Transitioning from a Pilot to a Private Equity Associate – Managing Director at Google

Darren and I talk about his career going from a pilot to PE associate to 15 years at McKinsey and now Google. Darren leads a team of 600 at Google. We discuss his advice on how to get to get there and the skills and attitude that will set you apart. We finish with how to find happiness in where you are now and what you need to do to get a job at McKinsey or Google.

Here is the complete transcript of the podcast.

Alex Grodnik: Hi, you’re listening to the Wall Street Oasis Podcast, a podcast about breaking into the world of finance along with interviews with those who have. I’m your host, Alex Grodnik. Today we are speaking with Darren Pleasance. Darren’s the managing director for Google’s global customer acquisitions group. We’ll get into exactly what that means in one second. Let me first tell you that Darren has an MBA from Anderson. He worked at McKinsey for many years. Now he flies his airplane to work at Google. Let’s jump into it.

Darren Pleasance: Pleased to be here. Thanks for inviting me.

Alex Grodnik: Yeah, so you – I met you in business school. You came and gave a presentation, a really incredible presentation in a class I took on innovation. I was just so enamored with your presentation that I had to get you on the podcast. That’s what this is now. I think our listeners would love to hear about your background.

Darren Pleasance: Yeah, happy to share it. Today what I’m doing, and I’ll go backwards and talk about the journey to this point, but today I lead a team at Google called Global Customer Acquisitions, which is essentially responsible for bringing in all new advertisers to Google’s business. We go out and look for companies around the world who don’t yet use Google’s digital marketing products, AdWords and all that. We work with them to help them understand how digital marketing might help them, and work with them then to shift some of their advertising spend to digital, and then help them be successful with that. That’s my job now. I’ve got teams in little over 20 countries around the world. My goal is to work with those teams to help introduce digital advertising to companies everywhere.

Prior to this, I was at McKinsey and Company for about 15 years. I was a partner there leading a bunch of work in our marketing and sales practice, did a lot of work around sales and channel strategy, a lot of work in small and medium business, SMB. Basically, through that experience was able to do a bunch of work both in technology as well as in other industries for whom small and medium businesses were a big part of their business. That’d be banking, credit cards, some sorts of retailers, and so on.

Prior to that, I was working in private equity in a small private equity shop down in Santa Barbara. Nanco Enterprises, it was called. Prior to that, I was a pilot from about – started when I was 13 years old and became a flight instructor, then a charter pilot, and ultimately flew for corporations and wealthy individuals. I flew for John Travolta for a while. I went to Alaska, was a bush pilot flying off of glaciers and other parts of Alaska, and then ultimately landed a job as a corporate jet pilot for a private equity firm in Santa Barbara, which then led into that private equity job that I mentioned a moment ago.

Alex Grodnik: Right, and that’s just an incredibly interesting background. I definitely want to hear more about how you get new businesses to advertise on Google. Let’s start at the beginning there. You were a pilot. You were a pilot instructor. You soloed when you were 16 years old. You took that job being around, I would say wealthy individuals who were involved in private equity, to wiggle your way into a private equity fund. Tell us how you did that.

Darren Pleasance: Yeah, I think that was largely the fact that when we weren’t flying – in general, the way it works for pilots is when you’re not flying then you have time off. I was in my 20s at that time. I was interested in what happened at the private equity firm. The principal, who was the founder of the private equity firm and the person I spent the most time with, was encouraging of me to come into the office if I was interested, and work with the CFO, and begin to understand different parts of the business, and learn some of the skills. In that process, I learned how to build cash flow models, do business valuation work, review purchase contracts. The company also owned quite a bit of commercial real estate. I had the opportunity to start helping to manage some of that. Basically, over the almost five years I was there, I went from an associate just beginning to understand stuff, to actually very active in the business, to where at the end I was probably 20% pilot, 80% private equity associate, whereas at the beginning it was 100% pilot, no private equity activity.

Alex Grodnik: That’s great. That’s an inspiring story. I think a lot of people want to get into private equity. They think they have to go do investment banking or consulting first before you can get into it. You did an entirely different path.

Darren Pleasance: Yeah, I think a lot of it was good attitude, the fact that I was willing to learn. I’m guessing it was as much that, right? I had the opportunity for sure, which came via the flying angle. I had access and exposure to these individuals. Then the fact that I raised my hand and asked to be given the opportunity – they didn’t have to pay me any more to do that. It really just – it was an investment of my own time. That investment ended up paying off substantially. I think it made for a fantastic set of experiences and learnings that I wouldn’t have got otherwise. It absolutely made for more interesting stories. When it came time to apply to business school, I’m sure to some extent my stories stood out from others in that I had had a pretty interesting path to that point in my life, and think it demonstrated a bit of initiative taking, and willingness to enter a world of pretty high ambiguity, and just try to figure it out.

Alex Grodnik: Right. Then what was the thought process – now you’re working 100% of time at this PE firm, what was the thought process of why business school?

Darren Pleasance: A lot of it came down to – I was always this weird anomaly inside the PE firm where I’d be the pilot. All the senior execs that I would fly around would often laugh that I was this pilot who, oh, by the way, could also build a spreadsheet and figure out the value of business. I always felt like this weird anomaly, which is fun, but it also felt like I was not really real. Nothing in my background suggested that I should have been qualified to be doing that because I was a – undergraduate was in mechanical engineering. I had worked at a couple of startups, mostly aviation related, and had done all this flying stuff. I really didn’t have anything that would suggest that this should be a legitimate brand of mine.

I just felt like going to business school would give me something in my background that legitimized some of the stuff that I was learning on the job. What’s interesting is I fully expected to come back to that job. I kept that job while I was in school part-time. I would go to school Monday through Thursday and then spend many Fridays and maybe a part of Saturday up in Santa Barbara, which is basically a large part how I chose UCLA and Anderson was because it was close and I could do that commute.

What was interesting is when I got to Anderson though, of course, that exposed me to a whole world of other opportunities out there that I had never even known of including consulting. I looked at investment banking, a whole bunch of different roles that were pretty new to me. Ultimately, that led me into the consulting path despite having assumed I would go back into that private equity path leaving business school.

Alex Grodnik: Right, so out of school, you went to work for McKinsey. You were there for a long time. Did you think, okay, I’ve got it now? I’m going to go work for McKinsey. I’m going to build my career here, my life here. I’m going to be a partner here, which you did. You thought, this is it, right?

Darren Pleasance: Yeah, I’m going to answer your question in two parts. I’m going to add a question to your question, which is, how did you end up at McKinsey? There is actually an interesting step, and to the extent that some of your listeners are in career change mode or perhaps even in business school, I think this is an important piece of the story. I was actually interviewing – I’d learned about consulting. I thought it sounded exciting, a chance to see the world, a chance to learn new things, a chance to work with Fortune 500 companies, which was something I hadn’t done at that point. I started interviewing. I interviewed with Deloitte, and Accenture, and A.T. Kearney, and all of the firms, including McKinsey. I essentially got dinged by all of them, including McKinsey. In the case of McKinsey, I got to second rounds, but then got dinged.

As luck would have it, Arthur D. Little came in, another consulting firm. There’s a longer story about how this exactly happened. I ended up getting an offer to join Arthur D. Little back in Cambridge, Massachusetts, their headquarters, which I took and then moved to Cambridge. I worked there for two and a half years. It went great, really enjoyed myself. Then McKinsey called again and asked to hear what I was up to. It turns out that apparently I’d done fairly well on the interviews but my background, relative to other candidates they were looking at, really wasn’t at all relevant to what they were looking for despite having thousands of hours of flying time. That didn’t matter much to them. Even the PE work was interesting and intriguing, but not exactly what they were looking for relative to candidates that had perhaps worked in other Fortune 500 companies.

They were checking in to see what I’d done and in that process discovered I was in consulting. I was doing stuff relevant to what they were trying to do at that time. They put me back into the interview process. Through that process I ended up getting an offer to join McKinsey. I subsequently left Arthur D. Little and joined McKinsey and was then there for 15 years, so. It’s an important step in that part of the story to McKinsey that I thought is important to share because it is stressful in school. It’s stressful any time you’re making a career change. For me, at that moment in school, the fact that I didn’t get into McKinsey did feel pretty disappointing. It’s just a few years later that things completely turned around for me.

Then back to your original question. I was at McKinsey – I thought I’d be there for just a couple of years like many people are and move on. Instead, I was there for 15 years and have built a great network, really enjoyed what I did, was doing well at what I did. I built a brand around the topics of sales and channel strategy, around small and medium business, and really wasn’t looking to leave. Then Google approached me. They had been searching for someone to lead a global team mostly focused in the small and medium business segment. They wanted somebody who had some consulting experience since there was a lot of strategy involved as well as sales execution.

Darren Pleasance: If you read the profile of the type of person they were looking to hire, it couldn’t have been more closely matched to the experiences I had over the prior 15 years. It actually worked out perfectly. I ended up deciding that for me, it would be a more interesting life story to have spent 15 years at McKinsey and then X years at Google than to have spent 20 or 25 years doing consulting. That was ultimately what led me to choose to come to Google.

Alex Grodnik: It’s interesting how you say these opportunities came to you. That’s how I found it in my life too. A lot of the opportunities don’t come from where you think they’re going to come. You probably never thought, I’m going to go work at Google. You were happy working not at McKinsey but then these things present themselves. Life has its way of figuring itself out.

Darren Pleasance: I think there’s a bit of serendipity, probably a lot of serendipity that happens in anyone’s career. I think to me is actually – I think it’s nice to remember that. You don’t have to be overly stressed about exactly how your career is going to unfold. I always tell people when I talk about career management. There’s only three things you can control pretty much in your life, certainly in your career but really probably in your life. Focus on those. The rest of stuff just happens. Those three things are skills. You can focus on what skills you build and how you invest your time to get better at certain things. My bias is you should invest in skills that you’re excited to have as opposed to investing skills you think will make you a lot of money or will be impressive to your family or friends.

The second one is relationships. You can invest in getting to know people. You can invest in helping other people in almost every situation. It was relationships that occur to those types of investments that ended up opening doors that I could then step into. Third is the attitude. I find I work with people who are glass half empty types of people. They’re always looking for why something happened to them or what’s bad about the situation. There are people, like I am, which tend to look at pretty much any situation and try to figure out what’s good in it. Many times, that has been what’s resulted in me being given opportunities that might not have otherwise come my way. The good news about all three of those is those are three things that are 100% in your control.

Alex Grodnik: That makes great sense. Thanks for the background piece. I’d love to hear more about your work at Google now.

Darren Pleasance: I lead a team of about 600 Googlers and then over a thousand dedicated vendor reps that sit in call centers around the world. We work closely with our marketing team and our engineering team to sift through the roughly 150 or so million businesses in the world to find the few million or even less sometimes of companies who will become Google customers in that year. Although say a million customers sounds like a lot, out of 150 million, it’s still a very small percentage and kind of a needle in a haystack problem. A lot of the work I’ve been doing has been around how do you take advantage of the massive amounts of data and analytic power and computing power we’ve got, married with the super-talented people we've got who are great at whatever role, whether it’s the sales role, whether it’s the marketing role. How do you marry those in a way that allows us to drive high volume, high quality customer acquisitions, so new customers, in a way that’s very efficient and effective?

In a sense, it taps in to all of what I did in consulting, a lot of analytics. It taps in to what Google is known for and really good at, which is utilizing information in a way to help drive business performance. I believe strongly in the products we sell. Our products are designed to help businesses succeed. It feels good when you help introduce Google AdWords to a company. They start using it. They discover they can basically access the whole world through digital marketing. Through that, grow their business far faster than they thought they could. We have amazing stories especially in the small-medium business phase of someone who might have had a hobby doing something, discovered digital advertising. Through that, converted a hobby into a profession and they are now able to put their kids to college and do things they couldn’t have otherwise done. It’s an inspiring role to be in as well as personally satisfying building on all the things we’ve built on.

Alex Grodnik: In class, you talked about integrating technology into the sales process. That’s been a big piece of what you’ve been tasked with.

Darren Pleasance: It has been, yeah. We call it science to sales. It has been saying, how do you take a sales funnel and look at every piece of it all the way from you’ve increased sales. You could talk about all the lead gen upper funnel awareness building consideration and so on. How do you take that entire end-to-end process and layer in technology to try to make it as efficient and effective as possible? The answer for that differs depending on what types of customers you’re going after. If it’s the head, if you will, the top customers that may be more sales heavy and less marketing heavy and more human engagement heavy as opposed to technology engagement heavy. In the long tail, maybe just the opposite. Much more self-service, much more marketing intensive, much less sales or human intensive.

Stitching that together in a way where technology is basically playing a role in every one of those stages for every one of those sales models has been super challenging but also very rewarding. We’ve had some amazing successes and achieved a lot of what I’d hoped to do when I was in consulting. Now I’m in a position to be able to actually do it with the teams we have around here at Google.

Alex Grodnik: Talk about the difference between being a high up at McKinsey versus being a high up at Google. Do you have more of an ownership mentality on the company side?

Darren Pleasance: Yeah. You [15:45] more decision rights. I’d say there’s a lot of similarities. Consulting is all about influence. You have almost no decision-making power. As a consultant, a lot of your success is driven by your ability to engage with executives across an organization and help convince them on what path they should take. If you’re effective at that, they’d make those decisions and they move forward. It’s not that different even in a company like Google. Almost every large corporation has some degree of matrix where not everything rolls up to one person other than maybe the CEO. Therefore to get anything done at a place, you’ve got to be effective at influencing key stakeholders. Many of whom don’t report to you. I think the skills I built in consulting have played very well in the world of Google. I guess I would call that very similar.

What’s different though is I do have more, I guess two things. I do have more ability to set the agenda and drive what I want to versus what sometimes the client wants to do in the consulting environment. Two though I think is also very important. I have a time horizon that’s different than consulting. Consulting is often three months, that’s a project three, maybe six, whatever, which is often get to an answer. Then you have all the other work that has to get done to land something. I guess in this environment, I enjoy the ability both to help come up with the answer, the recommendation but then see it through in the implementation, which some cases maybe six months, some cases maybe several years. That’s a longitudinal view on stuff to me has been very satisfying.

Alex Grodnik: That makes great sense. You spoke in my innovation class. Google is probably one of the most innovative companies. How do you think about that? What do you attribute it to? How do you innovate in your group?

Darren Pleasance: Reality definitely starts from the top. I mean, if you were to talk to Larry Page and Sergey Brin, the two founders, you would see that from them on down, there’s a huge ethos around innovation, around failure, around an expectation that in process of innovating, failures will occur. That’s actually a perfectly fine thing. I found a much higher appetite here at Google to try things. If they don’t work, declare they don’t work quickly but then move on. You’re not penalized with that type of thing. Part of it is just cultural and acceptance and an expectation around continuing to push limits.

We have a language here around 10x. It’s not good enough just to tune something and make it better. People expect you to think about how would I 10x it? How would I make it 10 times better, not just 10% better? Not everything lends itself to that. It’s a helpful and I think a healthy lens to put on almost any problem of substance, any meaningful area of opportunity. If you take a 10x lens to it, it definitely pushes you to think dramatically differently.

I mean those are probably the two biggest differences, just the overall culture and then the mindset. When you add – you take all of that – that’s more the mental approach to it. Then you add to it amazingly talented group of people. We've got engineers and marketers and sales people and analytic people who all want to drive to the next level of capability or whatever dimension of innovation you’re looking at. It’s not hard to get an engineering team to mobilize behind and you go do something important if they are also equally inspired and believe that really could be game changing if they were to be successful.

Alex Grodnik: In the beginning we talked about your passion for flying in airplanes and behind you, there’s pictures of airplanes. How do you incorporate that passion into your life now?

Darren Pleasance: I’ve been super-fortunate in that sense. It’s very much a part of my life. I live in Bend, Oregon now which was a decision I’d made back when I was at McKinsey. Most people like to tell reasons. I just thought it would be nice to raise kids in a place where they could ride their bikes to school and spend time on a ski mountain, and hike, and bike, and fish, and do all the things that I did growing up.

Since with consulting, I was on the road all the time, four days a week. It didn’t really matter where I live. I optimize for quality lifestyle and quality of life. When I came to Google, that was just part of the conversation with them, was that I was not going to leave Oregon. That was too important to me. However, I did commit that I will spend a lot of time, either in Mountain View or some place else in the world with the teams. I wouldn't be an absentee manager. What that's meant is that I've been on the road probably as much in my Google career as I was in my consulting career. The main difference is that I get to control when I go somewhere, so there's some power and choice.

To your question, I've had my own plane for a lot of years. I put it to good use every week. I fly myself down to work in Mountain View or wherever I'm going typically on Monday, and I fly myself home on Thursday. If it's a long distance flight, I'll fly myself to the closest international airport and catch a flight to Dublin or Singapore, wherever I'm going. That basically keeps me very active in aviation despite the fact that it's no longer the career that I'm pursuing.

Alex Grodnik: I think that's so cool. You talk about passion and balance in life. It's great at your level that you're able to bring those back into the picture. When you were starting off at Mackenzie and for the advice for the listeners that are beginning their careers, they're passionate about something, it's important. They want balance in their life, that's also important. How do you think about getting those things?

Darren Pleasance: I can't share the chart with you just because of the medium here, but I have a point of view. I basically said there is no such thing as balance, which sounds a bit extreme. This epiphany came to me at Mackenzie probably three or four years in where everyone was struggling with work/life balance and everyone was working crazy hours.

There's often weeks where it's 80, maybe even 100 hours a week. Everyone wrestles with those things. It occurred to me that all of us have the same 168 hours in a week. It really comes down to how do you choose to spend those hours, and what does good look like and being really thoughtful and conscious of what good looks like? How much time is spent on sleeping, on eating, on relationships, on things you do for fun?

I broke those 168 hours into those kinds of things, around health, and happiness, and relationships, and work. I kind of put a stake in the ground and said what does great look like? What does a perfect week look like? Then what I use that to do is to guide myself or help calibrate myself when I was off. More often than not, I was not living that perfectly aligned week, which is why I say there's no such thing as balance.

Balance implies a level of stability and consistency. That's just not the real world. I think you're always being pulled in different directions, especially if he has kids or other responsibilities in addition to work. I think the main takeaway that's kept me very well grounded was that happiness line I mentioned in there. That was all about me. What time do I need every week that I find important to regenerate and to rejuvenate my own energy and really stay happy?

A lot of that for me was around flying. I just make sure that I would allocate four or five hours on a weekend and go flying. My wife prefers horses. She would go do horses. We would just find ways to make sure that those things didn't get taken away.

What I found is that often people get into a busy career, and the things that go away first are the things that they love doing themselves, the happiness line I would call it. The other thing that goes away is often sleep and health. They don't go to the gym, they don't sleep as much. That may be okay for weeks on end or even a few months on end if there's something really important. Often people let years go by without any real grounding on the fact that they are, in fact, living a life that's very different from what they would construct if they had drawn that chart that I had talked about.

To me it's about choices. It's making choices on how you spend your time. It's about realizing that moments in time it may be completely fine to be off balance in an unhealthy way, but then know that it's not right and be making corrections back to what's good over time.

I guess the last point I'd make on this theme is I have a friend who says he revisits his career every October 7th, and he asks why every October 7th. I found there were just too many ups and downs over the course of the year and that any one of the downs I was tempted to just quit and move on to something else. Then a few months later it would be an enormous high, and he was thrilled to be doing what he was doing. He found that those ups and downs were consuming a lot of energy that really wasn't very productive.

He said instead what he would is every October 7th he would look backwards and say am I happy I was here for the last 12 months, and do I feel like I grew and I learned and that I'm better off today than I was a year ago? Similarly, am I confident enough about the year ahead that I think I will achieve the kinds of things I would like to over the next year? If the answer to that second question is yes, then he commits to the next year and doesn't entertain any conversation in his own mind around whether he should come or go over the course of that year. I think those have all served me very well in a very challenging, intense kind of lifestyle that pretty much all of us are needing these days.

Alex Grodnik: I think that's a great story. Darren, I'll get you out of here on this. What does someone need to do to prepare themselves to get a job at Google?

Darren Pleasance: We look for several things. I think at the core we look for leadership. This would be true of Mackenzie too, and I think it's probably true of most high-performing organizations. One is evidence of leadership. What have you done in your past and also through the interview process that can demonstrate that you are someone who makes things happen, operates effectively in teams, but is not just reactive but proactive in helping to shape the outcome that's a huge importance on leadership?

We look for GCA, general cognitive ability. You can call it how good a problem solver are you? That's what we used to call it at Mackenzie. We want people who are good at taking ambiguous situations and can structure it in a thoughtful way to take basically complicated and make it simple as possible. Then through that structuring think about how one might go about solving a problem.

Problem-solving skills are definitely important. I guess the one there that tends to knock most people out is to Googling this, and that's probably the least clear, certainly people outside of Google, but there's definitely a cultural fit question that comes here. There's a distinct effort here not to just hire people that look like us. We want a diverse workplace, and we're putting enormous energy into that.

What we want are not people that look like us, but the people that thrive in an ambiguous environment that enjoy that kind of uncertainty that goes with life here at Google that do like working as members of the team and don't feel the need to be the person on top or the person that shines. They're fine celebrating wins as a team as opposed to an individual, kind of a no-ego type of approach to life. I'd say by and large we're pretty successful at that.

If you work with people around Google, they're almost all fun, low-ego, super smart, thrive in ambiguity, love the fact that it's unclear exactly how the world's going to look even in six months here at Google. That's what keeps them going. If describing your attributes or you can hone those kinds of attributes, you're likely to be a good fit for Google.

Alex Grodnik: Darren, this was so much fun talking with you. Thank you very much.

Darren Pleasance: My pleasure. Thanks for inviting me. I'm pleased to do this.

Alex Grodnik: Thanks again. Thanks for listening. If you liked listening to this, you should subscribe. You can find it on iTunes or at WallStreetOasis.com.

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