Ep. 191 – Time Doctor COO, Michael Koenig

Our guest today is Michael Koenig, the Chief Operating Officer of Time Doctor, a remote company made up of 150 people spread across 40 countries. He was brought on in May 2020 to operationalize the company during a phase of explosive growth and to scale the organization.

Michael is a passionate promoter of remote work. He got his first taste of it as an early employee at Automattic, the makers of the website platform WordPress, where he spent six years helping increase their market share to power over 35% of websites.

Through his years of leadership experience at Automattic, Time Doctor, and Sweet, he participates as a Techstars mentor and serves as a board member and advisor to startups and nonprofits.

In This Conversation, We Discuss:

  • How Michael was able to lean on good mentors for guidance
  • Lessons learned from working remotely
  • The benefits of helping your employees excel in their roles
  • How someone who wears a lot of hats in a company is able to succeed
  • What Michael was able to get right as COO through experience


Connect with Michael Koenig: LinkedIn

Time Doctor – https://www.timedoctor.com

Tech Stars – https://www.techstars.com/

Connect with Cameron: Website | LinkedIn

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The post, Ep. 191 – Time Doctor COO, Michael Koenig, appeared first on COO Alliance.

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Michael Koenig is the Chief Operating Officer at Time Doctor, a remote company made up of 150 people spread across 40 countries. He was brought on in May 2020 to operationalize the company during a phase of explosive growth and to scale the organization. Michael is a passionate promoter of remote work. He got his first taste of it as an early employee at Automattic, the maker of the website platform WordPress, where he spent six years helping increase their market share to power over 35% of websites. Through his years of leadership experience at Automattic, Time Doctor, and Sweet, he participates as a Techstars mentor and serves as a board member and advisor to startups and nonprofits. 

Michael, welcome to the show. 

Thanks for having me on. I’m delighted to be here.

I would love to go back into some of your past and then I want to talk a little bit about what you’ve pulled from being involved in Techstars as well. Why don’t you walk us through where your career started and what got you here? 

It’s been quite a serendipitous route, to be honest. What I mean by that is I studied Philosophy in college, which, as one of my friends says, prepares you for everything but also prepares you for nothing. When I got out of college, I played the bass guitar and ended up falling into a band with two other venture capitalists and some other famous folks. It was an “80s punk cover band. I hated the music, so they named it the Michael Koenig Experience to spite me. They liked me and took me under their wing. One became my mentor, and he got me into tech. Going from philosophy to tech, it’s pretty serendipitous there in terms of making that connection and finding that first mentor to bring me in.

Beyond that, I started off in early-stage tech companies and had the opportunity to wear many hats, which is something that you always get to do in those early companies and early days where it’s all hands on deck. Everyone needs to do what they have to do. I was fortunate to learn from some great folks along the way and go through a couple of M&A activities on both the sell and buy sides. Eventually, I landed at a company called Automattic, which, as you mentioned, makes WordPress. That was a real journey in terms of being a very early employee and helping build this company that was entirely remote. When we joined, I was twenty. We were 30 people and spread across 25 locations without an office.

Seeing that company and being part of the journey to build it to a couple of hundred people across a couple of hundred locations and helping turn that into a juggernaut for web publishing was a real eye-opener. It started to train and prepare me to move into that COO role. You mentioned Techstars. The way I joined Automattic was through the acquisition of a company called Intense Debate, which came through Techstars the very first year back in 2007 in Boulder, Colorado. Techstars is a mentorship program. It provides initial capital but is about helping develop the business model and tell the story. Sometimes, first-time entrepreneurs and sometimes, experienced entrepreneurs build out their companies. It’s something that I’ve been a part of since 2007.

In 2014, I had the opportunity to join a company that I had been mentoring. First, as their VP of Business Development, so I have a lot of experience on the go-to-market side and then later as the Chief Operating Officer there. That was my first time entering into the COO role. It’s quite eye-opening. Lots of serendipitous connections and folks that have been generous with their time over the years to teach me.

What do you think that you picked up then through your time? By the way, quick question on studying Philosophy at the university. Are you sure you studied Philosophy? 

I don’t know. It’s possible that I was a brain and a vat being stimulated.

Are you even sure you were at college? 

I am sure. Who knows?

That’ll keep you awake. Making that transition and getting into early-stage tech and then some of the experience at Automattic, what do you think the experience that you pulled out of Automattic was that you carry with you now? I want to go into your first COO role before we go over to Time Doctor

There are a lot of different experiences. One of the things that have stuck with me, and I’m very fortunate to call the former CEO a mentor, was those early-stage companies are quite turbulent. It can be a rollercoaster where you have lots of ups and downs. One of the things that I pulled away from Automattic was the steadiness of the leadership, where you knew that if there was a fire, these folks could put it out. We had full confidence that we were in good care. That stuck with me over the past decade in terms of the role of leadership in providing that stability and keeping everyone focused. That’s part that is applicable regardless of the stage of the company that you’re in.

The role of leadership is about providing that stability and keeping everyone focused.

Certainly, there were lots of lessons learned from scaling, growing the company, and being in tight competition with other blogging and website platforms out there. The first thing that comes to mind is the steadiness of the leadership. I asked Toni, the former CEO, “How did you guys do it?” Toni reminded me, and he said, “It’s all about focusing on the long-term strategy. When things get turbulent or you see a new upstart within your field who has great, very cool features, and they’re getting tons of press, or you lose a big customer, it stays steady. Focus on the long-term vision. Let’s not get distracted and let’s remember what we’re doing. Our strategy is sound. Our tactics are great. We’ve built something amazing, and we need to stay focused on where we’re going in the long-term.”

That’s a huge lesson. It’s interesting that you brought it up so early as we were talking. I was thinking when you mentioned Techstars and Brad Feld. Brad has spoken a lot about the bipolar nature of entrepreneurs and how so many entrepreneurs are manic-depressive. Brad has struggled with bipolar. I’m bipolar. There’s a lot of medical history around the medical community called Bipolar Disorder, the CEO disease. 

I don’t think it’s a disease. It’s actually one of our strengths. The mania is why people quit their job and join us. It’s interesting that you saw that team and the steadiness and you brought that with you. Let’s flip over from there and then talk about your first time as a COO. What was that like in getting involved with an early-stage company as a COO and starting in your first role in transition into a COO? 

The initial role of business development was something that I was very comfortable in and had been essentially training for over the past decade. That was a very easy transition in terms of some of the operational aspects that weren’t solely focused on the go-to-market. I’d had exposure to legal and contract negotiations, understanding different data privacy laws, and things of that nature, which were pretty nascent at that time. I hadn’t had a whole lot of experience in HR, for instance. I’d had great people that had taught me and I had seen HR working at scale. It was very much a trial by fire, but I had seen it done well, so I knew where I needed to get us to.

It was like, “Here’s the end goal. What are the tactics to make that happen, create an amazing employee experience, or make sure that we’re compliant with all of the different applicable regulatory items.” Looking at what’s the financial health. Certainly, that was something that I’d had exposure to previously running different PNLs. When you take that mantle of leadership and the responsibility for all of the GNA, that was definitely eye-opening. I leaned back on my mentors and said, “How do I do this? What’s the guidance like?”

I was very fortunate that it wasn’t a particularly rocky transition. I have been very embedded in the company to date and have fostered a great relationship with the CEO. We had gotten to the point where there was implicit trust between us. That made things much easier where it was, “You have certain domain expertise. I’ve seen you operate. I know that you have this experience. I’m not entirely strong in this part, and I need to remove myself from those day-to-day operations so I can be that figurehead.” I’m speaking on behalf of the CEO. That also made it an easy transition as well.

You mentioned something that I thought was interesting. I may be paraphrasing, but it seems like you felt you needed to have some of the hands-on experience to understand the business area of HR versus the theoretical experience. Do you think that a COO can actually function well as a COO without having been through some of the battles? Can they study it in an MBA program and come out and say, “I can be a COO?” Do they need to go through some of the actual practical hands-on to get it?

I can’t speak to an MBA coming out. There’s certainly something to be said for having that firsthand experience. More importantly, it’s about hiring the right people and bringing on an experienced team who you can hand over the reins and say, “In the instance of HR, there’s no way that I’m going to get the practical experience that a seasoned HR leader has.” I may be able to fake it until we make it and get to that point. There’s no substitute for bringing on people that are better and smarter than you. It becomes more along the lines of managing, making sure they have all of the resources they need, and an environment in which they can operate, execute, take risks, and have the psychological safety to fail. You can only get so much operating experience before you need to bring in a specialist.

SIC 191 | Time Doctor

Time Doctor: It’s about hiring the right people and bringing on an experienced team to who you can hand over the reins.


You mentioned leaning on some of your mentors. How would you lean on them? How would you reach out to them? What would you say, and how did you find good mentors?

I come back to that serendipity, but that’s not always repeatable. If you are looking for mentors, what I found to be very effective was to know specifically what I was looking for advice on. More often than not, people were very willing to hop on a call with me because most COOs that I’ve spoken with have had a similar situation where they were a beneficiary of having great mentors to share that advice. That’s also part of the Techstars ethos of give-first of that mentorship. In terms of finding those mentors, it was about positioning myself to be around those experienced folks. Techstars was certainly a phenomenal platform to be able to meet folks.

Beyond that, it’s almost cold calling, sending a message on LinkedIn, guessing email addresses, like Cameron@COOAlliance, and reaching out, but with a very pointed and specific question of, “I’m going through X. This is the stage of my company. Here’s what I’m thinking. Could you even take five minutes to review this and respond with two sentences? I’d be grateful for it.” More often than not, people were willing to give me those few minutes and get back to me with good nuggets.

It’s almost impossible for someone not to respond when you structure it in such an easy way and short ask. You frame it in such a good way that it’s hard. You’re right. Everyone is successful and has had someone that has helped us get there as well. Part of being human is the desire to help others. We have hardwired in us that we want to help others as well. There’s something there. Let’s change direction a little bit and tell us about Time Doctor. What does Time Doctor do and how did you get involved in that organization? I want to go around in a couple of circles here in a second.

Everyone successful has had someone that helped them get there. Part of being human is the desire to help others.

Time Doctor is a time tracking and productivity Software as a Service. What we do is we give both employees and companies visibility into where they’re spending their time. There’s very much a mentality of, “You can’t change what you don’t know.” When I started using it, it was quite eye-opening where I was spending my time. Also, as a COO, I was able to track the categories of the work that I was doing.

For instance, if I was spending too much time on legal, that’s not necessarily the best use of my time and maybe it’s time to bring on someone to augment what I’m doing. Time Doctor is very much a work insights company that shows you what you’re doing and how to improve. In terms of how we got connected, I’ve been a passionate promoter of remote work. As I mentioned, Automattic is completely remote.

For me, when I joined Automattic, it was freeing that I could now control the environment in the four walls of where I was working. I started having a different work-life balance. I could move around the country without fear of losing my job, but also the opportunities that it created for folks outside of the United States to work for a San Francisco-based tech company. Remote has the power of breaking down those geographic barriers where you don’t need to be within a 25-mile radius of a headquarters in order to have an opportunity. That was eye-opening for me in terms of the different cultures that I got to interact with. I hadn’t thought of it like this, but I was talking with one of our team members at Time Doctor who’s located in Turkey.

One of the great things he said about working at a remote company was he gets to interact with people from all different countries and walks of life and cultures. He likened it to traveling the world in every conversation. I thought that was so interesting to put in that frame because when else would I have had the opportunity to day in, day out work with someone in Sophia, Bulgaria or in Japan, Tokyo? I found it so rewarding, and I always consider it, “Don’t discriminate based on geolocation. Take the best talent wherever they are. Let them work from wherever they are.”

SIC 191 | Time Doctor

Time Doctor: Don’t discriminate based on geolocation. Take the best talent wherever they are and let them work from wherever they are.


What year did you start at Automattic?

This was in 2008.

It was pretty early in the whole digital nomad or remote workspace. The internet and the WiFi had been around for a couple of years, but the ability to have laptops, digital access, be global, and Zoom was still new. I don’t think Zoom was around them, but Skype was early. You were pretty early in. What did you learn from being a remote company back then that still works because people are just learning it now, and you’re thirteen years into being remote? 

I think about the success of Automattic. It is rooted in open-source technology. WordPress itself started off as an open-source project. If you think about how open-source works, a lot of people from around the world contribute towards the same project. That happens remotely and asynchronously. It’s very rare that you get to interact with those folks that you’re developing a product with. There’s an inherent toolset that you use and a mode of operating. This is back, as you mentioned, before Skype. We were all in IRC and working together on that. For Automattic, it was very natural to continue on with that open-source framework.

Matt Mullenweg, the CEO, was a pioneer and continues to be a pioneer in remote work and saw the value of being able to collaborate with the best minds in the world and build great products. Oftentimes, especially with the early team, predating my arrival, they hadn’t met each other. I recall a story that had been shared by Matt, where there was a developer, Nikolay, who had been working in Sophia. They all thought that Nikolay was 28 years old. That first-time years-in to having worked together, they met, and Nikolay was seventeen years old. Think about that.

This is a massive piece of software that changed the internet. I can’t think of another instance where Nikolay must have been fourteen when he started working on WordPress, where you have a fourteen-year-old working with seasoned entrepreneurs and engineers. Think about the interview process. Nikolay’s resume was probably nonexistent or washed out immediately. He became and continues to be one of the most important core contributors to WordPress and to building Automattic.

Matt was one of the early-stage uber-successful entrepreneurs in the digital space. What was it like working with him? 

The lesson that I took away from Matt is his patience. Matt is so disciplined in the long game, the big picture, and thinking about what he wants to be as a company and, importantly, what he doesn’t want to be. There were a lot of potential business models that he could have pursued. I don’t know his mind necessarily, but this was my read. There were lots of business models that he could have pursued around WordPress. If you think about the nature of WordPress, creating the freedom to publish, having the ability to build a site, get on the internet, and have that outlet, in some cases, freedom of the press within authoritarian countries. There was a real focus on the product versus maybe becoming a hosting site. That could have certainly been a lucrative opportunity that he could have pursued.

Matt, very early on, said, “We’re not a hosting company. We’re a software company. We’re here to democratize publishing.” WordPress is years old now, and the software has never gone away. His patience and focus on the long game were truly remarkable, and especially the team focused on rolling out complimentary products that contributed to the ecosystem. These weren’t necessarily products intended to generate profit or revenue but were rather products that contributed to that ecosystem. I always took away those patients and focused on the long game that he’s had.

Certainly, for some of those products that may be 6 or 7 years into their existence, there were monetization opportunities. He didn’t start off with the concept of, “I’m going to build this, and it’s going to bring in X dollars of revenues.” It’s more along the lines of, “This is going to enrich the ecosystem. Maybe there’s an opportunity to make money off of it at some point, but this is going to be good in the long run.”

That is the core of what made him successful or what made it successful. It’s funny that you mentioned the hosting because I was going to mention that one of the very first clients I coached for two years was the CEO and the leadership team at Media Temple. WordPress would send 10% of Media Temple’s clients. I coached Demian Sellfors for two years. He’s the CEO there and he was always talking about the partnership with WordPress and how well it went. 

I was always in awe that he could have ever pulled that partnership off. He’s like, “We were both small companies. I talked to Matt and Matt thought it was good. He wanted to do this and I wanted to do that.” Go back into the early stage tech world and the fact that you were wearing many hats in your roles. What allows someone to succeed when they’re wearing all these different hats versus the people that fail at it? Not everybody can run at that pace, manage the different complexities, have all the different hats, and be successful. What do you think made you successful there, or what are the lessons you can impart that will help people in that jack-of-all-trades, master-of-none early-stage role? 

I keep coming back to this focus where when you’re early stage, you are fighting to be alive every single day. It’s easy to have lots of fires that pop up and can consume you. However, not all fires are going to burn down the house. You have to choose which you’re going to let burn and you’ll put up. In the early days, it is sometimes whack-a-mole, and you’re constantly trying to, “Let’s put out this problem.” It comes back to the conviction you have around who you are as a company and what your product is. When it came to handling the customer-facing roles, one of the things that I focused early in on was customer service.

SIC 191 | Time Doctor

Time Doctor: When you’re in the early stage, you are fighting to be alive every day. It’s easy to have lots of fires that can consume you. However, not all fires are going to build and burn down the house. You have to choose which you’ll let burn and which you’ll put out.


Providing customers with a great experience and the knowledge you can get about who’s using our products successfully? Where’s this resonating? Who is our core beachhead market that ideal customer profile? Starting to understand that and taking those lessons to direct product development and creating that conduit between the voice of the customer and your engineers and designers, but also starting to identify that pattern matches around who is into your product. Using those lessons to drive business development, drive sales, strategic partnerships, and positioning.

This wasn’t intentional. It was based on need. I found a lot of value in that case. As I mentioned, I was mainly focused on the customer experience and on the go-to-market side at that time. I do think that there is a need to at least focus on what core competency you’re going to develop. The rest comes up based on need. That’s where you come in for that mentorship. Dating back to 2007, that first cohort of Techstars, the whole purpose of Techstars was to create a network you could rely on and go towards when you needed that help.

What do you think the core competency is that you’re working on developing then right now, or what has it been? 

I’d say that the interesting thing about Time Doctor is that we’re 150 people spread across 40-plus countries. While Automattic was and continues to be distributed in those early days, a good portion was in the United States. Time Doctor was founded by an Australian living in the Philippines. Of those 150, there were only 12 of us in the United States, and those are recent additions. The core competency I’ve been developing is around interacting with different cultures, which can be vastly different if you are interacting with folks from the Philippines versus folks from Ukraine or South America. The challenge is around communication and making sure that you are conveying a message that resonates across the entire company.

It’s easy to fall into the trap of speaking to North Americans versus changing how you interact and how you speak to folks from the rest of the world. I thought that I had this huge tool belt of how to work remotely. Here I am at Time Doctor and I’m learning something new. That has been exceedingly important and a real learning experience for me. Beyond that, it has been taking what I’ve seen work at Automattic and applying it to a company going through explosive growth. Time Doctor has been around for over a decade now. It started to pick up momentum.

It’s always been a tool for remote teams, but when the world went remote, this was a trend that we’ve been seeing gaining speed over the past decade. Suddenly, there are ten years of remote work adoption over the course of a month. The challenges around very quickly operationalizing a company that has been used to operating at a certain level but is now 200% bigger in terms of a customer base. The competency that I’ve been working on a lot has been around change management.

I’m over your shoulder. I see my favorite book Atlas Shrugged. I would imagine that most of your global team has not read Atlas Shrugged. Is Topgrading on that same shelf? 

It’s not. It’s a mix of spy novels, business books, and random things. I’ve got a book on fish. It’s an eclectic mix.

I want to go back to the part where you were in the COO role for the second time. What do you think you got right the second time around? What do you think, as the COO at Time Doctor, you’re doing better than maybe the first time around? 

The first COO role was gradual adoption. I had been used to operating within a company. Now I’m going into a very established company that has a certain operating cadence and system that has worked for it. Maybe it needs to change slightly, mature, and move into something that can support scaling a team and setting the company up for the future. In terms of what’s different this time around, I hit up a mentor when I first started, and I said, “I’m coming into this company. It’s getting huge adoption and growth. It has this history of not necessarily having the DNA that you would expect in a US tech company. They’re very different ways of operating. What would you do in my situation?”

He said, “It can seem overwhelming or a big operation and a lot to do, but it is all about four words. Who, does, what, when. Figure that out, go department by department, map the machine, and you’re going start to see what’s working well and what needs to change.” I found that to be a somewhat calming mantra that I have taped on my monitor here, along with a number of other things.

It can seem overwhelming. It can seem like a big operation and a lot to do, but it is all about four words: who does what when.

I’m sure my team is quite sick of hearing that from me. That has been highly instructive. Things can seem complicated, but they’re quite simple at the end of the day. You have to break it down to its simplest form. I’d say that that’s one of the things that I got right this time around. Certainly, there have been missteps, but the other aspect has been making sure we have the right people in the right seats.

It’s always critical for sure. I love what you’re doing with Time Doctor. In one of our COO Alliance Events, we did an exercise called an Activity Inventory. We pretended that people had videoed themselves for a month and wrote down everything they did on the video camera. We recorded everything and then tried to categorize all the stuff as to whether they were incompetent, competent, or had a unique ability. We tried to help them get some stuff off their plate. 

It was a unique exercise because people often look at what they’re doing, but they don’t look at the waste in terms of money. If you’re paying a COO $250,000 a year, you’re paying them $125 an hour. Why are they doing $30-an-hour jobs? You’re paying them eight times that they should be off their plate real quick. I want to go back to the 21 or 22-year-old Mike Koenig. You’re graduating college and you’ve got to reach out to a mentor who’s the current you. What advice would you give your younger self that you know to be true now? 

That’s a doozy. Another that I have taped on my monitor here is to stop and think. When I was younger, I would race to do something quickly. One of the things that I’ve learned is that something may seem pressing, but it’s going to be there tomorrow, and you don’t need to rush to get it done. There are very few instances in which you absolutely need to rush to get something done. It’s on my monitor because I continue to remind myself. It’s always something I’m working on because, as someone who is very action-oriented, it’s very easy to make the wrong decision. While there are always benefits to learning from that wrong decision, sometimes those can be very costly mistakes, so stop, think, and don’t rush.

What will the ramifications be further down the line, or is this important? We may have a very large customer screaming for something. If you rush to meet that need but don’t step back and look at it in the larger context of the business and the product you’re building, you might make the wrong decision and start to steer the company down a costly path.

Often, you can fix that one issue for one customer. If you don’t solve the root problem, now it’s being created for nine other customers the next week. If you haven’t solved the issue, you took care of it for one person. Mike Koenig, the Chief Operating Officer at Time Doctor, thanks very much for sharing with us. 

It’s my pleasure. Thanks for having me on.

I appreciate your time.


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About Michael Koenig

SIC 191 | Time DoctorToday’s an exciting day at Tucows; we welcome a new group of folks into the herd. As I think about our new employee experience, I’m reminded of something that drives me crazy.


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