Meet the CTO who doesn’t shy away from conflict

The big picture

Arguing at work is healthy

This is the latest installment in Protocol's Calendar Series, where we take you inside a day in the lives of the world’s biggest tech execs: the meetings on their agenda, how they manage their time, their best productivity hacks and what they prioritize in a busy day. Read the rest of the series.

Marcelo Cortes is a co-founder and the CTO of Faire, an online wholesale marketplace connecting mostly small brands to independent, local retailers. It’s also a rare Series G company, with a $416 million funding extension to its latest funding round in May that put its valuation over $12.5 billion.

A lot of Cortes’s meetings are about fixing growing pains. “With our growth, things break very often. Processes that worked for 100 people stop working for 200. They definitely don’t work for three or four hundred, which is where our engineering org is right now,” he explained.

This philosophy extends to his office hours, which are open to anyone at the company. If nobody has any questions for him, he’ll turn it back on them: “What’s not working?” he’ll ask, adding that he can only help fix problems that he’s aware of.

As a leader, Cortes doesn’t shy away from conflict. His weekly meeting with the rest of Faire’s executive leadership team is called “Debate,” because “we want to send this message to the company that debating is a thing that we should be doing.”

I spoke with him about a typical day in his life: in this case, Monday, May 16.

His schedule has been edited for brevity and clarity.

8:30-9 a.m. | Carolyn/Marcelo: Weekly kickoff

Carolyn is my EA. Every Monday, the first thing we do is meet to go over the week: anything that’s very important that we need to accomplish. We resolve conflicts in the calendar; there are usually two or more conflicts that we need to figure out what to do with. Which one do I keep, which one do we postpone, or can I replace myself with somebody? There are always conflicts, because people add things to my calendar that will overlap with something else.

9-9:30 a.m. | Planning block

The planning block is me cleaning things up on my own. Especially Monday mornings, there will be a ton of messages on the weekends, emails, Slack, texts. I won’t answer them all, because there is no time. But I look through and pick at least the ones that are very high priority or important, and I try to deal with those.

This is also the time I have for myself to think about if I’m presenting something at one of the meetings that I have later in the day, to prepare myself to [do] it, think about what I’m going to say, write it down or something like that.

9:30-10 a.m. | Ryan/Marcelo

Ryan [Fioravanti] is one of our directors of engineering. At Faire, we have what we call pods, as well as pillars that encompass pods. Engineering, product, data science and design. Ryan currently leads two of our pillars, and I meet with him every two weeks. We always discuss, if something is broken, how to fix it or how to improve processes.

10-10:30 a.m. | Mark/Marcelo

Mark leads our brand pillar, so the same meeting with another person.

10:30-11 a.m. | Jeff/Marcelo

This could have been Jeff [Kolovson], our COO, or Jeff [Hodnett], one of our engineering leaders. More likely on Mondays I meet with one of our engineering leaders, like our head of engineering, Paul Poppert. But typically, I go over any People issues that we’re having, or we’ll discuss, for example, our feedback and promotion cycles.

11 a.m.-12 p.m. | CTO office hours

During COVID, we kept growing, and we hired a lot of people. After two years of not meeting people in person as often, I started to feel disconnected from the org. Before COVID, I knew every single person in the office. I had met them in person. We had spent at least some time together. I felt like I lost some of that connection.

Office hours is one experiment to try to close some of that gap. It’s very random. Anybody in the company can join. I don’t send the invites to everybody in the company and don’t advertise it too much, only to Engineering, though everybody’s welcome. People might ask about fundraising, about engineering strategy, about problems that we have, something that is not working or working well. They might ask about the interviewing process.

The number of people who join goes sometimes from 10 people to 20 or 30.

12-12:30 p.m. | Lunch

When I do have a lunch break, I will make sure to eat in the lunch room, because, again, I will find a spot that I can see people I haven’t interacted much with before, so I can get to know them and spend some time again with random people in the office.

12:30-1 p.m. | Weekly Leads

Weekly Leads is when cross-functional leaders from around the company meet. We pick a few random people to talk about personal things, how they’re feeling as well, if there’s anything top of mind for them that they want to share with the group. We don’t have time to do everybody, but we pick four or five people every week, and then Max [Rhodes], our CEO, shares his top-of-mind, the things that are most concerning to him, his priorities for the week. It’s also a venue that we use to communicate to the company any important information that we need to share or something that’s happening or coming.

1-1:45 p.m. | Debate

Debate is my most important meeting. This is the core team — our executive team — and sometimes a few other people join. It’s the weekly meeting where we have a very long list of topics that we keep that are important for the company that we discuss how to handle — from fundraising to big media events — or if there’s something that we need to address with the whole company, we will discuss there.

We know one of our values is to be kind, and we are very kind and respectful of each other. But we think having open debates, people exposing ideas and debating, discussing, arguing about them is a very healthy thing that we want to promote. In the early days, it was just three or four of us getting into a room and debating any topics that people would bring up, and we kept that name.

1:45-2 p.m. | Think break

Usually this time gets taken over by something that I need to deal with, an employee who needs to talk with me or some urgent issue or something’s on fire, and I need to deal with it. But if not, it’s my time to go to the washroom.

2-2:45 p.m. | Zoom interview: Director, Engineering

I usually do, on average, five to seven interviews a week. We haven’t slowed hiring, and we have very aggressive hiring targets for this year. We interview a lot. It’s hard to keep up.

I have a framework for assessing people at this level. There are specific areas that I try to ask questions to see how they score: One is how they think. The other is how they execute, how they lead, how they influence and their EQ.

Basic questions I ask include, “Tell me something that you did that you’re very proud of. And why are you so proud of it?” Or, “If I were to meet with people that report to you directly today, what are they going to tell me about you? What do you need to improve on? What do you do very well?” Or turn the question to say, “What if now I were to meet with your leaders, executives in your company? What would they tell me?”

2:45-3 p.m. | Interview buffer

3-4 p.m. | Zoom interview: Senior front-end engineer

I don’t do too many of these anymore. Only very rarely if we’re really on the fence about the candidate, or if it’s someone very senior, I might interview them myself. But that’s a very technical coding interview.

4-4:15 p.m. | Sync: Neervi/Marcelo

There probably was a topic that we needed to deal with, which could be engineer compensation bands or some People issue that we have. I meet with Neervi [Shah Patel, Faire’s head of People] almost every week for about half an hour to go over everything that’s happening in HR, People or the Talent team.

4:15-5 p.m. | Bi-weekly engineering all-hands

This is a venue for us to communicate with the whole engineering team. We will introduce new hires to the company, do shout-outs, recognize great things that have been achieved in the past two weeks, and a manager might highlight an example of somebody living our values or building something really cool. HR might have something to tell the whole company about some adjustments or some change. Usually I close it with some topic that I want to bring to the attention of everybody.

6-7 p.m. | Family dinner & PM workout

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