Riding the Tech Wave with Corey Lambert

Beth Davies, host:    Conventional wisdom tells us that if we want to be successful in our careers, we need a clear goal and a plan. This however, leaves many people worried that they're doomed to fail if they don't have a grand master plan. Well, here's a fact for you. You can build a successful career without a plan. Our guest today is a great example.

Welcome to Career Curves where we talk to people who have interesting careers and explore how they got where they are.

I'm your host, Beth Davies.

Today we're joined by Corey Lambert, who since graduating college in 2006 has held roles at some hot companies including Square, Lyft and now Cloudflare. Corey shares how he found his roles, what he learned about himself, and how this led him to make changes until he landed where he is today. Spoiler alert. He's done all this without a plan.

So happy to have you.

Corey Lambert, guest:  Yeah, I'm excited to be here. I'm a little nervous. I've never had a conversation about my career before, so this should be pretty interesting.

Beth:    I'd like to start with you back at the beginning and if you could tell me some about your childhood: where you grew up, tell me about your family and were there any messages that you were getting as a child about what you should be when you grew up and your career?

Corey:  Sure. So, I'm from Michigan. Midwest boy. I grew up in a relatively small town. Both of my parents were in their jobs for a long time. My mom 28 years...

Beth:    What did she do?

Corey:  She worked for a title insurance company. She was in marketing.

And my dad was an engineer at the power plant in our town. They were both in those same jobs, at the same companies for the whole time they were working.

Beth:    As you were growing up, were there conversations about expectations for you, your life, your career?

Corey:  Well, my mom was very much, "Follow your dreams, do whatever you want to do." And was very supportive of that always. And my dad, while very supportive, was more like you have to put food on the table. So a more practical approach.

Beth:    So dream but be practical about it.

Corey:  Yeah, exactly.

Beth:    In your family, was there a message and an expectation that you would go to college

Corey:  Yeah, there was actually. And I struggled with that. After high school, I don't think I was ready to go to college and my parents kind of pushed me. They were like, "This is the next step. Go to college." Which ultimately was the right choice. But for me it didn't feel like the natural next step at the time.

Beth:    Was that because you just didn't even know what you wanted to do?

Corey:  Exactly. I had no idea. 

Beth:    And so then what did you end up deciding to major in.

Corey:  I was an English major. I figured if I had to spend four years doing anything reading and writing sounded like how I would love to spend that time.

Beth:    Did you have any internships or jobs during college that had an impact on you?

Corey:  I had a pretty cool internship my senior year at NYU. I was a campus consultant for Sports Illustrated, so they would send us out on campus to promote this Sports Illustrated on Campus magazine that was relatively new then. And so we would give out schwag, host video game parties. I very much just enjoyed coming up with sort of these creative concepts, a way to promote the magazine. I was actually kind of shocked that this was someone's job.

Beth:    How did you start planning for your career? What were some of your thoughts as you're coming out of college?

Corey:  So there was no plan. Like, I'm going to be very clear about that. I still think there is no plan.

I ended up graduating a little bit early and so I was sort of forced to make a decision quicker than I thought. So I went home to Michigan and spent a few months roofing houses while I sort of figured it out, which anyone who knows me would think that's insane, right? Like that's not in my skillset whatsoever, but I needed to earn money, so I did that.

And then I decided to move to Chicago. No job. Student loans coming due soon. And I was just like, "I'm going to figure this out."

Beth:    Did you graduate with a lot of debt?

Corey:  I graduated with a fair amount of debt. I was lucky my parents helped some, I had good jobs in college that paid the rent so I wouldn't have to take out even more loans. And I graduated early, which helps save money. But yes, I graduated with a fair amount of debt.

Beth:    And so you get to Chicago and what did you do when you got there?

Corey:  So I actually thought...this is how naive I was as a 21 year old. I went downtown Chicago one afternoon. It was freezing cold with a stack of resumes. Like I was just going to walk into buildings and hand out my resume. Like, that's ridiculous if you think about it now. So in order to get warm, I popped into this theater, the lobby of the Oriental Theater, I think Wicked was playing there at the time. And I saw this woman walk in with just a box of flyers advertising all the shows in town. And I saw her stock all of the little flyer stands in the lobby. So I went up to her because I like theater. I'm like, "This could be cool. I'm sure she makes money doing what she's doing." So I went up to her and I said, "Hey, like who do you work for?"

And she told me, "Broadway in Chicago," this theater production company in Chicago.

And I said, "Oh, do you guys have any openings?"

And she's like, "I don't know. Follow me back to the office."

So I followed her back to her office. I sat in the lobby and her boss came out and was like, "What's all this about?" I told her I was looking for a job. I applied and a week later she's like, "Sure, come work for us." And it was 32 hours a week. It paid next to nothing, but it was a job in Chicago.

Beth:    What did you learn about that work and yourself from that particular job?

Corey:  So I had enjoyed myself. The crew I was working with were young and passionate and funny and smart. But it didn't pay as much. The loans start coming due and you're like, "Wow, I actually have to make some money." And so while I enjoyed that, I started to have to get more practical about how I would spend my future.

Beth:    So what did you do next then after that internship.

Corey:  The woman who had hired me had left the company and so of the promotional interns, they were going to promote me into her role. I saw what she was getting paid and I was like, no, I can't do this. It was just marginally more than what I was making. And then that was gonna sort of be my track if I had stayed.

So I actually went to a job placement service and they quickly found me a temp role, another marketing temp role, that paid a few more dollars an hour. It was with a startup in Chicago called Errand Solutions. I figured I would be there for a couple months and then find something that paid more in a similar role. And then the recession hit and I ended up being there for three and a half years.

Beth:    Had the recession not hit, do you think you would have wanted to stay there or was it a necessity play?

Corey:  Necessity play. Yeah, I mean, again, it was a really great opportunity, but it was small. There wasn't much room for growth in that company. And so I tried to get jobs. A lot of companies were not hiring, especially someone with almost no experience. So in a job that I thought I would stay a few months, I ended up staying in for three and a half years.

Beth:    How did it finally come to an end? Why did it finally come to an end?

Corey:  Sure. So this is actually, I think, a little bit of an interesting story. So I was at home one night. I was watching Youtube and a YouTuber at the time was making a video or had made a video about a Square Card Reader. So it was just this like little, black, rubber prototype. And she was like, "I've been asked to test this out," and I think she like bought a Coke can for herself or something.

And so I was like, "Wow, this, this is amazing." Like you can take payments on your cell phone. This is incredible. And so I looked at the website and they weren't really hiring outside the Bay Area and they had sort of an admin position open. And I was like, you know what, I might as well just like shoot for the moon and try. So, using my English degree, I wrote a cover letter in Haiku and just submitted it. And a week or so later they called and they were like, your cover letter was funny. Like talk to us. Yeah, that kind of got the ball rolling on my career in startups.

Beth:    That was pretty bold to send off a cover letter in Haiku. What was the self-talk going on at the time?

Corey:  I mean, I had absolutely nothing to lose. I had spent three and a half years in a role with a good company. I wasn't miserable, but I knew it was not how I wanted to spend the rest of my life. And so I just figured I'll try something different. I'll just throw a hail Mary pass.

Beth:    Any idea how you landed the job? What was it about you that had them say, "Yes, Corey, we want you."

Corey:  Well, okay, so something actually was happening in parallel. So I was part of this now defunct social media website called DailyBooth, where you just post a picture every day and people can comment on it. And I had a pretty big following. Like I had like 22,000 followers. And so one of the people that I mutually followed had just gotten a job at Square, like after I had watched this YouTube video. And so I messaged her and I was like, "Your company sounds great. Can you put in a good word?" And so I had already had an interview with Square and then she kind of put in a good word and I just so happened to be traveling to San Francisco with the company I was with in Chicago on a business trip.

And so this DailyBooth company, this social media company, had just raised a round money. And so I tweeted, "Just landed at SFO" and their social media person reached out to me and said, "Hey, we're having a party tonight because we just raised this round of funding. Will you come?

And honestly, you guys, I know that this sounds insane, but the person that I interviewed with on the phone at Square was at the party. And so she's like, "Wow, you're in San Francisco. Come to the office tomorrow. Meet Jack. Talk to the team." And, that was it. Like, seriously, I was packing my bags three weeks later.

Beth:    What were you saying to yourself internally to motivate yourself, to give yourself the confidence to step in this and present yourself the way you want it to present yourself?

Corey:  Yeah, so I had been thinking about doing a big move like this for awhile.

One thing that I'd sort of left out of my post-college story is I'd interviewed with Google for a role in Chicago. The role got filled while I was interviewing. And so Google was like, "You were still a good candidate. Would you be interested in moving to Mountain View potentially?" And I said, "Sure, let's try it out." So I came out, I interviewed with Google. As we got toward the offer stage, I decided I wasn't ready to leave Chicago, so I was just like, "Thanks for letting me interview, but I'm not interested."

And so, fast forward, three and a half years later, this opportunity with Square came along and I already knew I was ready to make this move. You know, I had thought a lot about it several years before – the pieces weren't there – and so Square just happened and I knew I was going to do it.

Beth:    Did you move into a marketing position at Square?

Corey:  No, I was on the facilities team, the original like office admin team. There were two of us.

Beth:    So tell me about that. So stepping into a whole different area of the company, how did you learn that? Did you ever even feel like you were in an imposter place? How did you step into that role?

Corey:  There wasn't a ton of learning. As long as you were willing to roll up your sleeves and work hard, you could do this job right. It was stocking the fridge, ordering lunch, getting mail, scheduling conference rooms. Very entry level. Funnily enough, it paid more than my non-entry level job at Errand Solutions. So yeah, there wasn't a whole lot to learn. If you were willing to, to do the work, you could do the job.

Beth:    So it sounds like for you it was really, in this particular case, not about that particular work, but more, "I just want the opportunity. It's a great opportunity, great company. Let me come out. I'll do anything."

Corey:  Right, exactly. Yeah, I was just like, I wanted to do anything to get my foot in the door with this company and Beth, it just so happens that this ended up being what I wanted to do with my life. Like I loved how different every day was. I loved that while I had these like brilliant engineers building these products, my job was to sort of help the company scale from a physical perspective, right? Like make sure everyone had a desk and a chair and a computer. And this was my first taste of that.

Beth:    What you just said is so important because I think a lot of people look at what you first described as sort of the office errand person as not a critical role and two things. One is you actually found out that you had passion about it and you recognize how critical it is. So that it keeps that whole operation running and helps the business scale. So how did you grow your career within Square?

Corey:  So I was in this admin role for six months and again, I loved it. But I think my ambition got the best of me. The company had opened up a new role as an internal testing coordinator. It had never been filled before and it was just something new that they were trying out. And the product manager in charge of this role reached out to me and was like, "Hey, I think you'd be a great fit." It came with a higher salary and more stock options. And so I took it, ignoring the fact that I was super happy doing what I was doing as an Admin. Because an Admin, it doesn't look as good on a resume. I wouldn't say it's less respected, but it's just not as sexy as what I thought this other role would be. And again, the pay and equity. So, yep, I switched even though again, I was very happy doing what I was doing.

Beth:    Did you enjoy this next role?

Corey:  For a time I did. I stayed in it for 18 months. Honestly, it was so challenging because I was in these meetings all day, every day with these engineers and it felt like they were speaking a different language. And so while the role was fun and challenging, without a technical background and without a desire on my part to gain that expertise, there wasn't much room for me to grow. Going into work every day and feeling like you're completely out of your element, it can get pretty exhausting.

Beth:    So you were in this operations role that you love. Now you move into this testing role where you're feeling out of your element. How did you reconcile this? How did you take care of yourself in this moment? What did you do?

Corey:  So first of all, it was hard to even think about leaving Square, right? I had moved across the country. These people sort of felt like my family. When you spend as much time at work as you do when you're at a small startup, the people that you work with are your closest friends. They're the people you go to, your support system. And because I was nowhere near home, that served doubly for me.

And so when I started to actually think that I would leave Square, I had no idea what I was going to do. I wanted to go back into the facilities realm. And again, I think I stayed in the testing role for so long because I was waiting for something to open up back on the office team so I could go back and nothing did in that time.

A colleague of mine at Square had left to go to this little known company called Lyft and they were hiring an office manager and so she reached out. And so I decided to go and do that. And again, I loved Square so much and I believed in it so much. It was just such a hard decision to leave.

Beth:    How did you manage those exit conversations? Because a lot of people end up feeling stuck because they don't want to go back and tell these people that are their friends and that they love and that they're connected to, "Hey, I'm out of here." What did you do? How'd you manage those conversations?

Corey:  You know, I don't think my manager was super surprised. I was constantly asking how I can do better, what I can do differently? I was trying to get out of him how I could make myself feel better in this role. And so I think after a while that got a little bit exhausting for him.

Beth:    If the role is a misfit for you, there probably is no answer that your manager could have given you that was going to change that. Right?

Corey:  Yep.

Beth:    So you tell your manager. Your manager's not surprised. What about your peers? How did you message this with them?

Corey:  I don't think they were super surprised either. And they were certainly bummed, but I was staying in San Francisco so they were happy about that.

Beth:    So the friendships are going to continue anyway.

Corey:  Yup, absolutely.

Beth:    So you move into this little known company called Lyft. Back in office operations. You had mentioned before that office operations / facilities may not have the prestige that testing or something more in engineering or in the product has. What made you decide that you were comfortable going back into an operations role knowing that it didn't have that kind of cache.

Corey:  It took a bit of maturing on my part to just ignore the title and the responsibilities and just do what made me happy.

Lyft was really good for me in a lot of ways. So they were in hyper growth mode. I think I was the 80th employee. I was there for 13 months and they were 400 plus. And so we moved offices several times that year. So I gained a bunch of experience in moving and in construction projects and I got to work with furniture companies, just things that I didn't get to do as much of in my limited time in this role at Square. And so while staying at Square another year would have been much more lucrative than my year at Lyft, this year at Lyft really I think launched my career in facilities.

Beth:    You know, sometimes people have many years at a company, but they have the same one year of experience over and over again. And it sounds like in one year at Lyft you had at least four years of experience.

Corey:  Oh yeah. Yes.

Beth:    Yet you only stayed at Lyft for a year. Why did you decide to go?

Corey:  So I wasn't actively looking. Again, I loved Lyft. I loved the mission. I believed in the company. And they were well funded. They weren't going anywhere. The job felt safe. But I was approached with what I felt was an even better fit. It's a company called Cloudflare and it was smaller than Lyft and as I had mentioned, Lyft had gone from 80 people to 400 plus in the year I was there. And as things gained more structure, I felt a little less creativity, a little less fun in my role. And so I wanted to go back to a smaller company where I felt like I could add more value and things were more ad hoc and I could help create these processes that Lyft was already starting to solidify.

Beth:    Was there anything about Cloudflare that you knew was making it a good culture fit

Corey:  If you walked into the early office, like I walked into my interview and I was just like, "Wow, this company could really use someone like me." Like the office environment was an afterthought. And so I was just like, I can make a big impact very quickly on this company.

Beth:    It's a great reason to make a move, frankly. It's a great reason. So you've been at Cloudflare now for five years. How do you keep the role interesting and challenging and how do you keep yourself motivated in the role now.

Corey:  Cloudflare is on the same sort of fast growth trajectory as Square and Lyft. And I think this time I was just prepared for it. So I've been fortunate to be able to hire my own team, which is important. And the company is still growing very quickly. When I started again, they were less than a hundred people and they only had two offices and now we have more than a dozen around the world. And so I always just have interesting projects to work on and motivation is never hard to find.

Beth:    You've been at Cloudflare now for five years. One of the things we hear a lot from millennials is that it's all about shifting jobs every year to 18 months and you're bucking that trend because you're in this role for five years. Is there any voice in your head that says you're doing something wrong or do you think that that wisdom is wrong? How do you reconcile your five years with this story that gets told about millennials?

Corey:  Honestly, this is just the right fit for me right now. When I was leaving Lyft after only a year, I called up a mentor of mine and I said, "Can I do this?" Like, can you jump from one job to another after one year? And he said to me – and he's a respected venture capitalist in San Francisco and he's held roles at some very prominent companies –and he said to me, "This is absolutely not an issue." And in fact, he was like, you should go to Cloudflare for two years and then you should jump to another company for two years. He sort of had this path drawn out for me. He just sort of knew that this was kind of the way that your career should progress.

And so that had been in my mind as I was approaching the two year mark at Cloudflare and then the lessons from Square, like you always have to follow ambition, like you can just be happy for a time. And so I was just like, I'm still happy here, so I'm going stay. And so again, five years on, I'm still happy, so I'm gonna stick around.

Beth:    You just mentioned that you went to a mentor. Have mentors played a big part in your career as you've been navigating?

Corey:  Yeah. I used the word mentor, but they're more friends. Just people I know I can go and ask these questions and I know that they're gonna give it to me honestly. And that their experience, there's going to be some weight behind their advice.

Beth:    As you've made the moves that you've made in your career, were there times that you felt lost and how did you get through this?

Corey:  Yes, for sure. And I know I've referenced the recession a couple of times. But that really was tough not to feel like I had options. Especially with the weight of student debt crushing down on me. That was just a really tough period of my life. I felt like I worked really hard. I'd gone to a good college. I got good grades. I was like, I checked all the boxes. Why isn't this easier? And it's just kind of a waiting game.

Beth:    When you think about your past, were there opportunities that you didn't take that you look back and regret?

Corey:  I honestly wouldn't use the word regret. There are a lot of "what ifs." Since I've been at Cloudflare, a handful of companies have approached me that have IPO'd in the last few years and every time one of them has a successful IPO, it stings a little bit with "what if". But I definitely haven't regretted not going to any of those companies.

Beth:    I'd like to talk a little bit more about your career in startups because that's a really appealing, sexy place. A lot of people are thinking that that's where they should go, especially if they're coming out of college like you did with debt, that a startup, and if a startup hits, that's the way to get the magic eraser and clear the debt. How much has working in startups helped you address the debt challenge that you were facing?

Corey:  So I'll start off by saying, when I went to Square, I had no idea what equity was. What potential upside there could be if the company went public. I just wanted to go work for Square. I thought it'd be cool to work for a startup and Jack Dorsey and...

Beth:    Cool products.

Corey:  Yeah, exactly. And so as you get into these companies and you learn more and more about equity, you want more of it, right? Like I had mentioned being super happy in this office management role at Square and then realizing I could switch roles and get more equity in this testing coordinator role. It ended up being sort of a bad move for me at Square, but that equity was really life changing. Like the amount change from the office team to the product team was a huge upside for me. And I hate to be motivated by money, but...

Beth:    But there's a certain reality, right? I mean, you graduated from college with a certain amount of debt and you're in San Francisco, an incredibly expensive place to live. And so there's just a reality of what money does.

Corey:  Yeah, exactly. And this just was a nice surprise, I guess for someone who just came out here not knowing anything about it. And then, two of the companies so far that I've worked for have gone public. And so yeah, it's just sort of a nice extra.

Beth:    So you said that you really didn't understand equity and know about equity. What is it that you now understand about it that if somebody else were to say, "Wait, hold on Corey, I'm lost like you were. Help me understand it." What would you tell them about it?

Corey:  Yeah, so if I could go and be 26 year old Corey moving to San Francisco for Square again, I definitely would have had a different conversation around salary versus equity. I definitely would've fought more on the equity side.

Beth:    Essentially what happens in startups, and probably any company, is your compensation package can include not only just your pay, but also equity, which is shares in the company, which from a day to day of paying the bills may not help, but if the company is successful, it's a successful roll of the dice.

Corey:  Yeah. And then absolutely. And I've been lucky, right? All three companies, knock on wood, are doing well. And two of them, like I said, have had successful exits to becoming public companies. But on the flip side of that, I've had friends who have worked for companies that don't exist anymore. And when you go to a startup, you typically take a lower salary because of the potential that the equity brings. And so those friends of mine spent three, four or five years vesting shares that eventually were worth nothing.

Beth:    Yeah, so here they're working super hard at a lower pay on the hope that the shares are going to hit and then they're worth nothing. So it is a gamble and I think to your point, sometimes people think I'm just going to do this startup because they all hit.

Corey:  Right.

Beth:    But they don't.

Corey:  People except for me. I was just like, "I'm going to do this startup cause it's cool." I had no idea that this potential upside existed.

Beth:    In the startups that you've been in, you've had a chance to work with some really distinguished executives, some founders and CEOs. What has that experience been for you and what have you learned working with these luminaries?

Corey:  Sure. So it's been different at each company. Because of my role, a lot of executives don't necessarily take a big interest in construction projects or furniture selection. And so like I said, it's been different at all three companies. Lyft, for example, John and Logan were heavily involved in the design choices for the first base that we built out, so I got to work pretty closely with them. They were in a lot of the design meetings and they weighed in on a lot of the choices we ended up making.

And then pretty similar early on at Cloudflare, although I've been there for so long and I feel like I have Matthew and Michelle's trust and so they're not necessarily as involved in these decisions as they once were. But when I tell my friends, "I was in a meeting with Jack Dorsey today," or whatever, they do think it's pretty neat.

Beth:    You just mentioned almost off the cuff that you had the trust of your senior executives. How do you build that trust?

Corey:  I work hard. I think that they know that I'm always going to make decisions that are the best for the company. And I've done a lot of projects at Cloudflare and I think they've been successful.

Beth:    Does this mean that you haven't made mistakes?

Corey:  Oh no, I've definitely made mistakes. I'm very honest about the mistakes I make. And I'm very honest when I don't know something. Startups are very competitive, right? So I've seen a lot of people, there's a term for it. It's "fake until you make it," I guess. And I'm not good at faking it. So if I don't know something, I'm very open and forward about it and I don't have any problem asking questions. The fact that I'm that open and honest just helps build that level of trust.

Beth:    So you started off your career not knowing what it was that you wanted to do. As you sit here now and think about the years ahead, what is it that you think you want to be doing?

Corey:  So I guess true to form, I have not put a ton of thought into next steps. I know that's silly considering every step of the way I've told you that I had no idea what I was doing next. But yeah, right now I'm happy and content. I'm learning a ton every day. And if that continues, I'll continue to stay the course and if that changes I'll make some changes.

Beth:    So as you talked about what's next, I didn't hear in there that you're still thinking about the financial side. Does that still factor into your thinking about your career and your career moves?

Corey:  Oh, absolutely. I don't mean to harp so much on the impact the recession has had on my career, but I remember this one story my dad told me. Just before the recession hit, a colleague of his retired and took his pension in a lump sum and invested it back in the market and lost most of it and had to go back to work. And I think that has just impacted the way I think about earning and saving and investing, myself. It was such a formative time in my career when I had no money and was so stressed about getting money, that's something that will, I think, stay with me throughout the rest of my career.

Beth:    There's a couple of times that you seem a bit apologetic about the fact that you don't have a plan, but frankly, as fast as the world is moving right now, I think you're a really good example of the fact that being open to the opportunities and open to it is in fact a strategy that works and it doesn't always have to be about having a plan.

A couple of last questions for you.

Corey:  Sure.

Beth:    What would you say is the smartest career move you made, whether intentionally or accidentally?

Corey:  Going to Square, for sure. It was a huge leap. I mean, moving across the country somewhere where you don't know anyone, for a company that could go out of business. But taking that leap was easily the best decision I've ever made career wise.

Beth:    And if you could have one do over, what would it be?

Corey:  Oh gosh. I probably would've stayed at Square a little longer.

Beth:    Why is that?

Corey:  I think because they were growing so fast, if I were a little more patient, I could have made my way back to the office management / facilities realm instead of having to go elsewhere to find that.

Beth:    What's one piece of career advice you wish you could have given to your younger self?

Corey:  Be patient. I think there have been two what I consider to be long periods in my career so far where I felt lost and hopeless. The first being during the recession and sort of the second during the 18 months I was in a role that didn't fit me super well at Square. And so I would just tell myself, "Just be patient. Things change so quickly. Again, stay the course and things will happen."

Beth:    And last question. How do you define success?

Corey:  I think if you would have asked me that five years ago, it'd be much different than the answer I'm about to give you, but I think working with just a diverse group of people on something that I enjoy working on feels like success to me.

Beth:    Great. Corey, thank you so much. I've really enjoyed getting to know you, so thank you for your time.

Corey:  Yeah, thank you so much for having me.

Beth:    A quick epilogue, since my interview with Corey, his company Cloudflare went public on the New York Stock Exchange, and the stock was up 20% in its first day of trading.  That makes Corey 3 for 3, following similar experiences at Square and Lyft.    

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