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"You Name It, I Did It": 10 Startup Employees Recall the Early Days

In the First 100, we're introducing Mashable readers to employees 1 through 100 at 100 different companies. Last week, we introduced you to employees 1 through 10, from companies like HowAboutWe, Groupon, Reddit, Barkbox and Quirky. Today, we introduce you to employees 11-20, and we hear about how a company evolves in the period of growth from 10 people to 20 people. While the companies below range from software to fashion to media, they share common themes — a growing need for specialization, a willingness to take on any tasks that need to be done and a focus on hiring slowly and thoughtfully.
"As you get bigger, the problems you face start requiring specialists. You hire a MySQL expert and a CFO, and you wonder what you did without them," says Tim Clem, #18 at Github.
Read on to meet 11 through 20, and stay tuned to The First 100 to meet the rest of the group over the coming weeks.

Image: Casey Driskill
On the ground floor... Previously I was a designer at Alexis Bittar. I liked the idea of creating a line almost from scratch and determining what the aesthetic would be. The Founder and CEO of Chloe + Isabel, Chantel Waterbury, is very passionate and knowledgeable about jewelry and wanted to make sure that what we had was different from what you could find out in the market at a similar price point, and that the inspiration was visible in every piece. Storytelling is an important part of everything we do, and that makes the creative process more fun.
Taking on more responsibilities... I’ve worked on everything from jewelry design to product development to merchandising, and now, marketing and brand creative. A lot of times the different roles stemmed from just being at a start-up, and the inherent need to be scrappy and get things done. I’ve always felt I had the independence to take on new responsibilities here and work on projects that didn’t necessarily fall right into my silo. About a year after I started I was promoted to design director, and a little over a year later I became creative director. When my world was jewelry design I felt confident about my decisions because I knew my field well from working my way up. In the creative director role I work with the marketing team, which is completely new to me. I’m constantly learning while I’m managing.
More specialization... We've recently hired a number of people for roles that were once simply a component of someone’s job. It’s nice because you bring in a new level of expertise and you get to see how teams improve overall and the output multiplies when someone can focus on a function that didn’t really exist before.
Doing a lot in a little time... What keeps me going is thinking about how far we've come in the past couple years. I'll look at something we did a year ago and it feels like ancient history, which makes me wonder where we'll be in a year.
Chloe + Isabel now has 75 employees.

Image: Josh Kill
The road to Squarespace... I had my own web design firm in the Seattle area that I started with Tyler Thompson, the former Creative Director of Squarespace. We had worked on Squarespace sites before, and had also done some contract work with Squarespace, so I was pretty familiar with the product. To be honest, it took me a long time to even start using Squarespace because I was a big believer in hand coding and building my own websites. Once I gave in, though, I realized how much it allowed me to focus on design and client work. That made me believe in Squarespace. I came out to new York to visit Tyler, and ended up with a job offer on the table. The possibility had never really crossed my mind before, but after getting a taste of the company culture and getting to know the founder, Anthony [Casalena], it seemed like a natural fit. It was clear that he was legitimately interested in solving problems and not just building a company. That was inspiring to me and ultimately what motivated me to join Squarespace.
An evolving role... I was hired because I knew about design, but could also code. I started out as a designer working with the Creative Director on specific projects — overhauling how the interface looked, designing new templates, etc. Then my role morphed into more of a web developer. I became the middleman between back-end developers and front-end designers, making sure we were using the best solutions when it came to HTML and CSS. Eventually, I was building out the front site, designing and building templates, and even adding features to the product. I now manage a team of ten as the Director of Platform. My value to the team is that I understand the high-level picture of a project and make sure the team is on the same page. We also spend a lot of time on that final 10% of a product, really perfecting it before we share it with the world, and I can provide some guidance on what that should look like.
Designing templates that stand the test of time future of the web... I'm constantly on the watch for what’s next and what’s being built. I try to stay engaged in what’s happening around the web at all times. It’s like a diet — I don’t go through a cycle of “Let’s spend two weeks of R&D to come up with a new concept”. You have to be consuming this stuff everyday. Not only do you have a good sense of what the current design trends are, but you also get a sense of when a trend is played out.
A "flat" company... We always describe our company structure as ‘flat’ but that doesn't fully convey what I mean. At Squarespace, you actually have the ability to work on what you're passionate about. What I liked about Anthony when I was first getting to know him, and it’s still true today, is the fact that he’s always looking for the best solution and he doesn't care who it comes from. He’s constantly asking for other people's feedback and opinions. Through careful hiring, we are able to create a company with a full range of people who all care about different things, and everyone plays a very important part in the company's success. i look forward to the company doubling in size and still having that be the case.
Squarespace now has 262 employees.

Image: Patricia Korth-McDonnell
Joining Huge in 2005... The company was small and felt like somewhere you could really make an impact — but at the same time, had an incredibly impressive leadership team. The founders were personally running all of the projects, and they were these incredibly passionate, dynamic guys who had amazing pedigrees. And of the kids working for them were the kind of people you really wanted to be around — super smart, ambitious, talented and not jerks. I actually applied for about four jobs over the course of 6 months before Shirley Au, now our President and COO, finally hired me as their second project manager. The real question is why they hired me.
Stepping up to the plate... I was able to participate in a lot of client-facing pitches and presentations, which helped to hone my skill set early on. Regardless of whether or not I was technically qualified, I was present and willing. When you're part of an entrepreneurial environment, you have to learn a thousand things in order to fill in the gaps and get the work done. I wrote code, conducted content audits, developed copy, did endless QA scripts, etc. — you name it, I did it. I actually think this is less about agency size, though, and more about attitude. Some big shops get really precious about what "roles" do what and don't allow people to get their hands dirty. In a creative environment, you can and should work to preserve freedom for people to use their brains outside of their job title's purview, no matter what size company you are.
The importance of passion... It's hard to answer this without sounding cliched, especially in an agency environment, I think the most important lesson has been that the work is only great when the people doing it are passionate about it. You have to choose the right work and staff it with the people who will kill it out of love, not just because it's their job. That, and also to trust your gut when hiring to build your team quickly. No matter how good someone appears on paper it's really all about how they will integrate into your team and make it stronger.
Jack of all trades... The company has grown from a 13-person digital shop in Brooklyn to a leading global agency with more than 750 employees in eight offices, across three continents. My role has evolved pretty organically with the company, as opposed to a linear career path you might expect from a larger shop. I started as a project manager, worked both on the PM and account sides, and at one time even led Huge's Client services team in New York. I also had a couple of stints in the Business Development group, founded our Product Strategy team and spent half a year in Europe opening offices. I moved to L.A. a year ago to lead the office over here and to focus on Huge's growth on the West Coast. I guess "organic" is a nice way of saying that my role has been diverse, but I feel like I've found my forever home in my current role.
An irreverent work mantra... "Calm the f*ck down." One of our Creative Directors told me a few years ago that I was great to work with, but was terrifying everyone on the team with my intensity. He said if he could give me one piece of advice it would be to calm the f*ck down. I've kind of made it my mantra whenever things get hectic and it has helped me to be a better manager, leader and partner to our teams.
Huge now has 750 employees.

Image: Rachel Sklar
Going to work with Arianna... My HuffPo offer changed my life and I knew that it would. I had developed a relationship with Arianna while I was at Mediabistro's FishbowlNY, and when I left she hooked me up to Kenny [Lerer] and I had dream offer inside a week. I accepted the day Arianna was going on the Colbert Report, and joined the staff in the studio audience. Afterward she hugged me and told me she was so glad I was coming. She looked me in the eye and said, "We are going to change the world."
Building a media company... I started as the Media & Special Projects editor — I launched, wrote & edited the first stand-alone vertical at HuffPo, "Eat The Press." I wrote on media at ETP and on politics, entertainment and culture on the main blog. Eventually ETP grew enough that I was able to hire some great contributors, like my current co-founder Glynnis MacNicol — our relationship incubated over Gchat as we went back and forth over her posts. I was also tapped early on to be a face of the brand (Kenny called it being "a mini Arianna") — as we grew, Arianna couldn't be everywhere, so I was lucky enough to step into the breach, becoming a frequent guest on MSNBC, CNN and Fox. I was also tasked by Kenny to recruit heavily since we were growing aggressively, so I spent a lot of time assigning and editing and recruiting new contributors. The company went from a small, scrappy startup contained on one side of a loft in Soho to adding more and more desks, taking over another floor, spawning a whole other editorial wing and just growing and growing. We launched the section verticals in May 2007 — Media, Business, Style, Entertainment to start — and just started massively covering the zone. Then we added Politics shortly before the 2008 presidential election flurry kicked in. It was dizzying and exciting and amazing.

Image: Julianna Bass
A new fashion concept... My initial interest in Bow & Drape stemmed from my fascination with the novelty of the concept — it was a superb idea with incredible potential. I had been in the fashion industry in New York for a while and have had the privilege of working with big names — but Bow & Drape excited me on a different level. I know plenty of designers working in the traditional fashion industry who feel as though their creative energies get stifled — Bow & Drape, by far, is so different in contrast. The company had a foundation that can be built upon and a concept that was unique — what excited me the most was that Bow & Drape is an upscale alternative to DIY — and nothing is more enticing to me than smart fashion. Of course, as with anyone who joins a small company, there were naturally some reservations. However, the idea of being involved in something and watching it flourish quickly overshadowed any fears I had.
A fast-growing team... The ladies at Bow and Drape are great — I've grown to really love them as people and that is always a good thing especially when working with a small startup team. Not only that, but the team really respects my position as a designer. My opinion and experience is valued, and they don’t hesitate to tell me so. These ladies started a fashion company that came from an incredibly novel idea. Now, they have diligently taken things to the next level at a pace that most don't reach so quickly. Bow & Drape wants to make a mark on this industry and they are eager to do whatever it takes to make their dreams a reality. I know exactly how they feel, and that is what keeps me going with B&D!
Bow & Drape now has 16 employees.

Image: Richard Murby
The road to ChallengePost... Prior to joining ChallengePost, I worked in the Innovation Lab at the World Bank. I was designing initiatives to help harness the problem-solving capability of technologists who work on some of the world’s biggest problems, and I used ChallengePost to power our Apps for Development Challenge. The competition encouraged people around the world to create apps using open data from the World Bank to address global issues such as poverty, hunger, and education. During the process, I became friends with the founder, Brandon Kessler, and we stayed in touch over the following years. When I was considering what to do next in my career, I went to talk to one of my mentors, who, like myself had spent time in both startups and governmental roles. I told him that I was thinking about going back into startups, and he asked me one question: “Is there a startup out there that you wish you had founded and believe you could have a transformational impact at?” I set up coffee with Brandon 10 minutes later.
Working on a small team... It’s not for everyone! Small companies are amazing places for self starters who don't need much direction. However, you also need to be comfortable being evaluated very directly on results — there aren't many places to hide when we're all pushing each other to do our best. And, don't forget, you have the opportunity to shape your own role, how you contribute, and the entire company.
A culture of reflection... Our office is relaxed, but with quiet focus. One high point of our culture is the ability to look critically at ourselves, a practice that manifests itself most at our weekly retrospective meeting, or "retro." At the end of every week, the entire company sits in a big circle to highlight accomplishments, recognize team members’ contributions, and suggest opportunities for improvement. We then assign team leads to address each of those areas, to make sure that we're delivering the best value to our users.
ChallengePost now has 17 employees.

Image: Anna Elwood
The road to ZocDoc... Before ZocDoc, I was working in the NYC public school system, teaching at CUNY. I was also waiting tables, working at an Apple retail store, and had a nonprofit on the side. I joined ZocDoc because I wanted to work for an organization where I would be able to make an impact on the world. Beyond that, I was looking for a place that offered me the opportunity to grow, where I would be constantly challenged, and where I could interact with a diverse set of people on a daily basis.
Doing whatever it takes... I was hired as one of ZocDoc’s first Operations Associates. The role included everything from answering the phones and helping patients, to training new doctors on our service, handling office manager duties, teaching new team members, helping launch new markets, creating methods and processes, etc. Now, the Operations team has grown to be one of the biggest in the company! This group is dedicated to upholding our core value of ‘Patients First’ and makes sure both our doctors and patients have a seamless ZocDoc experience. As the Director of Operations, my role now primarily consists of managing this team of rock stars, helping them grow professionally, and building out operational best practices as we continue to scale (we now have growing teams in multiple locations). We've come a long way, and I'm excited to continue to ease patients’ pain points and witness our continued rapid growth.
Taking on new roles... Since the beginning, I was always asking “What can I help with next?” after completing a project. I would volunteer for new opportunities when they were offered and identify areas for improvement on my own that I would be excited to take on. I saw it as a win/win — I was always looking for new professional challenges, and simultaneously, I was able to find new ways to improve our service. The beauty of being a part of ZocDoc is that you have the opportunity to work on different projects that interest you and while also having real impact on the company’s goals and mission.
A mission-driven environment... ZocDoc is incredibly mission-driven, and our culture maps back to our seven core values. We pride ourselves on creating an environment that encourages openness and collaboration, where everyone is allowed (or rather, expected!) to speak up and make their voice heard. Each day, we work hard together in our mission to improve access to healthcare, and we have a blast while doing it. Our #1 core value is ‘Patients First’ and everyone here is excited and inspired to do the work we do because we’re making an impact on patients’ lives every day. ZocDoc has also created an atmosphere where we not only hire great people but always continue to celebrate them and their hard work, and give them opportunities to grow.
ZocDoc now has 500 employees.

Image: Tim Clem
The path to Github... I was previously working at a Denver based company called Blue Dot that specialized in enterprise mobile software. GitHub was exciting because it was something I'd discovered on my own and begun using for personal projects before converting the entire development team at Blue Dot over. GitHub drastically changed how we worked on software together — I'd never seen anything like it and had been agonizing over the various terrible methods of versioning and collaborating on software with a team of people. I joined the team at GitHub because I fundamentally believed in the core mission and values. I loved the product, but even more than the product, I loved what it was enabling in the world. It felt like a huge leap forward in the way people worked together to build software, and I wanted to be a part of the consequences of all that. GitHub felt small, exciting, risky and buzzing with potential.
Taking on new opportunities... My role has changed a ton since starting in 2011. I came on primarily as a developer, but as with any small business you tend to take on whatever work needs to be done. Opportunities came about very naturally as part of being willing to understand the next most important and valuable things going on in the business and GitHub's unique and open organization structure has always done a good job of surfacing opportunity. The first major thing I worked on was v3 of the GitHub API, which is still going strong today. From there I moved into launching the first versions of our native applications: GitHub for Mac and GitHub for Windows. I was the product and development lead on GitHub for Windows and did everything from the initial prototyping to writing code and hiring the team that shipped 1.0. Most of those projects came about from talking to founders and early employees to understand what was important to GitHub and where we wanted to be in the next couple of years. From there I picked up a variety of responsibilities: building and leading teams around different parts of the product, working with the founders on our internal structure, and opening up and communicating internally valuable information around strategy, finances, hiring, and importance. At my core though, I'm a product person and I keep leaning back towards the product. GitHub's taught me that to build great product, you have to build a great company first.
The GitHub culture... GitHub has always valued passionate individuals who do work that affects real people for the better. We value openness and honesty. We don't fear change. We demand high fidelity communication and because of our global and remote workforce, written communication is especially important. We approach conflict by assuming the best of people. We argue well, but with an open mind, to make the best possible decisions. We work to get things out in front of the world as soon as possible because all your planning means nothing compared to seeing someone use (or not use) your product.
A growing team... One of the biggest things that changes as you grow is you start to have to hire specialists. When you are small, everyone has to have a broad range of skills to keep the product and company up and running. You've got to know how to both migrate the production database and analyze the quarterly finances. As you get bigger, the problems you face start requiring specialists. You hire a MySQL expert and a CFO, and you wonder what you did without them. Plenty of other things change as well, that are perhaps less interesting. You run out of office space, you watch employees introduce themselves to each other at non-GitHub events, you go through cycles of exploration and cycles of focus, you start understanding why bigger companies have process and red-tape, you fight to keep information open and processes transparent, you no longer know what everyone does in the company, you can no longer read the GitHub commit log, you are delighted by each new outstanding employee who seems way more qualified for the job than you ever were, and you realize how vital growth is for creating new opportunities and challenges.
Github now has 240 employees.

Image: Katherine Griffiths
The road to BuzzFeed... I heard of BuzzFeed and was intrigued by what they were doing. I knew it was a great opportunity to be part of a startup where I could learn a lot and get my hands dirty. I really loved the idea of being able to wear a lot of hats (and still do!), so I took the chance and left the Gilt Groupe, where I was working in the Customer Service department. At the time, it was a risky move to leave Gilt, and go to a smaller company, but I truly believed in BuzzFeed and have no doubt that I made the best decision. Sometimes it takes a leap of faith, but when it's something that you're passionate about, it's usually always worth the risk.
From a studio office to a global brand... BuzzFeed has grown tremendously since I first joined where I did everything from trafficking ads to creating invoices to managing client communication. Our first office was in a small studio space in Chinatown and now we have over 400 employees worldwide and our New York office overlooks Madison Square Park. It's exciting to see also how recognizable BuzzFeed has become. A few years ago, no one knew what it was and now when I say I work at BuzzFeed, I'm practically a celebrity. One thing that has remained the same though is the culture. We hire smart, quirky people with many different backgrounds, who can bring a lot to the table. This is certainly a big part of what has made BuzzFeed so successful.
Why I love it... The people that make up this organization are some of the smartest and most passionate individuals that I've ever met. BuzzFeed is an environment where everyone has a voice and our ideas are grounded in a desire to remain dynamic, relevant and always on top of what is happening in the social space. Being part of BuzzFeed is a lot of fun; we work smart and play hard.

Image: Anna Frenkel
Getting to Foursquare... In 2010, I was fascinated by how mobile was disrupting culture and communication. Smartphones were making it easier (for geographically-challenged people like myself) to navigate cities. I just moved to New York’s East Village and downloaded Foursquare to explore my new neighborhood and it was the first time I had ever used a piece of software to enhance my experiences in the physical world. It felt like magic. As I discovered local hidden gems based on the tips of people in the area, I got hooked and realized Foursquare was on to something big. It served as a bridge between the online and offline world as you roamed around the city. I was a fan of the Foursquare brand and story and was an evangelist from day one — getting all of my roommates and friends to use it, and convincing my favorite local coffee shops that they should provide incentives for loyal customers. That's when I knew it was time to leave the corporate world and fully get behind the Foursquare mission.
Spreading the Foursquare gospel... As the consumer and partner marketing lead, my role was to help tell the Foursquare story and to bring Foursquare to new audiences all over the world. During a big product redesign where local search and discovery was made front and center in the app, I helped develop new branding, messaging and positioning in tandem with our comms team. When we rolled out a brand new advertising platform, I worked on the launch plan and logistics with the sales and product teams. When we noticed organic growth in other countries, I worked closely with our business development team to bring Foursquare to different devices and platforms to make Foursquare accessible to people all over the globe. On a functional level, I always ask myself “What is the most impactful thing I could be doing right now?” to drive awareness and acquisition, and to do this in the spirit of our brand.
A collaborative culture... I'm lucky enough to be surrounded by incredible coworkers and friends who genuinely care about the problems we are solving, and realize how huge of an opportunity this is. Openness and transparency have always been the norm; product roadmaps and corporate matters are openly shared with employees at the company meetings, and the exec team holds weekly office hours to answer all questions on any subject. People are always open to feedback and everyone wants to do the best job possible, to push the company forward.
Helping people live better... At the heart of our brand has always been a strong desire to help people live fuller, more adventurous lives by helping them find interesting places and experiences nearby. I got to experience the meteoric rise of the company as we grew into a global brand and solidified our place in the local search space. Though we started as “just the check-in app,” we've taken all that data to help send personalized recommendations to people. We've grown into a full-fledged business, and every time someone uses Foursquare, our real-time map of the world gets better and better. It’s a huge honor to play a part in that.
Foursquare now has 170 employees.
Meet employees 21 through 30 of the First 100 next week!

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