Ep. 82 - Building The Right Team And Company Culture With HelloSign COO, Whitney Bouck

Ep. 82 - Building The Right Team And Company Culture With HelloSign COO, Whitney Bouck

Having a grand vision doesn’t mean anything if you don’t have the right people to execute your ideas. Whitney Bouck, the COO of HelloSign, joins Cameron Herold this episode to discuss her experiences from all the companies she’s been with and has helped grow. She talks about company culture in its entirety, and how practicing the right values can propel a company to success. Having formed countless top-notch teams throughout her career, learn as she shares the foundations and criteria you need to take into consideration when hiring for your team. Know some of the most effective strategies on being an effective COO, whether on a startup or an established company.

Whitney Bouck 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 HelloSign, 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 fifteen years with Documentum and EMC via acquisition and held a variety of leadership positions including CMO of Information Intelligence and other divisions of 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 World’s 100 Most Innovative CMOs. She’s recognized with the Silicon Valley Women of Influence Award in 2009 and she received the Top 40 Under 40 Award in 2003. Whitney, thank you for joining us.

Thank you. It’s a pleasure to be here. I’m looking forward to this whole conversation.

You’ve got a ton of insights to give us. My whole reason for starting the show was I’m getting tired of hearing the CEO story. Everyone interviews the entrepreneur, the CEO of the company. We hear their perspective and I’ve always wanted the rest of the story. It’s going to be your opportunity to tell us a little bit about what you have been doing with HelloSign, but also what you feel makes a great COO that everyone can learn from as well.

I appreciate exposing some of the other executive perspectives. You’re right, everybody wants to hear from the CEO, especially, in the startup world in Silicon Valley in particular, where many of the companies are founded by a product visionary. They’re the ones with the great idea that got the whole thing going but there’s a whole lot more to building a great company than just the idea.

If you asked my dad how did he raise his kids, he’d have a true story. If you asked my mom how did she raise her kids, she’d have a true story also, but they’re completely different. Even though we were all in the same household together, they were completely different stories. That’s where I’m coming from on this. Tell us a little bit about your journey. Maybe go back to the Top 40 Under 40. That’s a 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?

It was 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. I was there through IPO and acquisition by EMC eventually. I earned myself a reputation for one, being part of what it takes to scale to a successful exit or more than one in the case of Documentum. I’ve also been able to do a good job of building a brand reputation in the market. Somewhere early on, I decided that I enjoyed turning light bulbs on for people and helping connect what the company has to offer with the problems that solve for people. I’m good at that so having some visibility in that way and getting recognized from when I talked about it and I get it. It’s the two things that have worked to my advantage.

They’ve tracked with you then. I totally agree, when you get some of those early successes, they tend to start to mirror the rest of us. Partially because we get painted with that brush and also partially because you’ve done it, so you can start to replicate that. Tell us a little bit about HelloSign so we can 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 below 40 employees at the time and the high but single-digit millions in revenue. We were acquired in 2019. The founders and I ultimately decided to sell the company to Dropbox in February of 2019. That was an opportunity for us to grow the business much faster than we could do as a standalone company. At that time, we were about 130-ish employees and in gap revenue, we contributed about $20 million in fiscal 2018 to the Dropbox numbers. That gives you a rough idea of how we grew over the course of those three years. That’s a respectable growth in a relatively short time and also pretty hefty employee growth. Coming into the Dropbox world, the whole motivation there was to grow faster and to be a growth engine, not just for the HelloSign business but also to add more value to the Dropbox portfolio so that they can deliver more value to their customers.

That’s the growth spectrum that we’re talking about. As far as what we do, because many people may not know, HelloSign were in eSignature in the digital transaction platform. Our job is to help take these complex close to revenue and super important transactions that eventually at some point, need a digital or electronic signature as part of them to bind the agreement. We make that process seamless, intuitive, easy, cost affordable and also to be able to do it in the context of a larger business process where appropriate. We’re one of the only vendors in our space if not the only one that focuses on embedding our technology into other people to make it easy. We white label, meaning we’ll remove our branding if it’s to the benefit of our customers to preserve their brand in front of their customers. Many people have used HelloSign and not even known it.

Do you make your money on the number of documents being signed per month that the company pays for? Is it a per seat basis? How do you make your money?

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

You saw this company at a pretty early stage but you’d already been 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 my MO. I mentioned I joined Documentum in its early stages. It was a little bigger, but not as much as HelloSign when I joined. I joined Box at about 100 people, pre-public. Even before all that, when I joined Sybase, we were only about 200 to 250 people, so pre-IPO as well. I like that. That’s my sweet spot. I join when it’s small and I’ve been fortunate in picking companies that have got the right product, right product-market fit and right leadership team. We’ve grown big and successful.

If you look at Oracle, Sybase, Documentum, EMC and Box, they’re all big successful companies, but they weren’t when I joined. That was part of the draw for HelloSign. It’s part of what I love to do. I’ll be honest, I looked at 28 companies when I was on my hunt for HelloSign. I was picky and it wasn’t the size and the great product, although those were a big part of it. This is my first COO role. For me, part of it was the partnership with the two founders. They were looking for a third founder. Hopefully, it’s fodder for more of our conversation about the second in command perspective, but they were wise in recognizing that they had built a phenomenal product and company with great product-market fit.

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 operate the business as a trio. That’s the way we run the business. We’re a partnership. It’s fantastic. That was a big draw and I also like being the underdog. There’s no denying in the eSignature space that DocuSign was a front runner and they’ve got a lot of mindshare, but we have a better product. Our customers are happy and the market is untapped. We’ve got every chance to take the top position. I love being at the underdog.

I liked that you looked at 28 different companies. That’s a classic COO move as well. Honestly, I’ve never dated in my life. I go from one relationship to the next or I go from one company to the next. I find the next thing and I go, “This sounds good, let’s do that.” How do you slow yourself down to be analytical enough and what did you look for? How do you narrow it down from 28 to 5 to 1? What did you do?

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, “I’ve got connections. I get introduced to this opportunity. It sounds like a great fit. I’m going to go and do it.” I want to be at the best possible place that can best leverage my skills and I can learn the most and have the most fun. It behooves me to do some due diligence and not every company and opportunity is what it appears at the surface. A lot of those 28 companies are companies I did engage with in some way about a real opportunity. Some of them went further than others naturally. First, I had some criteria. I learned it when I became part of EMC. I’ve done two database companies, Oracle and Sybase, so I’m deep in the infrastructure side of things, not with the user touches directly unless you’re a database program or admin.

I was at Documentum which was an end-user product that was much more close to the tip of the problem that was trying to be solved. We became part of EMC, which was primarily a hardware company then edging its way into software through acquisition. I learned in that transition that I care about products that touch people as opposed to things deep in the infrastructure that is below the hood. I couldn’t bring myself to care deeply about how fast disks spin on a hardware server. I couldn’t quite get there. I had a similar list of criteria. I knew I didn’t want to commute anymore. I’ve always commuted about 45 minutes to 1 hour each way my whole career.

I live in the city. Tech is now in the city, meaning San Francisco. If I’m going to take another job, it’s going to be in the city I live in. I’m not going to commute anymore or at least a shorter commute. It was in the city. It was in 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 the potential to be big and I can help. Those were my criteria. As I dug in, either culture, market opportunity or location ruled it out or something. It was one of those things that didn’t quite work.

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

SIC 82 | Building The Right Team
Building The Right Team: When you’re new in a company, building relationships and trust should be a part of your learning tour.

 

We’ve had this conversation a few times and they’ve been asked that before too in their own interviews. What they’ve said is one, they knew they needed somebody with the skillset 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. There was that but it was also Joseph, in particular, the CEO and one of the cofounders has a deep commitment to building a great culture. He’s taking a methodical and deliberate approach to building a culture that has some key values. One of the values in the culture that I had never seen before is empathy. This is part of the draw for me to HelloSign. It’s empathy for each other and empathy for our customers.

Two of our other values is to make our team and customers awesome. Those things mattered so they were looking for somebody who fits well within that construct and would help embody those values and attract additional talent that would fit with that as well. I’m an empath so there are a lot of things there that works so it meshed well from a communication style perspective. The third thing was they were looking for somebody who had leadership skills and who could lead the company through the next set of transitions as we scale to larger growth. We do that with empathy, understanding and good communication. It’s bringing people along for the journey as opposed to telling them to get their butts moving toward the end game. It worked. It was a yes on all sides.

You selected them and they selected you. You’re coming in and that first 90 days or whatever, but how did you in the early stages establish the trust, communication and good healthy conflict with them to get the relationship to kick into gear?

I asked Joseph, the CEO, when I first started. I said, “I want to reprieve from making any big decisions for the first 60 days at least. I need to get to know what’s working, how the business runs, how the product sells.” Until I know some things, I can’t add a lot of value other than help contribute an opinion. Don’t let me decide without the context. A big part of it was going on a learning tour and part of that is building relationships with people and building trust. There’s a big part of that was a concerted effort on my part. Especially starting in a company in a C-level role, when there are only three of us in C-level roles, those titles imply things, keeping expectations and fears and all sorts of stuff that I wanted to defray. I spent a concerted effort to let people get to know me, be vulnerable, to share personal things about myself and to not be shy about that, and to make myself approachable. Funny enough, I go by Whit even though my name is Whitney.

I was coming into HelloSign and part of that thought process was, “Every single person that knows me well calls me Whit. Why don’t I go full Whit? It makes me more approachable anyway and it’s what I would prefer.” This is the first job where my email is Whit@HelloSign.com. Everything about me here is Whit. That’s helped too. It’s a lot of concerted effort to build trust, be vulnerable, listen a lot, learn a lot, and respect what’s been done to get us here and start to add value about what’s going to get us there.

Talk to me a little bit about the vulnerability side. What is it you’re doing to get the vulnerability going?

It’s being genuine, for one. You can’t fake that stuff. I’ll give you a real example. In the first company meeting where I was introducing myself to everybody, we still do every Friday, all-hands meetings with the whole company and make sure everyone’s in the loop, in the know and celebrates our great milestones and things like that. In that meeting, where I was introducing myself, I had at one point been exposed to something called a journey line. Are you familiar with that concept? If you drew on a slide, a PowerPoint slide or Google slide. It’s like a graph or chart overtime where the middle line is ground zero, where the positive moments are above the line and the negative moments are below the line. You pick the most impactful moments and chart them over time.

We call them lifelines.

Journey line or lifeline, it’s the same idea. I had done that for a prior exercise somewhere along the way so I updated it and use that as a way to introduce myself. Mine includes not only career milestones but personal milestones. The two in particular that I shared, hopefully, I don’t get verklempt here because it’s one of the moments I cried in front of the whole company as I shared this story. One of the low points of my life was my cousin. I called him my Broco. He was much closer to me than my own brother in lots of ways. We were tight. He lives in Boston and he got cancer at 30 and it was a two-year ordeal. It was awful. He finally recovered. It was great and he ultimately had some relapse issues and passed away on Christmas Day. When I started with the company, he was still living and talking about that eye-opening moment when he was in ICU, close to death and all sorts of crazy things. That was a real level setter. There’s no way you go through that.

We’ve all had tragic things happen in our family and friends circle. Those things have a way of setting priorities in line and it made me 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. That’s one of the things I shared in my lifeline or journey line. The real high moment that I shared that was personal was meeting my husband. 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. I can go tackle mountains. I couldn’t if I didn’t have him to back me up. He’s the one that has pushed me to take some risks that I may not have taken on my own and vice versa. It’s the same for him. It’s sharing things like that. They’re true, genuine, real and they have a lot to do with who I am as a person.

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

Totally. If we don’t, we’re kidding ourselves.

They’ll know anyway.

They probably know better than we do. Honestly, that’s a big part of hiring decisions. Where am I lacking in skill? I credited Neal and Joseph, the Cofounders, for recognizing where they needed skill that perhaps they didn’t have directly. I’ve 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’ve got to rely on people who are better than I am.

Talk about building trust with the two founders and what is it you need to do in the early stages so that you had that implicit trust that you could make decisions or have access to bank accounts? What do you do to get that? 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. Before even joining him, we already had a huge trust, so it was easy for me. I’m curious about what you did.

As any new relationship, it’s something you build over time that whole let me get to know what’s working and how we got here first. Giving that all its due respect was a big part of that. It’s obvious that Joseph and Neal built the company that I joined. I wasn’t here to contribute to any of that. 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. What got us here won’t get us there. Part of it was getting a whole lot of healthy respect and real curiosity to 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. A lot of listening, learning, absorbing and respecting was part of it. The other bit is proving over time that I am worthy of the 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. That’s what earns my right to carry a copy of the keys to the castle.

You’ve got the trust being built up. You’re building that vulnerability and relationship with the team. What did you start doing? What was your first big decision? How did you get the approval or the nod to go ahead and do those?

One of the first things was hiring a Head of Marketing, which was in process when I was being hired, but I was ultimately part of that final process. As you expect with any startup, it’s going to be fairly remedial. Thankfully, we’ve got a viral product and we had early integrations with Google that led to massive user growth and adoption, which was great. That only carries you so far. You’ve got to start to build some rhythm and an engine that’s going to carry you to scale. We had revamped everything from the ground up and build from scratch, marketing stack and system instead of lead generation programs and things like that. What we had wasn’t going to work at all and that took about a year and a half to do.

That’s part of what they hired me for. It was the recognition and experience that I bring to the table so there wasn’t permission involved in that. You brought me in because I know how to do this and this is what we need to do to get to where we need to be 2, 3, 5 years down the line so let me do it. That was a big one and obviously building out the team with the right marketing skill. Similarly, on the sales side, there was a sales leader already in place who stayed with us until early 2019. He grew with us from zero sales reps all the way up until we bring somebody else in and he moved on to another opportunity. It’s the same thing there. We’re building up the right skillset, team and processes. There was a whole other set of leveling up we needed to do in that arena.

The third big area that was a key focus was operationalizing more of the company. 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. First of all, let’s set the goals. Let’s tell everyone what they are and let’s hold people accountable to the things that are going to get us to those goals. That was a cadence we didn’t have in place in any systemized way. It’s the same thing on the financial side. Certainly, there were revenue targets and things like that. It’s getting more in-depth behind how we forecast, 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 all that stuff. Putting real process and rigor behind that are the big things that were the focus of my first real six months here. It needed two years to get to where I wanted them to be.

SIC 82 | Building The Right Team
Building The Right Team: Be genuine with the people you work with when it comes to showing vulnerability. You can’t fake that stuff.

 

All those are all big systems. Was there any pushback on that stuff at all? How did you get the buy-in if there was pushback?

There wasn’t any pushback. It was all stuff we recognized was needed. It’s funny, the area that I can think of where there was pushback, what was not an area that directly reported to me. I’m thinking more about 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 Neal’s support to make it happen for the company. You hit some interesting challenges when you crossed the 50-employee line and you go to the 100-employee line. Some of them are legal related and some of them are systems related.

I remember when we first had to start doing things like having an acceptable use policy, a code of conduct, an employee handbook, all those things, come into play when you roughly pass the 50-employee line. Those take a lot of thought because those are culturally big shifts and can be seen as big brother controlling stuff. We’re no longer the fun and scrappy startup. We were 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.

That was something that took a lot of thought and we did get some pushback and we made some mistakes. The first one of those things we rolled out 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 going to tell them, and then tell them what you told them.” We could have done more of the telling what we’re going to tell them a whole bunch before we got to the actual telling them part. It was more of a surprise than it should have been to people and we could have done better. We did do better after that. That’s one area I can think of that we definitely had a little employee pushback that we had to think through hard.

What do you look for with your employees? You have had to do a lot of recruiting growing by another 200% and grow another 80 employees in the last couple of years. What have you had to do and what have you looked for on the culture side of employees, not the skillsets as much?

It’s funny with culture because if you buy into the principles of diversity, which we all should, and that’s the diversity of every angle of cultural, educational, business, ethnic, religious background whatever, diversity brings varied perspectives that help you make better decisions. If you buy that for a moment, what you don’t want to do is have a cookie-cutter approach to hiring because you’re going to hire one and another that looks like that one and you get this sameness. You’ve got to start early on diversity and diversity breeds diversity. Part of it is yes, we look for values in people and demonstrated past experience of how they might use those values and work like integrity, empathy, radical candor, whatever you want it to be or 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 had a good background in nonprofits and wanted to look at how we can serve that sector of customers better, that’s an interesting example. If we don’t have that already in-house, that brings a different perspective for us to weigh. That’s one good example. We had a couple of hires in close proximity that had worked in the retail industry and management roles. It brought 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. That’s the stuff I’m talking about. It’s the diversity of experience that brings new insights.

You’re building out this team and you’re starting to put all the systems and the stuff in place. You’re dealing with Gen Y that certainly aren’t joining a company for 20 or 5 years. They’re joining a company project by project or maybe eighteen months at best. That tends to be at least what we’re hearing. How do you deal with that in that cohort? How are you dealing with keeping and retaining people in such a competitive job market like the Bay Area?

Not to mention through an acquisition, which is usually is a tough thing to keep people through. First of all, my experience with the generation you’re referring to is largely about having a clear path for them to have career growth. If they don’t have a line of sight on how to get to that next role, whether it’s next week, next month, next year, they’re going to move on. We all know that 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.

First of all, if you provide a great culture that is a big way to keep people and especially if they’ve ever worked in a culture that wasn’t so hot, you value that a lot. There is providing a great place to work. There’s the real transparency around career growth and identify levels whether you qualify them or not, your systems are immaterial. 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 having those conversations on a regular basis. That is the biggest demand area I see out of the younger generation. It’s knowing how to grow themselves in their career. We’ve done a ton of investment in that and did from early on. We’re thankful that frankly, Dropbox has done that in spades and now we get to leverage all of that as part of Dropbox.

That brings me to the whole acquisition thing. Interestingly enough, we also do 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 how we’re doing quarter to quarter. If things are getting worse, not better we talked about it openly with the company and several times, we’ve put together a task force of individual contributors and managers to brainstorm how we can fix this. Let’s get some real ideas on the table and show the rest of the company that we’re listening to them and taking action on their feedback. It’s that act of transparency and action that means a lot to that generation. Those are the things that will keep them, assuming they’re paid decently.

It’s like Maslow’s hierarchy of needs. There has to be a level of base pay, security and acceptance but there is that value in their work in an open, trusting environment, safety and good communication. That’s why they leave. If that stuff is in place, then they can go to the next level.

I’m proud to say that we literally retained every single employee throughout the acquisition.

How did you do that? What communication? How did you talk to them? What did you share?

This is funny. This is an area where I have to say we have done such a good job of all these things that I’m talking about that we had a lot of trust and goodwill with our customers. Our employee engagement scores are crazy. The market average is about 70% engagement score and we’re in the high 80s. We had invested a lot in that stuff. In hindsight, we were doing it because we knew about the acquisition. That helped. It was the single biggest contributor because in an acquisition, especially by a public company, you can’t talk about this openly. The circle of trust of the people doing the due diligence process was extremely small. It was seven of us. We weren’t telling the whole company. We had to tell them the day that it was announced.

The interesting thing is we had done this incredibly thoughtful plan about, “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 executive.” We had this whole day planned. We had good transparent communication as much as we possibly could. CNBC blew the embargo and put the news out at 1:00 AM instead of 1:00 PM. It completely threw everything into havoc. People found out exactly the way we didn’t want them to. I would love to say that we kept 100% of the employees because we had such a great communication plan, except that that wasn’t what it was. It was all the work that we did up to that point.

SIC 82 | Building The Right Team
Building The Right Team: The only way you’ll be the best at your job is if you have the best people at what they do working for you because collectively you’re a whole that’s much greater than the sum of the parts.

 

You stumbled onto one of my little known press hacks and that is you find the press organizations that don’t honor embargoes. You’ll find them, they’re easily searchable. TechCrunch is one of them. You send them something and say, “You can’t release this until 5:00 Thursday.” They’ll release it early and you take that initial jump and push that out to all the other outlets saying, “Sorry, they didn’t know the embargo. They clearly jumped on it because it’s big news and everyone else circles and wants to run the stories.” I use it against them. I’m like, “I’m not going to fight against you out. I’ll use you. I don’t care.”

It’s such a smart idea.

Where are you headed right now as an organization? What do you have to do to get there? If you’re going to go through some changes with this acquisition, what do you have to change?

Things are going great. I’ve been part of seventeen acquisitions in my career. Two being on bought side and one was Documentum, HelloSign and the other is on the acquiring side. This is by far the best I’ve ever seen. We have similar cultures which help a ton. Trusting, open, transparent, curious, and respectful, that’s worked well. The rationale of the acquisition on both sides was because we wanted to grow this business faster and get eSignature tools to anybody and everybody who wants them and preferably integrated with their tool of choice, Dropbox.

The rationale was all good and things are going well. Our whole aspiration of doing this was to grow the business faster than we would have on our own. That’s all about how do we leverage our parent company to take this product much more broadly to the world in a faster way than we could have. That’s a global exercise. How do we enable the Dropbox selling team to take this market into the Dropbox install base? How do we accelerate the things that we were doing as a standalone business? Those are huge movers. We’ve been deep into planning for 2020 and it’s all around these three angles of how do we grow the business faster. Thankfully, we have a ton of support, investment and help from Dropbox to do it.

You mentioned that this was your first role as a COO. You moved from another C-level. Was it a CMO?

It’s funny the roles that best set me up for this world too. I had two GM roles in my background, one at Documentum and EMC when I ran 2 of the 3 business P&Ls for Documentum. At that time, I had every function except for sales because we had a unified salesforce. Also, I was GM of the enterprise business at Box which is my first role there before taking over CMO building the enterprise business from the ground up. There I ran every function except for engineering. Those are probably the best roles that set me up for COO because I had such a cross-functional overarching view of a business and P&L. CMO twice because I was CMO at EMC and Box. Those things gave me a deep understanding of go-to-market and how to map the need of a product, market requirements and customer requirements together in a meaningful way. Those are the things that best set me up.

Where do you think you’ve struggled in your career? What have you had to work out the most?

It’s shifted a little bit over time. I remember in my first job out of college I was not a computer science major, although I did take a bunch of programming classes because I enjoyed it. I loved math and science. I remember I was at Oracle and feeling like I was with a lot of engineers. I was working in the engineering department effectively. I felt like I wasn’t technical enough so I went and took a bunch of programming classes. I remember that was a weak area for me. I fixed and moved on from that. I felt like I had what I needed there.

Later in my career, I felt that my EMC and Documentum days, certainly early at EMC, I hadn’t operated as an executive in a large organization. EMC when they acquired us, we’re about 25,000 employees from $20 billion-plus in revenue. 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 didn’t understand the operating at that scale and how to get things done in an organization that large. How do you bring in the right people at the right time and not bring everybody in that slows everything to a grinding halt? That was a real learning experience that served me well. In this job initially, I’d never run finance before or legal and I was running both of those functions for us. It’s getting deep into how do we financially manage a company and what does that look like. That was a learning area for me. It has shifted over time.

It’s interesting. Harvard wrote an article years ago called The Misunderstood Role of the COO. It’s amazing. It talks about the seven distinct types of COOs. I talked about it with members from all over the world of the COO Alliance. Some run finance, some don’t. Some run engineering, some don’t. Some run marketing, some don’t. The COO is running everything the CEO sucks at. In some companies, the CEO is outward-facing. If you think about Shopify, everyone knows Harley Finkelstein. Harley is the COO. Tobias, the CEO, is inward engineering-focused. You have to pick it up as you go and learn the skills or hire great people.

The CEO varies a ton and you’re right. It’s one of the things that the CEO isn’t good at and needs to round out and the skillset. It’s my job other than the finance legal part and corporate planning. I’m more of a CRO or Chief Customer Officer because I’ve got customer support and operations, marketing and sales and biz dev, everything that touches a customer from start to finish. The CRO is a growing role because of the need to tie those things together more closely. There are lots of different definitions for COO for sure. It’s the Chief Other Officer.

We’re also the ones that typically have to be the ones with the bad news or the hard decisions. The entrepreneur, our job is to make them iconic so we often get to roll out the bad news and they get to roll out the good news. Is that similar to you?

I’ve never thought about it that way. I don’t think it is. At least at HelloSign, I don’t feel that’s true. Maybe it’s the strong partner dynamic that the three of us have. We all feel like we all own it.

When you’re a larger company, if you’re a couple of hundred or more, you’re pretty solid in your role and knowing that you’re leading teams and strong confident people that are experienced sometimes way more than you and you’re good with that. How does a leader who is maybe a second in command or a leader in any business area where they’re starting to hire the 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?

This gets back to the principle of A’s hire A’s and B’s hire C’s. This is about ego. It’s 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. If I hire people that are only me or less skilled than I am, then I’m sure changing the company. To your point, I don’t have a problem with hiring somebody who’s way better than me. I feel that’s my job. I’ve met plenty of people who are in executive ranks that don’t feel that way and are threatened by people that are better than they are at something working for them. Therefore, I do think they shortchange the company and either the company fails or they eventually learned the lesson and figure it out or they get replaced.

You’re the seasoned exec who’s done all these acquisitions, deals, transactions and multiple companies you’ve been able to help scale. If the Whit of now would think back to the Whitney at 21 or 22 graduating college, what advice would you give yourself? Other than shortening your name to Whit. What advice would you give yourself back then that you wish you’d known them but you now know to be true?

I’ve given this advice as I’ve gone back and talked to my alma mater or as I mentor young people in their career. By accident more so than on purpose, I ended up with a nonlinear path in my career. It wasn’t a step one, move up, step two, move up, step three, move up. I meandered a lot in different roles. I moved up along the way but 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 that thing or that thing. In hindsight, I’d love to be able to say that I purposefully took risks and left at the opportunities where there was the most opportunity for learning and challenge. That wasn’t on purpose at least initially. It was by accident. If I could go back and tell myself all over again, I’m lucky that I did that and great.

What I tell young people now is don’t overthink it. You don’t know where you’re going to end up ten years from now. Don’t try to plan too hard because otherwise, you may totally miss the best ever that could have happened to you. Be opportunistic, build your network and 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. You can start to focus on those things. I feel fortunate I end up where I did, but I wish I’d known that early on.

Whit Bouck, the COO of HelloSign. Thank you very much for sharing with us. I appreciate this time.

Thank you. What a great conversation. I enjoyed it and I love this whole show. It’s great. Thank you so much for including me in it.

You’re welcome. Thanks for giving us the rest of the story. I appreciate it.

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About Whitney Bouck

SIC 82 | Building The Right TeamWhitney Bouck joined HelloSign as COO in 2016, where she is responsible for growing and scaling the company in partnership with the CEO, CTO, and the executive team. Before joining HelloSign, she ran the 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 the Information Intelligence 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 World’s 100 Most Innovative CMOs, previously recognized with the Silicon Valley Women of Influence award in 2009, and received the Top 40 Under 40 award in 2003.

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