Sara McCaffree, UX Designer, from YouTube to O.School

Sara was born at Bethesda Naval Hospital and raised in Oklahoma City. She attended Northwestern University in Evanston, IL hoping to pursue a career as an actor and worked in the entertainment industry in Los Angeles for a while.

Later, she applied for a position as the EA to the CEO of YouTube (just after the Google acquisition) and was lucky enough to get it, putting her on her current path in the technology industry. You can now find her at coffee shops around San Francisco working on her Sketch files.

You started your career as a program manager at Showtime, then transitioned into an assistant role for companies like Google, YouTube, Twitter. How was your experience of transitioning to tech?

I’d never even thought about having a career outside of entertainment, but I knew I needed to make a life change when I was offered a job in LA and was afraid I might throw up. Sometimes our bodies make our choices really obvious! I remember getting back to my email and seeing the link for jobs at Google and I thought, “they probably need *someone* to do something!” I was looking through a bunch of different jobs and found one that literally hit on everything in my resume so I applied and thankfully got the job being the EA to the CEO and CTO of YouTube.

I found transitioning to the tech industry fun and enlightening. I am so glad to be working in this industry. One of the things I love about the people I meet working in tech is that so many are really intelligent and very kind (that’s a bit of a subtweet — I did meet nice, smart people in LA but unfortunately, it was not the norm).

My day-to-day at YouTube was really a blast.

It was a teeny company (I was around employee ~85 in the building) and still functioned as a start up. Google left us alone for the most part. I loved the people I worked with and the job was great. I got to throw events, install a disc-golf course, plan our beautiful new space, make sure we got a pizza oven…it was different every day.

When I left YouTube, the project management aspect of the job — the part I really loved — went away. That’s when I realized it was time for a career change. I knew I wanted to stay in tech and I wanted to help solve product problems while having some creativity in my job, so I eventually decided to transition into a career in UX.

In September 2015, you pursued a 10-week intensive program to learn User Experience at General Assembly. What drove that shift of career path?

I remember walking into Google for new hire orientation ten years ago and thinking, “Finally, I am with my people!” I knew I was in the right place and industry for me. That being said, I always wanted to contribute more than I could in my role as an EA. Don’t get me wrong — I had lots of fun — but I wanted to learn more about how technology works so that I could solve problems for the products that I loved.

I also wanted my job to have some creativity so I decided that UX was better for me than, say, learning Ruby. I took some online and night classes over the years but I realized that I couldn’t change my career trajectory without completely jumping off the cliff and starting my career all over again. I looked at a few bootcamps but I’d been at GA before and really enjoyed it, so I decided to quit my job and focus on UX full time. It is a great feeling to finally use my brain to work on meaty challenges!

During the UXDi program at GA, you worked on several projects. What are some of your main takeaways from the program?

GA was a really positive experience for me and I’m still in touch with my teachers and the people I worked with (in fact, I hired one of them to help me design the site for my current company, O.school). We were taught the theory behind UX really well. I was so lucky to have the best teacher, Susan Wolfe, who is as passionate about teaching as she is about User Experience.

We all trained on Sketch (in a previous GA UX class they had us use OmniGraffle). We also had to take an HTML/CSS class. We had 5 projects to work on during our 10 weeks. The last one was a project where we solved a problem that a real tech company had which was great training for life after GA. I think every tech company should have students from a bootcamp work on a project because we were all chomping at the bit to do a really good job!

It’s been already a year since the program has ended and you have since done consulting for different companies. Do you think the General Assembly program was successful at giving you the keys to enter the workforce?

It really depends (hopefully my GA UX cohort is chuckling at my joke ;-) ). Before doing this, I had an extensive network that I built over 10 years living in the Silicon Valley and the only UX jobs I’ve been hired for have come to me through that network.

GA did a great job of hammering home that your network is everything and it is pretty unlikely that students will get jobs from cold submissions.

I can tell you that every job I submitted to online rejected me. For some people who didn’t have a good network, the job search was harder. There are also the variables of interviewing well, being a “culture fit”, etc. that are hard to quantify. I would tell anyone interested in doing this that changing careers is never easy, and the first year will likely be rough, especially if you’re in an area saturated with talent the way we are here in the Bay Area.

I had the advantage of knowing I was going to do this for a few years and I was prepared to go for a while without a salary. If someone asked me if they should quit their job, go to a bootcamp and then pursue a career in UX I would absolutely encourage them, as long as they think they can keep a roof over their heads while doing it.

If you had the power to go back in time, what would you have done differently?

This is such a hard question for me to answer. I try never to think about what I would do differently because even though I went through some really hard times, I learned valuable lessons that brought me to where I am. From one very bad career decision I made, I learned that I need to advocate more for myself.

Another one of the big lessons I’ve learned over the last decade working in tech is that culture is very important to me. At this point in my career, if I walk into a space that is full of pool/ping pong tables and nerf darts, I’m going to nope right out of there, because I know it will absolutely not work for me. I’m glad I learned those lessons, so I wouldn’t necessarily change anything, but if I could go back in time, I’d want to give myself a big hug.

What’s next for you?

Right now I’m working at a startup called O.school. I’m the design lead and I also do ops. We just had our alpha launch, which went over really well. Now we have lots and lots of work to do to get to our beta launch! Our goal is to launch this summer. It’s been so cool to create a product from scratch and I’m looking forward to debuting it to the world soon.

Finally, who should we interview next?

I loved my teacher at GA, Susan Wolfe. I think she’d have a lot of great things to say to people looking to do a bootcamp. In my capacity doing UX at the start up, I was able to hire one of my favorite GA colleagues, Nicole Gottwald, to do design with me. She’s also a fantastic photographer.

Christina Brodbeck has a lot of interesting things to say about design and technology in general. Andi Galpern is doing wonderful things for the UX community through Cascade SF and is multi-talented. I’d love to also hear from people who say they’d never hire a bootcamp student but of course I don’t personally know anyone who feels that way!

Connect with Sara on Linkedin, Twitter, and discover her work.

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