What I've Learned After Four Years Working At ClassPass

Screen Shot 2019-02-27 at 10.50.38 PM.png

Four years ago on this day I had my first day at ClassPass, my first job and company out of college. I had just moved to NYC from San Francisco where I had attended SF State University and all I wanted was a job where I could talk to people a lot and where I could learn a bunch of stuff.

Before applying, I had not heard of ClassPass, but from the moment I walked into the office, I knew it was where I wanted to spend my time. In a post that I wrote announcing that I had gotten the job in 2015, I remember talking about how drawn I was to the people at the front desk, to the generous nature of everyone I was talking to, and to the vibes of the office itself.

I was the thirteenth or fourteenth member of the customer experience team at ClassPass, and I loved the team I started with. We were in charge of answering emails from users as they came in, and that’s what we spent our time doing, when we weren’t going out for coffee at the nearby Starbucks. We had about 100 employees total and not enough space to fit everyone. We had company team meetings where everyone sat on the floor, and later where we rented out small theater spaces as we grew larger and larger. We had team outings that included almost every employee, and we all felt jitters when our founder was featured in the magazines and TV shows we all knew and loved. I knew everyone’s name, and I made my name and started my reputation at karaoke one night. It was an awesome place for me to start my career— I got to learn what it meant to have a purpose at work, to take things on and get things done on my own, and to be a part of one of America’s fastest growing start-ups.

At ClassPass, a lot of things have changed and evolved in the past four years, but one thing that hasn’t changed is that I am still a part of the team that is now almost at 450 employees across countless countries.

When I first started, I remember thinking that I wanted to make it ‘at least a year’ on the team before I moved onto something new. I was so wrong— Since my first job on the Customer Experience team in 2015, I’ve been able to move into a role on the HR team as the Learning and Development specialist, and I’ve loved the journey I’ve had and everything I’ve gotten to do. I’ve found a job that values me exactly for what I am, and allows me to bring my whole self to work- and that’s the good stuff.

I’ve learned so much more than I could have imagined I would, and I’ve come to understand the world differently than I saw it when I was 22 years old.

When I first started at this company, I didn’t have a real vision for how I wanted my life to unfold. I didn’t know what kind of work I wanted to do, I didn’t know what I was going to be passionate about, and I didn’t know what kind of impact I wanted to have on the world. I now understand that it’s totally uncommon for 22 year olds to have a grasp on what they want to do or who they want to be- and I now understand that I was doing the right thing by jumping into something with only the desire to learn in my mind.

Four years later at 26, it’s easier for me to understand that maybe I don’t have all the answers and maybe that’s okay. These days I spend my time jumping into all kinds of cool things and chasing various things in all different directions. I’ve learned that growing itself is the substance that people are looking for.

There isn’t going to be a time when I’m done learning— that’s a new thing for me. I always thought that I one day would ‘become’ something- that one day I would activate and I would all of the sudden be something that I was working to be. I now know that even someday when I feel like I’ve made it, it won’t be enough- because there is always more I can do with my life.

After working at the same company for 4 years, I’ve learned the value of change and failure. I now understand that failure is the only way to succeed- that the only way to make something that works is to first make something that doesn’t work. I’ve also learned that it’s okay to fail as long as you have a plan to move forward, to fix things, to make new versions of things, and to get up and try again. So many times I have tried things that haven’t worked and never has someone yelled at me- because for the most part, people get that failure is just a part of success- at least in the ClassPass world.

I’ve learned the value that feedback and discussion has. I’ve now come to understand that my idea isn’t always the best idea- that sometimes my ideas combined with someone else’s are better than my ideas alone, and sometimes someone else plainly has the better idea- and it’s okay to get excited about someone else’s idea too. In the same way that failure is necessary to succeed, I’ve learned that feedback is necessary for any kind of improvement.

I’ve learned the power of taking action. And in the power of just doing things without needing everyone to sign off. Sometimes people don’t have the time or energy to help you with your thing, and you should just put it out there and make it happen on your own.


Contrary to everything I’ve ever thought in the past, nobody is an actual expert on anything and everyone is learning at the same time and pace that you are. My younger self would be shocked by this. The people who end up winning are the people who believe that they can do something and then they just do that thing. You can never know everything so you just have to take a leap and believe that you can learn along the way. Everyone is faking it at least a little bit, so you may as well join in and try things. As long as you’re willing to put in the work to find an answer, you’re good to go.

Something that I’ve also come to understand is that most people are good people who want to help you, and everyone wants to laugh. People want to feel a connection with other people, and they want to love what they do. Sometimes we can get caught up in the tasks we do and we forget to take a step back and enjoy who we are, what we are doing, and the awesome people we know.

It’s crazy that people spend time doing things they aren’t passionate about, and we should all be doing everything we can to support one another and make each other’s lives better. I’ve learned that helping and supporting another person is truly the best way to feel fulfilled at work and in life. People just want to be happy and feel like they are doing great work. Compliments and acts of kindness go a long way and people like people who have good intentions and help other people do their best work and get the most out of life.

It’s crazy to think that 4 years ago, I didn’t know any of this. The final thing that I’ve learned, and the lesson that I now understand to be the most important to me, is that a lot can happen in short bursts of time. People make decisions and take actions that can change things drastically from one day to the next. I’ve learned that the best way to feel that you are continually growing, that you are continually evolving, is to hold on tight to change and never let it go.

Growth happens when change happens. Learning happens when new things come at you, when different things challenge you, and when things start to fail and succeed. I never knew how important change would be when I first started at ClassPass. I never knew that resistance to iteration, to evolution, and to new ways of thinking would be what would block my own ability to become better. And now that I’ve learned that, I feel strong. I feel confident in my ability to stay passionate and driven as my life moves forward- both in and out of my career.

I’m right where I need to be in life and I’m grateful to have had all of the opportunities, to have met and become friends with all of the smart, talented and accomplished people, and to have learned what is most important to me in my life and my career. It’s all so good and I can’t wait for what the coming years will continue to teach me.

Thanks for reading! Want more? Check me out on Twitter or Instagram.

Benjamin HawesComment