Shaping Teams and Cultures | HelloSign COO, Whitney Bouck (Podcast 82)

A's hire A's and B's hire C's. I mean, this is about ego. It's really blatantly about ego. The only way I'm the best at my job is if I have the best people at what they do working for me. Because collectively we're a whole. That's much greater than the sum of the parts. I mean, if I hire people that are only less skilled than I am, then I'm shortchanging the company.

Whitney Bauck joined HelloSign as COO in 2016 where she's responsible for growing and scaling the company in partnership with the CEO, CTO and the executive team. Before joining hello Signs, she ran global marketing organization at Box and built Box's enterprise business from the ground up, helping pivot the company from being an SMB oriented product. Whitney also spent 15 years with documentum and then EMC via acquisition and held a variety of leadership positions, including CMO of Information Intelligence, another division at emc. Previously, Whitney held a variety of technology and leadership roles at both Sybase and Oracle. She was recognized in 2017 as one of the top 40 women in revenue, in 2015 as one of the 100 most innovative CMOs, previously recognized with the Silicon Valley Women of influence award in 2009, and she received the top 40 under 40 award in 2003. So, Whitney, thank you for joining us on the second in command podcast.

Thank you. It's a real pleasure to be here. Looking forward to this whole conversation.

Yeah, you've got a ton of insights to give us. So my whole reason for starting the Second in Command podcast, it's funny, I don't actually often say this, but I was kind of getting tired of hearing the CEO's story. You know, everyone interviews the entrepreneur or the CEO of the company, we hear their perspective. And I've always wanted the rest of the story for you. Today it's going to be your opportunity to tell us a little bit about what you guys have been doing with HelloSign, but also what you feel makes a great COO that everyone can learn from as well.

I actually appreciate exposing some of the other executive perspectives because I think you're right. Everybody wants to hear from the CEO, especially I think in the startup world in Silicon Valley in particular, where so many of the companies are founded by product visionary, they're the ones with the right idea that got the whole thing going, so. But there's a whole lot more to building a great company. Yeah, just the idea, right?

If you asked my dad, how did you raise your kids, he'd have a very true story. And then if you asked my mom, how did you raise your kids? She'd have a very true story. And they're both completely different. But they're both, even though we were all in the same household together, they were completely different stories. So that's kind of where I'm coming from on this. So tell us a little bit about your journey. Maybe go back to the even the top 40 under 40. I mean that's a pretty great award to be getting at a younger age. What was it do you think they identified in you as a strong leader back then?

I guess by luck and by effort, I've been associated with companies and helped scale companies from a pretty early stage. I joined Documentum when we were dozens of people, was there through IPO and acquisition by EMC eventually. And I think I just earned myself kind of a reputation for one, being part of what it takes to scale to a successful exit. I think I've also been able to do a really good job of building brand reputation in the market. I still somewhere early on I kind of decided that I actually really enjoy turning light bulbs on for people and helping connect what a company has to offer with the kind of problems it really solves for people. And I think I'm pretty good at that. And so I think having some visibility in that way and getting recognized for wow when I talk, to wit, I get it as I think the two things that really have worked to my advantage.

I totally agree. When you get those, some of those early successes, they tend to start to mirror the rest of us. I mean, partially because we get painted with that brush and then also partially because you've actually done it so you can start to replicate that. Tell us a little bit about HelloSign so we understand the scope and the size of the company and what kind of company it is.

Let me take you back to when I started in early 2016. We were kind of below 40 employees at the time and in the single high but single digit millions in revenue, we were acquired earlier this year. The founders and I ultimately decided to sell the company to Dropbox in February of this year 2019. And that was really an opportunity for us to grow the business much faster than we could do as a standalone company. And at that time we were about 100% employees. And in the roughly, I think in gap revenue, we contributed about 20 million in fiscal 2018 to the Dropbox numbers. So that gives you a rough idea of kind of how we grew over the course of that Three years. So pretty pretty respectable growth and a relatively short time. Also pretty hefty employee growth. And as I said, you know, coming into the Dropbox world, the whole motivation there was really to grow faster, to be a growth engine, not just for the HelloSign business, but frankly also to add more value to the Dropbox portfolio so that they can deliver more value to their customers. As far as what we do, because many people may not know HelloSign, we're an E signature and digital transaction platform and our job is to help take these complex, close to revenue, super important transactions that eventually at some point need a digital or electronic signature as part of them to kind of bind the agreement, if you will, and make that process seamless, really intuitive and easy, cost affordable, and also to be able to do it in context of a larger business process where appropriate. So we're one of the only vendors in our space, if not the only, that focuses on embedding our technology into other people's.

And then you make your money. What is it just on the number of documents being signed per month the company pays for, or is it a per seat basis? How do you make your money?

Both actually. We offer our product in a couple of different ways. We can either offer it as an end user product. So you sign in, you set up documents to send out. Maybe you're a lawyer, for example, in your corporate legal team. So you log in, you've got templates you use, you set up documents for signature, you send them out to the parties involved, et cetera. And in that case it's just on a per seat basis and you can send as many documents as you want, no volume limitations at all. But in the case where we do embed into other people's applications, there isn't usually a named user that's logging in. It's a systematic thing that's happening as part of a larger process or application. And in that case we do charge by volume.

You saw this company at a pretty early stage, but you'd already been pretty successful in some parts of your career. What was it that got you to join a 40 person company? What did you see?

You'd never know this from my LinkedIn profile, but that's kind of my M.O. i mentioned. I joined Documentum in its very early stages and a little bigger, but not much than HelloSign. When I, I joined Box at about 100 people pre public and I joined, I think even before all that. I think when I joined Sybase we were only about 200, 250 people. So pre IPO as well. I like that. That's my sweet spot is join when it's small. And I've been very, very fortunate in picking companies that have got the right product, the right product market fit, the right leadership team that we've grown big and been very, very successful. So if you look at kind of Oracle, Sybase, Documentum, EMC box, okay, they're all big successful companies, but they weren't when I joined. They weren't that draw for hellosign is part of what I love to do. But I'll be honest, I looked at 28 companies when I was on my hunt for hellosign and so I was really picky. And it wasn't just the size and the great product, although those were a big part of it. I think this is my first COO role and for me, part of it was the partnership with the two founders. They were looking for a third founder. And this hopefully is fodder for more of our conversation about the second in command perspective. They were, I think, very wise in recognizing that they had built a phenomenal product and company with great product market fit. And we're at a stage where having somebody that came in with scale experience and go to market experience would round out the skills that they had and that the three of us could really operate the business as a trio. And that's the way we run the business. We're a partnership. And then I also like being at the underdog, honestly. I mean, there's no denying in the E Signature space that Docusign was a front runner and they've got a lot of mind share. But I think we have a better product, our customers are happy and I think the market is untapped and I think we get every chance to take the top position. So I love being at the underdog.

I really like that you actually looked at 21 or 28 different companies. I mean that's a classic COO move as well. Honestly, I'm like, God, I've never dated in my life. I just go from one relationship to the next or I go from one company, I just find the next thing and I go, oh, this sounds good, let's do that. How do you slow yourself down to be analytical enough? And then what did you look for? How do you narrow it down from 28 to 5 to 1? What did you do?

I think I've refined this process a little bit and I've shared it with a lot of people because it is a different mind shift. I feel like most people follow what you described kind of a, hey, I've got connections. I get introduced into this opportunity. It sounds like a great fit. I'm going to go do it.

Go for it. Yeah.

I think there's the. I want to be at the best possible place that can best leverage my skills and that I can learn the most and have the most fun. It behooves me to do some due diligence. Right. And not every company and opportunity is what appears at the surface. So, you know, a lot of those 28 companies, those are companies I actually did engage with in some way about a real opportunity. First I had some criteria. I learned, I think it was when I became part of emc. So I'd done two database companies, right, Oracle and Sybase. So kind of deep in the infrastructure side of things, not what the user touches directly, a database programmer or admin. And then I was at Documentum, which was an end user product that was much more close to kind of the tip of the problem, if you will, that was trying to be solved. And then we became part of emc, which was primarily a hardware company, then kind of edging its way into software through acquisition. And so I learned pretty in that transition that I really care about products that touch people as opposed to things deep in the infrastructure that are sort of below the hood. I really honestly couldn't bring myself to care deeply about how fast disk spins on a hardware server. Just couldn't quite get there. So I had a similar list of criteria. I knew I didn't want to commute anymore. I've always commuted about 45 minutes to an hour each way my whole career. I live in the city. Tech is now in the city, meaning San Francisco. Gonna take another job. It's gonna be in the city I live in. I'm not gonna commute anymore, or at least shorter commute. So it was in the city, it was in software, enterprise software, not consumer, because that's what I do. It's something that touches users, that solves real problems and is meaningful in the world of business with an awesome culture and a great team and has potential to be really big and I can help. Those were kind of my criteria. And so as I dug in, either culture ruled it out, or kind of the market opportunity ruled it out, or location ruled it out or something. It was one of those things that kind of just didn't quite work.

So what do you think the two founders saw in you then? Because they were clearly looking as well. What did they look for? What did they see?

We've had this conversation a few times. And they've been asked that before too in their own interviews. And I think what they've said is that, well one, they knew they needed somebody with the skill set that I bring to the table, the scale experience and the go to market side of the house, because those are the things they didn't have. So there was that. But I think it was also Joseph, in particular. The CEO and one of the co founders really has a deep commitment to building great culture, has taken a very methodical and deliberate approach to building a culture that has some key values. And one of the values of the culture that I had never seen before is empathy. Empathy for each other and empathy for our customers. Two of our other values. Make our team awesome. Make our customers awesome. Those kinds of things mattered. And so I think they were looking very much for somebody who fit well within that construct and would really help embody those values and attract additional talent that would fit with that as well. And I'm an empath, so there's a lot of things there that just works well from a communication style perspective. And then I think the third thing was they were looking for somebody who had leadership skill and who could lead the company through the next set of transitions as we scale to larger growth. You could do that with empathy and understanding and good communication and, you know, bringing people along for the journey as opposed to telling them to get their butts moving toward the end game. It just kind of worked. It was a yes, yes, yes on all sides.

Awesome. How did you, in the early stages, establish the trust and the communication and good, healthy conflict, you know, with them to really get the relationship, relationship to kick into gear?

Well, I think first of all, I spent, I literally asked Joseph, the CEO when I first started. I said, hey, I kind of want to reprieve from making any big decisions for the first 60 days at least. I need to just get to know what's working, how the business runs, how the product sells. There's like, until I know some things, I can't add a lot of value other than just help contribute an opinion. But like, don't let me decide, have the context. So a big part of it was going on a learning tour and that part of that is building relationships with people and building trust. And so I think there's a big part of that that was a very concerted effort on my part. I've also, especially starting in a company in a C level role, when there's only three of us in C level roles, those titles imply things and people have expectations and fears and all sorts of stuff that I really just wanted to defray. And so I spent a concerted effort to let people really get to know me and to be vulnerable and to share personal things about myself and to not be shy about that and to make myself approachable. And so kind of funny enough, I go by Whit, even though my name is Whit. It was really coming into hello sign. Part of that thought process was like, you know what? Every single person that knows me well calls me Wit. Why don't I just go full wit? Like it makes me more approachable anyway and it's what I would prefer. And so this is the first job where I've really literally. My email is witellowsign.com so everything about me here is wit. And I just, I think that's helped too. So a lot of kind of concerted effort to really build trust, be vulnerable, listen a lot, learn a lot, respect what's been done to get us here and then start to add value about what's going to get us there.

Talk to me a little about the vulnerability side then. What is it you're doing to kind of get the vulnerability going?

Well, I think it's being very genuine for one, like you can't fake that stuff. Two, I'll give you a real example. So I think in the first company meeting where I was introducing myself, I had at one point been exposed to something called a journey line. If you drew on a slide, a PowerPoint slide or Google Slide, whatever kind of a graph or chart over time where the middle line is kind of the, I guess, ground zero. And the positive moments are above the line and the negative moments are below the line line. And you kind of most impactful moments and chart them over time.

Yeah, we call them lifelines.

Journey line, lifeline. There you go. So I had done that for a prior exercise somewhere along the way. And so I just updated it and used that as a way to introduce myself. And mine includes not just career milestones, but personal milestones. One of the really low points of my life was my. He was my cousin, but I called him my Broco. He was my. But closer to me than my own brother in lots of ways. We were very, very tight. He lived in Boston and he got cancer at 30 and it was a two year ordeal. It was awful. And he finally recovered and was great. And he ultimately had some relapse issues and passed away. It'll be two years ago this Christmas on Christmas Day. But when I started with the company, he was still Living and talking about that eye opening moment when he was in ICU and close to death and all sorts of crazy things. That was a real level setter. Right? I mean, there's no way you go through. We've all had trag things happen in our family and friends circle. Those things have a way of setting priorities in line. And it just made me really treasure work, life balance and family and close friends in a way that I was doing, but not to the same degree as I have ever since that moment. So that's one of the things I shared in my lifeline, journey, line, whatever. And the real high moment that I shared that was personal was meeting my husband and I met him later in life. We didn't meet until I was in my late 30s. There's something about having the right partner by your side, that one plus one equals five. Man, I can go tackle mountains I couldn't if I didn't have him back me up. He's the one that I think has pushed me to take some risks that I may not have taken on my own and vice versa. I did the same for him.

Do you share some of the vulnerabilities that you have in your work roles at all? About your struggles with certain areas of the business or things you suck at or.

Honestly, that's a big part of hiring decisions. Where am I lacking in skill? I mean, just like I credited Neil and Joseph, the co founders, of recognizing where they needed skill that perhaps they didn't have directly. I got to do the same thing. And that's all about figuring out where I'm weak and where I don't know what I need to know to be successful. I got to rely on people who are better than I am.

Let's talk about building the trust with the two founders then. What is it you needed to do in the early stages so that you had that kind of implicit trust that you could make decisions or have access to bank accounts or like, what do you do to get that? I mean, when I joined as the COO for 1-800-GOT junk, the founder was my best friend and he'd been my best man at my wedding three months before. So before even joining him, we already had huge trust. Right. So it was easy for me.

Curious what you did as any new relationship. I mean, it's something you build over time. That whole kind of let me get to know what's working and how we got here first. And frankly, giving that all its due respect, I think was a big part of that. I mean, Joseph and Neal Built the company that I joined, right. I wasn't here to contribute to any of that. So really respecting what they've been able to build and figuring out what they did that worked so well. Because what worked there may not work here and what got us here won't get us there. So I think part of it was giving a whole lot of healthy respect and real curiosity to really understand how we got here and what things they did that worked and what lessons did they learn that didn't work and where the biggest business challenges were from their perspective. So a lot of listening, learning, absorbing and respecting I think was part of it. And then I think the other bit is proving over time that I am worthy of trust, that I am part of this, that I'm totally committed, that I'm here for us to win. I'm never going to demonstrate any lack of integrity. I mean, that's kind of what earns my right to carry a copy of the keys to the cast.

So you've got the trust being built up, you're building that vulnerability and relationship with the team. Then what did you start doing? Your first kind of big decisions, what were those? How did you get the approval or the nod to go ahead and do those?

Well, I think that one of the first things was hiring ahead of marketing, which was in process when I was being hired, but I was ultimately part of that final process. And really looking at, you know, as you expect with any startup, it's going to be fairly remedial. I mean, thankfully we've got a very viral product and we have had early integrations with Google that just led to massive user growth and adoption, which was great. That only carries you so far. You got to start to build some rhythm and an engine that's going to carry you to scale. And so really had to kind of revamp everything, everything from ground up and build from scratch a marketing stack and system instead of lead programs, lead generation programs and things like that, that really what we had just wasn't going to work at all. And so. And that took took about a year and a half to do. But I think that's part of what they hired me for, right Was recognition that that's experience that I bring to the table. So there wasn't really a permissioning involved in that. It was a brought me in because, you know, I know how to do this and this is what we need to do to get to where we need to be. Two years, three years, five years down the line and then obviously building out the team with the right Marketing skill. And similarly, on the sales side, there was a sales leader already in place who stayed with us actually until earlier this year. So grew with us from zero sales reps all the way up until our most recent and only recently did we, did we bring somebody else in and he moved on to another opportunity. But same thing there though, of building out the right skill set and the right team and the right processes. I mean, there was a whole other set of leveling up we needed to do in that arena. And then the third big area that was kind of a key focus was operationalizing more of the company. So let's do quarterly objectives and key results and let's have regular processes for checking in on those things and hold people accountable to goals. Well, first of all, let's set the goals, let's tell everyone what they are, and then let's hold people accountable to the things that are going to get us to those goals. That was a cadence we didn't really have in place in any sort of systemized way. And same thing on the financial, financial side. So, you know, certainly there were revenue targets and things like that, but getting more depth behind how we forecast and how we determine what our growth targets are going to look like and how do we set quarterly goals around that and set sales targets and think all that kind of stuff, putting real process and rigor behind that was those are the big things that were the focus of my first real kind of six months here and needed two years to really get to where I wanted them to be.

But for sure, oh yeah, those are all big systems. Was there any pushback on that stuff at all? And how did you get the buy in if there was pushback?

There really wasn't any pushback. I think it was all stuff we recognized was needed. It's funny, the area I can think of where there was pushback, what was actually not an area that directly reported to me. I'm thinking more about like the growth of the company. And where did we hit milestones that we had to shift Things that needed to have Joseph's mind and Neil's support to really make happen for the company. It's fun. You hit some really interesting challenges when you go when you cross the 50 employee line and again when you hit the 100 employee line. Some of them legal related and some of them, you know, kind of systems related. And I remember when we first had to start doing things like have an acceptable use policy, have a code of conduct, have an employee handbook. All of those things kind of come into play when you roughly pass the 50 employee line. And those take a lot of thought because those are culturally big shifts and can be seen as very kind of Big brother controlling stuff. We're no longer the fun scrappy startup, and we were really looking for a way to do those things without losing any of the fun, scrappy bits that made us the company we were at that time and still are. And so that was something that took a lot of thought. And we did get some pushback and we made some mistakes, quite frankly. The first one of those things we rolled out, I think, was the acceptable use policy. And we could have done a lot better job in hindsight of telling. It's that whole tell them what you're gonna tell them, tell them, and then tell them what you told them. And I think we could have done more of the telling them what we're gonna tell them a whole bunch before we actually got to the actual telling them part. And so I think it was more of a surprise that it should have been to people and we could have done better. So we did do better after that. But that's one area I can think of that we definitely had a little employee pushback that we had. Think through hard.

What do you look for with your employees? I mean, you obviously have had to do a lot of recruiting, growing, you know, by another 200%, grow another 80 employees in the last couple years. What have you had to do and what have you looked for on the culture side of employees? Not the skill sets much.

It's funny with culture, because you don't. I mean, I think if you buy into the principles of diversity, which I think we all should. And that's diversity of every angle, right? So cultural background, educational background, business background, ethnic background. Diversity brings varied perspectives that help you make better decisions. So if you buy that for a moment, then what you don't want to do is have a cookie cutter approach to hiring, because you're just going to hire one and then another that looks like that one and another that looks like that one, and you just kind of get this sameness. And so you got to start early on diversity. And diversity breeds diversity. And so part of it is, yes, we look for values in people and demonstrated past experience of how they might use those values in work, like integrity or empathy or radical candor or whatever you want it to be, whatever the values of the company are. We look for examples that show that people embody those kinds of traits. But we also look for people that bring value, add to the culture, that are going to help Us continue to evolve and morph in a positive way. If somebody came in who was really had a good background in, say, nonprofits and wanted to look at how we could serve that sector of customers better, that's an interesting example where if we don't have that already in house, then that brings a different perspective for us to weigh. So that's one good example. I think we had a couple hires in a close proximity that actually had worked in the retail industry industry in management roles, brought kind of a different set of management philosophies to contribute, and it didn't change the way we thought about management training and things like that, but it added value to the process. So that's the kind of stuff I'm talking about.

You're building out this team. You've started to put all the systems and stuff in place, and then you're dealing with Gen Y that are certainly aren't joining a company for 20 years or five years. They're joining a company project by project or maybe, you know, 18 months at best. That tends to be at least what we're hearing. How do you deal with that in that cohort? And then also, how are you dealing with keeping and retaining people in such a competitive job market like the Bay Area?

Well, and not to mention through an acquisition, which is usually a very tough thing to keep people through. So I think, first of all, my experience with the generation you're referring to is largely about having a very clear path for them to have career growth. If they don't have a line of sight to how to get to that next role, whether it's. Whether it's next week, next month, next year, they're gonna move on. Because we all know that you can go once you've got some level of experience in a given role under your belt, you can use that as a way to go outside and find a role that's perhaps a step up or certainly pays you a little bit more. You provide a great culture that is a big way to keep people, especially if they've ever worked in a culture that wasn't so hot. You value that a lot. So there is providing a great place to work, and then there's the real transparency around career growth and identify levels. Whether you codify them or not in your systems is kind of immaterial. But clear levels and clear expectations of those levels that can be communicated to people so they know how to get from A to B and then be having those conversations on a regular basis. That is the biggest demand area I see out of the younger generation is knowing how to grow themselves in their career. We've done a ton of investment in that and did from early on, and we're thankful that, frankly, Dropbox has done that in spades. And now we get to leverage all of that as part of Dropbox. And that brings me to the whole acquisition thing, interestingly enough. And then we also, by the way, do very regular quarterly employee surveys where we ask a ton of questions about engagement and how much they believe in the mission and how often do they think about looking for another job. We ask those hard questions and we gauge kind of how we're doing quarter to quarter. And if things are getting worse, not better, we talk about it openly with the company. And several times we've put together a team task force of individual contributors and managers to, hey, go brainstorm how we can fix this and let's get some real ideas on the table and then show the rest of the company that we're listening to them and taking action on their feedback. And it's that kind of, again, that act of transparency and action, that means a lot to that generation. And those are the things that will keep them aside, assuming they're paid decently.

And, you know, it's kind of like Maslow's hierarchy of needs, right? There's got to be a level of base pay and security and acceptance. But then, yeah, there is that value in their work and an open, trusting environment and safety and good communication. That's really why they leave that stuff's in place, then they can go to the next level.

And I'm so, so, so, so proud to say that we literally retained every single employee through the acquisition.

The acquisition. So how did you do that? What kind of communication? How did you talk to them? Like, what did you share?

This is funny. So this is an area where I have to say, I think we had done such a good job of all these things. I'm talking about that we had a lot of trust and goodwill with our customers. I mean, our employee engagement scores are crazy. I think the market average is about 70% engagement score, and we're in the high 80s. So we had really invested a lot in that stuff. And that it turns out in hindsight, we weren't doing it because we knew about the acquisition, obviously. But in an acquisition, especially by a public company, you can't talk about this openly. I mean, the circle of trust of the people doing the due diligence process was extremely small, like 7 of us. So we weren't telling the whole company. And so we had to tell them the day that it was announced. And the interesting thing is we had done this incredibly thoughtful plan about, oh yeah, we're going to send this early morning email. We'll have a morning town hall, we'll have one on ones, we'll have office hours, we'll have the Dropbox execs. We have this whole day planned of like really good transparent communications as much as we possibly could. CNBC blew the embargo and put the news out at 1 in the morning instead of 1 in the afternoon. And so it just completely threw everything into havoc. People found out exactly the way we didn't want them to. And you know, I would love to say that we kept 100% of the employees because. Because we had such a great communication plan, except that that wasn't what it was. It was actually all the work that we did up to that point.

You just actually stumbled onto one of my little known press hacks and that is you find the press organizations that don't honor embargoes and you'll find them, they're easily searchable. TechCrunch is one of them. And you send them something and say, you know, you can't Release this until 5 o' clock Thursday. They will, they'll release it early. And then you take that initial jump and push that out to all the other outlets saying, sorry, they didn't own the embargo. They clearly jumped on it. Cause it's big news and everyone else circles and wants to run the.

Love it.

I just use it against, I just use it against them. So I'm like, all right, I know, yeah. I'm like, I'm not gonna fight against you. I'll use you.

I don't care.

So where are you guys headed right now as an organization? What do you have to do to get there? Because you're go through some changes now with this acquisition. What do you have to change?

Yeah, well, we're eight months in now to the acquisition, so things are going great. I've been part of 17 acquisitions in my career. Two on the being bought side and one was Documentum now hello sign and the other is on the acquiring side. And this is by far the best I've ever seen. We just, we had very similar cultures, which helps a ton. So trusting, open, transparent, curious, respectful. That's worked really, really well. And rationale of the acquisition on both sides was because we wanted to grow this business faster and get e signature tools to anybody and everybody who wants them, preferably integrated with their tool of choice. Dropbox. So anyway, the rationale was all good, so things are going really well. But you know, as I said, our whole aspiration of doing this was to grow the business faster than we would have on our own. And so that's all about, you know, how do we leverage our now parent company to take this product much more broadly to the world in a faster way than we could have. So that's a global exercise. How do we enable the Dropbox selling team to take this market into the Dropbox installed base and how do we accelerate the things that we were doing as a standalone business? And so those are all big movers.

Big, huge, yeah, big, huge movers.

And so there's really the last three months or so we've been very deep into planning for next year and it's all around these three kind of angles of how do we grow the business faster. And thankfully we have a ton of support and investment help from Dropbox to do it.

Now you mentioned earlier that this was your first role as a coo. You moved from another C level. Was it a cmo? Where do you think you've struggled in your career? What have you had to really work at the most?

It's shifted a little bit over time. It's funny, I remember in my first job out of college, so I was not a computer science major, although I did take a bunch of programming classes because I enjoyed it, honestly, I loved math. I remember I was at Oracle and feeling like I wasn't technical enough, so I went and took a bunch more programming classes. So I remember that was a weak area for me. I kind of fixed that, moved on from that, really felt like I had what I needed there. Later in my career I felt like, like my EMC days, documentum days, certainly early at emc I hadn't operated as an executive in a very large organization. And EMC when they acquired us were about 25,000 employees, I don't know, 20 plus billion in revenue. So the years I spent doing that, about the five years or so that I was in an executive role at emc, were incredibly instructive. I just didn't understand kind of the operating at that scale and how to get things done in an organization that large. And how do you bring in the right people at the right time, but not bring everybody in? That slows everything to a grinding halt. So that was a real learning experience. I think that served me very well. And then I think in this job initially, you know, I'd never run finance before, but I was or leased and I was running both of those functions for us. Really, really getting deep into kind of the how do we financially manage a company and what does that look like? That was a learning area for me in this role. So it's really shifted over time.

Harvard wrote an article about 15 years ago called the misunderstood role of the COO. And it really talks about the seven distinct types of COOs. And then I talk about it with, we've got, you know, members from all over the world of the COO alliance. And some run finance, some don't, some run engineering, some don't, some run marketing, some don't. You basically the COO is running everything. The CEO sucks. At some companies, CEO is very outward facing. Right. But in some cases the coo. Like if you think about Shopify, everyone knows Harley Finkelstein. Harley's the coo, Tobias. The CEO is very inward engineering focused.

You're right. It's one of the things that the CEO isn't good at and needs to round out in the skill set. And it's funny, I view my job other than the finance legal part and the corporate planning. I mean, I'm really more of a CRO or chief Customer officer. Right. Because I got customer support and operations and marketing and sales and biz dev and kind of everything that test as a customer from start to finish. But I think the CRO is a growing role because of the need to tie those things together more closely.

And how does a leader who is maybe a second command or a leader in any business area where they're really starting to hire their first people that are truly smarter than them in those functional areas, what's the mental hurdle they need to get over to feel comfortable? And they're not going to lose their job by hiring smart people.

A's hire A's and B's hire C's. I mean, this is about ego. It's really blatantly about ego. The only way I'm the best at my job is if I have the best people at what they do working for me. Because collectively we're a whole. That's much greater than the sum of the parts. I mean, if I hire people that are only less skilled than I am, then I'm shortchanging the company. I don't really have a problem with hiring somebody who's way better than me. I feel like that's my job. Yeah, but I've met plenty of people who are in executive ranks that don't feel that that way, who are very threatened by people that are better than they are. At something working for them. And therefore I do think they shortchange the company and they end up. Either the company fails or they eventually learn the lesson and figure it out or they get replaced.

If you were to think back the wit of today, to think back to the Whitney, I guess, of 21, 22, graduating college, what advice would you give yourself other than to shorten your name? To wit, what advice would you give yourself back then that you wish you'd known and then but you now know.

To be true by accident, more so than on purpose. I ended up with a very non linear path in my career. It wasn't a step one move up, step two move up, step three move up. It was very much a kind of like I meandered a lot in different roles and yes, I moved up along the way, but I actually think that was a great thing for me. I don't know if I would have ended up in this role if I hadn't tried tried that thing or that thing or that thing. In hindsight, I'd love to be able to say that I purposefully took risks and leapt at the opportunities where there was the most opportunity for learning and challenge. But that wasn't on purpose, at least initially. It was by accident. And I think now if I could go back and tell myself all over again, I mean, lucky that I did that and great. But I think what I tell young people today is first of all, don't overth it. You don't know where you're going to end up 10 years from now. Don't try to plan too hard, because otherwise you may totally miss the best thing that ever could have happened to you. Be opportunistic. Build your network. Keep looking for new opportunities to learn. Surround yourself with people that can teach you things. Those opportunities will present themselves and they will teach you what you love to do and therefore what you're best at. And then you can start to focus in on those things. I feel very fortunate I end up where I did, but I wish I'd known that earlier early on.

Wit Baouke the COO for HelloSign. Thank you very much for sharing with us today. I really, really appreciate this time.

We complement each other's skill set, so that's very important. So we don't overpower each other's discussions, especially when we know it's not our forte. So we, we stick to our territory. Let's say his territory is marketing, mine is business. So we sort of have created our own playfield which is existent in his mind. And my mind as well. So that playfield and that distinction is very important.