby. Go to the receptionist. I’m like, “Hi, I’m Godard Abel from Big Machines. I’m here to see Don Ken Turner.” She was like, “Funny, Don isn’t here today.” We had an appointment. He didn’t even bother letting us know he wasn’t going to be there.

Needless to say, we were going to leave without the deal. I remember my co-founder and I, we were just silent in the car driving back towards Chicago. Also, I remember that year my twins were born. They came out nine weeks, two days premature. I’m driving back Chicago, and they’re in the NICU intensive care. I’m like, “Man, my life can’t get any worse than this.”

[laughter]

Godard: Somehow I felt obviously, very down and very scared. I had this constant fear of failure, because also my first investor was my father. Then I’m like, “Oh, man…”

[laughter]

Godard: “I’ll lose my dad’s money. The company’s going bankrupt. I can’t sell, and my kids are in the hospital.”

[laughter and applause]

Godard: When I had that realization I was in my car. I’m like, “Oh well, things can only get better.”

[laughter]

Godard: From there, luckily they did. My boys actually did really well. Four weeks later they came out of the hospital. Today they’re 13, and they’re doing amazingly well.

[applause]

Godard: Also, Big Machines, ultimately we did learn how to sell. Actually, about six months later we went back to see Don and he signed the deal.

[laughter]

Godard: The weird thing is, he never apologized. He just acted like it never happened.

[laughter]

Godard: Eventually, the company had success and Oracle bought it. It became a very spiritual journey. I remember all those years I felt like I had a cloud of anxiety on my forehead, which was my company. It would never leave me.

Eventually, I met a conscious leadership coach and started working on my own consciousness. Luckily, my second or my third company I no longer had that cloud of anxiety, and it’s still a struggle. Learning how to deal with own emotion and growing spiritually through the journey, that’s probably been the biggest thing I gained from that struggle.

Craig: Yeah. Thanks. One of the most interesting things for me is seeing how in a lot of cases companies have to make a couple of hard pivots on their path. It’s not just the really early stage companies that are trying to find that product/market fit.

Sometimes even after you find that initial product/market fit, you have to do something meaningful and different after that either how you’re positioning the product, what market you decide to go for upmarket, downmarket, how you’re going to go out and sell the product. Let’s dive into that.

Maybe Yvonne, a thing about to either New Relic or Airware experience? Has there been a pivot that you’ve had to make along the course as you find that sweet spot of growth and the right model for you guys?

Yvonne: Yeah. I foreshadow a little bit a couple of the pivots we’ve made in Airware and New Relic. What I’d like to call out, people talk about pivots like they’re black and white like, “Did you make a pivot or did you not?”

[laughs]

Yvonne: The reality is, I think we need to appreciate that there are pivots that are black and white. You’re either in hardware or you’re not. When you’re making a decision like that and it’s truly a market positioning decision, make it and be done with it. Don’t drag it on. Don’t get all emotional about it.

You’re trying to figure out the right answer for the company. Its product/market fit, how you’re going to scale and you’re going to have to make some hard decisions. Rip the band-aid off and move on. That in my mind is a hard pivot. Airware made that around hardware.

I joined the company six months after the layoff and they were still mourning. It was like I cut off an arm and a leg. Now, we’re thriving and we’re healthy as the people who left still think well of the company and their shareholders. It all turns out OK.

The other type of pivot is important to understand may not be that severe. For New Relic, for example, we had developer love. When we sold into the enterprise, what we realized is it wasn’t, “we’re never going to sell to developers again.” It was really much more of an extension. It was much more of, “We’re selling to developers and they’re really important to us.”

By the way, “We can also sell there are these people up here who can write really big checks and how cool would that be?” [laughs]

Yvonne: What we had to learn was how to balance that and how to transition the company over time and really what I would say expand it so not throw the baby out with the bathwater.

To me, when I think about the decisions that I make at Airware, I try to get really clear with the executive team on it was a bad decision or it was a good decision until now and now it has to change and we’re really going stage left, or is this we need to expand into new areas and what is that transition time and what does it have to look like? That thought process has served me well.

Craig: All right. Marc, how are you? I know through our experience with Zuora there’ve been a couple of different growth phases.

Marc: Right.

Craig: What did you have to change or do differently or find your way into the better position?

Marc: It’s a very interesting question. Before joining Zuora, I thought that I went every cycle somehow for a company possible.

Even if I join PTC probably when the company was already public, that we scale from as I said almost $150 to $100 million to $1 billion in eight years with one single product, then we acquire the number one and we pivot the business more toward enterprise software from one individual product too.

At Zuora in a little bit than four years, the speed of the market today is so fast you have to be able to make a decision really quick.You have those forces, you have the market forces and the competition forces.

Your people, every day, come in with new ideas. I believe you have the ability somehow to think about all that and do what is right. To keep really focused on what is working is really important for your success.

Earlier I was talking about that moment when we try to move up markets and you should surround yourself. It’s never alone. You need to have that core team within the organization that you trust. They went through this. They can filter this message and give you the right information. Get together and think about what you should be doing there.

Godard, we were a partner. Then when Salesforce acquired SteelBrick, we said, “Should we keep it? Should we do something different?” I remember spending that weekend with the team thinking about what we should be doing here.

You have absolutely to understand what are your sweet spots, why your customers are really buying your technology. Regardless of the size of the companies, this is who we are. You have absolutely to stay focused around that core and don’t try basically to go everywhere.

Our success today at Zuora, if I’m looking where the company is today and where the company was a couple years ago, we had probably 10 comparison markets. Zuora five years ago was the same size of a lot of other startups.

I believe the reason why we really won is because we focused on the customers, which problem you are trying to solve. If it’s a big problem, don’t try to solve everything. Solve what really does matter the most to your customers and then from there scale.

You have the ability to stay really focused on keeping the entire organization focused. Despite all those forces that I was talking about before, this is really the leadership. This is really important. You have a vision. You have really a strategy.

You need to have the execution arm. That shouldn’t be disrupted by anything else. It’s really around the execution around that vision and that strategy. I believe this is what’s made Zuora who we are today in the subscription revenue management and revenue management market.

Craig: Godard, how about you? What things either at Big Machines or SteelBrick did you have to change and adjust along the way or even make a hard pivot to find a new space or positioning?

Godard: I think Big Machines was more we started way too wide and this was still a dot-com business. I remember when I started Big Machines because we said, “Hey, we’re going to sell big machines on the Internet.”

The Internet was still pretty new, and actually my father had a pump manufacturing company. He had complex engineered industrial pumps and we said, “Hey, we’re going to sell those online.” At the time I said, “Not only are we going to help him sell it through his website, we’re going to create a marketplace. We’re going to help buyers of machinery.”

We called it eBuy. We had about four products as our vision. I remember kind of one by one after about a year we were like, “Oh, marketplace isn’t going to work.” The next year it was like, “OK, eBuy isn’t going to work.” Then we’re like, “OK, direct to customer isn’t going to work.”

[laughter]

Godard: We kind of just wound up all we’re going to do is a little configurator to help these company’s sales rep sell their product better. It was like a massive narrowing.

I recently actually watched Peter Thiel. He has a great video on building. Well, he says everything is a monopoly or a commodity. His point is you’d rather be a monopoly, which actually seems obvious.

[laughter]

Godard: His point is the more narrowly at the beginning you define your market…In the Big Machines I did it totally wrong. I went after really big tien. His point is, “Hey, the more narrow you start…”

That was more like SteelBrick. SteelBrick had started by Max Rudman, an entrepreneur. He started very focused. He said, “All I’m going to do is” — He called it code quickly initially. — “just code quickly just for Salesforce customers, just on the Salesforce platform, and just for mid-market growth tech companies.” It was very narrow. He built a perfect product for that.

Then when I partnered with him we kind of had the luxury of starting very narrow and then over time we expanded. Eventually we went to enterprise and eventually we got a little bit in the billing, although it never went very far.

[laughter]

Marc: Thank you.

[laughter]

Godard: I think it was a lot more fun starting very narrow. That’s probably why he’s an entrepreneur now. I think the narrower and the smaller you start I think the better. It’s much more fun to grow your vision than to have to shrink it because it was way too broad to begin with.

Craig: One of the interesting things looking at the stories from your companies is and I wonder, is it natural and is it a good thing? That as you make that big ramp from the kind of company that’s doing well, one to ten million, and then figure out how you grow from ten to thirty and from thirty to 100, is it natural that things are just going to break? Is that a good thing?

Maybe, Marc, you can start off with this. Is that a good thing? How do you chart?

Marc: It’s good. It’s all good.

[laughter]

Marc: You have those. I would call them the “oh shit” moments. Wow, it’s bright in here. It’s good. This is what I said earlier, those moments they are the best somehow at least for me they are the best moments at the company.

When I’m looking back to the last couple years, the more difficult the problem was and having a team working with you to solve that big problem then implement a solution, see the solution working, and then the company scale again, this is the most rewarding moments in your professional life.

I want to have more of those moments. Actually, today I’m like you. I am extremely paranoid when the people they come to me and say, “Marc, everything is fine.” It cannot be fine. If it’s fine, it means it’s going to break somewhere and it will and I’m extremely paranoid.

[laughter]

Marc: When it’s fine, most of the time I will call for a meeting to go a little bit deeper and say, “Let me understand.” Then you will find out something that doesn’t work and that is really extremely rewarding. After the older rewarding moments when you work through that difficult time from the business perspective.

I was with Tien, our CEO, he called me at the end of the court. He told me, “Marc, how is it going for the court?” because he is not involved that much in the business where he used to be deeply involved. Let me tell. Maybe it’s good news. I am not that much involved neither in the business. I believe I’d touched probably only four deals. We have a team running the business. He likes to do that.

He calls one sales manager and the sales manager tells him, “Yes, everything is fine.” It cannot be fine. Last quarter it was fine. That’s when you can see the level of maturity of the company.

You have to stay extremely paranoid until you have implemented the solution. The people, the processes, tested the process, the solution, that idea that it is working before moving to the next, I will say, production challenge or future challenge of the organization or the company. I love those moments. Actually, this is probably what I love the most about my job is those difficult times.

Craig: What are some of the things that broke that you had to reinvent quickly at that company. Then we’ll go to Godard and Yvonne. Give people a sense for maybe that natural creative destruction process.

Marc: I believe the product. I remember, I would call it, the pivot moments for the company. We have a econ. Every month we had one econ. That one was about the products organization. We moved up markets. Lot of requirements. Solutions start to break. We had the energy organization, the print organization.

I remember that afternoon we had our head of the organization say, “Marc, we cannot go up markets. It’s putting too much stress on the people and on the product. The product cannot do that.” This is exactly what you want to hear. This is what I will call.

You need to really make sure that you have those positive frictions in the system. Positive friction, for me, is a customer that is within my sweet spot coming there and saying I need this, and this, and this because the product cannot do that. You need those moments. They are really important to push the envelope of the company.

From that time, I remember Tien and I, I believe that we pivot the entire organization from the leadership perspective because we understood at that time that the people, they are getting drained. They cannot change after change. Few people they can really reenergize themselves and retackle those problems. You have to bring different people to be able to bring the company from one level to another one.

I believe the change that we made at that time at the products engineering organization, a lot of change in the marketing organization, the management legion really helped us to move to the next level. The solution and the company wouldn’t be who we are today if we didn’t have that difficult time.

Craig: Yvonne, what have you seen? You’ve been at smaller companies and you’ve seen them grow big, like in New Relics case. You’ve been in big companies like VMware. That’s a massive change in what those organizations are like. What things break and fall apart that you have to figure out and retool along the way?

Yvonne: Pretty much everything.

[laughter]

Yvonne: I think the hardest part is getting your stuff to sell. Finding product market fit, getting people to want to buy your product, and making sure a competitor doesn’t undercut you, that’s problem number one to solve. What most people don’t realize is once you’ve solved that problem the next big problem you have is, “Oh my God, you’re successful” and things break.

The simple analogy I’ll use it that you’re writing a piece of code. That’s great. I’m writing code. I’m not going to comment the code. That would be stupid. I’m writing it. I know what it’s supposed to do.

Then I bring in you guys and you’re going to help me. We create this really successful app and it takes off like wildfire. All of a sudden, my buddy Marc goes on vacation and the thing breaks. We can’t figure out what went wrong. We’re like, “I can’t believe he didn’t write comments in this code.”

Craig: It’s always Marc’s code. [laughs]

Yvonne: I know. It’s always Marc’s code.

[laughter]

Yvonne: He comes back and all of a sudden, he’s like, “OK.” We make a deal. We’re all going to write. We’re going to comment the code. All of a sudden, we’ve got scalability problems. We have to realize, and we have to break the code base into separate services and create APIs.

Well, this is fundamentally what happened to the product code base as the successful software company scales. You kind of cut a lot of corners when you’re younger. Then you grow and you scale. Engineers leave. You have to create protocol because you have a problem. It’s usually problems that create that.

The organization is no different. I always would use this analogy at New Relic. My maddening moment is nothing was written down.

[laughter]

Yvonne: That’s fine when you’re 20 people. When you’re 400 people spread across two different offices and you’re growing hand over fist, you have to write decisions down. It was this, I use this analogy. I’m like, “Gosh, it was just like this. You have to comment the code.”

One of the gentleman came in my office and he goes, “Yvonne, you’re right. I have to start writing stuff down.” He was an engineer. He said, “But I’ve done the math.” He goes, “If I write stuff down after every meeting, that’s going to take me 10 minutes times X number of meetings. That’s Y amount of productivity that I’m losing out on.”

[laughter]

Yvonne: I’m like, “OK, the company is scaled. You can’t think about it that way. What you have to realize is your job changes as a manager and as a leader. You don’t write everything down but write the important things down.”

Those are just a couple of examples. It is always changing. For the economists in the room, there’s complexity and there’s volume. There’s indifference curves of pain. Through complexity and volume of the business you’re going to hit an indifference curve and your communication, your organization’s structure, things are going to have to change.

It’ll be smooth sailing until you hit that next indifference curve, but that’s healthy. That’s growth. It happens whether you’re a million dollars or whether you’re 100 million.

Craig: Godard, what have you seen? What things break and how do you work through that when you’re building up companies, as you’ve led and done with Big Machines, New Relic, and now G2 Crown?

Godard: I think, and Yvonne mentioned it, but to me it’s usually the organization structure and the people. I think especially going one to a hundred just thinking about sales. Zero to one, you can just be an entrepreneur selling and you probably should be, right? Then one to ten, you probably need now one sales leader. Maybe a five-person team that can manage well. Now you have a two-tier organization.

Frankly, finding that first sales leader is already super hard. I remember at BigMachines I had three VPs of sales. Then I had to become the VP of sales.

[laughter]

Godard: Luckily, I hired Matt Gorniak, who became my business partner and sales leader. By the time he just started selling. We figured it out together. First of all, even finding one good sales leader was really hard.

Then we realized once you get to 10, 20, 30 million, all of a sudden Matt could only manage — I don’t know — seven, eight, nine reps. Now you need regional VPs or segment VPs. Now you need multiple sales leaders.

Matt had to go to a higher level role more as a CRO and manage themes across multiple teams. Matt has scaled extremely well. A lot of people don’t. Then again, it’s also hard as an entrepreneur when you have to explain to some people that were with you from day one that have done really well as an individual contributor, but you don’t believe that they’re ready to be the leader.

I think somewhat they feel entitled. You feel you owe that to them. Having those conversations with people, “Hey, you’re amazing. I love what you’re doing, but you’re not ready to scale to that next level yet. I have to bring in a different leader.”

Keeping that organization aligned. It keeps breaking as you get bigger. I was amazed when I was at Salesforce, obviously, Marc ended up with 10,000 of people and hundreds of layers of organization. You have to keep breaking it and keep fixing it with new leaders. That’s always been a massive challenge for me.

I think we’re going now through a G2 crowd where it’s going through that transition from one sales leader to multiple. Then getting the right leaders in every function. It’s always hard.

Craig: Let’s go back in the time machine now. We can take you back 5, 10 years before, what do you want to tell yourself that you didn’t know back then. That you say now with the experience, the ups and downs and the big success that each of you have had, “Wow, I really wish I would have known that.”

There’s a lot of us in the audience who are looking at that. They’re staring at how do they go up one to 100 mountain for the first time. Or wondering if it’s always this hard. What would you really wish that you could go back in time and tell yourselves now that would have made it easier or given you different insights. Yvonne, let’s start with you, then we’ll go down.

Yvonne: We kind of joked about this earlier. I have this conversation with myself all the time. I went from a company that I helped take public that was much larger down to a small startup. It was a great perspective.

The things that I tell myself every day, the smaller the company — we were talking about it earlier backstage — the more extreme the emotions, the highs and the lows. What I tell myself, whenever you hit that low, whenever you have that oh-my-God moment in the car or for me, on the evening train, you have to remind yourself everybody goes through that.

When you’re small, everything feels like life or death. It helps you be agile in your thinking. It helps you focus. One thing I take with me is just a lot of calmness. There’s a lot of things that seem like they’re life or death. They’re really not. Just maintain perspective. Surround yourself by smart people and work through that.

The second thing is have conviction in your decisions. It is better to go full on and take a risk. We all take risks in small companies, but go full on. Any of this wishy-washy stuff, you’re doomed for failure.

It may not be the right thing, but take the risk, have measurements in place, and be open-minded that if it doesn’t pan out the way you thought, you can change. Don’t be wishy-washy. Those are probably the two biggest things I take with me.

Craig: Marc, how about you? We put you in the time machine, what would you want to know back then?

Marc: People. People management. You are somehow in an extensive human business. People will make it or break it. I learned it in a hard way. My first management job I was 25. I was the youngest manager at PTC, at that time. At 31 they promoted me to be the SVT to run the Japanese operation for PTC, moving from managing 15 people to having an organization of almost 260 people.

I hadn’t been trained to do that. I didn’t have any coach to do that. That experience of dealing with the people and in a completely different environments. You need to have interpreters. You have to develop different senses somehow. You have really to look at the people and sometimes the body language says more than the people they are saying there.

That is probably my most important and my biggest asset when it’s come to the people. I can make decisions really quick. I don’t need to spend hours and hours in a meeting. I can understand where it does work. Every time, when it’s a problem I will every time go back to the people. The people are creating problem or basically success. When you have a problem it’s all most the people.

Smaller the company is, you don’t have any processes. It’s people. The bigger it is, it’s processes and people. The people, people, people, people. It’s really the key success factor. I’m really getting good at that now, but I learned everything the hard way.

[applause]

Marc: Thanks. Thanks.

Craig: Godard, what would you tell yourself back then? I know you had chance to take a lot of the hard fought lessons, the ones through big machines, and put them into practice at Steel Brick and now into G2 Crowd. If you can go back 5, 10 years, what do you wish you would have known through those experiences that you’d tell yourself now?

Godard: I think a lot of it was what Yvonne said, but if I were to put it in one words it’s breathe.

[laughter]

Marc: It’s silent.

Craig: There you go.

[laughter]

Godard: I did get an iPhone for Christmas from my wife. I’m not wearing it today, but it has a nice breathe app that’s automated it.

[laughter]

Godard: I think, for me, getting greater consciousness and self-awareness. I think for me it didn’t happen until I was 40. My guru Jim Depthera, I think he says as a male that’s common. I think I didn’t even grow up till I was 40.

[laughter]

Godard: Those of you that are younger, I hope you can get there sooner.

[laughter]

Godard: I have a daughter and I can already see she’s 10 and she’s probably more emotionally mature than my 13-year-old boys. I think women probably get there sooner.

For me, it took till 40 to get some self-awareness consciousness. I do think whether it’s my work, my family, any part of my life just being more conscious, more present, taking care of myself, which then allows me to deal with whatever challenge comes along.

Craig: That’s great. Well, look, hopefully, this has been helpful for everybody. We can show three amazing enterprise tech leaders that have gone through a lot, have done a lot, and accomplished a lot. You can see some shared experience. It’s not always easy. It’s not usually easy at all. Yet, that’s how great companies are built. That’s how you pioneer a new market or disrupt an existing one.

I want to really thank our panel for being real and sharing the stories, the insights, and the hard-fought lessons.

Marc: Thanks.

[applause]

[silence]

Published on June 7, 2018

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