All CEOs had to start somewhere, and whether they were bussing tables or photographing concerts to pay their rent, there were quite a few lessons to be learned along the way.
We spoke with some of Boston tech's CEOs about their first jobs, what they learned and how these gigs shaped their paths to becoming CEOs.
Ted Chan, CEO and founder 
What was your first job?
My parents are Chinese immigrants and my first job was at their Chinese restaurant, The Wok, in Wellesley, MA. I started bussing tables and washing dishes. My father is a Joyce Chen-trained chef and my mom ran the front of the house. I love the restaurant and service industry.
What lessons did that job teach you?
The only day my parents took off all year long was Thanksgiving. My parents came from Hong Kong with nothing and made a great life for me and my sister. They never complained about work and always had a positive outlook no matter how tough times were. They took a risk, bet on themselves and sacrificed everything to make it work.
Some of my parent’s best employees have also made a lasting impression on me.
I remember a lady in her seventies who was an amazing dishwasher. She never got behind, always looked calm and even had extra time to make dumplings. When she went on vacation to visit her family in China, I had to do her job on weekends. I got soaked and couldn’t keep up no matter how hard I tried; however, it definitely looked like I was working hard with all of the water splashing around me.
After realizing I didn’t know how to do the job, I decided to observe her going forward. She had a process. Every dish had a place. Panicking when there was a rush didn’t help anything. To this day, I try to assess employees by what they get done, and not by how hard it looks like they are working. At CareDash, we have a relaxed, process-driven and thoughtful corporate culture. Some of our best data scientists take their time and have their own unique ways of working, but ultimately know how to get things done.
What was the hardest obstacle you faced?
My parents worked 12 hours a day, 7 days a week, 364 days a year and never carried their emotions or exhaustion on their sleeve. To this day, my mom is always cheerful, every customer gets greeted and she does her best to remember their names. I carry these lessons from my mom with me today. As CEO, the tone you set at the top is important from a cultural perspective. I learned so much from that first job about how to stay composed, control my emotions and present myself as a leader and manager.
What leadership values did you learn and how did it shape your path to becoming CEO?
Great chefs are amazing leaders and each one has their own style. My dad works harder than anyone I know and doesn’t view himself as above any task. I can see how much people respect that and it makes them work harder and contribute to the mutual success of the restaurant. It also takes great discipline, focus and a willingness to try new things. Some CEOs pay lip service to the “chief bottle washer” executive, but I firmly believe in it. That is, the notion of someone who is in charge, but understands the smaller and menial tasks, understands why they are important to creating a great product or service, and in a pinch, can get it done.
Kevin O’Brien, CEO and co-founder 
What was your first job?
My first "real" job was working for @stake back in the early 2000s. @stake was a cybersecurity company, and most of the l0pht team — a Boston group of hackers, many of whom are still active in the security industry — was part of @stake. I was young, arrogant and in reality far less skilled than everyone else there, but I loved being around so many smart, talented and creative people.
What lessons did that job teach you?
I didn't realize it at the time, but in hindsight, it taught me the value of surrounding oneself with incredibly intelligent and passionate experts. It provides unbelievable opportunities for learning how to do things more efficiently and effectively, but it also creates a culture where the whole is greater than the sum of the parts. @stake set out to "make a dent in the universe," and what made it possible for that team to do so was what happened when you assembled so many brilliant and dedicated minds.
What was the hardest obstacle you faced?
Back then, I was still basically a kid. I thought I was pretty hot stuff, but of course, I wasn't — I was lucky to be there, and I didn't realize it. Nearly two decades later, I'm still incredibly grateful that one of the leaders there pulled me aside and told me that I wasn't meeting her expectations.
It wasn't pleasant at the time, but of course, it was exactly right. I can't recall how I reacted (mortified, probably), but learning to both provide and listen to honest feedback, incorporate it, and grow from it is one of the key lessons you learn when you move from individual contributor to leader. I've never had the opportunity to thank her for her feedback, but I both deserved and benefited tremendously from it — and it's stuck with me for a long, long time as a result.
What leadership values did you learn and how did it shape your path to becoming CEO?
Outside of the office, I spend a lot of my time training in various martial arts. It's interesting how similar those lessons and values are to what I see when I'm in a suit instead of a gi: success is never a straight line affair. It's a matter of trying and failing repeatedly, and not internalizing either to the point where you become stuck. No great boxer, judo player, or MMA fighter has ever gotten there by NOT losing; in reality, it's quite the opposite.
When I reflect on my time at @stake, and that (at the time) uncomfortable dressing down, it's strikingly similar to when I'm tapped out or rocked on the mats. If you're not open to mistakes, you can't get better. The trick is to both recognize where you're wrong and then make new mistakes the next time, as well as to correctly recognize how to push the people who work for and with you past their limits in ways that afford them the same opportunity.
Jeff Ernst, CEO and co-founder 
What was your first job?
I kinda fell into my first job in the tech industry by chance. It was a Customer Support role at Software 2000. I had used the company's financial software when I was an accountant at Fidelity, and realized I was way more enamored with the software than I was with the monthly grind of accounting. I was incredibly passionate about this job. It was extra special because it combined 3 different roles that are usually done by different folks...on-site consulting to onboard new customers, teaching classes on how to use the software and solving technical problems on the support hotline.
What lessons did that job teach you?
I got to know everything about our customers, their challenges, their aspirations, and how technology can help them do their jobs. I also learned every nuance about our software...the good, the bad and the ugly. This role taught me just how important the customer experience is because I was the primary touchpoint that many of these customers had with the company. It was up to me to make sure they made the right strategy decisions and set up the system in a way that ensured a smooth monthly closing process because otherwise we both failed.
What was the hardest obstacle you faced?
Playing this role made me an advocate for the customer, always looking out for their success. But this sometimes put me at odds with others in my company. When we hit a bug, I'd do battle with the developers to get the customer a patch right away, when the developers would have rather just fixed it in the next release (remember this was long before SaaS). If an upgrade installation corrupted their data, I'd have to convince my boss to let me go onsite and fix it. Having lived in their shoes, I knew what it was like when you have to close the books and report to the board, and your software doesn't work as expected.
What leadership values did you learn and how did it shape your path to becoming CEO?
This experience made me customer-obsessed, and now running a software company, I have made being customer-obsessed one of our core values. Especially now that we are Sofware-as-a-Service, we have to earn our customers' business every day. And I don't believe in just meeting their expectations, I believe in blowing them away with an outrageously great customer experience. I lead by example in my company, my folks all know that I'm going to challenge them to wow the customer, because that's what's going to get them to share their experiences and success with others.
Jen Andre, CEO 
What was your first job?
My first real job was working tech support for IT for my university. Studying computer science at the time, I was passionate about computers and technologies, and thought it would be a good fit for my skills.
What lessons did that job teach you?
Working tech support at a university, you have to support a variety of different applications and environments — everything from unix environments, to windows, and applications that ran from mail applications to technical software like Mathematica. It’s far less defined than doing technical support for a product company, for example, and because of this, it required you to be resourceful to try to solve problems for a user — e.g. doing searches on your own for the solution, trying to reproduce the issue yourself, rather than relying on canned troubleshooting documentation or scripts. Being resourceful and self-driven was one lesson I take with me in every job.
What was the hardest obstacle you faced?
There were several times users would be on the phone extremely upset because they lost their data, or could not get an application working for a school project looming against a deadline. Even though it was no fault of the technical support person, they would often take it out on you. It was hard not to take it personally when a user was frustrated and blaming you for their problems. Calming someone down enough just so they would answer your questions and follow your steps to troubleshoot was often half of the battle.
What leadership values did you learn and how did it shape your path to becoming CEO?
Keep a clear head in the face of obstacles and find a way to move past them.
Katherine Hays, CEO and co-founder 
What was your first job?
My first job was on Wall Street in investment banking and then in Equity Research covering major media companies. I learned that I was passionate about media, but not necessarily banking or equity research.
What lessons did that job teach you?
The job taught me about the media industry — a foundation that enabled me to identify a market need and a way to solve it when building my first start up, Massive Inc., and now at Vivoom, a Shared Media platform that is revolutionizing mobile video marketing.
What was the hardest obstacle you faced?
The media industry was in the early days of its digital transformation. People were starting to ask questions such as, “Would digital music take off?” and "How will print media and advertising be impacted?" When considering the start of the digital era, predicting the future for companies across multiple industries was the biggest challenge and also the most rewarding part of my job. Ultimately, it's what led me to start my second company, Vivoom. With Vivoom, the business challenge we are solving for is the need for an entirely new video advertising model on mobile. We believe that, in a few years, the idea of simply buying an audience will sound dated and highly inefficient. Instead, brands will enable their most influential customers to shoot and share content with an audience of their peers with the brand inserted in a non-intrusive way.
What leadership values did you learn and how did it shape your path to becoming CEO?
I learned critical lessons about how to build and lead a team. My former boss was a partner and in a senior role at Goldman Sachs, yet he did some simple things I now recognize were deliberate and helped him build an extremely high performing and loyal team. For example, he had a big round table in his office and everyone ate lunch together which quickly built a strong sense of “team-ness” and made all of us much more efficient in our jobs. When an offer was given to a new team member, everyone would all get on speaker phone and share our excitement about them joining our group. Simple things like that make a tremendous difference. Importantly, I also learned the power of transparency and fairness. Building company culture can be difficult, but I truly believe it's simple things like this that make people look forward to coming to work. I'm proud to say we are building this culture at Vivoom today.
Alex Kubicek, CEO 
What was your first job?
My first job was packing parachutes at Sky Knights Sport Parachute Club in Wisconsin. While folding fabric wasn’t a huge passion of mine, it was constantly interesting and required a great deal of discipline.
What lessons did that job teach you?
Prioritization. Multiple types of parachutes would come in and we would need to make sure that we had the right types packed to keep first-time clients on time. At the same time, parachuting regulars would ask to be repacked, and keeping them happy was a priority as well. This constant juggling would keep us on our toes.
What was the hardest obstacle you faced?
Management. We would always need to ensure the safety and reliability of every single packed parachute. I made a difficult decision to open and repack our entire inventory after a mistake was found on a few parachutes. After a scramble, our team was able to repack all parachutes and keep everything flowing well.
What leadership values did you learn and how did it shape your path to becoming CEO?
Stress management for myself and for team members was the most valuable thing I learned. Our team was responsible for the safety and experience of all skydivers. We needed to be able to balance our quality with execution speed. Stress was always at high levels and regulating it was always important. Understanding that it is a "marathon and not a sprint" stands at the core of our company and shapes who we are and how we do things. Our team celebrates each other’s successes and the positive impact everyone is having. Our company also strives to give back to our communities we serve with educational programs for schools and team volunteer time.
