Employee #1: Warby Parker

by Craig Cannon11/30/2016

A conversation with Mara Castro, Warby Parker’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Mara Castro was the first employee at Warby Parker. She currently is the Director of Customer Experience.

Discussed: Working at a Nonprofit, Finding the Job Posting, Interviewing with the Founders, Starting Part-Time, Figuring Out Operations, Moving to New York, Going into Retail, Building the Brand, and Learning to Manage People.

Craig: So the easiest way to start is just to explain what you were doing before and go from there.

Mara: Sure. So I graduated from Texas A&M then went back to Brazil and was working with a former Formula One racecar driver, helping him set up his nonprofit. At that point I was pretty dead set on wanting to build a nonprofit that was going to do good for the world. So I started in Brazil but knew that I did want to come back to the US.

I was originally from Brazil but my father worked in oil so we lived around the world – UAE, Libya, Singapore, Venezuela – then I ended up moving back to Philly for business school and from there started working at a nonprofit called the Food Trust. So I got a lot of exposure to how nonprofits work in the US.

I loved the work that I was doing but felt like I wanted to do something more with a little bit more of a business background. I felt like I could add more value to the world instead of spending so much time fundraising and policy writing and that kind of stuff. As I was trying to look for something different, Jeff Raider, one of the co-founders of Warby Parker, put out a job description looking for an operations manager.

At that point the four founders were still in business school. It was November of 2009. Warby Parker was really just an idea. They didn’t have a website or anything but they knew that they wanted help from someone to set up customer service and operations in general.

Craig: Where was the job posting? Was it on Craigslist?

Mara: I think they had posted it in quite a few places but because my ex went to Wharton business school, it had been shared there to all of the students and he shared it with me.

Craig: Gotcha. Okay, so you email him and then you meet up. How does that go?

Mara: It was great. Jeff is one of those guys that’s just incredibly charismatic, super fun, really smart. We talked about everything that I had done before, what I was hoping to do in the future and it was just very, very natural–just casual conversation about what my experience was and then what the idea of Warby Parker was at that time.

Craig: And was the idea the same as it is now?

Mara: Yes, that’s one of the special things about Warby Parker is that from day one, they really spent a ton of time thinking through what the pillars were for the brand. They really wanted this company to be a lifestyle brand that was going to be here for the next hundred years. They wanted it to really revolutionize eyewear industry and they wanted to prove that for-profits could do good in the world. Those three main pillars are still the ones that really reign the company to this day.

Craig: Did he convince you with that in the beginning?

Mara: The pitch was really just that they’re four really smart friends with this great idea to sell glasses online, so many other companies were selling products online that never had before –you shouldn’t have to pay the price of an iPhone for glasses.

I started wearing glasses when I was maybe 12 years old and so I knew how expensive glasses were and how limited the options were. It just seemed to make a lot of sense plus, with my background of wanting to work somewhere that was going to do good in the world, it was just awesome to see how it wasn’t a marketing ploy. It was part of the brand and who they really wanted to be from day one.

Neil [Blumenthal], one of our co-founders (and current co-CEOs) was one of the first employees at Vision Spring before he went to business school and he had really set up the whole program and how that nonprofit worked. And we were just going to partner with them so that we could do work in a way that they knew how to do it best and we were just going to help them and achieve that in the best way. It just really felt very authentic, very natural so at that point, I was just like, “Okay, you guys need to hire me.”

Craig: [Laughter] Okay, so what happens next?

Mara: We were still just talking about it because they didn’t even have the glasses yet. They didn’t have a website. It was really just an idea at that point but they knew that they wanted help soon thereafter. And so we continued talking. And I think they received the glasses maybe at the end of December or January of 2009. They started doing some trunk shows with their friends and I came to a couple of them, got to see the glasses, got to meet the other co-founders, and actually did an interview call with Dave Gilboa who is currently my boss. They decided to launch in the beginning of February and I started February 1, 2010.

Craig: Did you move to NY at that point?

Mara: No. So they were still in school in Philly and school was going to go through June. So on February 1st, we were launching but not necessarily the website. It was more of launching the fulfillment process. So we were still doing trunk shows with their friends and I was helping process orders with our tech consultant, set up the whole process through NetSuite which is an ERP [Enterprise Resource Planning] that we were using at the time, and really just help set up the foundation. Then we fully launched on February 15th with the website and features in GQ and Vogue

For the first two weeks in February I was part-time, 15 hours a week, just helping with anything that came up. The launch of the website kind of kicked us into crazy mode. And that’s when my role turned into a hundred hours a week and basically that’s what it’s been since then.

From that point, it was just like, “Okay, this is really going to work. Let’s figure out how to make this work in the best way. I think it was April when we decided we were going to move to New York and started prepping for that move.

Craig: And so were you handling fulfillment in the beginning?

Mara: I was helping with a little bit of everything, right. At first it was just me but then we quickly hired four other people and also I helped train all of the founders’ families everyone we knew could help, because it got really crazy really fast. I was in charge of setting up all of the training materials, managing all of the folks, setting up the culture, working with inventory, supply chain and then helped with all of the talent on HR, setting up all of the assistants as well and office management. It was a startup, right? You do what’s needed.

Craig: Right, exactly. The job description doesn’t exactly match the job. So had you guys raised money at that point?

Mara: No. So it was all from the four founders’ savings at that point.

Craig: Ok. How many styles did you launch with?

Mara: That’s a good question. It was twenty-seven plus our monocle. At that time, a few very big, bold styles which were in at the moment and then a few toned-down frames. And then, of course, the monocle.

Craig: [Laughter] I didn’t even know that was a thing. Do people actually buy it?

Mara: We do get a lot of orders for groomsmen. But, I mean, it’s not our bestseller. [Laughter]

Craig: [Laughter] I figured. Ok, so you moved to New York and then what? Had you lived in New York before?

Mara: I had not, no. I feel like everybody has a dream of living in New York so it was very exciting to move here. So we moved to New York. We worked out of Neil’s wife’s back office. She had a jewelry line that she ran out of the garment district. So it was this tiny inventory room which became one of our first showrooms. Our first showroom was actually Neil’s apartment. [Laughter]

So we moved to her back office and then from there, we moved in August to our first real office in Union Square. At that point I think we had maybe 10 employees or so on our team.

Craig: At that time were you able to get a sense if it would last or if it was just this crazy startup thing that might implode?

Mara: No, we were definitely filling a need in the market for sure. Just from customer conversations I could tell it was a thing. We always wanted to make sure that every employee (and our founders) were interacting with customers. We had phone and email initially and we responded to each and every person individually even when we got the crazy spike in March. We were all working from 7:00 to 4:00 a.m. really responding to every customer. People would reply to the 4:00 a.m. emails being like, “I get it. You’re a startup. That’s totally fine. Take your time, but would love your glasses. This is amazing. This is such a great idea. Don’t know why nobody has tried this before.”

So it definitely felt like we were filling a need in the market and that we just had to figure out the kinks of growing pains to make sure that we had enough inventory for everyone.

Craig: I imagine the actual manufacturing process is pretty time intensive–learning how it all works and figuring it all out, especially in the beginning.

Mara: Yeah, definitely. So Neil did have some experience in manufacturing glasses through Vision Spring, the nonprofit where he had worked. He knew some of it.

The way our manufacturing process works is we get the materials from either Italy or Japan. We manufacture the glasses in China and then we ship them to the US. Now we have six labs across the US. They then cut each lens specifically to each customer and then ship those glasses, the completed glasses, to the customer directly from our labs.

It is a pretty complicated process and, honestly, none of us had worked in retail before, including the four founders. Setting up the technology that was necessary to track all of that inventory, to manage our customer orders in the best way, wasn’t easy. Do you know about the Home Try-On?

Craig: Yeah, but you should explain it anyway.

Mara: Cool. So the Home Try-On program, the way it works is you select five pairs and we ship them to you to try on and then you return them and can purchase your favorite on the site. So the first lab that we ever partnered with was in New York and they used to do not only do fulfillment of the glasses but our Home Try-On program as well. The way that it would work is that they would send out the Home Try-On glasses from their lab and then everything would get returned to Neil’s apartment in Philly.

Initially, it was just me going through everything and double-checking, making sure everything was good, cleaning everything and then putting it all in boxes and just carrying it over to a UPS to send it over to our lab so that they could start the whole process again.

Craig: [Laughter] That’s insane.

Mara: [Laughter] Yeah, it was pretty insane.

Craig: Were there other bottlenecks? How established were the labs and the manufacturers that you were working with?

Mara: The way that labs usually work is that they partner with an optician at a company like LensCrafters and they fulfill the glasses but then send it to that storefront who then dispenses the glasses in person to a customer. Our process was completely new to them. They had never gone through the fulfillment process of quality checking everything and making sure it was the way we wanted it to before sending it to the customer directly. We were definitely establishing that through our company and teaching all of our labs how to do this.

Craig: Were you ever involved in those conversations? Convincing the lab, “Hey, now you do this, too.”

Mara: So the lucky thing about that is there was one person at the first lab that we partnered with that really believed in our idea. It took some convincing with him but then he was really the one that was able to get all of his lab on board. Of course, it took us a lot of work to establish all of the partnerships to set up all the processes in a way we wanted.

Craig: Cool. So back to the story, you moved to New York and things are ramping up. What happens after the summer? How does it go?

Mara: I mean, so we went through the period of just crazy explosive growth in February, March, April. Then we were moving to New York and, of course, in any startup in the beginning you have step function growth, right. With us, we didn’t do any marketing in that first full year. We really grew most through word of mouth, We were really just focused on “How can we learn as much as we can from the experiences that we are providing to our customers? What can we be doing differently?” And that’s what we were really focusing on: so building all of the technology, how to build out and manage all of our inventory, how to make sure that we were running the company in the best way. We were hiring a few more people at that point. We hired our first tech employee.

Craig: Wait, what?

Mara: Yeah, so we were only working with a consultant until the end of 2010.

Craig: [Laughter] So the whole first year was on some consultant guy’s website? That’s amazing.

Mara: Yeah, so it was on NetSuite. Our contact there made it all work. But at that point we were still answering all of our phone calls through Google Voice to our cell phones. Everybody was in one inbox in Gmail.

Craig: [Laughter]

Mara: It was pretty insane. You know the labels that you use in Gmail? We would use labels with our names. Just put a label and say, “Okay. Royce, Brian, Lee, Colleen, Mara.” And you would just assign the top 10, middle 10, things like that. And we would just make it work.

Craig: And so now are you becoming more of a manager?

Mara: In March of 2010, I was already a manager but still very much a doer because I was managing the operations team but still doing office management and talent and inventory and all of that kind of stuff as well. I think it wasn’t until much later on that I was fully able to hire for all of those different roles. It was very much just managing all of our folks within the operations team to make sure that we were just fulfilling orders and managing our customer’s experiences as best as possible.

Craig: You’ve been there for six years at this point. How’s your role changed?

Mara: A lot. I mean, it’s been an awesome journey, lots of learnings along the way. I think what’s been most exciting about Warby Parker is that we continue to grow at this crazy pace and we’re just always going through growing pains and trying to figure out what’s the next big step and how do you deal with that next big step. Going from startup mode and being very reactive to everything that gets thrown your way because you don’t really know when to expect that next big push, that next big craze. It’s been awesome to be able to have more processes in place, better systems that we can count on. We’re not just on one inbox anymore and we have a real phone system with lots of hard data which is awesome.

Craig: Okay, and how many people are you now?

Mara: So companywide, we’re over 900 people and that includes our employees from our 40 retail stores that we now have.

We started thinking we were only going to sell online but then through lots of different experiments with the showrooms we found that our customers did really like getting access to all of the glasses and getting that assistance in person and that we could also learn a lot from those interactions in person with those customers. So we started experimenting with a few stores. We launched our first store in 2013 and then have been expanding since then.

Craig: So what did you learn from customers trying on in a store vs the Home Try-On data?

Mara: First, observing them and what glasses they’re gravitating towards, how they shop. So usually, people in the past have gone through face shape but a lot of people don’t even know what their face shape is. It is a little hard for people to understand that. So do you organize by bolder and more classics? By different color styles? So we were able to see how customers interacted with those glasses and how we were setting them up in person allowed us to further understand how to couple those glasses together and how to talk about them, how to create better stories around those types of glasses.

Craig: Do you have thoughts on what your personal future ambitions are?

Mara: To be honest, I never thought I would stick around at a company for more than two years, right? Everybody jumps around every two years, nowadays especially. So it’s been six and a half years and I continue loving it as much as I did in day one. It’s just a combination of continued learning and growing and the amazing culture. That just keeps me coming back for more and I know that we do have a lot of really exciting plans for the future (we’re opening our own lab in upstate New York soon) plus this continued expansion into retail. We opened our first store in Canada this year.

There’s just so much more that we can do. Our brand awareness in New York, in California, is pretty high but throughout the rest of the country and potentially rest of the world, there’s a huge opportunity there. It really feels like we’re still just getting started. And there are so many more opportunities for the company and so many more opportunities for me to continue to learn and develop myself and continue to add value to the growing organization. So that keeps me around.

Craig: What does that mean? How do you want to continue to develop yourself?

Mara: I mean… I have about a 150 people on my team. I’ve never managed a 150 people before. Actually, Warby Parker was the first experience that I had managing anyone. So continuing to grow my team and scale my team, making sure that we’re investing in our employees in the best way while we continue to learn how to scale the organization in the best way, and the way that I do that is making sure that I’m a better leader every day.

I just continue to expose myself to other companies that have gone through this growth before, have done what we have done before, continue to read a lot of books, just developing myself in any way possible.

Craig: Most people in the world have not managed 150 people. And, I mean, you’re easy to have a conversation with but I imagine there are other things that aren’t your strong suit, right? So what did you have to learn along the way?

Mara: Everything.

Craig: [Laughter] Okay. How about–what was counterintuitive for you?

Mara: I don’t know. Let’s see. That’s a really good question. So I am very much a planner and I like to be very organized in everything that I do. I think in the beginning it was a lot more stressful to not be able to have everything planned out. You just have to roll with the punches and you just have to figure things out as they get thrown at you. And so eventually you then get used to that culture and then you have to break out of that and go into process mode and make sure that you have really great processes in place so everybody in the organization is empowered to take action in a way that’s consistent throughout the entire organization.

A lot of what I learned is around lean, Six Sigma thinking and how to implement it into daily practices. You have to realize that everything isn’t going to be exactly the way you want it and how you would do it. But if you are able to have enough processes in place and enough structure in place with enough guiding posts like strategic objectives and milestone metrics and core values, then you empower everyone to take action, to make decisions and learn on their own. Then you can then help them learn through the great decisions or bad ones and, of course, correct from there.

That’s been more of the learning challenge. As you grow into a leader and, of course, as the team continues to grow, making sure that those ideas seep through to all of the layers of the organization.

Craig: Yeah, each person on a hundred-person team is not as effective or easy to evaluate as each person on a ten person team, right? So you’re not 10X more productive and managing that process does make a lot of sense. As your ambitions scale, do you feel that you have founder-type ambitions in you at some point?

Mara: Potentially? I mean, I’ve learned so much here and I feel like if I did want to, that I would be able to start a company myself. Nothing planned for the moment but potentially, one day.

Craig: Anyway, so the founders were all dudes, right?

Mara: Yep.

Craig: So you were obviously the first female hire. What’s that dynamic like?

Mara: I don’t know. I think it’s just hard to really put myself in those shoes just because in every experience I have had even before Warby, I haven’t had that much of an issue with being the only woman in the workplace and having to just work that much harder to speak up or to assert myself or something like that. Once we moved to New York, the two other guys became board members and stepped out of day to day operations and it was really only the two co-CEOs that stayed on board. And so maybe that’s why it didn’t feel very daunting.

Craig: Interesting. Ok, let’s move on then. What books are you reading right now? Are you a business book person?

Mara: Yes, most recently I’ve been reading a couple of HBRs business books which are compilations of great articles – HBR’s 10 Must Reads on Managing Yourself and HBR’s 10 Must Reads on Managing People – and my personal favorite which I’m having my entire team read right now is How to Win Friends and Influence People.

Craig: Cool. So we usually ask people about lessons learned. Maybe you could break that up into first employee learnings and general learnings?

Mara: Sure. So learnings from early days, first. I think that the most successful people that I’ve seen in startup settings are people that have no ego. They just know that shit needs to get done. You really just need to put your head down and figure things out and just make it work. So hauling boxes to UPS or cleaning glasses or when we got a batch of bad glasses, going through them and realizing that they were all bad and counting them up and then sending them back. So you just need to make the time and you just need to do it and you need to figure out how to do it in the best way. But working at a startup is really hard and it’s more than a hundred hours a week. It’s all consuming and you just have to be ready for it.

I think that those are sort of just my general learnings from startup life. It’s not for everyone. And I guess in terms of growing into the position that I am today and moving forward, I think part of the learnings that I’ve taken away from the last six and a half years in terms of hiring for your team, is that you need to focus more on the behaviors that you’re hiring for.

We really believe in hiring passionate, curious, proactive people rather than people that have the specific skills or experience that maybe you’re hoping to get because in the end, if the person doesn’t fit into at least those three behaviors at Warby Parker, they’re just not going to be successful. And we are a company that moves quickly and we want to be able to depend on everyone to be a problem solver and to think in a proactive manner. You can always teach the other things. I can always give somebody exposure to going to a conference or sitting down with somebody from a different company that has done these specific roles before. But you really do need to hire for behaviors and if you make a mistake, it’s better to call it quits sooner rather than later.

Craig: And what about hiring people that aren’t like you?

Mara: It’s also a very much of a learning process and you have to learn how to manage to everyone’s personality. You have to understand what you’re hiring that person for and then how to manage them in the best way to use those skills that you really hired them for and then supplement what they don’t have.

Craig: Last question. Would you consider yourself a good manipulator of people?

Mara: That is a really bad way of putting it.

Craig: [Laughter]

Mara: You mean like influencing people?

Craig: No. I mean, you can call it whatever you want but I think “manipulation” is unfairly cast in a negative light and is different. I think it’s actually one of the strongest skill sets someone can have. I think “influence” might work toward a similar output but the input is different . Anyway, I look around and there are certain people that are obviously good at it and certain people that aren’t great and certain people where you’re like, “I don’t know if you’re really good or terrible.”

Mara: So, honestly, I’ve learned how to be better in the last six years. I know initially the whole political games in an organization killed me. It really killed me to think you had to speak in a way or you had to manipulate people to get your job done. But through the advice of a colleague I read “How to Win Friends and Influence People” by Dale Carnegie and learned that it’s not necessarily about manipulating people to get your job done, but how to influence others in a way that everyone wins in the end.

It’s hard, but a lot of practice has helped me get better. I think I can still get better, but I’ve definitely made a lot of strides in the last few years. I feel like it’s something that people just have to continue working on…

Craig: Well, I mean, perhaps this is obvious but these things, these interviews, are like therapy sessions for me as I’m figuring shit out.

Mara: [Laughter]

Craig: [Laughter] But really, that challenge of figuring out how steer a group of people that you may not completely vibe with is fascinating to me. Anyway, this has been super fun. Thanks so much for your time.

Mara: This was a lot of fun.

Craig: Totally. Thanks Mara!

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  • Craig Cannon

    Craig is the Director of Content at YC.