Ep. 260: Whitney Bouck is the COO @ HelloSign (now a part of Dropbox). For those that do not know, HelloSign is the company reimagining how you approach your most important business agreements with their award-winning e-Sign solution. As for Whitney, she directly leads the organization’s go-to-market efforts, including sales, marketing, business development and customer operations. Whitney is also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership and execution. If that was not enough, Whitney is also on the board of Ekata, building the global standard in identity verification. Finally, prior to HelloSign Whitney spent close to 5 years at Box where as SVP Global Marketing & GM Enterprise she took on all of marketing globally for Box and was responsible for reshaping the company brand from SMB to enterprise.

Pssst 🗣 Loving our podcast content? Listen to the start of the episode for a promo code to our upcoming events!

In Today’s Episode We Discuss:

* How Whitney made her way into the world of SaaS originally with Box and how that led to her coming one of today’s leading COOs with HelloSign. What were Whitney’s biggest takeaways from seeing the hypergrowth of Box? How did that change her operating mentality?
* What does truly successful exec leadership look like in Whitney’s mind? When is the right time for founders to think about building out their first exec team? What common mistakes do they make in the process? What can founders do to attract seasoned SaaS execs to their early-stage company? What are the questions that suggest an individual has a startup culture to them? What are the indications that they are a “big company” person?
* What does Whitney believe is the new role of the CIO? What has changed about their tole and what has driven this change? With their coming front and center in the org, how does that change both the reporting and operating structure of the business? What are the nuances and intricacies of this role that many do not often consider?
* COO is thrown around as a term today, what does it really mean to Whitney? What does Whitney believe separates good from great when it comes to COOs? When is the right time for founders to start looking for their first COO? What should they look for in their first COO? What is the optimal onboarding process for any new COO?


Ep. 261: Tom Bogan, CEO of Adaptive Insights, a Workday company, will review the key principles to building a successful SaaS company. From team to vision to metrics to funding and more, these principles provide the framework for high-growth, high performing SaaS companies.

How can you develop a winning culture? How can you set aggressive but realistic goals? What’s needed to build the right team in SaaS today?

SaaStr’s Founder’s Favorites Series features one of SaaStr Annual’s best of the best sessions that you might have missed.

This podcast is an excerpt of Tom’s session at SaaStr Annual 2019.

Missed the session? Here’s what Tom talks about:

  • The important maxims about team building
  • Insights on fundraising and why you might not want to always raise at the highest valuation
  • Personal stories from his time building Adaptive Insights

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Whitney Bouck
Tom Bogan

Below, we’ve shared the full transcript of Harry’s interview with Whitney Bouck.

Harry Stebbings: We are back on the official SaaStr Podcast with me, Harry Stebbings, following our week away, and my word, it is so nice to be back. But now we’re back, I want to make the show better than ever. And so hit me, what can I do to make it better for you? Let me know on Instagram, @HStebbings1996 with two Bs, and I would love to see you there.

Harry Stebbings: But to the show today, and obviously I would never have favorite guests on the show, that would be wrong. But I’m totally thrilled today to welcome a personal favorite of mine in the form of Whitney Bouck, COO at HelloSign, now a part of Dropbox. And for those that don’t know, HelloSign is the company re-imagining how you approach your most important business agreements with their award winning e-sign solution. As for Whitney, she directly leads the organization’s go-to-market efforts, including sales, marketing, business development, and customer operations. And Whitney’s also an advisor to companies funded by the YC Continuity Fund, focusing on enterprise strategy, go-to-market strategy, leadership, and execution. And if that wasn’t enough, Whitney’s also on the board of Ekata, building the global standard in identity verification. And finally, prior to HelloSign, Whitney spent close to five years at Box, where as SVP of Global Marketing and GM enterprise, she took on all of marketing globally for Box, and was responsible for reshaping the company brand from SMB to enterprise.

Harry Stebbings: Now you’ve heard quite enough of Harry, and so now I’m very, very excited to hand it over to Whitney Bouck, COO at HelloSign.

Harry Stebbings: Whit, is is absolutely fantastic to have you on the show today, I’ve heard so many great things from many different people, but thank you so much for joining me today.

Whitney Bouck: Oh, thank you for having me, I’m thrilled to be able to talk to you today.

Harry Stebbings: Well I’m the excited one, but I do want to start with a little bit about you. So tell me a little bit of context, how did you make your way into the wonderful world of SaaS, and come to now be one of the leading COOs with HelloSign?

Whitney Bouck: Well, I started in SaaS really at my time at Box, which I joined in early 2016. And that was really the timing in the market where the SaaS evolution was taking place. Box was then a quite small, private company, and I joined to help build the enterprise business for them. They’d been predominantly selling, at that time, into SMBs, and that was kind of the wave of change from on premise software to SaaS software, mostly I think founded and I guess the ground broken by Salesforce. And it was just starting to take off, but it was still the time when there was a lot of confusion and fear, particularly on the part of CIOs of oh, really, can I put my data in a server that I can’t touch? I don’t know.

Whitney Bouck: So it was an exciting time to be on the front lines of the new and emerging trend in technology.

Harry Stebbings: I absolutely love that in terms of that taking off of the technology itself and the company. I do have to ask though, you saw some incredible hyper growth during that period at Box. How do you think that experience maybe impacted your operating mentality, and were there some big takeaways for you?

Whitney Bouck: Oh, a lot of big takeaways. I think the scale and rapid growth is, first of all, one of the most exciting things to experience, at least for me. I love fast paced, I love high energy, I love change. So for me, that’s the perfect environment for me to be in. But I think the takeaways for me are that you also have to watch for burnout. You can sustain that pace for a long time, at least for me I can do it for several years, but at some point, hey, you do need to take a break and realize that it’s not normal to run a million miles an hour 24/7 weeks and weeks, and months and months on end. So that was one of the takeaways, I think it does … it’s good for the body, it’s good for the mind to every once in a while kind of take a small break. Even if it’s a day to just recoup, and refresh, if you will.

Whitney Bouck: And then I think another key takeaway was that those kinds of periods of fast growth and scale are the way to potentially earn your unfair share of a developing market. And so there are windows of opportunity to be taken advantage of, and not to be overlooked. So I think there’s kind of a combination of run fast and rest once in a while that I think is really a great learning for me out of that period.

Harry Stebbings: Well I knew we’d go off schedule, I didn’t quite expect we’d go off schedule this quickly, but I’m too intrigued, because we have employees both in the fund that I have and then also with the show, and often they say, “No, I’m fine, I’m just tired.” My question to you is when kind of observing your teams today, how do you determine between tired and potential burnout? How do you determine between the two, because they’re very different, and what are the signs of the burnout?

Whitney Bouck: Yeah, really good question. I think part of it is when I see somebody that’s falling a little bit too much into routine, and maybe resisting taking on a new challenge, or kind of a lack of engagement where they’re withdrawing a little bit, and at the same time they feel tired or seem tired, that starts to me to reek of burnout. And that’s where I’d love to just say to that person, “Hey, you seem like you could use just a little bit of time off. Maybe take a day and go do something where you’re not on technology.”

Whitney Bouck: It’s funny, I had a really great aha moment earlier this year where we’d just been through a mass period of crazy work schedule, and I went skiing in Lake Tahoe in Northern California, and I was on this ski slope thinking about wow, you really can’t be on your phone and ski at the same time. Like you’re kind of forced off the grid, and it just makes you appreciate nature, and it was just a wonderful afternoon. I just felt like I got all this refreshment in a few hours. It was so powerful.

Whitney Bouck: So, I don’t know, I think there’s something kind of magical about that, and it takes one who’s maybe experienced it to show one who hasn’t that, hey, do this once in a while, it’s a good thing.

Harry Stebbings: No, I totally love that realization when it comes to skiing, and I have to admit, I struggle to ski without the phone let alone with the phone. [crosstalk 00:07:21] I think that’s a bad thing, but I do want to start this day on a topic that I know we’re both very passionate, and it’s the theme of exec leadership. And I guess starting really from a base level, I’d love to hear, in your mind, what does truly successful exec leadership look like to you?

Whitney Bouck: You know, there are so many books written about this topic, and I’ve come to perhaps my own view on this that I think a great, successful executive leader is somebody who has the following combination of skills. Is an outstanding communicator, a very active listener, an empathetic and vulnerable leader, so that they can really bring people along for the journey. There are so many executives that I feel are so focused on success and the end game, and maybe their minds work faster than most and that’s why they’re in the position they’re in, but they forget to bring everyone else along and make them part of the journey. And so while it’s so important for a successful leader to set a North Star, to really establish that vision and communicate that vision, it’s just as important to make sure that your people are also seeing what that North Star is and why it matters to the company so that they can rally behind you, and rally with you, and be with you in the trenches when times are not as easy as others.

Whitney Bouck: So I feel like all those things, of really connecting with your people, bringing them along and being empathetic and a great communicator is just … those are the things that stand out to me as the most important.

Harry Stebbings: Can I ask, how can you check with your team in terms of their continuous alignment with you towards that North Star? What are the signs that maybe they’re not as aligned as you are, or they’re not in step with you in terms of that progression to the North Star?

Whitney Bouck: Great question. I feel like setting goals that are aligned toward that North Star are really important. And goals are … I know a lot of people whine about having goals and it seems like a pain to have to put them together, but in actuality, they are the way to ensure that … particularly as a company gets bigger, that everyone knows what we’re doing and why we’re doing it, and how it ladders up to the ultimate mission and goal of the company.

Whitney Bouck: So first of all, set great, clear goals and make sure people understand what their work contributes directly toward that North Star. If they don’t feel aligned to the goals of the business, then they’re going to get disengaged, they’re not going to be as passionate about it, so make them feel like their work is really worthwhile, show them why it’s worthwhile.

Whitney Bouck: And then I think the way to tell when things maybe aren’t working is if you’re in tune enough to know the things your people are working on, and the kind of obstacles they’re hitting, then if those are not the things that are directly aligned to the goals we already talked about, then we’ve got a problem. And then we just need to realign and recalibrate. So I think there’s … that’s also part of the great communication, right, it’s got to be two way, and make sure that the dialogue is happening regularly enough to know if things are going off track.

Harry Stebbings: I am totally agreed in terms of remaining on that track. I guess, again, off schedule, so, unfair of me, but I’m always struck when kind of setting goals and really structuring them, how do you get that balance of ambitious, but slightly achievable and still possible, but then also not too easy that they’re hit within a much smaller timeframe. How do you get that right balance in the middle?

Whitney Bouck: Oh, god, it’s so hard. It is really hard, and we have not always gotten it right. I haven’t always gotten it right. It is finding the balance, and that means you’re probably going to stray on either side of the right line. If you make them to aggressive, you risk morale, right? Because you won’t hit the goals, but if you … to your point, if you make them too easy, then there’s no motivation.

Whitney Bouck: So I think you kind of have to triangulate, and at least this is the way I think about it in my head, for example, if I’m trying to figure out the right revenue target for the next year, then I’m going to look at well, if we were just on the same trend line we’re on today, where would that put us? That’s one input. If I look top down at like the really ambitious goal and the desirable top down goal, the aspirational goal we’d like to hit, that’s another point of input. And then there’s sort of the bottoms up, of given the capacity we have, the bandwidth, the other priorities, what do we actually think we can accomplish with the resources we have? And that’s sort of a third input. And then I sort of us those to triangulate and find the right middle ground between them, and that seems to have worked pretty well for me the last several years. So that’s been my latest technique that seems to get me as close to that right balance as I can, which is not to say I’m perfect by any stretch, but it seems like we’re getting better at it.

Harry Stebbings: I mean, it is such a hard question to ask, and then to ask it when it’s not on schedule, I mean, what an incredibly [crosstalk 00:11:29] interview. I do want to ask about the team behind the goals themselves, and especially the exec team who sets them. Because a lot of founders who I meet in the very early stages of company building have a lot of questions when it comes to hiring the exec leadership, and really there’s three that predominantly come up. The first is when is the right time to really start building up my exec team beyond just us the founders? How do you think about the right time?

Whitney Bouck: Well I think, first of all, and I’ll credit actually the founders of HelloSign on this front, part of is recognizing when you as founders have perhaps run out of runway in a certain area of the business. So for example, Joseph and Neil, who were the co-founders of HelloSign, Joseph is really the product visionary, and Neil is the technical visionary, and the two of them did a phenomenal job of building a product that got very early product market fit, high levels of traction and growth, and I think their realization of wanting to bring me in as COO was well, we haven’t skilled an organization at this level before, and we’re growing really fast. So that’s piece one.

Whitney Bouck: And piece two is I think they realized as well that it was the time to start investing in sales and marketing, and that was an area of expertise and experience they didn’t have. So from their point of view, they were looking to bring in a partner, third partner, who brought the exact skills they didn’t have. And I think that was a really, really wise and, I don’t know, timely thing for them to do when they did. And at the time I joined, we were about 40ish employees, and just kind of single digit millions in revenue. So that’s kind of, I think, what a good founder or set of founders need to be thinking about, is when are we starting to hit a bend in the curve on growth that’s going to challenge the capabilities and experience we have where we’d benefit from outside experience and knowledge to pair with our own.

Harry Stebbings: So I totally get that inflection point, and my next subsequent question is, okay, you see that kind of bend in the road and that potential inflection point, but you’re still a small, very fast growing, but still a small startup with 40 people. How does your [inaudible 00:13:20] Joseph of the world convince an incredible, seasoned status exec like you to join a small startup at the time? What would your advice be to founders in terms of bringing on those incredibly talented, experienced execs who’ve seen and done it before?

Whitney Bouck: Well, I think it depends on the exec. I do think that there are some executives who feel they do their best work and are happiest in a very large scaled organization once they get there. And I don’t know that all executives will naturally scale down to startup level. You have to be scrappy, you have to build from scratch, you have to adapt as you go, and you don’t have all the same resources at hand when you’re in a small startup that you do when you’re in a big established company. So not everyone will make that journey.

Whitney Bouck: I think the ones that will, and the ones that can be attracted by the startups like HelloSign, this is certainly true for me, are the ones that show so much promise, and have a product that people clearly resonate with, that there’s some level of proof of revenue and product market fit. That’s like an enticing opportunity for someone like me. I’ve done that several times now, that’s kind of my MO, actually. Join a company that is small, help it grow and scale, go through a successful exit, and then go and do it all over again. And I’ve kind of done that three or four times in my career now, and so that’s what I want to do.

Whitney Bouck: And I think that there’s a myth that the really seasoned executives will only look at already proven, even still early stage companies like the unicorns in the Valley, and I actually think the most seasoned execs that do really well in the scale environment are looking for the pre-nicorns, right, the ones that are not yet the proven unicorn and can be the one to help make it such. And certainly that’s where I’m at.

Whitney Bouck: And the other thing that motivates me is I love looking for the underdog. If I really believe that a company and the product have the wherewithal to take the leadership role, or take the very, very unfair share of the market, that’s exciting too. Because then you get to prove to the world why this thing is better than the thing they thought was the best thing. You know what I mean?

Harry Stebbings: I totally get you, and it’s awesome to hear. I guess the one point that I’d love to expand on and hear your thoughts on, is as you said, sometimes it doesn’t always work when a seasoned exec spins out from the large incumbent, but they think it will do, and they think they want to work in startups. So my question is to you, if you were putting yourself in the shoes of a founder, what questions do you think would reveal whether a seasoned exec who wants to join a startup has that startup fabric and culture within them to be the adaptable and flexible, and kind of ownership centric person that you need to be maybe more in a startup?

Whitney Bouck: I don’t know if I know the exact questions, but I think what I’d be looking for if I were the CEO hiring people and testing for that, I’d be looking for answers to questions like, “Okay, we’re trying to launch this new product. It’s never been launched in our organization before, you have a resource team of two and a budget of X,” which is some small number of dollars, euros, or whatever your currency is, “How are you going to launch and make this as successful as though you had a million dollars to spend?” Answers to that kind of question, or the questions that come back to a question like that are really telling. If somebody just can’t think out of the box about how to do this without a team of 20 and a budget of a million or ten million dollars, then you’ve got the wrong person.

Whitney Bouck: I mean, I think the kinds of things I would want to hear are questions from that individual like, “Okay, if I only have a team of two, can I have them full-time for a month to really plan the most optimal launch? What other successful avenues of launching products have you done in the past that maybe I haven’t seen before? Can we leverage the investor community that we have to go take this … ” I mean, just a whole slew of questions that might uncover, yes, a lack of experience in doing something in a really scrappy way, but might uncover a sense of curiosity and willingness to consider, and creativity. And I think those are the qualities that really matter when you’re trying to look at somebody who’s coming in to a smaller organization.

Harry Stebbings: No, I totally get you and you really see that kind of mental plasticity with that thought process revealing. But I do want to move though one layer down, because that’s going to be advice itself on scaling out and building that initial exec team. But we’ve seen recently the rise of a certain role, and you mentioned it when we spoke before, and you said there’s the new role of the CIO. So talk to me, what is the new role of the CIO?

Whitney Bouck: Well, it’s been a really, really fun thing to watch over the course of the last 10 years, because I think it’s not like CIO is a new role, it’s been around for a long time as we’ve become more and more dependent on technology to run our businesses. But I think if you look pre 10 years ago, the CIO was typically reporting in to the CFO, it was very much a cost center, the whole goal was to run as lean and cost effectively as possible, and choose the technologies that solved the most critical problems. And by the way, the user experience was a total afterthought. And we’ve just seen the role completely shift. And I think largely because of the emergence of SaaS software, and smartphones, and apps. So the whole consumerization of IT phenomenon, where users get to choose what they like, and they know how they like to work on their personal stuff. They bring those expectations to the workplace. And couple that with now the ability of a technologist, or CIO, to be able to try software before they buy, or to listen to the whims and the delights of their users of what tools they like to use the most, that’s a great informant that they didn’t have before.

Whitney Bouck: And so now I feel like the CIO, who often is reporting direct to the CEO and has a seat on the executive team, is a guide toward what will make the user experience best, not only for the employee but for the customer. And if you can make an awesome experience for the customer, then you’re more likely to win their business, and that has a direct impact on revenue and growth. So it’s no more a cost center, but a potential revenue generator and innovator. And that’s just a complete fundamental flip from where we used to be. And as often as CIO stands for chief information officer, I think it also now stands for chief innovation officer. And I think that’s just a very exciting place to be.

Harry Stebbings: Can I ask, with this … I totally agree with you in terms of the excitement around that, but with that kind of very transformational shift into potential revenue driver, almost, how does that change its position within the structure of the C suite, and particularly with the communication pathways that it has, and maybe even its relationship to the COO?

Whitney Bouck: Yeah. So I think it definitely has changed the reporting structure. I think maybe five, six years ago we started to see a shift where CIOs were less and less reporting in to the CFO for the reasons we just talked about, and more frequently reporting to either the COO or direct to the CEO. And I just think that means that CIOs finally sort of have this freedom to impact the world in a way that they couldn’t before. And they do become a strategic driver of the business strategy, and how does … we’re seeing also the emergence of the chief digital or chief transformation officer, which are kind of in a similar vein of looking at how do we take age old processes or ways of doing business, or ways of engaging with customers and flip it on its head? Let’s turn this around and make it all about the experience of the end customer, or partner, or whatever, to attract more business and more engagement.

Whitney Bouck: And that, to me, is just completely different than how we used to look at it, where it’s like okay, well, I’m just going to pick the system that’s the safest, and we’ll train the users on how to use the stuff they hate later. So that has really changed, I think, the perspective of the CIO but also how the rest of the C suite looks at the CIO.

Whitney Bouck: And I think we’ve also seen an emergence where the CIO becomes the strategic business partner to the line of business leaders. So the head of marketing, for example. Marketing has never been more technology centric than it is today, and the marketing leaders need a really strong partner in helping to evaluate, and deploy, and optimize the technology that supports the marketing efforts. So now you’ve got the CIO, instead of locked in a basement somewhere in a data center trying to save money, is now the most strategic partner in helping to figure out how technology becomes a strategic tool and weapon. So completely shifted.

Harry Stebbings: No and listen, I love the shift, and as you said, I couldn’t agree more in terms of the excitement around that shift. I do want to discuss though also the role of the COO, because I had Claire Hughes Johnson on the show before, and we discussed how to differentiate between good and great when it comes to COOs. So I’d love to hear your thoughts. For you, what do you think separates good from great in terms of the CEOs available today?

Whitney Bouck: Well first of all, I think we kind of have to talk about what COO even means, because I’ve found it varies pretty widely from company to company. And in some cases it truly is the O is for operations, right, chief operation officer. I feel like in many companies it truly is about operations. And then you’re talking about corporate planning, and finance, and legal, and the things that really make the business run smoothly under the covers. And in other cases, like mine for example, the COO does have the corporate planning stuff, but also has some or all of the go-to-market functions. In my case, that’s sales, marketing, business development, and customer experience. So the definition matters, right?

Whitney Bouck: So in my case when most of mine is about scale and go-to-market, then I think good to great means something about really looking for opportunities to put processes in place, but god, not for processes sake. Like just enough process to make things more efficient so you can move faster, but not so much that it slows people down. And I think that’s a bit of an art form, to be honest. So I think that’s one element of good versus great.

Whitney Bouck: I think another is really being a great partner with the rest of the business. For me, going back to my partnership with the founders, Joseph and Neil, the three of us really run the business as a partnership. And we recognize in each other the strengths we have. Joseph really looking at product vision and how to take product to market, and Neil with what technology and architecture needs to look like, and how we build great quality product. And for me, it’s how we market, sell, and service our customers. So those three things coming together are pretty magical if we can treat them like, wow, the three of us are better than one plus one plus one. You know, one plus one plus one in this case does not equal three, it equals 10. And so how does a great COO interact with the partners in the business to really try to get a whole that’s greater than the sum of the parts, I guess. It’s not very practical advice, I suppose, but for the way I see it.

Harry Stebbings: No, listen, I love that kind of the whole being more than the sum of its parts. I do want to ask though, you said about implementation of processes there, totally needed in the scaling kind of journey, so to speak. I guess my question to you is, and it’s quite a granular one, in terms of the implementation of a new process, how long do you determine is long enough to really know the effectiveness of the process, and how do you think about whether to stick or twist, so to speak, on a new process when you’re not sure it’s working or not?

Whitney Bouck: Yeah, this is where emergence of agile computing … bear with me for a second, because I swear it’s relevant. Agile development has introduced a totally new model of building software, right. So we used to build in six, nine, 12 month release cycles, release the stuff, and then figure out what was wrong with it, go back and fix it. But if you were waiting for a new feature, or a fix to an important thing, you might have to wait for another six, nine, or 12 months. And of course, with agile development we’ve moved to a model where we iterate, and we move very rapidly, and we release new software every two to three weeks. And it just gives you a constant ability to check in, and you set milestones, or sprints, or whatever along the way, and you can course correct much more quickly. And I think that same methodology is very appropriate for planning and processes. Why wouldn’t we have near term short milestones that are effectively progress bars that let us check in and say, “Is this working? What’s working, what’s not working?” And course correct all along the way.

Whitney Bouck: And it may look like a more crooked path, I guess, when you get it to the end game, but the journey is much more satisfying, and I think you’re much more likely to get to a good end point. So let me give you an example, when we started looking here at HelloSign for … let me back up a step and give you some context, we’re very, very fortunate in that most of our sales are driven from people expressing interest and raising a hand and saying, “I want to talk to someone, I want to see a demo, I want to try the product.” That’s a very luxurious position to be in that will certainly not last forever. So we needed to put in place a process to start doing outbound sales, so reaching out to companies that don’t know who we are, or haven’t yet engaged with us, or haven’t raised a hand, and educating them and helping them understand how they can benefit from what we have to provide them.

Whitney Bouck: That’s a totally different motion and a very different kind of engagement model. And the last thing I would want to do is say, “Oh, well let’s start this tomorrow,” and then a week later go, “Did it work?” This is a months, if not years long, journey of developing that muscle. And so instead, we look at can we identify early successes where maybe it’s just the rate at which an email gets opened, or maybe it’s … from there, how often does an email get responded to? If we had an email responded to, what’s the likelihood someone will pick up the phone if we call? Those are all kind of progressive milestones that indicate we’re on the right path.

Whitney Bouck: And I think you have to do that with any process that’s more than super simple. And I think it lets you kind of figure out if it’s working over the long haul, and you kind of make decisions along the way rather than wait for one big event to tell you if it succeeded or not.

Harry Stebbings: It’s super interesting to hear you say that about the nice position of excessive inbound, but also kind of realizing the need to build outbound. My question to you is often we hear the importance of the need to hire for six months ahead of where you’re at. Given your kind of many incredible experiences in different hyper growth situations, would you agree with that hire for six months ahead? Would you say actually if you’re early stage, you can’t always have the luxury of doing that to your burn rate, or would you say actually it needs to be 12 months? How do you think about that hire for six months ahead?

Whitney Bouck: You know, I actually think it’s more like … let’s talk at what level we’re talking about. I think at the individual contributor level, it’s probably more like three months ahead. Because, exactly, you don’t have the money as a startup to have the luxury to hire that far in advance, you just don’t have the bank account. So when I think of support, for example, customer support or technical support where you have to have staff to answer tickets, and answer phone calls, that’s probably a three month ramped time for someone to come up to speed, so hiring three months in advance is just fine.

Whitney Bouck: I think the same thing is true for a salesperson. Engineers, probably a little closer to six, perhaps, before they really start making full impact. Executives are definitely a six month lead, because it takes a long time to actually put things in place that really start to show success there. And so I think maybe it varies a little bit, depending on the level of role, if that makes sense.

Harry Stebbings: No, it totally makes sense, and it’s actually a brilliant segue, because I did want to ask, in terms of [inaudible 00:27:18] time and really making sure someone’s ready and prepared for success in the organization, when it comes to the COO, I often hear founders say, “I’ve never hired a COO before, and so I’m not really sure what the onboarding process should be, how it should be structured, what it should look like.” How do you think about kind of best practices for onboarding a new COO?

Whitney Bouck: Oh, and Joseph did such an excellent job when I came onboard, so the good news is I have a really good model to draw from. I think the first thing was we were super clear early on what we were going to do to split duties and functions. So we had clarity of role and responsibility. And I think that was so key. If we were just partnering on everything together, and neither one of us really owned anything, I think that would’ve been really difficult.

Whitney Bouck: So clarity first, of roles and responsibilities. And then what Joseph did so well was for the things that he was handing off to me, he did a very thorough documentation of where he saw those functions standing, where he saw things that were working well, where he saw things that weren’t working well, respective on the individuals and the leaders within that organization. What his hopes were for where the organization would go, and was able to walk me through that function by function, which just gave me incredible insight into what he’d been able to accomplish so far and where he saw the need for bringing someone like myself on board.

Whitney Bouck: So I think that was crucial to us getting off on the right foot. And then I think it was my job to pick it up from there, and ensure that I was doing those same things I talked about earlier, about the qualities of a great leader, active listening, being an empathetic leader, starting to establish what is the North Star and how are we going to get there? Went to each of the individuals and managers that are in the functions I took over, asking them what they thought were the right things for that organization to do.

Whitney Bouck: And I think that the last thing I would say there about successful onboarding, is make sure that you don’t make decisions too soon. I asked Joseph when I came onboard for a 60 day decision making reprieve. I am not going to know enough to make good decisions, and if I make decisions without the right insights or information, or whatever, I’m going to make wrong ones. And I don’t want to do that too early. So will you give me the latitude of not making any decisions for the first 60 days? And trust me, it was really hard, because I like to move fast and I like to get stuff done, but I did my damnedest to hold onto that and to really take my time and bounce my thinking off of Joseph and the people that I worked with to try to get a handle on how do I do this job in a way that’s going to keep the company moving in the right direction, not yank us off course, accidentally or willingly, not make any massive shifts that might cause morale issues, or whatever. It was a journey. And I had to take my time doing it, and I think that’s one of the best things that a CEO can do for an onboarding COO, is to let them participate and experience that journey and support them along the way.

Harry Stebbings: I absolutely love that 60 day decision reprieve, and couldn’t agree more with you on that. I do want to ask though, because you said there about the structure and the metrics of what has to put in place, and you’re all kind of moving forward. I guess my question to you is, when I spoke to Claire at Stripe, she said actually her biggest challenge post the onboarding period was keeping up with the insane hiring demands in terms of just numbers and velocity. So would you agree with Claire there, and how do you think about such the difficult balance of the pace of the hiring, yet also the maintenance of that quality high bar with hiring every new candidate?

Whitney Bouck: Oh, it’s so hard, Harry. And especially I think in Silicon Valley when you’re trying to hire engineers, there is such contention for hiring great talent there, it’s really, really difficult. So yes, I totally agree with Claire that that contention of trying to hire quickly, and maintain the high quality bar, and I think there’s a couple things, one is going back to your earlier question of do you need to hire six months in advance, or three months in advance, you’ve got to make sure you have hiring capacity. And that means you’ve got to be thoughtful about how many recruiters you need to have on staff, or how many external agencies you work with, to make sure that you can feed that pipeline for hiring. That is like critical.

Whitney Bouck: And the second thing I would add to that is that there has to be an agreed upon framework up front for how many people you need to have in the interview process. There’s tons of studies that show anything more than like six is a waste of time. So don’t have four repeated on site visits with four interviews every time, right, it’s just exhaustive for no purpose. So have a designed process that you agree to up front with the various hiring managers on how many people are we going to have, what representations do they represent across the organization, what kinds of qualities are we looking for in the role, get alignment on the role definition, and then move as fast as you can.

Whitney Bouck: And the last bit, is make sure there’s no friction in getting to the offer stage. Because in an area of high contention, you can get all the way through the interview process, but if it takes you a week and a half to get an offer out, you’re going to lose the candidate to somebody else. And so I think the whole point of all that is how do we streamline to move very quickly, and all that alignment up front with the cultural elements, and the job requirements, and who’s interviewing is key to making sure we hire the right quality individuals on the other side.

Harry Stebbings: You know, I absolutely love that in terms of streamlining the process. I guess my question too, is you said there about minimizing friction, this is the last one before the quick fire. You said about minimizing friction, where does friction normally come into play? Is it a difference of opinion on the quality of the candidate, is it a difference of opinion on terms, where do you find the barriers to actually producing the offer sit in the process?

Whitney Bouck: I think there are a few. I think one is if you have too any approvers in the mix. And in a small company that’s not usually going to be an issue, and chances are the CEO’s still approving all of the offers. But in a large organization that can certainly be in the way. I honestly find the worst of it is lack of alignment about the level of role, and therefore the skills and experience that are applicable to hire to that role. So to give you kind of a real example for us, we were hiring a ton of engineers … we’re still hiring a ton of engineers, by the way, so all great engineers please apply. But maybe a year or so ago, I think we just weren’t aligned on what the definition of a junior, a mid range, and a senior engineer were. And so we would be hiring for, say, a senior engineer and we’d get somebody in who was a middle engineer, and so they didn’t really qualify and we would rule them out. But it’s like why? They’re a great mid level engineer, why are we not assessing them as a mid level engineer and hiring them that way?

Whitney Bouck: And so once we had that realization, we fixed it, then we were able to move really, really quickly and hire much faster. So it’s all about that alignment on expectations, I think, up front that can really get in the way and slow things down. You just end up in this mire of dialogue and trying to figure out who’s right and who’s wrong on whether this is the right candidate.

Harry Stebbings: Yeah, no, I agree with you there in terms of too many cooks in the kitchen. But I do want to finish though on my favorite, which is Whit’s 60 Second SaaStr. So I say a short statement, and then you give me your immediate thoughts. How does that sound?

Whitney Bouck: All right, I’ll do my best.

Harry Stebbings: Okay, so what motto or quote do you frequently revert back to?

Whitney Bouck: Okay, I have to give you two. One is focus, focus, focus. I just can’t say enough about … and that’s not just for an individual, but for the team. I feel like if you don’t have a deliberate set of priorities, going back to our goal setting conversation, then people will be all over the place, and you have less likelihood of being successful if they’re lacking that North Star, right? And the focus and determination to get there. So that’s one. Make sure you have focus.

Whitney Bouck: And I guess the second one, I’m truly an optimist at heart. I like to say I used to wear rose colored contacts. I don’t wear contacts anymore, I had surgery, but now I wear rose colored glasses. Believe that we can do anything if we put our minds to it. I think when you’re in a startup, you have to have faith. And you haven’t yet proven that you can be a really successful big company, and faith goes a long way. And so I think as a leader, we can inspire faith and belief in the people we work with. And that’s something I just love to do.

Harry Stebbings: What’s the most challenging element of your role with HelloSign today?

Whitney Bouck: I think it’s not different than it was a year or even two years ago. It’s still about scaling and growing and maintaining the high quality bar of product, customer experience, and hiring.

Harry Stebbings: Tell me, what are your strengths and weaknesses? A hard one on self reflection.

Whitney Bouck: My strengths are that I have tremendous energy. I don’t need much sleep, I can go a long day, I can do it for a long time, and I’m an optimist, so I think I bring happiness to people around me. So those are I definitely think of as strengths, but I also have a tremendous ability to focus and get stuff done. I’m kind of a … I guess in Myers Briggs terms, if people know that, I’m an ENFJ, so that means I’m kind of a doer, but I have feeling, and compassion, and empathy along with it. And I obviously have a lot of experience in go-to-market type of stuff, and so I think I bring that expertise to the table. So those are a lot of the strengths I bring.

Whitney Bouck: And I love to help, I really love to mentor people, and bring them along which kind of speaks to why I like to invest and advise with other companies. Sorry, this is a really long answer, Harry.

Whitney Bouck: A weakness is obviously I talk too much. But the second one is that I think I like to take on a whole lot of challenges, and I love new, fresh challenges, so if I’ve been doing the same thing, which you need to do in running a business, by the way, for three years straight, I tend to de-prioritize those things and I have to make myself make sure that those come to the top of the pile.

Harry Stebbings: That is hilarious, and listen, most people don’t have the self awareness to know about the 60 seconds, so I think I rank self awareness in the strength, by far. I do want to ask though, you mentioned the element of kind of mentorship and investing there. In terms of the angel investing, how does investing also change the way maybe you think about your operational role today and how you really act upon it?

Whitney Bouck: Well, it’s funny, I think of an investor role much the way I do as a board member role, and I’m also a board member on a company. It does you shift your mindset, for sure. I think when you’re an operator of day to day, you’re thinking about how do I get the best thing done, how do I get it done fastest? You’re in the weeds a lot of the time. And I think when you’re an investor or a board member, your job is to advise, and to guide, and to be a sounding board, and to be a problem solver, but not to do. And that’s a totally different mindset. And so I think I’ve gotten better as a leader because I’m an investor, advisor, and board member.

Harry Stebbings: No, I totally agree with that in terms of getting better and improving with the different insights that one gets. I do want to finish on the toughest of all, I think, but is my favorite. And is what do you know now that you wish you’d known at the beginning? Now this can be at the beginning of your time with Box, it can be the beginning of your time with HelloSign itself, but at the beginning of dot, dot, dot chosen time, what do you wish you had known at the beginning that you now know?

Whitney Bouck: In a funny way it kind of goes full circle back to the beginning of our conversation, Harry, about that take a break once in a while. I love running hard for weeks, months at a time, but every once in a blue moon, you’ve just got to kind of step back. So I guess I would sum it up to say it’s a marathon, not a sprint. So train, run hard, rest, do it again.

Harry Stebbings: I absolutely love that. I think I could do with taking some of that advice, I have to say, I am actually very young but I look a bit like Benjamin Button. So clearly I need that help. But [crosstalk 00:37:30]-

Whitney Bouck: I don’t buy that for a second.

Harry Stebbings: But I do want to say, Whitney, thank you so much for everything you’ve done with this episode, seriously, I’ve enjoyed it so much, and I’m really–

Whitney Bouck: You are such a wonderful interviewer, thank you so much, this is one of the most fun interviews I’ve ever done.

Harry Stebbings: What can I say, I told you Whit was amazing, and if you’d like to see more from her, you can find her on Twitter @WhitneyBouck, likewise it’d be great to welcome you behind the scenes here at SaaStr on Instagram @HStebbings1996 with two Bs. And as always, I cannot thank you enough for all your support, and I can’t wait to bring you a very, very special episode next week.


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