From EM to Founder and VP of Engineering

Ana Rosas, Co-Founder & VP of Engineering, Valued

The leap from engineering manager to VP of Engineering while also being a co-founder can feel big. It can also feel like just the right challenge like in the case of Ana Rosas, Co-Founder and VP of Engineering at Valued. We talked about her early career aspirations, what made her take the risk to co-found an early stage startup and her advice for other founder leaders.

Hello friend. We've known each other for quite a while and so I'm not even going to pretend like I don't know you. We've known each other for five years I think.

Yeah, or more maybe.

For people who don't know you, can you just give us a quick introduction of yourself?

For sure. My name is Ana. I'm from Mexico. I'm a software engineer. I've been working in tech for around 13 years now, on and off. I had some breaks in between my master's degree, but I've been around for a while now. And now that I'm thinking, I met you back in 2018.

Yeah. We met through Travis. You started your career as a software engineer. Was becoming a manager and a leader a career goal in those early days or when you went into software engineering, was there a career plan that went into management leadership?

Not really. I was doing small plans at the time. When I graduated from Mexico, I was thinking more about the short term. So my main goal at the time was to live abroad, study abroad, and get some international experience. My next goal once I graduated from my other school was to have some international work experience and get actual professional experience. It was more on those two years, three years, and short-term goals. And then management came along after some years of professional experience, so it was more like baby steps and then just started thinking about the future.

It sounds like you had this clear idea that you wanted international experience.

Yes, that was for sure. That was like, oh, I want to either work abroad or work in an international company, work with people that have very different backgrounds, not only technical but cultural backgrounds. I think it's more, I don't know, it's more interesting but also, it gives you other types of ideas, another way to tackle problems. I really like that environment, to have people with different mindsets.

You and I both. I love those different mindsets and cultures. It’s the soup of being human.

Exactly.

You became an engineering manager at Travis CI. You became one before I officially started at the company. How did that come about?

By then I had been working at Travis for almost three years, so I had a good grasp of how the tech stack was working, how things were working, and how teams were working. I wasn't getting bored, but I was getting curious about seeing other things. When I started working at Travis, the team was smaller and we didn't have engineering managers back then, so it was mostly a tech lead and the CTO who were driving the teams. We had not complex organizational issues but we had some organizational issues. We weren't sure what things we should be focusing on and those types of things.

A couple of months after I started, the team hired an engineering manager. Before Travis, the other company I worked for was small as well. I was working directly with the CTO who was the one who was managing the team. So this was a change. It was the first time I worked with someone as an engineering manager. I got to experience what an engineering manager does, all the problem-solving for the organization, for the team, setting goals, and helping people reach their personal goals as well. It was interesting to see and I got more interested in that part. 

Two years after this person started, there were more managers but also the company was growing. One of the managers left. I’d talked with my engineering manager before this about being interested but sometime in the future. So when this manager was leaving, it came up in conversation, "Hey, probably it's too soon but if you're interested, here's the opportunity." It was the CTO who asked me directly. So I was like, "I don't know. Maybe." I gave it a thought. I talked with other managers to see what they were thinking and how the work was and all of that. It was a good opportunity and I already knew the team that I was going to be working with, so I was like, "Sure. Why not? Let's try it."

How was being an engineering manager different than you expected?

You change your role completely. Being an engineering manager is a new job. It's very different from being a software engineer, or an individual contributor. You don't have the time to do as much code as you were doing. Sometimes you don't even get the time to code. I was fine with it and I knew about that so I didn't have an issue with that. 

I used to work with computers and solving technical problems and then moving into management, you get to solve other types of problems. It's not only computer problems. Sometimes you help your team develop things, but also you need to help your team solve conflict and organizational stuff. There are other types of problems that you get to solve. That was not the tricky part, but it was something that I had to learn how to deal with.

You're right. Stepping into management is a new role. 

Yeah, it's a different job. It's a very different career. Of course, having your tech background helps a lot in being an engineering manager. That's for sure, but it's a different role.

I want to skip ahead to what made you become a founder and VP of Engineering. Was that an experience you had been looking for? 

Yes. I forgot to mention that in my introduction. We started the company a little more than a year ago. Of course, we started with a very small team. From the beginning, we decided to assign roles to the people that were founding the company because it's better to know what you should be focusing on. So I'm the VP of engineering of Valued. We're still a startup so we haven't launched yet, but we're building a product analytics platform. 

What made you become a founder? Was that something you were looking for? How did that come about?

It was in my mind for a while. After I became an engineering manager at Travis, I later worked at another company, Canonical. That was my first experience with a way bigger company. Before that, I worked with companies of less than 60 people. When I got to Canonical there were about 500 people. So it was a big change. I got to see and work with VPs and directors for the different departments. I got to experience more about how a company is managed and how it's developed. It made me curious that probably it's something that I would like to try one day, but I wasn't looking for it when this opportunity came up. It was in the background of my mind like, "Oh, one day, I should do it." But no, it was not something I was looking for, but I'm very grateful it landed at the time it did. It was perfect timing.

If you wouldn't mind talking a little bit more about how it came about? What was the idea? Was it the chance to work with the people you knew? What drew you to this opportunity?

It was a mix of things. The product idea was cool because it was something that we could have used at Travis. There was a chance to work with former coworkers who are also really close friends of mine. Working with people that I know are very experienced and I also know how they work, and how they like to manage the company. I knew their expectations and their goals when founding a company. 

Some of them are previous founders of Travis and part of the team is also new founders, so we have a mix. So it was good. It was exciting to have that and also to get to work with them again because I enjoyed working with them back in Travis. So yeah, it was a mix.

Did you have any trepidation or concern about becoming a founder leader? Or were you like, I'm ready to jump in? 

I thought, “Is this going to work? Is it a good idea?" I guess it's risky, right? A startup is risky, but I was like, "It's a good opportunity and it's something that I wanted to try." I also had more experience as a manager. I had a lot of ideas for things that I wanted to do as a manager and founder. I knew that being a founder would allow me to do those things. There was not another level that I needed to convince, "Oh, we should try this way of hiring. We should try this new policy." It will be on me to propose it to my fellow co-founders. I knew that I would have more impact at a company, even if it was a smaller company. I felt I was ready for that. 

How has it been working with the friends? Has it been what you expected it would be or is it different?

It's been really good. I’ve gotten way more support than I was expecting, but also, being friends helped with that. When I have needed to take some time off because of personal things, I have been really supported by them. When I wonder if I’m doing leadership right, I get feedback, and knowing they’re being honest is really good. That helps a lot. When your friend is being honest, it's easier I think. You can get the harsh truth and it's okay. For sure, we are humans and sometimes it's not easy to give that feedback but it helps.

How has being an engineering leader at a stealth startup matched your expectations?

I didn't have expectations. I knew it was going to be a lot of change because we are building something and as we are building it, we're discovering if we are right or wrong on our hypothesis. There's been a lot of adapting to those changes. It feels like it has been a rollercoaster, trying to get a new thing developed. You wonder, “Is this the right thing that we need to be working on?”  

I also knew that being a leader in a startup means wearing a lot of hats. It's not only engineering leadership. It's hiring, not only for engineering. We have to make a lot of decisions. Is this the right moment to hire someone? Is this the right role that we need to hire for? Is this what we really need or not? There's the strategy part, and as well, even some HR stuff like, are we doing this right? Are our contracts correct? I’m doing many different things that I haven't done in previous roles, but it's been interesting. It's been great. 

I get the impression that you like to challenge yourself and continue to grow, and this offers a great opportunity for you to grow as a leader, business person, and human.

Yeah, exactly. I think that's a good way to describe myself. I always like to challenge myself. Okay, I already did this. What's coming up next?

What's been most challenging about leading an engineering org that's pre-product market fit?

Developing a product from scratch has been a bit challenging. Getting everyone on the same page on what we're building, and growing the team as well while developing the product. All this cycle repeats. This is our goal, this is what we should be working on, and this is what's important. I feel like humans, we are creatures of habit so we need to repeat a lot of what we're doing and why we're doing it. Now that we have some employees, we have been working a lot on how we work as engineering and product teams so that, again, we are all on the same page, that people are working on what they should be working on and that we are building our product the way we want to build it. 

Being a founder and an engineering leader is a lot of organizational work. All the things happening at the same time is the thing that has been challenging.

We have a great team. I think they complement each other a lot in their different skills, but it has been challenging to get to know how they work and how to adapt the best workflow that works for everyone. While at the same time, we're building something because it's the first time I'm building something from scratch. For example, in previous jobs, the product already existed, and already had customers. We were building new features. In this case, we’re building the base of a new product. So that's as well, that has been challenging with growing a team, making sure everyone is on the same page in workflows and such.

Having that all happen at once seems challenging. Is it knowing where to prioritize and how to focus? Is it decision-making? What's hard about having so many things all at one time?

Knowing what to prioritize, like what I should be focusing on is hard. Should I be focusing on making clear the product part, setting milestones, or working with product to set the milestones, or should I be focusing to help the team find a workflow that works for everyone? Should we be focusing on getting updates from everyone? Deciding what's important? So that has been challenging.

We are very spread around the world, so time zones have been a bit hard because we have people in Europe, the Americas, and in New Zealand. For a while, we tried to have synchronous meeting updates. At least have engineering things synchronously because it's important right now. Things are changing so much that we need to make sure that we are all on the same page and that someone is not building something that they shouldn't or that we already thought should change from what we first said.

Yeah, that's critical at the beginning when you're this small, scrappy startup. You don't have a lot of room to just build anything or something that sounds fascinating.

Yeah, exactly. That's also another thing that I have learned, smaller milestones and reducing scope so that it's clearer and easier to tackle. We're working on it. 

Time zones are a big deal too. The spread is big. 

That spread means sometimes either Europe has very late calls at 8 PM, or 9 PM or New Zealand has early calls. I think it works a bit better for the Americas, but it can be very tough for the other time zones. We were hoping asynchronous meetings would help, but right now, it's working better to have actual meetings. We try not to do them every week and spread them out, but it's something that we are working on and trying to adapt as we see it.

When I was at Travis, I was in New York and Eastern Time, and people would chuckle when I'd say I would never have done that role in any other time zone. I didn't have to flex my schedule that much. I got Europe and I could also catch the Pacific Coast Time folks in the states.

Totally. It's tough. I had to have late calls last summer and I was just recovering from COVID and it was tough.

Those small things can matter especially when you're a small, scrappy startup that's trying to get started, making sure that your health is good. 

Yeah, for sure. I think being healthy is one of the things that will help you the most when you are building a company or at least having some kind of good health. We cannot all be a hundred percent all the time. 

Do you feel any more pressure as a co-founder than you did as an engineering manager? 

I do feel more pressure, but I also think I put that pressure on myself. It's different when you're a co-founder. You are trying to build your company, getting your baby growing and out to the world. When you are an engineering manager at a company, you're an employee. You don't have the same attachment to the company. You also feel responsible to your employees. You want them to be well, to succeed at what they're doing, and to have a good environment. It's so easy to mess up things and so you just try to have things right and help people reach their professional goals as well. It's a pressure to get everything in balance, and have the company succeed but also people feel they're succeeding as well.

What's been most gratifying about leading an engineering org at a startup?

Although it's been hard and challenging, building something from scratch and seeing it taking shape, is very gratifying. Thinking about what's next, what we should be working on next, what we should be planning, what resources we need, and what we should be working on. All of that, it's very exciting for me. That's really nice to see.

Also, building a team is gratifying. As I said, I think we have built, I think so far, a really nice team and they complement each other. It's really nice to see how they are working together, how they have adapted, and how they're interested to know more about what we're building and why. That's really great to see.

Building something from scratch is hard and it's also the most gratifying thing at the same time is what I hear you say.

Yes. Challenges.

Both oh my gosh, and also, oh my gosh.

Exactly. You have them both. Sometimes it's like, oh God, this is not working, and then, oh, this is working.

Yeah, I think it speaks to that rollercoaster. It's both the best thing and the hardest thing at the same time, which is my favorite zone of working.

Totally.

What advice would you give to other first-time founder leaders?

Making sure you maintain a work-life balance is important. You're going to do way more for your startup company by being healthy than burned out. It's very easy to find yourself in a cycle where, oh, I need to get this done, I need to get this done, and work on weekends or work long days. In the long term, it will just burn you out. So I think it's very important to keep that work-life balance. 

Talking with other founders is good. I think you can learn a lot from other people and you will be surprised by how many issues other people have already been through, and probably hearing them will avoid you from doing them. I don't know how to build a brand-new product. That's probably an issue other people have had.

Learning from people's mistakes also helps. In talking with other founders from other companies they may introduce you to people that will be interesting for you, for your company, or possible clients. Even just learning from what they're doing is good.

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