36 min read

Episode 7: Strategic leadership

How to strategically approach your career growth like, well, an ops person.
Episode 7: Strategic leadership

Operations means a lot of different things to different people, and nowhere is this more true than the COO role. I don't think I've ever met two COOs with similar backgrounds or scopes of responsibilities.

"You manage what teams?"
"You have what kind of background?"

Every leader brings their own skills and style to the role. And a lot of the company's needs are defined by the strengths and priorities of its CEO. This makes it a really interesting role, but also challenging to get insight into.

We already talked to one COO about her path to the C-suite on the podcast. Today, we're hearing a different perspective from another experienced leader.

What makes a great COO? How can a mid-level ops pro identify their skill gaps and fill them from their current role? And how do you leverage your existing network to find your next role?

We're digging into these questions and a lot more in this episode!

About Our Guest

Our guest is Barrett Brooks, COO of Good Coffee.

Barrett is an experienced operations leader who started his career in customer success and marketing before taking on the COO role at ConvertKit, a famously remote company in the email marketing space.

He retired from that role last fall and embarked on a rather public job search for his next career move, which led him to his new role as COO of Good Coffee.

Barrett has approached his whole career in such a strategic way—from the roles he’s taken to the skills and capacities that he’s built. I know his approach is one that all of us ops people will appreciate and learn a lot from.

About this Episode

In this episode, we chat about:

  • How Barrett has strategically grown his career to keep himself challenged at every stage
  • Why he left a famously remote company to start commuting again
  • The upsides and downsides of bootstrapping a team through huge growth
  • How the COO role is shaped by your CEO's background - and why Barrett ended up managing engineering at ConvertKit 👀
  • How to grow your career in operations by building a skills matrix and leveraging the access you have in your current role
  • The role of communities in building your career

... and so much more!

Listen Now

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Don't forget to join the Opsy community!
If you are an operations pro working in tech, or just want to learn more about operations, we'd love to meet you. Join our community.

Show Notes

Stay in Touch



Caro Griffin 0:33
In this episode, we're talking to operations leader, Barrett Brooks. Barrett built his operational skills in customer success and marketing before taking on the COO role at ConvertKit, a famously remote company in the email marketing space.

He retired from that role last fall and that's when I came across him. He embarked on a rather public job search for his next career move, which is something that I don't think we see a lot of folks do—especially non-technical people like all of us in operations. It was through this process that he found his current role as COO at Good Coffee.

Barrett has approached his whole career in such a strategic way, from the roles he's taken to the skills and capacities that he's built. I know his approach is one that all of us Opsy folks will appreciate and learn a lot from.

So let's dive in…

Caro 1:13
Alright! Well, thank you again for joining us today, Barrett. Really excited to dive into your kind of career path and all your thoughts about ops.

Barrett Brooks 1:20
Yeah, thanks for having me.

Caro 1:22
So, let's just start at the beginning. Tell us a little bit about your career path so far and how you got into operations.

Barrett 1:28
How I got into operations... All right. Well, I'll go back to the beginning of my career. I studied accounting and finance, double majors, in college and I had a certificate in organizational leadership and came out and wanted to be a Management Consultant, I thought. I did that for just under a year before I realized that it was mostly one big political game that I didn't want to be the winner of, and so I got out of that. I started my first company actually doing kind of career coaching and consulting for young professionals who wanted to transition to more meaningful careers than Fortune 500 pathways. That company failed, and I learned a ton in the process and that kind of set me on my path to where I am today. 

So, I went to work leading customer success and then marketing and growth at a company called Fizzle, where we provided online education for people that we now know as creators. At the time, we didn't really have a word for it, but people starting small online businesses around one of the things that they love in life, or are a set of expertise that they have.

Then I moved on from Fizzle to go to ConvertKit, which is an email marketing platform also serving creators—it's really grown into of a full marketing platform over time—and I was there for 5 years. I started off leading marketing and then, about a year and a half in, switched over to COO. I was our first COO there and did that for about three and a half years, from three and a half million in revenue to about 28 and a half million in Revenue at that time. 

And then, from there, I kind of took a career hiatus over the past six months. I was just very tired—leading through the pandemic was exhausting, I had been in my role for a while through a pretty hard stage of growth. And the company were just entering a different phase of, kind of, settling into its stage of scale and I was looking for something else. 

So, I spent some time doing a lot of writing, especially focused on climate tech and that whole ecosystem, which is something I'm still doing today. [Those are] long-form essays about climate tech companies, kind of breaking them down, looking at their business models and exploring that side of things. But I also have a full-time job that I started not too long ago as COO of a company called Good Coffee and we have five retail locations in and around Portland, Oregon and then we have a decent sized wholesale business and a growing e-commerce business. All of which I'll be overseeing in my new role.

Caro 3:42
Wow, so a pretty different company, or product then - going from email marketing to coffee, and like a physical good. So excited to dig into that.. but, first, I think we have a lot of people in the Opsy community who kind of think of themselves as having fallen into operations but you come from a pretty traditional background with accounting but then I heard you kind of slip in there that you started in marketing. I'm interested to hear, how did you get from accounting to marketing? I mean that's such an interesting and valuable skill set, I would imagine, for a COO, especially at an email marketing company.

Barrett 4:10
Yes, well, I can say that, while I studied accounting and finance and I was decent at it, I absolutely hated it. My grades weren't always the best, except for when I actually applied myself, and that was less often than some of my classmates, just because it wasn't interesting to me. It felt like a bunch of made-up rules about how the world is supposed to work created by humans. And I like human interaction, human psychology, just like the fundamental baseline for everything, of all of our kind of interactions and how we operate as people. I felt like marketing really got at the heart of that, and so marketing was interesting to me because it could be numbers driven, it could be creative, it could be brand, it could be conversion optimization... It was this like wide range of things that gave me so much more of a canvas to paint on. 

And, for me, at least, early career ops roles were just not where I felt like I could best use my skills. I felt like I could be much more of a revenue driver through marketing early in my career and then, as I got more senior and I got more experience across functions of companies, it actually made me more qualified to take on an even larger operations role later, when that gave me an even wider canvas to play with across the company. 

So, yeah, I did a bit of marketing and then got into ops, but I do feel like that kind of background in accounting and finance made me capable in a way that maybe a traditional marketing background type person might not be as comfortable in a COO-type role.

Caro 5:38
Oh my God, I'm so glad I asked that question because that's really interesting. I love how strategic you were about... you know, early career ops, that's not where I can make the impact, let's do marketing and then pivot. 

So, you ended up in the COO role at ConvertKit. What brought that change on? That seems like kind of a jump, but I imagine you had started taking on some of those operational things…

Barrett 5:54
I had, yeah. So, from the early days, Nathan Barry, who is the founder of ConvertKit, and I were friends for years before I joined the company. We had kind of been in a mastermind group, where the two of us and several other entrepreneurs met weekly, for years, talking about our businesses, our problems, what we were trying to achieve through our businesses... and, so, I'd always kind of been a peer mentor to Nathan, as he had been for me. And, so, I was able to step into the company with a lot of background and just a lot of knowledge of what went on there, even though I had never been working at the company to that point. 

I felt like, from early days, he kind of leaned on me, and we leaned on each other, to help define the mission, vision, and values, and like really put words to the belief system he had been instilling in the company early on. We talked about the brand strategy, who we were going to be, setting the vision and strategy. So, even when it wasn't my job, I was doing some of the things, and partnering on some of the things, that would end up being my job later. That kind of laid the groundwork but, to get to the heart of your question, the impetus for the change was that I was ready to grow and I went out looking for new opportunities.

A mentor of mine offered me a job to go to work for him and move to New York and I actually took it. I let Nathan know and we ended up having a conversation about me having an expanded role, playing a role across the entire businesses as COO. That ended up being enough of an incentive to stick around for several more years, almost almost 4 more years after that.

Caro 7:24
Wow, I love that you stuck around so long afterwards, that it really was, it sounds like, the right opportunity and not just like a Band-Aid for a few more months.

Barrett 7:31
Yeah. Yeah, totally. 

Caro 7:34
Yeah, you can tell you really partnered on that.

Well, you gave me the perfect opening to ask, because you brought up Nathan... I remember seeing on Twitter you talking about how the two of you worked on your relationship like it was a marriage. What did that look like in practice? 

Barrett 7:46
A lot like therapy at times, honestly. [Laughs] One of our secret weapons for our executive team was we worked with a great coaching company called Reboot, founded by a guy named Jerry Colonna. For anyone who wants to have a very high career trajectory, I would definitely recommend his book by the same name of Reboot. We hired them to come in and do executive coaching with each of our execs across the team. We spent about $12,000 a month on coaching for our executive team because we found it to be a foundational practice, both individually and then in groups at times when they're needed to be conflict resolved.

Nathan and I both did individual coaching, which is like business counseling and, honestly, a lot of times focuses on our emotional responses to the facts of business. And then, at times, we would do series of joint coaching where we would get together and say, "Look, we have this fundamental difference that we're working through right now. Let's get into it." It really gave us... there's this kind of attachment theory of relationships, especially with people we love and that we rely on for our sense of self-worth, our sense of belonging, our sense of well-being, and, in those relationships, we have conflict patterns. 

And so, much like a marriage, I think, business partnerships can very much have those conflict patterns. They are attachments. You have financial interests that are inevitably tied to one another, you have emotional experiences day in and day out together. So, we very much approached it in a similar fashion. It's not the same to counseling, I wouldn't say, outside of work. But it was a very similar process, in terms of identifying our patterns, working through those, and developing tools for addressing them, without needing outside help over time. So, that was one of our big tools. 

And then, overtime, we just got better and better at leaning into the discomfort of saying like, "Hey, here's what I'm feeling right now. I'm feeling super angry and frustrated in this conversation. I just need to air that out so that we can get into, like, the meat of the thing." Some of those practices and the ability to hit pause long enough to verbalize the thing that might have been going on in our bodies that we might have been feeling, just about the way a conversation was going, allowed us to address the surface level thing and then say, "Okay, understood. Now, let's go talk about the thing that was causing that." And that ended up being really productive over time.

Caro 9:57
Yeah, absolutely. You talk about coaching so much [like] the way I thought about it. After I started doing it for a little bit in my last role, I was like, "Oh, this really is like therapy." Sometimes you hit that button where you're like, okay, I'll save this for actual therapy, but this is really helpful... I think the best executive teams I've been on are ones where I can be like, "Okay, I'm getting really worked up right now and I just need a minute, but I'm going to keep going..." When you can name that, it goes so much further to build that relationship. So, yeah, it sounds like the ConvertKit executive team, in particular, really invested in that, which is so great to see. It's a big line item on a bootstrap budget. 

Barrett 10:32
We had a very strong perspective that... I don't think work should or can fix people. I think people have to fix themselves, to the degree that they want to. And there are very very strong crossovers between trauma attachments in our lives, emotions we experience in our lives outside of work, all of that stuff shows up at work. And you might not talk about it in the same depth, or in the same way that you would with someone that you were in love with or in partnership with outside of work, but you do have to be able to acknowledge it, see it, address it, and work with it at work, because the same exact emotions will show up in both places for similar reasons or triggers. And, if you're not working on that, and, like you said, I thought you made a great point... Identifying it, maybe in coaching, and sometimes [there's a] bridge like, "Okay, I got to go talk in counseling about that." But the learnings crossover entirely. 

There are things I learned at work that I apply to my marriage now, and there are plenty of things I learned in marriage counseling, which my wife and I have done since the day we got married, that apply in work. And, so, I think it goes both ways and they're both really healthy practices.

Caro 11:36
Yeah, of course. Obviously, y'all had a very close relationship as you worked together in the COO role. What did you find that you like most about being in that role?

Barrett 11:48
I think the number one thing I loved was the breadth. Of all the functions in the company—we had engineering, product, operations, marketing, and customer success. [Those] were kind of the five core functions at ConvertKit, and everything but Product reported in to me. So I got to lead engineering, marketing, customer success, ops, and data, actually, which was separate from ops. And, so, on any given day, I might be talking about everything from challenges building out a feature that we're supposed to deliver for the product team, to conversion optimization and ad campaigns, to how to get more efficient in our outsourced customer service function, to, like, our data infrastructure. All of that could just be literally one day. 

I found that really stretched my mind, it caused me to have to grow a lot to be able to serve all of those different functions. I learned a lot about things like technical infrastructure behind the scenes that allowed the app to run and that allowed us to serve our customers. I just thrive on that variety, basically, and, I think, being able to jump into anything. The challenge of needing to be well informed enough to be productive in a conversation, but also humble enough to be able to say like, "I don't get this. Can you slow down and explain it to me so that I can be useful here?" Really gave me this great balance of like diving in, but also... I'm not supposed to be the expert in any conversation. Really, my main role is ask good questions, provide global business insight to a given conversation, and then allow people to go do their jobs. 

Caro 13:10
Yeah, I think that's like the perfect definition of a generalist, right there. There's so much overlap between being a great generalist and being in an ops role, a lot of times, especially when you're overseeing that many departments.

I have to say, I’ve talked to a lot of operations leaders who oversee a lot of different things. You don't usually see engineering under operations. It doesn't sound like you had an engineering background and, I think, in particular that one tends to be siloed off, especially a start-up. I would love to hear more about how that happened, and I guess if there were any other challenges around that.

Barrett 13:41
There is a great book called Riding Shotgun by a couple of former professors from Georgia State University. It talks about the many different models for introducing a COO a role to a company. One of the main premises of the book is that every skill role is completely contingent on the CEO that they're partnered with and so I think a lot of what we tried to do was specifically to design for where can Nathan be at his best, where did he want to be working in the business day to day, and how could we split those duties up in a way that served both of us. 

In the case of engineering, he wasn't an engineer. He didn't have an engineering background, although he does have front end coding skills and deep design skills, so there was more overlap for him than me, but I was also excited about the challenge. I was very close to our engineering leader at the time—and that's a big part of what I think allowed me to succeed. We had fantastic engineering leaders. We had two while I was in the role of COO. The first one was named Grant, he was very, very technical, deep background in infrastructure, like, really understood how the app was built, why it was built that way, how we needed to deliver. And then our second, our VP of Engineering, was named Sarah. She came from MailChimp, she had a great people management background, really understood organizational design, was able to get into any given conversation... also not as in engineer by background, but a an excellent engineering leader by background. 

So, I think having those people in place was the first big thing. The second big thing that was me being up for the challenge. And then the third was just like that was all by design to step Nathan up to do the things that only he could do as our CEO.

Caro 15:21
Wow, okay. Well, we talked about the breadth of the role and that being a thing you really like. On the flip side, what was the thing that… I guess, I'm using past tense here but you're still a COO… I guess what's the thing you find most challenging about the role?

Barrett 15:30
Well, I think COO roles vary greatly from company to company. A lot of what I didn't like, I'm trying to solve for in this new role so that maybe even a good way to frame it.

The first one was that, at ConvertKit, we worked remotely. I've been working remotely for almost 10 years, a little over 10 years now and, frankly, I'm pretty tired of it. I'm interested to see if in, you know, five, eight, ten years, if we see a little bit of a swing back away from remote work. Just based on my personal experience, which is that it gets really old being at home every day for 10 years, just like plugging away, working super hard and never getting that people interaction.

So, for me, that was one of them. I actually did not enjoy the remote work aspect of the work by the time that I left and that's just largely driven by being an ambivert. I like my in-person time. I'm very good at reading people's body language and emotion. It's one of the things that I really put to use in helping manage conflict and get to good resolutions of problems in businesses. That's harder online, it's a lot more taxing to try and pick up on how people are doing without being in a room, and then just like the joy of celebrating. When you're working super hard, trying to scale a company, there's just a lot less fun when it's like... you log off and then you're at home alone, that's it. So that was a big part. 

The second thing was I got a little burned out on software. I think software can do a lot to make the world better and also, the fundamental things we experience every day, even working remotely, are physical. Our car, furniture, what we what we consume, what we drive ,like, all of the things where we live. I think we need a lot more smart and talented people working in the world, in the physical realm, of like building things that are sustainable, that are healthy, that are thoughtful... and applying technology to those spaces in a way that allow them to scale, that allow them to be profitable… so that was another one. I was a little burnt out on the idea of software as the end-all, be-all of all of our problems.

And then, third, is it's hard being in a role. We grew revenue 25 million. We grew the team from... When I got there, I was number 17. We grew it to a little over 70, and we did it all bootstrapped. That was very, very, very challenging. Especially the bootstrapped part. 

I think the there's a beauty and a curse to being bootstrapped. One of which is that the owners get to make all of the financial decisions about where money goes, which is beautiful. And the curse is you have a lot more limitations than a funded business whose mandate is very clearly to grow grow grow grow grow grow. And, so, in the end, that conflict over how much we want it to grow, what our ambitions were over the long term... I just think there was a little bit of a conflict over like what I was hoping for and what I really believed we were capable of and what I wanted to do in the world and what Nathan, as the primary owner, was excited about. And that's okay. The way I put it at the time was that we were like consciously uncoupling or trying to go out at the peak of our relationship rather than riding it down the backside of it when we already knew that we had diverging ideas about the future.

Caro 18:48
Yeah, and such a great way of approaching that. I've spent, I think, almost my entire career at bootstrap companies and it’s definitely hard and its own thing. And going from 17 to 70 in just a couple years is... a lot for a bootstrapped company. I was trying to think if I have encountered another one that's done something like that and I can't imagine.

I feel like you gave me the perfect segue here… I think I followed you on Twitter for a while but I think one of the things that really got me to like dive into your background and learn more about you was that, last August, you announced that you were retiring as the COO of ConvertKit and started a pretty public job search shortly thereafter. I love when people do this, but I don't see a lot of non-engineers do it, and I don't see a lot of people approach it with such a thoughtfulness and intention. You built this whole page on your website that's called a Request for Opportunities, and I'm going to link to it in the show notes so everybody else can see it as an example, because I think more people should do this.... I would love to basically start the conversation about this by asking, you know, how did you decide to approach your job search that way, as you were leaving ConvertKit? 

Barrett 19:47
Well, the first thing is that I was in a huge position of privilege. This is pretty widely known and Nathan's talked about it publicly too - we did a decent sized secondary sale of stock for employees at ConvertKit who had our own stock for some time, or had stock options, I should say. I participated in that and that gave me the flexibility to work without income for up to a year, was what my wife and I planned on.

I'll just start with... that is a massive lever for finding the right thing that most people are not afforded so that was an unfair advantage.

The second thing I'll say is we valued at ConvertKit, [and] I value personally, working in public. I value talking about therapy in public and I value talking about numbers in public, I value talking about the emotional hardship of relationships at work in public. Because I find that most people think they are the weird ones, they are the ones with the unique problems that they have, they are the only ones to experience anxiety or fear or whatever it might be related to work, or otherwise. The more we talk about it, the more it normalizes just life being challenging and that the beauty of life comes in the peaks in between the hard steps. Without that, it just ends up feeling like we're lonely and like, you know, going crazy on her own. And so a big part of it for me was being public about it. 

Most execs that you see leave a role hole up on their own, they like call in favors from their network, they never talk about why they left, or what they're looking for. I think it’s really discouraging, especially to earlier career folks, where it's like, “How do they do that?”

I wanted to be the opposite of that. I want it to be public. I also wanted to have a tool for generating opportunities that I might not have access to on my own.

Another aspect of remote work working at a bootstrap startup outside of the Silicon Valley ecosystem is the network is just not nearly as strong. I worked my tail off to help us recruit a great executive and general team at ConvertKit and that was very much a team effort. But outside of that, I leveraged my entire network to get us an incredible team at ConvertKit and, so, like, I didn't have a lot of connections outside of that that I could rely on, especially in the tech ecosystem. So, I wanted to generate opportunities and I also wanted something to point to—like, I didn't think of that post as, ‘this is going to create the opportunity I end up taking.’ I thought of that post as,
‘this is the thing I can send someone so I can send up the three-sentence email instead of a four paragraph email.’ And, if they want to read more and it's intriguing to them, great, they'll reach out. So those were kind of like my high-level goals there.

Caro 22:25
Yeah, yeah, no that's good. I've had some people reach out with like the Google Doc versions of it, but I love your build in public version, right? So, I guess, to get into some tactical follow-up questions—how did you decide what to include on the page?

Barrett 22:
Well, one of the things that will probably surprise most people, is how forthright I was about my weaknesses on the page. One of the things that I find is that in things like reference calls for candidates, or interviews, or just any working relationship at the outset of, well, any relationship period, is that people are not very forthright about their weaknesses. They're like little landmines you got to find out about later. I would way rather walk into a situation being very forthright about my goals and very forthright about my weaknesses.

You're going to hire me for all the other stuff... my strengths, the background, the experience, like, of course you're going to get into that, but I want to know that you're accepting me for my weakness, knowing that it's my job to work on those and that we are aligned on vision. So, those are two of my big things that I wanted to make sure to include there. 

The rest of it was very much geared towards helping people understand whether I might be the right fit for them. What would they need to know about me, based on my experience, my interests, what I'm looking for, to help them gauge whether they should reach out to me. It was like a sales page for Barrett.

Caro 2:44
Yeah, absolutely. It was great.

What kind of response did you expect and what kind did you get?

Barrett 23:50
The very specific response I was hoping for was from a relatively small and obscure set of climate tech founders who are starting some of the most interesting companies that, I think, will kind of define the climate movement over the next couple of decades. I did not get that response. I am not surprised that I did not get that response because I do not have the background for those roles. But, what it gave me the opportunity to do, is reach out to those folks and link to it, first of all.

Secondly, to have been public about it, as I started writing and sharing about climate tech, to build more of a reputation there, it often was something people landed back on [after] reading something else I had done, either from my Twitter feed or from my blog. That gave me much more warm conversations to kick things off with than if it had just been kind of like a cold, “Who is this guy?” type thing.

Yeah, so the response was way lower. I was very disappointed by that. I mean, I was very self self-conscious about my lack of connections and, honestly, my lack of ability to get direct response from founders where I felt like... there was this idea that there was this massive resignation happening, great talent was hard to find, climate tech companies are at the earliest stages of trying to figure out their shit, and I couldn't get a call back. It was like, okay what's going. My response to that was basically to put my head down and say, “What is likely the case is one of two things." 

One, they're busy and got a thousand things coming at them and I just am another person. And, two, I don't have a background at three climate tech companies where it's like… "That guy, that's the guy I need right now.”

So, I knew, if I went and built more of a reputation in the space, it would certainly be better over time. So, ather than getting all in my feelings and worried about it, I just went back to work, basically, simply knowing that I had set aside plenty of time.

Caro 25:40
Yeah, absolutely, and such a… I'm gonna say, an operationally
minded way to approach it. Like, no, I’m going to problem solve this and I'm going to make a plan and I'm going to execute it. I'm gonna build that reputation and that experience.

You already said earlier that you ultimately decided to join Good Coffee, a Portland-based coffee company as COO. You described this online as, “the most self-surprising career move you've ever made.” So, tell us a little bit about why you were so surprised with yourself in this move.

Barrett 26:07
I mean, in some ways, my wife would tell you that it wasn't that surprising. So, it's always interesting to have that kind of life partner to be able to reflect back to you things about yourself you can’t always see. But I very much centered my work since leaving ConvertKit, and my kind of search for either a company to start or a company to join, on solving climate change, and making that my next kind of chapter of my career. So, that was the first thing that was surprising... that this other thing that I couldn't have expected ended up coming my way and felt right to me.

The way that developed was the two brothers who are the founders of Good Coffee are also long time friends of mine and have been for years. We had kind of - the CEO and I had been kind of like meeting in a business roundtable kind of way, just like chatting about what's hard about scaling companies and... very similar actually to how I met Nathan.

Caro 26:58
I was gonna say! I feel like you're writing an ad for Opsy for me, like… "This is why you need a community of like-minded ops people..." [Laughs]

Barrett 27:06
It is! [Laughs] Yeah, it's just so hard to know. I had known Nathan for some years before I joined him and I've known Sam for so many years before I join Good. You can't engineer that overnight and so, whatever like long-term opportunities you want to create, you know, you don't go in building relationships with that in mind, but certainly, strategically, you look at, “Where do I want to be over time? Where do I think I might want to be? And how can I start building out a few relationships in that area so that, if something becomes available, I am top of mind?” And that was the case here.

In February and March, I planned to and did participate in OnDeck’s Build for Climate program, which was an eight-week, idea accelerator program for people who are interested in founding climate tech companies. Sam had approached me about joining Good and I had actually told Sam like, look, I'm going to do this accelerator, I’ve got a kid due in early May, my second kid is due in early May...

Caro 27:58
Literally, any day now.

Barrett 28:01
Yeah, exactly... I don't want to join a company and then make you pay me to be out on Parental Leave... like, why don't we check back in in August, after I have figured out if I want to found the company and had this kid. And I respected the living hell out of the way that he responded which was... he had printed my email that I had said all that in, we got together for coffee, and he let me walk through my reasonings, and was, like, “That totally makes sense. Also, I think, while you're going through this accelerator, we should do a trial run as COO of Good."

Caro 28:30
[Laughs] No pressure, just go through an accelerator, get a new COO role, get ready for a new kid, okay...

Barrett 28:
[Laughs] Exactly. 

He asked me how much time I was going to be spending on the accelerator, about half half my time each week, and so I did have a couple days available—although I intended to be writing during that time—and so the pitch made sense to me. It was like, yeah, I should not imagine one path while actively exploring the other. It would be great to actively explore both. 

So February-March, I went through the accelerator. In March, I did two days a week as COO at Good. What I found was that, on balance for my priorities in this chapter of life, of having two young kids wanting to be present in their lives, being in a fortunate financial place where I can take a little bit more risk, and then also the things that I wanted deeply at ConvertKit, of not being remote, maybe making something physical in the world… those things were showing up at Good. As we talked about me joining, I said, “Listen. This is looking interesting to me and one of the things I really would want to make a priority of mine over the next five years is to make Good carbon-negative as a brand. Would that be something you're open to?” And, so, creating a slice of my work that would be aligned with all of the research and learning I've been doing. And they were not just open to that, they were super excited about it. So, I think, that was the other thing that made me excited. 

I might not be able to like make a technological breakthrough that fuels a bunch of emissions drawdown. But, we might be able to be an example for an industry that is going to need a lot of work just like every industry is, and that in and of itself can be a very meaningful contribution, even if it's not like a global scale contribution. Which is something I really struggle with. Sometimes I'm like... I gotta change the whole world! And, instead, it's like, okay, I'm going to take my slice and I'm going to try and do a really good job. So that was kind of how I ended up there.

Caro 30:21
I think I struggle, and I'm sure a lot of us do, with that whole like zooming in, zooming out thing. You know, it's so easy to get distracted by like everything pressing down on you and all the things we should be worried about and thinking about and then, at the end of the day, it's like, okay... I just want to build a great place to work for people who can like give back in their community, and then like be present in their lives, right? And it's that ripple effect. 

So, yeah, I love how you were able to bring up the the carbon-negative thing to them and to carve that out. I was going to ask about that because I, again, have obviously stalked you online. [Laughs] I have a lot of follow up questions!

Barrett 30:55
Making of a great podcast post [Laughs]

Caro 30:56
Obviously, that's going to be one of your big projects. I would love to hear a little bit more about that. I mean, I know it's super early days but how are you thinking about even starting to crack that nut? It's a really big one in the coffee industry.

Barrett 31:05
It is a really big one! You know, any effective movement towards going carbon-negative for a brand starts with... Where are we? Where are the problems right now? So that's going to be step one. My goal is, by the end of this calendar year, in 2022, to define our footprint.

Carbon footprints for companies are defined in scope 1, 2, and 3 of emissions. Scope 1 emissions are the direct result of - what you do and how you make money. Scope two emissions are kind of like the ancillary effects of that so... I'll get it wrong if I go too far into it, so I'll just leave it at that for now you can. And scope 3 is the emissions of all of the suppliers and downstream companies that you work with. So, in order of importance, like, scope one is for sure the thing you need to address first. 

I think, for most brands don't go right at the heart of the problem, to put it kindly. They kind of like try and dance around the actual problem. So, for us, the scope one stuff is going to look like - the roasting of our coffee beans, like, that is a very, very natural gas intensive process with lots of emissions. We're going to need to look at that very closely. It's in the products that we sell, especially milk. Milk is a very big contributor to emissions, just because cows are. Our electricity, heating and cooling of all of our retail locations will be another big aspect of it… and so, you know, you can start to like see the ops mind go into effect here but, basically, the goal is to define the line items in order of importance. Then we need to start to translate that to what it will it cost us to eliminate that. Well, and is it impossible to eliminate it. 

So, something like coffee roasting. Is there an alternative to gas-fueled coffee roasting? Well, there may not be right now and so that might be a thing we have to find high-quality offsets to get rid of, whereas something like milk, if we're just serving conventionally raised cow milk right now, we could go to something, at minimum, from a local company like Neutral here based in Portland. They're all grass-fed cows, their operations are newly carbon neutral, and, when they come into our supply chain, we're starting from zero, basically. So things like that is what we'll be looking at.

Caro 33:23
Yeah, no, okay. I'm like… my mind again went to the operational part of all the line items. It sounds like a fun project and obviously a very meaningful one. So, what else are you looking forward to working on at Good?

Barrett 33:34
It's been so much. This is going to sound so weird for the point in history that we're at but, like, commuting to an office every day has been amazing. We'll see how I feel in a couple of years but, so far, I have a 25-minute drive each way. We're about 20 minutes outside of Portland in a little city called Troutdale. It's kind of the entrance to the Columbia River Gorge so I get to ind of see the river, just like be in this little small town right outside of Portland, but still close enough that it's super easy.

It’s been really fun getting to hear, see, feel, watch the coffee being roasted, coming in the door... all of that's been awesome. Our roaster and our HQ are in the same place and we have a cafe attached to that.

Caro 34:18
Ah! Very fun.

Barrett 34:18
The environment is very inspiring to me from that angle. And then the problems are super interesting. Good is at a scale that is very similar to ConvertKit when I started. We have about 25 total team members, mostly in our retail stores, a few in our roastery, and then a couple execs. Similar revenue scale... The problems today are very simple in definition but not always in solution and so, for me, having scaled something at this point, you know, not to astronomical heights but to decent size…

Caro 34:50
[Sarcastically] Yeah, decent size

Barrrett 34:53
Yeah, totally. Well, you know, some people would say hundreds of dollars of revenue is real…

Caro 35:00
[Laughs] Yeah, I feel ya.

Barrett 35:02
So, you know, right now, it's the problem assessment. It's [figuring out] where the opportunities for us to make the biggest difference in, to get more efficient. 

An example of an interesting problem I'm working on right now, is all of our wholesale business has run through either text message or emails to our CEO up to now. That's how people place their orders.

Caro 35:17
Wow, that stresses me out just thinking about it. The unread text on this person's phone…

Barrett 35:24
Totally! You know, he’s just been he's been grinding for seven years. He's been doing everything. It totally makes sense that's how it runs but I'm like, “Sam, you don't have to do this.” We can solve this. We can automate this.
And, of course, he's pumped about that. So, it's things like, all right, let's go find a Shopify Plugin app that works well to run our wholesale accounts through. Let's give people an online ordering platform, specific pricing, bill them immediately... like all of that kind of thing can be automated. 

It's those problems where, they feel obvious as solutions to me, but, for a business our size, that scale is huge leverage for the business to continue to grow. That will allow us to go from, you know, let's call it 20 wholesale accounts to 500 wholesale accounts and have it systematically work the same way all of our e-commerce operations do. It's things like that that are really exciting to me. 

Caro 36:20
Yeah, I mean, and that too is where that like diversity of thought and experience comes in, right? When you're one of 20 software guys, you're just another software guy, but when you're the guy who sees all these automations... it's skyrocketing potential for the business. 

I was recently helping a bike shop who makes custom bikes here in Mexico City and I was like... You're using paper receipts, and then like taking a photo? Like, we can we can fix this. We can automate those. It's great to be able to like be that person too, and that definitely gets me excited.

Obviously, you are a very growth minded person. So, I'd love to ask what advice would you give someone who is maybe in a mid-level, Head of, Director of Ops or something like that, and is looking to move into a more senior operations leadership role? It's a big question, I know.

Barrett 37:05
It is a big question but I do have thoughts on this. The further up, you know, the kind of ops totem pole you go...

You know totem poles is probably one of those phrases that I'm gonna eliminate from my vocabulary... I'll say the farther up the ops ladder you go...

Caro 37:19
There you go, yeah. I like that.

Barrett 37:21
Yeah, to correct myself there. I'll just do a plug for language awareness on that one. I think just being aware of where phrases come from, is something I've really worked on over the past few years but... Anyways, back to the story.

The breadth of knowledge you need across areas of any given business grows very rapidly the further up the ladder you go and, so, what I find for a lot of ops people who are kind of mid-career is that they'll typically have had one area of expertise, whether it's Finance, People, maybe even like some Biz Ops where they're kind of consulting across groups in a company... That's great and you're going to need a lot more than that as you continue to grow. So, I actually think Biz Ops people are often the ones with the best trajectory, because they get to see all the different units if they're positioned well.

But my baseline advice would be, regardless of what kind of vertical of ops you've been in, get some rotational experience, even if you have to do it on your own time. 

For example, let's say that you want to go from kind of like director of Ops to a C-level role. I would think about what business functions am I least comfortable with. How could I create space to show up in that function and help the team, the leadership, or whatever, in that function do their jobs better? [In a way] where I'm not costing the business anything, where I'm doing it on my dime. Maybe I'm going to the customer success teams weekly leadership meeting and my request of the leader there is to be like an observer. I'm just there to listen to the kinds of issues of issues you deal with and then, if you have an insight, and you can say, like, "Hey, I heard y'all talking about this problem and I just had a few thoughts on ways you might improve on it. I just wanted to offer that up as something that might be helpful." I think those are really great ways for you to start broadening your knowledge, getting to know a function a little bit better, and improving in your future ability to lead across functions.

That would be one big aspect. And then I think just like really brushing up on your proficiency in different areas. When I think about the core ops functions, I think about Accounting, Finance, often People and Data. Those are like the big, big ones, for me, at least.

Caro 39:35
Data? Interesting, okay. I really thought you were going to go to like legal, facilities, like security... like those are ones I hear a lot after like the same list and you took a pivot. I mean, I totally agree but very interesting..

Barrett 39:46
Some of that stuff starts getting into the like the blur between, I mean, there's like Biz Ops and there's like Ops Admin. I think some of the legal, facilities, all that kind of thing can sometimes get into the admin space. And so there's like a range.

Certainly, you're hearing my bias in terms of where I've been, and the other range would be equally valid too, but just thinking like... Okay, you know, where are my strengths? How can I emphasize those even more? If you're an Excel Master just like many people are in the Ops World... Well, are you?
Like could you level up there, could you be even better, could you get more comfortable with a things like Financial modeling and other aspects that you're really going to need as you continue to grow? So, really looking at where your strengths are, how could you double down on them. 

Then where are your skill-based weaknesses? I think about that differently than like personality or talent-based weaknesses. We all have like basic psychological background makeup that brings us to work in a certain kind of
package, and there's some weaknesses that you should just steer clear of, you should try and avoid interacting with those weaknesses as much as possible and that's the best strategy so you can double down in your strengths. Skills-based weaknesses is just learning you haven't done yet.

So, let's say you have like a really great background in People Ops but you want to be a C-level leader in the future. You're going to need some finance and account. It might make sense to think about going to get an MBA or doing some night classes or online classes to get more comfortable with reading financial statements, building financial statements, things like that.
I'd look at it as like almost a skills matrix just like you would build for a people organization. Say, all right, if I were designing a skills matrix for the role that I want. What are the skills that I can't check the box on right now? And which ones can I reasonably build to help me get where I'm trying to go?

Caro 41:35
Yeah, absolutely. I tell people all the time to look up the job descriptions of the job you want and then like see what requirements you don't have. I also love this advice because it's advice you took yourself, right? It sounds like what you did as you were looking for your new role.

So, on the flip side of it again... I'm sure, as a growth minded person, you already have a list in your head, but what are you working on this year that you'd like advice on? What are you trying to get better at?

Barrett 42:00
I think right now the biggest thing is just industry expertise. I'm in a completely new space. I have not worked in a physical products business before. I have not worked in coffee before. And, so, really, it's building expertise there to understand what's the baseline kind of industry expectation for things like profit margins, growth rates... What does it cost in cash outlay to build a new retail store? How much lead time do you need on signing a lease before you can be live in a space and making money from it? If we wanted to stay self-funded, how many stores could we fund on our own? What are the other levers we could call there in terms of lines of credit, debt, equity financing? so, really taking like everything I've learned in ops and applying it very specifically to the coffee industry, and what the industry generally accepts as true so far, then finding the places where...

First principles thinking would say, well, I understand why the industry says that but it that doesn't have to be that way. So, let's figure out if we can actually make that a competitive advantage of ours. That's a lot of the learning I'm doing right now. Let me do my homework and make sure
that I am aware of what this industry runs on, how it operates, what it looks like to be successful, before I started making assertions about... we can blow that out of the water and we can go get out and do so much better than all those other people. Because, often, industries are the way they are for a reason. And then sometimes there's like a 10% of it where there's absolutely no reason and that's where you can win. So that's kind of the search I'm on right now - what is that 10 percent?

Caro 43:28
Yeah, you got to learn the rules to break the rules, or whatever they say. 

I feel like that was definitely my HR/People Ops journey. Where I was like, Okay, let me learn all this HR stuff and then figure out like... I object to the fact that you're teaching me how to union bust, but I will learn it and then
we'll do it differently, right? 

Well it has been so great chatting with you today. Thanks so much for taking the time and really excited to follow Good and everything else that you're going to be up to in the climate tech space.

Barrett 43:52
Thank you so much. I appreciate you having me.

Interested in learning more about operations leadership?
Listen to our interview with Megan Bianco to hear how she juggles all the different aspects of her role.