Ep. 16 – Seva (Formerly ConvertKit) COO, Barrett Brooks

Whether you are a writer, a chef, a podcaster, or a blogger, regardless of how you identify yourself, you are a creator. Creators want to create, and Seva is giving them the opportunity to do just that. Barrett Brooks, the COO at Seva (formerly ConvertKit), says they are a bootstrapped startup that builds email marketing software on a mission to help creators earn a living doing what they care about. From coming up with a business idea to making that first product to selling what you make, Barrett explains how their email software gives you a competitive advantage.


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Seva (Formerly ConvertKit) COO, Barrett Brooks

Barrett Brooks is with us. He is the COO at ConvertKit, which is a bootstrapped startup building email marketing software on a mission to help creators earn a living. In the past, Barrett led growth at Fizzle.co. He also worked for bestselling author Seth Godin, who wrote the cover testimonial for my first book, Double Double. He founded a company called Living for Monday where he helps college students find jobs that matter. He is also a servant leader, sustainability advocate, optimist, writer and outdoor enthusiast based in New York City. He fundamentally believes that business is one of the most powerful forces for good in the world. Barrett, welcome to the show. 

Thanks for having me, Cameron.

I’m looking forward to this. Tell us about your journey as a COO. How did you end up where you are now and how did you get some of the skills that you’re using? Even before that, tell us a little bit about ConvertKit just so we can get a good frame of reference.

ConvertKit is a software company. We’re bootstrapped. We’ve been around about five years. All of our high-level metrics are public. We see part of that as being a goal of educating teachers and startup creators. I can share that we’re doing about $13 million in annual recurring revenue right now. We are a team of 37 people and our mission is to help creators earn a living. We think of creators as YouTubers, small-time makers, podcasters and bloggers. What’s interesting is they’ve got this online business that its goal is to help them earn a living doing work they love and that’s been the theme throughout my career. It’s personal work for me that I enjoy. We’re having a lot of fun doing it as a team. It’s a great audience and we’ve got some big players in the industry that we’re trying to compete with. That keeps us on our toes. That’s a little bit about ConvertKit. I’ll take you back to the beginning of my career which is where some of the skills I’m using now come from.

I started my career as a management consultant at Ernst & Young. They had brought back their consulting practice after having sold it off years before. I was one of the two staffers in the Atlanta office, which meant I got a ton of exposure to senior executives and clients and also to the partners at EY. That helped me develop this executive presence in the big business world. It’s the ability to be in rooms with people much more senior than you and carry yourself well. That was a big skill that I developed then that’s carried forward to now where I understand how to interact with people at different levels of organizations. How do I adjust my leadership style to different types of people in different scenarios? That was a big thing there, but as a management consulting, your job is not just to communicate with people but to fix problems and often pretty hairy problems. That helps to keep me in some good frameworks for evaluating problems, finding opportunities to grow businesses, then solving them systematically and not just with one-off solutions. It all started there.

What kind of training do they give you in the problem-solving process in the consulting that you’re doing?

I like to call it, “The drop you in the deep end training.” Being one of only a couple of staffers in that office as they were building that practice back out, they didn’t have a ton of training established for lower levels of the organization. They had a lot of partner and director training at the time, but they weren’t prepared to train the staffers up. It truly was just, “Go find a project that you want to get staffed on and pitch yourself to a partner and then get going.” That was my whole entrance into the business. Coming out of school, that’s quite a challenge but it was good. It taught me a lot.

Are you coming out of an MBA program into that? Are you coming out of an undergraduate degree into the work?

Undergraduate, yeah.

They throw you into the fire then.

They did, but now I think they’ve built out training. If you go to somewhere like Bain & Company or McKinsey or places like that, they’ve got intense training that they put people through. EY since built a great program now.

How long have you been with ConvertKit?

I’ve been at ConvertKit two years now. I started off in this floater, special projects role. We had a bunch of big ideas we wanted to execute on. We’re putting on a conference, doing a series of documentaries about our customers and things like that I came in and led at first. I moved into a role as director of marketing where I let all of our paid acquisition, all of our content marketing, all of our brand marketing and built a team out there before moving into this role as COO.

How many customers would you have?

We’re right at about 20,000 paying customers.

What growth have you had in the company since you’ve been there over a couple of years?

When I got here, we were at $300,000 in monthly recurring revenue and we’re now going on at $1.2 million.

That’s four times that growth. How many employees when you got there?

We were right in the twenty.

They did push a lot of their margin into hiring in the early days.

Compared to pure level organizations, we have not hired nearly as fast with that same growth. We’ve grown at 4x and grown the team a little under 2x at that time, which has been one of our greatest challenges. It’s keeping the team small but continuing the growth.

Do you outsource all of your employees in one office? How does your team make-up look right now at your office?

SIC 16 | Email Software

Email Software: You have to think from an execution standpoint. What’s the vision for the future? How do you make ideas actually work over time?


We’re 100% remote as a company. We have no offices. We have about 37 people that are spread out across 24 cities and seven countries.

Who would your big competitors be then?

We look at our biggest competitors in two groups. You’ve got your traditional email marketing software that is built for you to send a broadcast to an audience. That’s the core of it. There’s more like marketing automation platforms and we sit somewhere in the middle. On one end you’ve got MailChimp, Constant Contact, MailerLite, AWeber. On the other end of the market, you’ve got tools like Infusionsoft, ActiveCampaign, Drip and others that are built more as automation tools.

Who is setting the vision for the organization? Is that you or is that the CEO? What are the different roles between the two of you?

We’re both vision-oriented people in very different ways. Nathan, our CEO is a product designer by trade. He’s heavily involved in the product. He’s the product owner in the organization. Of the 37 people on the team, 33 of them report to me. That would be engineering, marketing, sales, customer success and operations. The two product designers on the team report directly to the CEO. He’s both CEO and team lead. He’s very much driving forward on the future-driven product, the ways we want to market, in terms of doing things like the conference that we launched and the series of documentaries that we launched. I’m very much thinking about the vision for it and how do we operationally work. How do we scale without scaling the number of people on the team? One of the big constraints we put on ourselves is we’d like to stay at 50 people or less overtime to keep this a family-oriented culture, to be able to take great care of the people that are here. I’m thinking very much about from an execution standpoint, what’s the vision for the future? How do we make these ideas work over time?

Do you know Ari Meisel?

I don’t know.

Ari is a guy who’s based on the East Coast. His book was called Less Doing, but he’s got a little bit of a model where he looks at everything that an organization does. He runs it through this little filter of can we stop doing it. Can we optimize it? Can we automate it? Can we outsource it? It goes along that line of trying to grow big and keep your headcount of around 50. We often get bogged down in just getting bigger for the sake of getting bigger, but without a mindset around optimization and automation and efficiency, even outsourcing to partners. Tell us about what are you doing then to stay small and to continue to scale?

One of the things that’s most important is setting the intention. Many companies and especially peer level companies in the startup world, measure themselves on the number of employees. We’re this big in terms of team size. Just by starting out with this intention to say, “We’re not going to measure and we’re not going to optimize for team size. We’re going to optimize for the opposite of growing team size.” That helps us focus on, “How can we solve problems without adding people?”

That’s a huge intention that anyone who’s reading needs to grasp. You said it that too often people use the headcount as a measuring stick, as a yardstick, as a symbol of their success. 

There’s some level of that if you want to get into a values-driven conversation about the opportunity to create jobs and all this. I think there’s an argument for it and I’ll acknowledge that.

I had a client in New York city called Elite SEM. Their CEO ranked as the number twelve company to work for in the United States by Glassdoor. I coached them for four years. When I started coaching them, one of their goals was to get to 100 employees. I was like, “No, you’ve got to remove that. That cannot be a goal. That’s not an exciting thing to drive towards. Let’s drive profitability, employee engagement, customer engagement and revenue, but let’s not drive the number of employees for the sake of getting bigger.”

When we have a problem come up, one of the most important things we do is we acknowledge the fact that the easiest thing to say is let’s hire to solve for it. That’s the first thing that comes to mind. The second dive in was the second level questions on is this a symptom or a problem? If it’s a problem, what are the different ways we could go about solving this with hiring being one of them? We go down the list of, is there a process? Is there outsourcing? Are there tools that we could be building to solve this thing for a scale that is going to grow over time? If hiring ends up being the only way to solve it, then we have a conversation about whether we should be adding a person to the team.

It needs to get done, but not necessarily a bias and not necessarily be by hiring somebody as well. That’s a great little filter to run it through. How do you guys make decisions on what to start? All the new ideas that an entrepreneurial company has, how do you make decisions on which ones to green light, which ones to red light or which ones to shelf for a while?

I’ll admit to you, Cameron, this is one of the things that we’re struggling to solve for right now as we speak. At this stage of scale is where decisions have to start having filters on them. To this point, the way we’ve made decisions is does this align with the leadership team’s vision for where we want to go? What that can often lead to is too many priorities at the same time. Over the past 18 to 24 months, what we’ve learned is we bite off more than we can chew more often than not. What we’re trying to do now is create decision-making filters so that we know whether something should be on the list of priorities or whether we should put it off for later. That’s a huge challenge.

I’ll share with you a tool called the decision filter that I created. It was based on a tool that Dan Sullivan, who built Strategic Coach, created. It’s called an Impact Filter. He does teach companies to decide which projects to say yes to based on their impact on the organization. I’ve taken it to the next level because I always feel like we can sell ourselves on every idea of having an impact. I want to know what the ROI is off of that and the ROI against our time, our people and our money. I also want to go after the projects that are the low hanging fruit that could get us into orbit faster. The ones that will create momentum. That momentum will continue building for us versus often companies get into the big hairy projects that can take a year versus cranking off seven quick small ones that will give us momentum. Tell me a little bit about employee recruiting, hiring and training process. When you’ve got an entirely remote team, that’s a pretty unique skill set. It’s becoming more and more normal now, but what do you guys use? What tools, what systems, how do you hire, etc.?

To me, the number one advantage to being a remote team is the ability to recruit from everywhere. That has opened us up to a talent pool. Nathan, our Founder, is from Boise, Idaho. He’s gone up there. His family is there. He loves it there. Recruiting the quality of people that we have on our team in Boise would be much more difficult. It wouldn’t be impossible, but it would be very difficult. The first thing is that everyone is a potential hire for us, which is fantastic. The second thing is that the hardest thing about is that everyone is a potential hire for us, which means we have to create our own focus filters so that we’re not going after everyone. We’re going after the right people. There are a couple of things that we’ve done that have helped us. Number one is we use software called Workable to manage our pipeline and recruiting process. All of our applications go into that system and we filter them there through the pipeline of hiring from application to hire.

The second thing is we found some great partners where we post our jobs regularly. A couple of sites that we post on regularly are WeWorkRemotely.com to exclusively for remote working jobs. We post on Hire Tech Ladies. One of our priorities is to make sure our applicant pool is diverse and inclusive. If the applicant pool is diverse and inclusive, then it means that we are much more likely to hire people who are diverse and inclusive. Hire Tech Ladies is a great one for us. People of Color in Tech is another great one. What we found is that those three sites alone produce an inordinate number of highly qualified applicants compared to everywhere else we might post. We’ve tried sites like Indeed, Monster and things like that. They tend to produce on average a very low-quality candidate. They’re in between. In LinkedIn, it can be hit and miss, depending on how you target the posting. We often target for New York and San Francisco when we post to LinkedIn because that’s where so much of the tech talent is concentrated. Other people will still be able to see that post even though it’s in those cities.

Do you have as a center point where you’ve got a few cities that you’re hiring people in or do you even look for that at all?

We don’t. The one priority that we’ve placed is on people in North American equivalent time zones. The reason for that is as you get an eight, ten and twelve-hour gap in the time zone between teammates working hours, it gets that much harder to collaborate and work together on projects. We don’t rule out hiring people outside of North America, but we do prioritize applications, just for the efficiency of the organization.

I coached CEOs in Australia. It gets tough because we’re limited for four days in a week that we can be doing coaching and only a limit of about a few hours a day. It strips away the availability of time. You go through the interview process and thanks for sharing those. It sounds like amazing tools to dig into as well. After you’ve got your applicant pool and you are using Workable to screen people through the process, what are you looking for in candidates? How do you run your interview process and have you done training of your people on interviewing?

SIC 16 | Email Software

Email Software: We could be much more efficient in screening applicants with things like software and tools.


We could be much more efficient in screening applicants with things like software and tools. We choose not to be right now because of our intention to hire so few people. We have a highly manual screening process where we’re looking for outliers and the way they communicate, the way that they put time into their application. Which would mean that an automated filter could easily rule people out that are the kind of people that are exactly who we’re looking for. When we’re going through applications, typically the manager who is hiring for the role is looking at each application. We’re specifically focused on what their cover letter looks like. We ask a couple of questions that are qualitative information. What kind of person is this? I would have to follow up for the show notes in terms of exactly what questions we asked for different teams. We’re looking for a type of person and then we’re looking for skill set. If we can get a person through the type of person we’re looking for a filter, which means that they’re going to be a huge contributor to culture, that they’re not just looking to work remotely.

That’s a huge challenge we have as a remote company is that it seems incredibly attractive to a lot of people who are not going to be high performers. We’ve got to filter between are you just looking for a remote job? Are you looking for a remote job at ConvertKit because you’re excited about this work? A big tool for this, that’s been a little bit of a hack for us has been that we published a page at ConvertKit.com/Mission. In it, we outlined our mission, a very detailed vision, our values as a team and then what we consider our competitive advantage, which is that we care so much about each customer that we serve. That page being linked to from job postings has been an interesting conversation piece where we know who’s done their research because a lot of the people who end up there end up mentioning it in their application. Those are the people that we find are excited about this work at this company, not just their next job.

I like that you’re intentional about your whole process as well. It’s not just happening by accident. You’ve got the people coming in. How do you onboard them?

Onboarding has been something that we spent a lot of time on over the past year. It went from it varied by the team for a long time to now we’ve got a pretty great process where we invite members from across the teams at the company to host one-on-ones with the new person on the team to show them the tool that we use internally. One person might have a one-on-one where they catch up a little bit and then they show them how we use Slack as a team. The next person might have a one-on-one and then they show them how we use Basecamp to project plan and communicate ideas as a team. A large part of the first week for any given person is centered around getting to know teammates who are also teaching them something that they’re going to need to know about how we operate. We found that to be incredibly effective.

I’m thinking a little bit about culture as well. The whole remote teams’ business and it’s working. There’s another client that I coached. It ranked as the number two company to work for by Glassdoor. They are a completely remote team of 85 people just like you guys are. How did you guys build a culture with these employees when everyone’s remote? What tools do you use and how do you develop that culture? It sounds like vision is a part of that and your hiring process for sure, but what else do you do? 

We had the heartbeat of the organization, which lives in two places. Slack is the synchronous day-to-day communication where everyone’s getting together. The other is Basecamp where we’re sharing ideas, pitching each other on a potential project we might take on and then planning those projects as we decide to prioritize them. On top of that is a layer of meeting structure that we found to be very meaningful. We try and treat meetings as culture builders as opposed to blocks of time that are wasted. Every Monday we have an all-hands meeting with all 37 people on the team and we’ll do ten, maybe fifteen minutes of updates across the teams, which we try to tie together with an overarching story from the leadership team about where we are and where we’re going over this next week. The other 45 minutes is a team conversation about something that matters right now.

One example of this is we are hosting our second annual conference. We had a call about the logistics of that conference. We invited ideas for how to make it even better in these last couple of weeks leading up to it. We had each contributor to the planning process share what they’ve been working on. It’s very participatory, but there have been other meetings where we’ve invited the entire team to come ready to give the leadership team candid and direct feedback about how we’re performing, how we’re leading and how we need to get better over time. That’s one huge culture contributor where people find it very odd how frank we are with each other when they’re coming from environments that might be more political or a little bit more reserved. That’s one aspect of our culture that we try and build throughout our meetings.

It’s pretty comfortable once you get used to it though.

It is. It gives you a lot less to be anxious about at work because people are communicating directly and honestly with each other. We do twice-a-year retreats. We get all 37 people in one physical location. We do one in the winter in February, we do one in the summer in August. They are in San Diego in the winter and North of Boise, Idaho in a town called McCall in August. We use those as an opportunity to dive deep on relationship building, on vision casting and on planning for the next six months. What I find is that those retreats are these lifelines, especially to the extroverts in the group. Almost anyone can make it six months if they’re disciplined and get that re-up of energy, connection and relationship building and then go back home and get back to work. It creates this nice balance of having these deep and meaningful relationships. If you’re in a place with a person for a week, you can learn a lot about them.

Are your retreats a week-long?

They are a week long. Our international teammates come in on Saturday prior to adjust to the time difference. We kick things off Sunday night with a big team dinner and then people fly out Friday morning.

That’s a huge commitment on culture for sure. I’m glad you mentioned the meeting rhythms as well. One of the books that I wrote a few years ago was called Meetings Suck. I was tired of people complaining about meetings when the reality is most people have never been trained on how to run meetings and even how to show up and participate in meetings. It’s good that you guys get it and they’re running them properly because they’re a huge part of giving people the tools to grow the company.

You have to stay focused on it because if you do it well, they’re great. If you get lazy, they fall apart.

Talk to it though, they totally fall apart. Tell us about the whole performance management side of the business. How do you oversee all the projects? How do we ensure that stuff is getting done and getting done quickly and getting done right? How are you growing the people?

This is another area where we’re continuing to evolve. I’ll share our process and then flaws that we see in that process. We set a strategy for the year and that strategy looks like three to four thematic strategies for the year across the company. One of our biggest strategic priorities is to be able to tie revenue to email activity in our application so that we can prove that creators are earning a living by using our tool. It’s obviously not worded long of a statement. We set things out like that. We have five individual teams. It’s engineering, operations, marketing, sales and success.

We take those strategic priorities and they say, “How did these apply to our work and what are the strategies we’re going to follow that roll up into these larger company strategies?” They set goals off of those priorities. Each team has its goals for the year and then each quarter, we adjust. The leadership team, there are seven of us. There are directors for each of the five teams, then Nathan and I as CEO and COO, and we go quarterly. When we have our team retreats, we buttress it on either the beginning or the end of it with our planning meeting. Three months in between each retreat, we get the leadership team together to plan for the quarter. That’s where we’re making the more fine-tuned adjustments and prioritizing the work for the following three months to make sure that we’re focused on the right things. That’s what goal-setting looks like.

What we have our directors do is they meet with each person on the team and they say, “How can you contribute to where we’re going as a company over this quarter? What goals do you want to pursue both as from a professional standpoint that we need you to accomplish in order for the team to accomplish its goals? Also, from a personal development standpoint, how do you want to grow as a human and as a professional this quarter? What are you going to focus on?” There is not a lot in that last quarter category because he can’t do too many things at once. We are looking for at least one thing from every person. How are you going to grow? That might range from, “I can create a physical fitness practice over this quarter because I see my health not being where I want it to be.” It might be, “I’m going to start a YouTube channel as a side project to learn more about content creation and everything in between.

How do you manage your team in terms of them wanting to have side businesses?

We highly encourage it. We have a channel in our Slack team that is for side projects. There’s a group of people who get together early in the morning about once a month to talk about their side projects and the progress they’re making. The reason we encourage it is we like to hire people who are creators themselves because we think they’re going to have more passion for the creators we serve if we do. If we take away their ability to be a creator by them working here, then we’re losing the magic of that. We see side projects as a way for our team to stay connected to the people we serve over time.

Where are you guys struggling?

We’re at an interesting point and scale where we’ve had tremendous growth and we built this wonderful culture that we all enjoy quite a bit. To go from 20,000 customers to 100,000 customers, the architecture that the app is built on is going to need to change. The way we handle things like spam detection is going to need to change because if we let spammers into our app, it affects all of our great customers at the same time. A lot of the things that we’ve been able to get by on with manual solutions to this point have to be automated. That’s a new area of growth for everyone on the team because we have to go from, “I can just apply more hours to this,” to “I have to apply different thinking to this.” That requires growth from everyone. Every individual has to grow in order to shift that thinking that way. I would say that’s the biggest thing. Maintaining a level of growth at scale is different from hustling to get that early growth that you see in a startup before you found the full product-market fit. That’s a challenge to continue growing at that scale.

SIC 16 | Email Software

Email Software: We like to hire people who are creators themselves because they’re going to have more passion for the creators we serve.


How do you guys do that? Do you decide what you want your growth to be and then reverse engineer that? Do you forecast what you think your growth is going to be and manage into it?

A little bit of both. We work with both models in terms of what we want and what we see as realistic. What we did after setting targets that ended up being discouraging for the team and past planning sessions is that we set a consistent pace we wanted to hit. We said, “This is the net new MRR that we believe is achievable.” It will get harder over time because as the customer base grows, churn grows in a nominal amount. We set it at a consistent pace that we wanted to hit throughout the year to prove to ourselves that we could create predictable success over time, which is a term that Les McKeown coined. We liked this idea of intentionally being able to create an amount of growth over time because that indicates to us that we can scale that if we want to.

I love the planning process and the rigor behind the planning and the meetings that you guys seem to have in your business. I know you also take that down to the one-on-one level in your one-on-one coaching. Walk us through your one-on-one meetings and how those work.

The first thing is that I see one-on-ones as the time for team members to express what they’re challenged by, what they need from us as leaders and what they’re hoping for from their work. We very much make one-on-ones driven by the teammates that we’re having one-on-one with. If done properly, that person’s put some thought into what kind of conversation do I want to have with my manager right now? If they haven’t had time for that, it’s still our job as leaders to say, “What’s going on?” Number one, how are you doing as a human? If you’re not doing well as a human, you’re probably not going to do great work. Number two, what are you struggling with and where can I help? Number three, if we get past your edge and then we get through those two questions, then I got a couple of things that I want to prioritize and talk to you about. If we’re not creating space for people to share what they’re struggling with, share their ideas, they’ll do the job, but I don’t think they’ll stay as engaged as they should.

How about yourself? What are you focusing on and where are you working on?

I’ve been in this role for a few months. We’ve intentionally set out a transition process where over time a new team is coming up under me for the reporting structure. What I’m focused on is getting it on the ground level with different people across the teams to see directly with my own eyes what their work looks like and not just see it but do it. For example, we have a team that manages customers coming over from competitors where if you have a large enough email list, we’ll do it for you. You give us your login to your old tool, you’ll tell us what you want your new set up to be, and we get it done for you. We don’t start billing you until it’s done. I’m doing one of these migrations for one of our large customers right now to see for myself the challenges that team might be facing. It’s almost like you’ll hear a new senior executive of a Fortune 500 company come in and they’ll do a year-long listening tour. They travel the globe, visits all of this. It’s the equivalent of that, but I’m doing the work so that I understand that better across the teams.

What about your personal growth as a COO over the years? How have you had to grow?

I have to grow every day. There are parts of this role that require different things than me. One of them is emotional growth. You have to put other people’s needs first and you have to be able to both make objective decisions and then communicate objective decisions in a way that connects with the humanity on the other end of that decision. Emotional growth as a leader is just EQ and interpersonal skills. I’m always being challenged by filtering my own emotions, communicating effectively, building interpersonal relationships so that there’s plenty of trust. That’s a big area for me.

Secondly is skill set. I’ve not built a company to this level of scale before and I’m having to level up my own skill set, my own knowledge of tools, processes and opportunities to automate things in a way that I’ve never had to. That’s exciting to me. That’s exactly why I love the role. It also means that if I’m not doing it effectively, the company’s going to lose out because of it. I’m constantly looking at where are my shortcomings, what are the processes I can learn about, what are the role models at an organizational level, we should be looking at and what can we learn from them.

We spend a lot of time at the COO Alliance talking about the CEO-COO relationship and the skill sets that have to be developed there with communication, handling good healthy conflict, growing. Normally for both parties, it’s the biggest company they’ve have run. How are you and Nathan as CEO, working on your communication skills and growing together as a CEO-COO team?

We have the great gift of having known each other for years before we worked together in being very good friends. That’s also a great challenge because it means that you bring existing relational baggage into our working relationship. That’s been challenging for us. It’s like a marriage. It’s that level of relationship in terms of how many hours you have to spend and how closely you have to work. In making this transition to COO, one of the key things that we did was we put in place a daily stand up for Nathan and I. We have at least 30 minutes every day where we’re setting an agenda. We’re having specific conversations about the biggest things that are changing in the business to make sure that when we go to the teams, we’re not having conflict in front of the team. We’ve already talked about the major issues so that we have alignment and we can facilitate conversation instead of he and I trying to figure out where we’re each at on the issue.

Walk us through how your daily stand up works then.

We’ve implemented this new practice. It’s the idea of a stoplight at the beginning of every meeting. We say, “How are you doing?” personally, green, yellow, red and why? We start every one-on-one with green, yellow, red. That tells us, our capacity on that day to have deep, challenging and conflicting conversations versus just needing to connect and hear each other out. Green yellow usually indicates that we can dive into pretty much anything. Yellow is saying we’ve got to be a little bit more careful about how abrasive we might be with one another on a given day. Red says, “We need to connect to touch base and then we’ll call it quits.” That’s the first thing. The second thing is we’ve already made an agenda. It’s nothing fancy. We maintain it in Google Doc. We had a new date at the top and we had our three or five bullet points and we run down the list. We prioritize by the most important issue for helping the teams move forward or that they need our input on. We take notes right there in that document and leave with action items at the end of it and then get onto the next thing.

It’s the rigor in that process and I love the head check just to make sure that the other person is ready. Do you do that in your one-on-ones with your direct employees as well? 

We do.

It’s such a powerful process because there are days when you’re not ready to talk about anything at all. There are others when you’re ready to dive in for sure. You mentioned a couple of times around how you’re using Basecamp and you use it as almost a place to build out the projects before they get proposed, not only to manage projects you’re working on as a company but also to build them up before they get pitched team. How do they use it for that?

One of the features in Basecamp that we love is their message board feature. There are two heuristics in Basecamp. One is teams and one is projects. Each team, the company has its own Basecamp area and then each project we’re working on has its own Basecamp area and each team has a message board. Each project does. Within teams, including the HQ team, which is everyone, anyone in the company can type up a proposal for an idea or share something that they’d like to share. We’ve used that for a variety of purposes overtime.

One of those purposes is that we’ll write almost like an internal blog where someone has a concept or a culture-building idea that they want to share with the rest of the team. They will write it up just like you would have blog posts and publish it there. Another one is that we might have an idea for a project we want to pursue. It would be like a project pits, overview, a summary of what it is, the objective of why we might do it, and the details of the idea. That allows for a comment feed afterwards for people to weigh in. We do that at different stages of projects. Once an idea comes in on a name for a new project or working on a logo or whatever, then there’s this opportunity for the rest of the team to comment on it as well.

It’s almost like because you’re remote, you’re being forced to have these amazing systems and processes in place for everything. You’re forced to use the design to be used. A lot of companies miss out on that because they are all local and in the same office. They get lazy.

You have to work very hard. We have to work very hard to communicate. The challenge that it does create on the other end of it is that at times there can be so much information flowing that it’s easy for things to get missed. The challenge we’re actively trying to address is how do we make sure the right people on the team get the information they need without being distracted by everything?

Do you use Zoom to communicate, like video conference with each other?

SIC 16 | Email Software

Email Software: Have specific conversations about the biggest things that are changing in the business to make sure that you’re not having conflict in front of the team.


All of our one-on-ones and team meetings are through Zoom on video.

That also helps with the culture side. The final question just dawned on me when right at the beginning you said you’re in the middle between all these different competitors. How do you as a company and how do you keep your employees focused on your vision of what you guys are as a company versus being distracted and pulled in all those different directions?

It’s a regular struggle. There is a certain amount of competitor analysis that’s healthy. It keeps you trained on what the market is doing and where it’s going. There’s a certain point where you have to say, “That’s great. We know what they’re doing, now we’re going to do us.” The thing that keeps us grounded is being connected to this specific group of people we’re trying to serve. It’s the YouTubers and the musicians and the photographers and all of the creators that make up our market. They will guide us. They will tell us what they need and what they need is often very different from what any given competitor might be building at any given time. The anchor we always try and tie it back to is know what the competition is doing, but always build the thing the creators need, not what someone else’s building.

That’s so simplistically brilliant too. I had dinner with a CEO over in India years ago and he said, “Americans are so crazy. You all try to build products that you love and sell things to people that don’t need them or haven’t asked for them.” I was like, “What do you do?” He goes, “We have a billion people over here. We just ask them what they want and we sell it to them.” It works. Barrett, thank you so much for sharing all your ideas with us and the wisdom. I really appreciate it. I guarantee I’m going to be coming to visit you and hang out with you when I’m in New York City.

That’s great. I would love that. Thanks for having me.


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About Barrett Brooks

SIC 16 | Email SoftwareI’m the COO at ConvertKit, a bootstrapped, $14M ARR email marketing software startup where we’re on a mission to help creators (musicians, filmmakers, chefs, outdoor adventurers, and others making original work that builds our culture) earn a living. We help creators create and grow relationships with their audiences and customers through email marketing.

I’m a servant leader with experience as a management consultant, founder, startup executive, and non-profit board member.

My superpowers are helping teams fulfill their potential, building community through meaningful relationships, bringing crazy ideas to life with remarkable quality, researching and teaching complex topics, and creating, communicating, and inspiring others to chase a big vision. I layer in my experience with process improvement, change management, finance, and accounting to help create strong operational efficiency.



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