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

Shawn Lane: All right. Hey everyone, welcome to the very first episode of the newest track of Seeking Wisdom: The operations track. My name is Shawn 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 this show called Exceptions, it's all about really unique B2B brands. They're all amazing. And 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 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. And 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 throws of hyper- growth, whether you're in ops or not, we want to give you role models and examples that you can point to and learn from along the way. So, my job, you could 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. And what better way to kick things off, then 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 be my boss. Now Will joined Drift early as like the 13th employee. And one of the things that I always think is interesting is how people in ops come to be in ops in the first place and 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 like a tech nerd to an extent, like I built computers growing up. One of my jobs in high school was setting up home wireless networks when like 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. And 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 like a great way to marry passion with day to day. And 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 like more of a fund manager. And 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 kinds of dynamics and less about like a really specific problem that I'm solving for a customer and just long- term passion. Like what did I want to spend my time thinking about? It was clear that it was more on the operations side and less on the investing side.

Shawn Lane: Did you find yourself while you were going through all of your diligence and looking at these companies, thinking about that? And visiting yourself at these companies?

Will Collins: Yeah, exactly. So one of the things that we did as associates is we'd do all this work, right? Six months to like source the deal, actually get it done, then you'd invest. And the beauty of like the associate role is then we'd come up with a hundred day plan. And the hundred 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. And it was like, we really need to figure out like what our gross and net churn are by these different divisions and then we need to set up a support organization to deal with that. And that was like an example of one of the operational problems that I would be on the ground solving with a portfolio company. And I really enjoyed that. And then I would like stop and go find the next one. And so that start and stop for me was painful and I like would do all this work and get this in a place that was like, ready to scale and I felt excited about it. They'd start to hire people and then I would like leave. And that was just not super satisfying for me.

Shawn Lane: It's kind of like the difference of people who are consultants versus people who work inside the company. Right?

Will Collins: You don't own a result. Exactly.

Shawn Lane: It's still a great training ground.

Will Collins: 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, like all of that lined up really, really well, but the day- to- day tactical was just not the perfect fit for me.

Shawn Lane: 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 MBAs. 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. So 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. So Will, who was used to picking companies for VCs was now 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 Collins: I did the original spreadsheet thing, which was like, I came up with 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. Like basically that was it. And 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. So I found out about this job because I had listened to Gearhart 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. He came over, he started Seeking Wisdom, I started listening to Seeking Wisdom before I found out about the job. It just so happened... I mean, luck and timing are real things. It just so happened that at the time, like I had turned down a couple of things, I'd come out of business school without a job, which is not, I wouldn't recommend that.

Shawn Lane: Not normal.

Will Collins: 99. 8% of my peers had jobs a year before that. So it was stressful, but I had been listening to Seeking Wisdom and that episode popped up and it sounded like a body guy. It sounded like a body guy.

Shawn Lane: Like one of the bullet points is like," Schedule my appointments."

Will Collins: Answer my emails. And honestly, I didn't even read it. Like I did, of course, I saw that bullet point, but like I did not read the job description for what it was. And I think, thankfully at least luckily my mindset was, it doesn't matter. 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? And 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. Like that is as good as I could possibly get at this point. And the rest are details.

Shawn Lane: 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 in the fire and at different points in time, owned everything from sales to CS to finance.

Will Collins: When I came in, the way that I thought about it was we have a really dedicated product team. Obviously both Dave and Elias are full stack engineers. Like they got that, like I'm not adding any value there. We got DG like a full fledged marketing team and let's face it, I'm not adding any value there, but like everything else was kind of like," Will, figure it out." And 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. So it allowed me to run around and do a bunch of things, which was great. 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 recruit Julie Hogan for a year. We could keep in touch with Jim Callowher and when the right time came, like add that person without sacrificing like the result of the business short term. Right? So, over time running CS and thank God for like Kara 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. And frankly like where my strength was, I felt was numbers, systems and those kinds of things. So slowly, like at one point I think I had 16 people reporting to me and I knew like that wasn't sustainable and nor am I like the functional expert, so I did my best to put us in a position to succeed and at least like cover the major bases. And 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 I could. But when those people came and it was clear talking to them, they were the right people, absolutely throw everything.

Shawn Lane: 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 like really tactical understanding and appreciation for the work that those people did. Right? Whereas I think a VP of Ops who came in let's say we hire 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. Like for me personally, I didn't go into a specifically operational role until I had already done customer facing roles for four years on both the post- sale and pre- sale side. And having done those gigs before gave me the appreciation. And I think also it gives you a little 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 Collins: 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. Like I get having a quota is not easy. It's very, very hard and it's easy from the outside to see the gong and see the music and like look at that and be like," I could do that." 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.

Shawn Lane: So, 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. So 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 servicing a bunch of different spokes.

Will Collins: I think there were two things. One, I think David and Elias' experience scaling companies to thousands of employees, I think what would they learned doing that was these divisions become their own companies. Sales gets so big, it becomes its own company with its own culture and its own norms and its own... 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 product, right? These big functional divisions become their own companies. And especially when you have ops there, when you serve the VP of Sales, like you're going to have the opinion of sales. If you're in marketing, you serve the VP of Marketing, you're going to have the opinion of marketing. So, 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. And these big tall walls ended up in friction points for the customer. And 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 Kmart was only able to do four? They had a super lean structured data model that they were to do from like a centralized location. Right? So that was, I think David and Elias' experience. My experience on the biz ops side was if you don't own anything, you become this like really weird policemen. Again, you report to the CEO or the C- suite whatever, and you run around, you give recommendations, but ultimately it's up to the division, whether or not they choose to do it. And you're supposed to be this team that like bridges gaps and streamlines process and all that stuff, but you can't actually do it. And so my experience there was we need to own it. And so 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.

Shawn Lane: 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, 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. Whereas a sales team focusing highly on its own might not care about like," Hey, we're going to do this thing. And then like CS will have to deal with it afterwards." Our 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 Collins: Yeah. And knowing that you can never make a decision, especially when it comes to systems, reporting, information flow or process that's in a vacuum. 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. 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.

Shawn Lane: 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.

Will Collins: 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 like the core of an issue. So 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. And so I'll do the minimum, like 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. So getting to like a root cause I'm definitely still learning on how to do that more effectively. And then the other thing is technology like is not always the answer. We have a tendency to get excited about tools and excited about shiny things that can solve all 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 always find myself like reverting to this is start manual, start small, do it-

Shawn Lane: Pen and paper.

Will Collins: 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 a monthly dashboard? I was on it every day, writing it on my calendar that DC gave me and I was like," Hey idiot, put this in the dashboard and send it out to everybody." But...

Shawn Lane: You felt the pinpoint yourself?

Will Collins: Yeah, it's true. So I think that those are two things I struggle with. And I think simplifying and coming back to like, what is the root cause of something? And if I need to run it by somebody, talk to reps, like 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 get feedback on it. I think that's the quickest way to fix it. And 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?" Work through it that way. Like I think feedback getting that sooner or more often, it's just like ultimately the way to get over those humps.

Shawn Lane: 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 Collins: Oh boy. Best book I've read in the last six months. I just finished The Everything Store. That's an amazing book.

Shawn Lane: Got it. Favorite part about working in ops?

Will Collins: Just exposure to the whole business.

Shawn Lane: For sure. I think that's going to be a common answer to that one. The least favorite part about working in ops?

Will Collins: It can be tough to predict. Your day can totally get away from you quickly. And when you're trying to accomplish big rocks, you got to be on your time.

Shawn Lane: Someone who impacted you getting the job you have today.

Will Collins: A guy Peter Barton. So I read a book that was called A Short Life Well Lived and it was all about, he ended up getting into the cable business with John Malone and he died at 51 and it was all about his life story and how he basically like triangulated and just said like," I don't know." This is actually a good story. So when I applied for the job, it was a Typeform. And 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." And 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 Intercom's is doing this?" Or whatever, just [ crosstalk 00:21: 11 ]

Shawn Lane: ...campaign.

Will Collins: And I was down here for another interview. I was driving back to school and it was 5: 00 PM. Like a month later, I'm like," This is it. Like this guy's never going to respond to me." I emailed him like," Hey, I'm in town." I had come down to see him speak at a founder collective event, heard his life story. And I was like convinced I just have to work here. And he finally responded," Let's get a beer." So like, that's how I ended up meeting with him. And then I slept on a friend's couch. I bought clothes, slept on a friend's couch that night, met Elias the next morning and like the rest is history. But I think because I read that book, I read that book and Peter said," I went into that meeting with John Malone..." And he had offers at Cisco and like amazing companies. But he's like," I learned about that guy and his history and what he was all about and like, I just talked to him and I knew that was somebody I'd worked for." Like, I had a similar moment to that. And that's ultimately like how I had the confidence to make the decision.

Shawn Lane: That's amazing. A Short Life Well Lived?

Will Collins: Yeah. Great book.

Shawn Lane: I've got to read that. And then last one, one piece of advice for someone who wants to have your job someday.

Will Collins: I would say like, I don't know, this is stupid, but just like put in the time. 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 like get comfortable with numbers and do your best to like 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. And if I didn't have that background, if I were in sales ops, like 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. And the more you get comfort with how the other divisions work, the better you're going to be in this kind of position.

Shawn Lane: Awesome. Will Collins, VP of Operations at Drift. Thank you very much. Appreciate it.

Will Collins: Thanks for having me. This was great.

Shawn Lane: 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 slane @ drift. com, 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 podcasts. 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.