How to Go from MBA to VP of Operations with Drift’s Will Collins


On the very first official episode of #Operations, host Sean Lane sits down with Will Collins, VP of Operations at Drift. Together they look inward to focus on operations at Drift – Will was employee number 13. So what exactly does it mean to work in ops at a hypergrowth company? You’ll find out in this episode.

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Full Transcript

Sean Lane: All right. Hey everyone, welcome to the very first episode of the newest track of Seeking Wisdom, the operations track. My name is Sean Lane, and I lead our Sales Ops team here at Drift. Now, if you’re a regular listener to Seeking Wisdom, you know that we’ve been expanding. In addition to our original show with DC and DG, we’ve introduced more specific tracks with more hosts, to cover more topics. We’ve got a marketing show, we have a product show called Build With Maggie, we have the show called Exceptions that’s all about really unique B to B brands. They’re all amazing.

Now, we have operations. Yes, you heard me right, operations. Here’s the thing, I’ve got this theory. My theory is that ops teams, and more specifically ops people, we have a branding problem. It’s not that we don’t have an identity, we do. And, it’s certainly not that we don’t have interesting stories to tell, we do. It’s just that historically, we haven’t done a great job of telling them. For every big splashy marketing campaign, or every rip of the sales gong, there’s a whole bunch of work that’s happening behind the scenes, under the hood, behind the curtain, whichever metaphor you want to use. But, when I looked around for other places, other podcasts that told me these types of stories, or tackled these types of topics, I couldn’t find any.

So, on this podcast we’re on a mission to confront that branding problem. We’re going to look under the hood of fast growing companies, to see what it really takes to build a company while going through hyper growth. To do that, we’re going to talk to the people who have been there, done that, so that for those of us who are desperately trying to build companies while in the throes of hyper growth, whether you’re ops or not, we want to give you role models and examples that you can point to and learn from along the way. My job, you can think of me as your tour guide, as we set out on this mission together. I’m going to do my best to ask probing questions, find some smart guests, and point out things that we find are interesting along the way.

What better way to kick things off than looking ourselves in the mirror? To do that I went to Drift’s VP of Operations, Will Collins. Who, by the way, also just so happens to me my boss. Now, Will joined Drift early, as like the 13th employee. One of the things that I always think is interesting is, how people in ops come to be in ops in the first place. Will’s story is no different.

Will Collins: I grew up in finance. I did investment banking originally. I got into venture because I’ve always been a tech nerd to an extent, like kind of. I built computers growing up, I used to, one of my jobs in high school was setting up home wireless networks when DSL was a thing. I’ve been a gamer. I just enjoy tech, and I geek out over systems, and gear, and all that kind of stuff. I realized quickly I didn’t want to be a banker, I got into VC because I thought, “Man, I love tech. I could do this for a living. That’s a great way to marry a passion with day to day.” I loved venture, but what I personally came to the realization of was like, I’d much rather spend my time working with a small team, like becoming an expert in something, and building something, and solving a problem, than being more of a fund manager.

As I was moving my way up in venture, the kinds of problems that I was spending my day thinking about were things like, what kind of return is this for my fund? Is this the right CEO? How am I finding the next deal? When do I need to raise another fund? Those kind of dynamics, and less about a really specific problem that I’m solving for a customer. Just long term passion, like what did I want to spend my time thinking about? It was clear that it was more on the operation side, and less on the investing side.

Sean: Did you find yourself while you were going through all of your diligence, and looking at these companies-

Will: Yeah.

Sean: … Thinking about that?

Will: Yeah.

Sean: Like, envisioning yourself at these companies?

Will: Exactly. One of the things that we did as associates, is we’d do all this work, right? Six months to source the deal, actually get it done, then you’d invest. The beauty of the associate role, is then we’d come up with a 100 day plan. The 100 day plan was like one, maybe it was like we need to find an independent board director. But, then like two, three, and four were all operational. It was like, we really need to figure out what our gross and net churn are by these different divisions. Then, we need to set up a support organization to deal with that. That was like an example of one of the problems that I, operational problems that I would be on the ground solving with a portfolio company. I really enjoyed that.

Then, I would stop and go find the next one. That start and stop for me was painful, and I would do all this work, and get this in a place that it was ready to scale, and I felt excited about it. They’d start to hire people, and then I would leave.

Sean: Right.

Will: That was just not super satisfying for me.

Sean: It’s kind of like the difference of people who are consultants, versus people who work inside the company.

Will: You don’t know how to resolve.

Sean: Right.

Will: Exactly. And-

Sean: But, talk about still a great training ground.

Will: … Oh, I mean working with entrepreneurs, people that are passionate about what they do is amazing. Early stage tech is definitely where I want to be. That kind of ecosystem. Disrupting industries, making better consumer experiences. All of that lined up really, really well. But, the day to day tactical was just not the perfect fit for me.

Sean: And so, Will left the VC world and went to business school to get his MBA. Which, if you have followed our CEO David Cancel at all in the past, or listened to Maggie’s show Build, getting your MBA is typically an immediate disqualifier for working at Drift. Simply put, and you can Google this, I’m not divulging anything new here. DC was on the record as not being a fan of MBA’s. But then in 2016, he wrote a blog post called, “Why I want an MBA to Join my Team at Drift,” where he outlined this amorphous role called Operator in Residence.

I decided to go back and read the blog post, and the job description is a healthy mix of part intimidating, part intriguing, and quite frankly part unappealing. Quote, “Do not apply to this job if you are concerned with work/life balance. Do not apply to this job if you’re afraid to get your hands dirty.” But, of course, there’s a bunch of incredibly appealing parts of the role as well. Will, who is used to picking companies for VC’s, was not about to graduate from business school, and needed to pick a company and a job for himself. And, he did what any good ops person would do, he made a spreadsheet.

Will: I did the original spreadsheet thing, which was like I came up with a list of 600 companies in Boston. I whittled that down to … Basically the two criteria I had were team and market. I wanted really smart people that I really wanted to work with and for, that were trying to do something really, really big. Basically that was it. I whittled it down to like five companies that I was super excited about. I actually, I did that before I found out Drift was hiring. I found out about this job because I had listened to Gary Hart when he was at HubSpot, DG, when he was at HubSpot. He did a podcast called Tech in Boston. I used to listen to that.
Will: He came over, he started Seeking Wisdom. I started listening to Seeking Wisdom before I found out about the job.

Sean: Wow.

Will: It just so happened, I mean luck, and timing are real things. It just so happened that at the time, I had turned down a couple things, I had come out of business school without a job. Which, is not, I wouldn’t recommend that.
Sean: Not normal.

99.8% of my peers had jobs a year before that. It was stressful, but I had been listening to Seeking Wisdom, and that episode popped up.

Sean: Yep.

Will: It sounded like a body guy. Like, it kind of sounded like a body guy.

Sean: It did. One of the bullet points is like, schedule my appointments.

Will: Answer my emails.

Sean: Yeah.

Will: Honestly, I didn’t even read it. I did of course, I saw that bullet point. But, I did not read the job description for what it was. I think thankfully, at least luckily my mindset was, it doesn’t matter.

Sean: Mm-hmm (affirmative).

Will: This company is going to change 50 times, this role is going to change 50 times. What matters is, am I passionate about what they’re trying to do, can I add a lot of value, and am I like aligned with the team? If those three things are true, they’re trying to build something big, even I can’t predict at that point whether or not it’s going to work. But, if I can genuinely say that after two years or whatever time I put into this, and I’m going to learn a ton, and work with people I really want to work with on a problem that I really care about. That is as good as I can possibly get at this point.

Sean: Mm-hmm (affirmative).

Will: The rest are details.

Sean: Am I passionate about what they’re trying to do, can I add a lot of value, and am I aligned with the team? Now, everybody has their own criteria for why they pick the job they pick, or why they keep getting up in the morning to go back to that job. But, Will had his. Now, there was no guarantee that this Operator in Residence thing was going to work out. But, early in his tenure at Drift, Will got thrown into fire, and at different points in time owned everything from sales, to CS, to finance.

Will: When I came in, the way that I thought about it was, we have a really dedicated product team that obviously builds data [inaudible 00:09:04] engineers. They got that. I’m not adding any value there. We got DG, like a full fledged marketing team. Let’s face it, I’m not adding any value there. But, everything else was kind of like, “Will, figure it out.”

Sean: Yeah.

Will: That was great for me, because I got to look at a bunch of different problems, and I had exposure to sales, I had exposure to CS, I had exposure to systems, and CRM, and finance obviously, and legal, and IT, and that kind of stuff. It allowed me to run around, and do a bunch of things, which was great.

Sean: Mm-hmm (affirmative).

Will: The other thing I think was good for the company was, we didn’t have to invest in people at the wrong time. We could wait for that person, we could-

Sean: True.

Will: … Recruit Julie Hogan for a year, we could keep in touch with Jim Kelliher, and when he … The right time came, like add that person without sacrificing the result of the business short term, right?

Sean: Yeah.

Will: I came, overtime, running CS, and thank God for Cara, and Michelle, and all of that crew for putting up with me, and even sales. Kevin, and Danielle, and Brandon, that whole crew. I knew I wasn’t going to be like a functional VP of Sales, of CS. I didn’t have 10 years of scaling a team doing that. Frankly where my strength was, I felt, was numbers, systems, and those kinds of things.

Slowly, at one point I think I had 16 people reporting to me, and I knew that wasn’t sustainable, and nor am I the functional expert. I did my best to put us in a position to succeed, and at least cover the major bases. Then, when we had the right person to help recruit that person, or help get them up to speed, or enable them from an operations perspective as best as I could. But, when those people, and it was clear talking to them they were the right people, absolutely throw everything.

Sean: Yeah. I think all the personnel benefits that you outlined are spot on. But, I think the other either intended or unintended consequence of all of that exposure that you had early was, the fact that you then gained this really tactical understanding and appreciation for the work that those people did, right?

Will: Yes.

Sean: Whereas, I think a VP of Ops who came in, let’s say we hired somebody today for your job, without having the experience, and the exposure that you’ve had over the last few years. I think that it really helps to not only give you context, but also empathy for the gigs that people had. For me personally, I didn’t go into a specifically operational role until I had already done customer facing roles for four years-

Will: Yeah, yeah.

Sean: … On both the post-sale, and the pre-sale side. And, having done those gigs before gave me the appreciation-

Will: Yeah.

Sean: … And also like, I think also it gives you a little bit of just not confidence, but like status or respect from people who are now in those gigs knowing that you’ve been there, done that in their shoes before too.

Will: Right. I couldn’t agree with you more. I think not only does it enable you to have a level of credibility that you wouldn’t have otherwise, but it also makes you just more empathetic. I get having a quota is not easy. It’s very, very hard. It’s easy from the outside to see the gong, and see the music, and look at that and be like, “I could do that.”

Sean: Mm-hmm (affirmative).

Will: never the case, never the case. It’s always more difficult when you’re in the role, sitting down, day to day, making a tough decision. There’s lots of gray area. I think it’s super critical to have some exposure to that, whether it’s a full-time role, or it’s six months in it, or it’s supporting somebody closely, and being on calls or whatever. There’s varying degrees, but I think it should be a requirement.

Sean: I think we’ve started to zero in on a key trait in the ops identity, empathy. Having empathy for your internal customers is just as important as having empathy for your external customers. And, Will’s unique path within Drift set him up to do just that.

Then, his next challenge was to set up the actual operations team itself. He had to make decisions about how it would look, and he landed on this idea of a centralized ops model. Like, the hub of a wheel surfacing a bunch of different spokes.

Will: I think there were two things. One, I think David and Elise’s experience scaling companies to thousands of employees, I think what they learned doing that was these divisions become their own companies.

Sean: Yeah.

Will: Sales gets so big it becomes its own company, with its own culture, and its own norms, and its owns … It just becomes its own entity. CS, the same way. Marketing, the same way. Finance, the same way. The finance is never that big, but like [inaudible 00:13:52], right? These big functional divisions become their own companies. Especially when you have ops there, when you serve the VP of Sales, you’re going to have the opinion of sales.

Sean: Mm-hmm (affirmative).

Will: If you’re in marketing, you serve the VP of Marketing, you’re going to have the opinion of marketing. I think their observation that, that happened, one, it got really hard to coordinate them. And two, I think what they would tell you is, the job of sales became throwing something over to CS. The job of marketing became throwing something over to sales. These big tall walls ended up in friction points for the customer. Some of the people that we find most inspirational from a company perspective, Walmart, Amazon, have frankly taken a different approach. Amazon’s two pizza rule, like how was Walmart able to open 50 franchises when K-Mart was only able to do four? They had a super lean structure data model that they were able to do from like a centralized location, right? That was, I think, David and Elise’s experience.

Will: My experience on the BizOps side was, if you don’t own anything, you become this really weird policeman.

Sean: Mm-hmm (affirmative).

Will: Again, you report to the CEO, or the C-suite, whatever. You run around, you give recommendations. But, ultimately it gets up to the division whether or not they choose to do it. You’re supposed to be this team that bridges gaps, and streamlines process, and all that stuff. But, you can’t actually do it. My experience there was, we need to own it. I think their experience of small autonomous teams, like their preference for that, and my preference for having something and owning it, and streamlining from a central location. The combination of those two is why we ultimately landed where we did.

Sean: Yeah. I think the other added benefit, that at least I’ve seen during my short time here, is the idea that again, you’re breaking down these silos that you’re talking about, right? So, these parts of the organization don’t become their own unique entities. But also, you have an appreciation for the impact that the changes you’re making, or the systems you’re adding, or the process you’re changing. You have an appreciation for the impact that it’s going to have on the other team, right?

Will: Right.

Sean: Whereas, a sales team focusing entirely on its own might not care about, “Hey, we’re going to do this thing. Then, CS will have to deal with it afterwards.”

Will: Right.

Sean: Or, marketing is going to throw stuff over the fence, and sales is going to have to deal with it. But, by having this kind of more comprehensive view I think of the org, we’re able to … Again, I think it just comes back to that idea of like comprehensive understanding, but also empathy for the other teams.

Will: Yeah, and knowing that you can never make a decision, especially when it comes to systems, reporting, information, flow, or process that it’s in a vacuum.

Sean: Yeah.

Will: It just doesn’t happen. But, because our systems are so closely tied today, because we can integrate whatever we want, we can use 50 tools, we can all have our own tool. It’s just, one thing cascades in ways that are hard to predict-

Sean: Yeah.

Will: … And, when you’re selfishly motivated, and you don’t have exposure to those other areas, it’s easy to make those kinds of decisions in a vacuum. When in reality, there are real consequences.
Sean: I think this is a good place to pause for a second, to dig deeper into something that Will is alluding to here. That, things don’t always go the right way. It’s easy to hear all the successes in these stories, but as someone who is here alongside Will every single day, I can tell you, we hit roadblocks, we screw stuff up, and we get stuck every single day.

I think there’s two problems I run into frequently. One is, I mean obviously stubborn and ego, like thinking I have the answer, is one. But, even that aside, I think one problem I run into a lot is not solving the core of an issue. Someone will come with a problem and say like, “Man, it would be great if we did this.” Or, “Why can’t we have this view?” Or whatever, and what it really is, is like a symptom of something else. I’ll do the minimum fix or whatever, but someone will keep coming back, and I’ll start to recognize like there’s four different problems that ultimately reflect something else.

Sean: Mm-hmm (affirmative).

Will: So, getting to a root cause, I’m definitely still learning on how to do that more effectively. Then, the other thing … So, the other thing is, technology is not always the answer.
Sean: Mm-hmm (affirmative).

A lot of, we have a tendency to get excited about tools, and excited about shiny things that can solve all of our problems. But, it tends never to be the only solution. You can always leverage technology, but I think the best thing to do, and I’ll always find myself reverting to this is, start manual, start small, do it-

Sean: Pen and paper.

Will: … And then figure … Literally, like it’s stupid but it’s real. Start with pen and paper, write it down. You know how I came up with the monthly dashboard? I was on it every day writing it on my calendar that DC gave me. I was like, “Hey idiot, put this in a dashboard, and send it out to everybody.”

Sean: Right.

Will: But it-

Sean: You felt the pain point yourself.

Will: … Yeah, it’s true. I think that, that’s something … Those are two things I struggle with. I think simplifying, and coming back to what is the root cause of something. And, if I need to run it by somebody, talk to reps. Man, talk to people on the front lines that are living and breathing it every day. You can sit in front of a spreadsheet or a system all day and think you’ve got some perfectly crafted thing, and it blows up day one, so give feedback on it. I think that’s the quickest way to fix it. If you think you have the right fix, go to somebody with it. Say, “Hey, is this really going to solve your problem, yes or no?”

Sean: Mm-hmm (affirmative).

Will: Work through it that way. I think feedback, getting that sooner and more often is just ultimately the way to get over those humps.

Sean: Before we go, at the end of each show we’re going to ask every guest the same lightning round of questions. Ready? Here we go. Best book you’ve read in the last six months?
Will: Oh boy, best book I’ve read in the last six months. I just finished The Everything Store, that’s an amazing book.

Got it. Favorite part about working in ops?

Will: Just exposure to the whole business, for sure.

Sean: I think that’s going to be a common answer to that one.

Will: Yeah.

Sean: Least favorite part about working in ops?

Will: Oh, it can be tough to predict. Your day can totally get away from you quickly.

Sean: Yeah.

Will: And, when you’re trying to accomplish big rocks you gotta be on your time.

Sean: Someone who impacted you getting the job you have today?

Will: A guy, Peter Barton. I read a book that was called, A Short Life Well Lived.

Sean: Okay.

Will: It was all about, he ended up getting into the cable business with John Malone. He died at 51, and it was all about his life story, and how he basically triangulated and just said like, “I don’t know.” This is actually a good story. When I applied for the job, it was a type form.

Sean: Okay.

Will: I wrote three pages. I kid you not, I wrote three pages. DC responded to me immediately and said, “I think you could be a good fit.” Then, ignored me for a month and a half. A month and a half. I would email him like every single week like, “Hey, I saw this article, I couldn’t agree more with this.” Or like, “Did you see that Intercoms doing this?” Or, whatever. Just like go-

Sean: Mm-hmm (affirmative), you had a modern drip campaign.

Will: … I was down here for another interview, I was driving back to school, and it was 5:00 PM, like a month and a half later. I was like, “This is it. This guys never going to respond to me. I email him like, hey, I’m in town. I come down to see him speak at a Founder Collective event. Heard his life story, and I was convinced, like I just have to work here.” He finally responded, “Let’s get a beer.”

Sean: Wow.

Will: That’s how I ended up meeting with him. Then, I slept on a friends couch, I bought clothes, slept on a friends couch that night, met Elise the next morning, and the rest was history.

Sean: Damn.

Will: But, I think ’cause I read that book. I read that book and he was … Peter said, “I went into that meeting with John Malone,” and he had offers at Cisco, and like amazing companies. But he was like, “I just, I learned about that guy and his history, and what he was all about. I just talked to him, and I knew that was somebody I would work for.” I had a similar moment to that.

Sean: Wow.

Will: That’s ultimately how I had the confidence to make the decision.

Sean: That’s amazing. A Short Life Well Lived?

Will: Yeah, a great book.

Sean: All right, I gotta read that. Then last one, one piece of advice for someone who wants to have your job some day?

Will: I would say, I don’t know, this is stupid. Just put in the time.

Sean: Yeah.

Will: It’s easy to get, whether you’re doing sales ops, or you’re doing CS ops, or you’re doing marketing ops today. Even if you’re functional in one of those divisions, get comfortable with numbers, and do your best to learn how other parts of the organization work. I think the benefit I had of being in finance and in venture was I had some of that exposure. If I didn’t have that background, I would … If I were in sales ops, I would be doing CS things, I would be doing marketing ops things, I would be learning how they report their metrics, and how they think about their business, and forecasting, and those kinds of things. Because, it’s going to be super critical, and you’re touching it whether you know it or not. The more you get comfort with how the other divisions work, the better you’re going to be, to be in this kind of position.

Sean: Awesome. Will Collins, VP of Operations at Drift. Thank you very much, appreciate it.

Will: Thanks for having me.

Sean: This was great.

We did it. That’s a wrap on our very first episode of the operations track of Seeking Wisdom. Thanks to all of you for listening, and thanks very much to Will for being our first guest. Before we go, I’ve got two quick asks for all of you. First, in order for me to be an effective tour guide and make the most of this show, I want to hear from you. I know the Seeking Wisdom community isn’t shy, so send me your feedback. The stuff you want to learn about, the people you want to hear from, topics you want us to cover. You can email me at Tweet at me, message me on LinkedIn, whatever.

Second ask, if you’re a regular Seeking Wisdom listener, you know what’s coming. We need you to show us your support for the show, and help me show DC and DG that this ops track deserves a spot by leaving us a six star review on Apple Podcast. Six star reviews only, help us out. All right, I think that’s it. I am out of here, we’ll see you next time.