How my co-founder and I structure ourselves as CEO and COO

For the first two years of Buffer we didn’t use C-level titles. In February last year it started to make much more sense for me to use the CEO title, and soon after Leo became CMO. We had grown up a little and were not just a bunch of people hacking on a product. There was a little more structure and it was helpful on the inside and from the outside to reflect that.

For half a year Leo used the CMO title, but it never felt quite right. The CMO role felt quite narrow and specialized, and Leo had much more to contribute than that. He had always helped me to think through other areas. In addition, Leo has a real growth mindset which made sense for marketing, but also for much more than that. The company was growing fast and it made sense for Leo to have more responsibilities than purely marketing.

How we initially structured the COO role

I asked Leo to become COO in November last year. I wasn’t really sure how that would work and what it would change, but I knew it would definitely be different. It felt right, and exciting.

Leo and I spoke and reflected on the key strengths he had and how we wanted to have him involved in all areas to push us further. The title felt perfect since I would describe Leo as someone who really thrives with operations. He will always get everything done in his list, no matter what. And he’ll always choose to have more in his list than anyone else. This is something I’m incredibly inspired by.

We structured ourselves with the analogy of a train. I would be thinking about laying the track ahead in the right direction, and Leo would help the train to run on time and move fast. In practice, this translated to Leo being in sync with every aspect of the company and helping us to improve (product, customer happiness, marketing, growth). He’d sync up regularly with everyone and be someone who could help with setting goals and brainstorming how to keep to them.

Some struggles and learnings with the CEO/COO balance

One of the things that spurred the role adjustment for Leo was that we were right in the middle of going through our quiet pivot. We had realized that growth had slowed with the vision we were currently on, and we made adjustments. In some ways we were moving at our slowest pace for some time and we knew we needed to make some changes. We adjusted the vision and it felt appropriate to rethink our roles too.

We spent about 3 weeks with the “Leo kicks Buffer into a higher gear across all areas” setup. I think it was a welcome change from everyone in the team, however right away something didn’t feel quite right for me.

Leo and I were both excited about his role being to help us move faster. I was happy to try and stay focused on figuring out where we need to go in various areas and with the company as a whole. The problem we found, was that it was almost impossible to clearly separate these two processes. If Leo was working with someone to try and set goals and keep to them, he inevitably had to make decisions which affected our direction.

It felt like with the new structure we were suddenly both involved in every decision. The goal of the new role for Leo was to speed things up, but with both of us discussing every decision, things were sometimes grinding to a halt, especially in cases where we didn’t immediately agree.

This put a lot of strain on our relationship as co-founders, and it’s probably the only time I can think of in the whole lifetime of Buffer so far where I’ve had some really tough conversations with Leo. It was exacerbated by the fact we were hitting some of our slowest growth months ever and both felt pressure to pick things back up. I was confused and needed to quickly figure out why it wasn’t working.

How we came to the current CEO/COO structure

In the first week of December we were in Thailand for our second company retreat. It was during our time there that Leo and I had a lot of lengthy walking meetings around Pattaya about the structure of our roles. We talked a lot. I couldn’t think of a more perfect setting for us to figure these things out. We’re both optimistic people and despite the tough conversations we knew we’d come to a conclusion about how things should work. We had gratitude for how lucky we were to be in Thailand and had built a company to a stage where this problem had arisen.

I’m the kind of person who likes to solve problems. I guess that’s why I naturally enjoyed programming (though I rarely code anymore). Therefore, I always like to try and talk things out until we can agree. As an introvert, however, I often do some of my best thinking and have inspiration when I spend time alone to contemplate. So, after several days of discussions with Leo, one evening I took to my room and started reading up everything I could find about the COO role.

I was surprised by how many different definitions of the COO role there were out there. This really confused me at first. For example, one person may say it’s the CEO’s job to motivate and manage the team as a whole and ensure execution of day-to-day tasks, whereas another person may say it’s the COO’s job to manage day-to-day running of a company and help the CEO have room to think on a higher level.

Everything became clear to me when I found this key insight:

"There is commonality across different businesses between the roles of CMO, CFO and most other executive functions, but not so with the COO, where the roles are hugely varied. Maybe the best way to think about it is that the COO does the things that the CEO doesn’t." - Nic Brisbourne

If you look at the job descriptions of various COOs, you’ll find that they could be completely different from each other, sometimes even opposing. The reason is that it all depends on the strengths of the CEO. It was starting to make sense to me that the best CEO/COO relationships are when the two are very complementary to each other. This got me excited since Leo and I have always found we excel in different areas.

"A COO’s value is designed to be complimentary to the CEO. The truth is that no CEO, no matter how experienced, can possibly cover the complex aspects of managing all the functions of a technology company. Its better to divide and conquer. By recruiting a COO, the CEO can focus on the aspects of the role that he/she truly excels at and enjoys the most." - Firas Raouf

So I got to work brainstorming all the areas of the company and which I felt confident about running myself. Once I did that, it became clear how Leo and I should work together. I hopped onto a call with Leo to explain my discovery.

What Leo and I do as COO and CEO

When I shared my learnings around the COO role and how we could work together, Leo was receptive to the adjustments and we were both really excited for the new structure. We’ve used this structure for the last three and a half months and it is working incredibly well.

The key thing we have done is to determine our key areas of focus and embrace the idea that we should not be the key person running anything. It was a key learning that if we’re running something ourselves, we’re not doing it as well as it could be done and we’re also neglecting other areas. So we aim to fire ourselves repeatedly and move to a position where we’re helping with higher level vision, coaching and we’re “being reported to”. This has started to work very well, and it feels like we’re moving faster than ever.

Here’s how Leo and I work together now:

For a while, and especially after the previous experience of stepping on each others’ toes, we tried to make these areas completely separated. Over time, we found there is a lot of natural overlap. Our advisor Hiten shared an analogy which helped us a lot (I’m paraphrasing here):

"Think of it like Batman and Robin. So if Product leads a project, it’s Batman and Growth supports with the right numbers and is Robin."

This is how we approach everything now. The Batman and Robin method helps us have one person who makes that final call, but we can both support each other too.

How do you structure how you work with your co-founder or business partners? I’d love to hear any thoughts, questions or advice you have!

Photo credit: Hans Splinter

The Yin and Yang of a great co-founder relationship

I’ve always found it interesting to think about co-founder relationships. I’ve been in a few myself, some which were not completely successful and then more recently working with Leo for the last 3 years has been an absolute joy. It’s fascinating to me how co-founders need to be different in many ways and at the same time have shared values they are aligned on. It’s a real art to find someone who you work well with and trust.

I recently watched a video of an interview with DHH from Basecamp and found the audience question on co-founders interesting and very in-line with my own experiences on what makes a good match.

Complementing each other in skill-set

"When two men in business always agree, one of them is unnecessary." - William Wrigley Jr

I think it’s super valuable to have different strengths as founders. I often see fantastic products from great engineers and product people, where I believe the product should be used by far more people. It’s probably because the founders are not naturally inclined to do marketing, and so keep working on the product.

"I see a number of startups where the founders are too alike. Either they agree on everything or even worse they do the same thing. Like starting a company with two programmers - I don’t think that’s a good idea. I think you need skills, and you need mentality, to complement each other." - DHH

In the early days of Buffer, I reached a point with the product where it had a couple hundred users and some paying customers, and I knew in my head that I needed to switch to marketing. There was validation that the product in the exact form it was in, was already useful to people. There was clearly more people out there who would find it valuable as well. However as a developer it was a real challenge to be effective at switching to marketing instead of fixing bugs or building out new features. Luckily for me, that’s when Leo came on board as my co-founder and had a massive impact since he was a great marketer.

It’s also useful to have different mindsets on the business aspects too:

"For me and Jason on skills, Jason was all about design and I was all about programming. So that was just a natural fit right there. On running the business, Jason is more of a risk-taker and I’m more conservative. I’m more about running the numbers and making sure everything’s alright, and Jason’s more like let’s just rip away everything and try something new and take a leap. I think you need both of those things to pull the business in the right way." - DHH

For me and Leo, we’re both scrappy and take the lean mindset. At the same time, Leo is probably more inclined to push something out of the door extremely early, whereas I like to be a little more calculated and logical and get the best balance of learning and not wasting time by building something out without validation, but still shipping something quite polished.

One of the most interesting ways Leo and I complement each other is on “doing” vs “reflecting”. I often joke that if Leo and I each have a daily todo list with 5 items on it, there is absolutely no question that Leo will get through his 5 tasks. For me, I struggle at times to get through everything. I work hard to be productive, however I also like to take time to reflect on the direction we’re going and ponder changes. We both aspire to be more like each other in this regard: I’d love to just crank through more, and Leo says to me he’d like to reflect more and sometimes realize not to do some tasks. We talk very regularly and help each other, and we end up at a nice equilibrium.

Aligned with each other on values and vision

"At the same time, you have to have some overlap too. Jason and I obviously share a lot of opinions about how to run a business and what is important and our values are incredibly alike, in terms of creating a sustainable long-term business that does well for both its customers and its employees. So you can’t just be polar opposites and expect that everything’s going to be daisy. There’s got to be overlap on important cultural values in the company, but outside of that seek as much diversity as you can." - DHH

The hard part of finding a great co-founder is that you want to sufficiently complement each other, but at the same time it’s vital to agree on fundamental values and what you want to do with the company. If one of you wants to flip the company within a couple of years and the other wants to make it their life’s work, it’s going to be difficult to agree on key decisions.

From an early stage it became clear that Leo and I were very aligned on many of the values which became the Buffer culture. I introduced Leo to How to Win Friends and Influence People and we spent countless hours discussing the principles and examples. Leo has always had tremendous gratitude for the opportunities he has had and is one of the most positive and happy people I know, and that was something I aspired to focus on more. I always enjoyed being very open and transparent about my learnings and progress and this came completely naturally to Leo too and he enjoyed pushing us further in that direction.

How did you meet your co-founder and what are the key ways in which you complement each other? I’d love to hear about your experiences

P.S. We need help with many areas of Buffer right now, to complement the existing great team. Check out our openings