A story of my career change, from sales to design

How I transitioned from business development at Google to product design.

DY Lee
Bootcamp

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Pretty soon I’ll be starting a product design internship at a software company called Braze. It was a long journey to change careers, but I learned so much through the process. Can I say long again? Maybe a capital L and bold font will do. Long.

To put things in perspective, it took 14 months, 200+ applications, 205 rejections, 6 interviews, and ultimately 1 design job offer to get here.

Through this article, I hope to do two things.

  1. Document the start of my design career to read in the future (hopefully as a more seasoned and wiser designer).
  2. Help aspiring designers who are considering a career change. I know that when I first started, it was really useful to read about other people’s experiences.

How it all began

For the past six years or so, I’ve worked in business development and software sales. Actually, my first job out of college was marketing frozen dumplings but that’s another story. Shout out if you’ve seen any of these at your local Costco.

A huge amount of this time was dedicated to finding new business for various technology companies, which sold products ranging from servers and IT services to enterprise software. Most recently, I was on the business development team at Google Cloud for the Looker product.

An accurate depiction of me as a business development rep in tech, eagerly cold calling an IT Director.

Outside of work, I’ve always been interested in technology and try to stay up to date with new devices, platforms, or tech news in general. A big thank you to Marques Brownlee, although he will probably never read this.

Looking back, there have been a lot of creative influences around me too. Many of my friends are designers, and I enjoy creative projects outside of the 9–5 like cooking videos and photography.

I guess all of these influences sparked an interest in Design during 2018, which is when I first moved to NYC and started casually reading design articles. Design was always interesting, but I never really had the chance to study it deeply.

One of the first videos that I watched on what being a UX Designer was like.

Fast forward to 2020 and like many others, I found myself spending way more time at home. I really wanted to try to be productive, so decided to learn more about design through a bootcamp.

Back to the books

After some research and hearing about it from a couple of friends, I enrolled in Designlab. It seemed like a good program, and I was also interested in learning from mentors that the bootcamp connects students with.

There are many design bootcamps out there, so I’ve linked a list with some recommendations.

There’s a lot of debate on design bootcamps, but I think the most important thing is that there’s a genuine desire to learn. In my opinion, a bootcamp is one of many ways to get into design.

Personally, I needed some sort of structure and access to mentors. The bootcamp provided these, along with a foundation for the basics which is exactly what I was looking for.

My enrollment email for the start of Designlab in June 2020.

I slowly progressed on the bootcamp projects during the evenings and weekends, while working my full time job. There were definitely times when I wanted to give up, but luckily I was able to graduate from the program in April 2021.

From start to finish, Designlab took me about 10 months to finish. For the part time track, the estimated completion time is around 6 months but this differs for everyone.

Screenshot from April 2021. Students need to submit their portfolio to graduate from the program. This was actually the second time I submitted mine, so it was a very welcome email.

While going through the bootcamp, I also sought mentorship from experienced designers. This was without a doubt, the most impactful part of my career change experience.

A huge thank you to Mariana, Cassandra, Mike, Anthony, Kenny, and countless others who helped me throughout the bootcamp and during the job search! If you are reading this, I’m extremely grateful for your help.

One of these mentors also curates UX Design Weekly, which is an excellent resource that I’d recommend to anyone interested in Design.

Another great resource is ADPList, which is a testament to how supportive the Design community is. The platform connects aspiring designers with experienced mentors around the world who are willing to help with portfolio reviews, interview prep, and career advice. Very solid.

After finally finishing the bootcamp, I was super fortunate to work on a 20% project at Google. You can read more about the 20% philosophy here, but this project was a wonderful opportunity to work with a product manager and engineers as a volunteer designer.

I would highly recommend supplementing a design bootcamp experience with volunteer work. Besides having the chance to help others through design, you will gain real life experience and can apply what was learned in class.

Several volunteer resources:

It was also really helpful to join online communities, which gave me a chance to connect with other designers and keep up with industry news.

The arduous job search

It took me about 3 months to find a design job after starting the search in May. I methodically tracked every application to gather data to look back on. This was also a habit from being in business development, where I tracked outreach to prospects to analyze where improvements could be made.

Tracking all of these details (including rejections) was tedious, but also surfaced some valuable insights.

My job tracker sheet, where I filled out details of job applications and additional notes.

For example, if I noticed that ideal job listings came from certain websites, I would spend more time on these. This job board from Ideate Labs was one of them. Or if there were job titles that yielded better results, I started using these as search filters. Things like “Jr. UX Designer” vs. “Junior Product Designer.” While looking at job applications everyday, I started to pick up on “design” language and phrases to infuse into my resume and cover letters.

I am also a big fan of automating content to deliver straight to my inbox. Alerts from Google or LinkedIn would send me job listings everyday based on preset filters like Job Title or Location.

I got this alert from Google every day, which linked to job postings across the web.

With each new conversation, I learned more about the general structure of interviews and things to expect. There are many resources on preparing for design interviews, but these are some that were especially helpful. Particularly for the dreaded whiteboard challenge.

A video that another Designlab student shared with the group. Extremely helpful for structuring a portfolio presentation.
I had never done a whiteboard challenge before, but knew they were notorious in design interviews. So I tried to absorb as much as I could from other designers who walked through mock challenges.
I also watched design challenges from a Product Manager’s perspective. Since designers work closely with Product Managers, I thought it would be helpful to try and understand design thinking from this angle. It is also likely that a Product Manager will be involved in at least one of your interviews.

Main learnings from interviews

Observe the data for patterns

After several interview cycles, I started noticing some common patterns.

These were specific topics and questions that interviewers asked, or parts of my presentation that sparked certain reactions. Eventually, some of these became predictable which helped me prepare responses ahead of time.

Overall, I tried to gather as much real life data as possible to help me improve for next time. I had never done design interviews before, so this was a good opportunity to test things out and change my approach based on feedback.

Some challenging questions that kept coming up:

Q: How did you handle conflicts with developers while designing?

Q: If you could go back, how would you approach this design differently?

Q: Were there times when you gave up something during the design process due to constraints? How did you approach this?

See each interview as a learning experience

Rejection is an inevitable part of the job search. What helped me from my time in sales, was getting used to rejection and knowing not to take it personally. Remember, when one door closes another opens.

Rock on. Coincidentally, “no” spelled backwards is “on.” Point is, it all depends on how you see it.

Job searching is an emotional rollercoaster, but rejections also provide valuable data that can be used to iterate and improve on for future interviews.

Plus, it is great practice and helps build confidence for next time. There is always another opportunity, so don’t sweat it too much if things aren’t working out at first. At least this is what I told myself, while anxiously refreshing LinkedIn Jobs every 30 minutes.

As I went through additional interviews, my presentation deck and flow started becoming a little bit more refined each time. Here is the exact template that I used to put together a deck to present design work.

Find common threads from the past

A big challenge was how to relate my past experience to a seemingly unrelated field (design). What could sales and design possibly have in common?

As it turns out, there are many overlapping areas and transferable skills.

These include communicating with other teams, presenting, negotiating, and pivoting quickly based on feedback. I also found out that the discovery process is almost identical in trying to better understand user pains, challenges, problems, and goals. From there, how might we help them solve the problem?

Looking back, I’m glad that my background is in business development and sales. This helped me build the confidence to clearly communicate ideas, and have human conversations about solving a problem together.

Also, I had the chance to fail miserably in sales calls and make plenty of mistakes. There was one time where I was so nervous, that I literally sweated and my hands shook outside of the view of the webcam.

Still, the world continued spinning and I learned that it’s really not that big of a deal. I can also approach problems from a different perspective and think about how design impacts the business.

It takes a village

I really couldn’t have made this career change without the help of numerous mentors. Below are several spotlights of the people who’ve helped me make it here.

If there is one thing that I’d emphasize, it’s the importance of seeking mentorships. This could be through mutual connections, a bootcamp program, working for the same company, online resources like ADPList, or reaching out to designers on LinkedIn.

Luckily, many designers are willing to help and share advice. All it takes is putting yourself out there, and being willing to learn.

Changing careers can take a long time. It took me 14 months and wasn’t an easy process. However, persistence pays off when paired with a genuine desire to learn. Eventually, opportunities will arise and with a bit of preparation and luck, everything falls into place.

I am really thankful to have learned from mentors who were willing to share their time and experience. If you asked me several years ago, I would have never imagined myself making this transition.

My career change was certainly a journey and extremely challenging at times. The highs were high, and lows were extremely low. There were moments when I almost cried or gave up. Not to mention many nights of looking out at the stars at night and being sentimental.

This might literally be me. Or a stock photo from Unsplash. I will let your imagination decide.

What kept me going through it all was encouragement from family, mentors, friends, and a vision of who I want to be in the future.

Trust me, if I can do this, anyone can. Good luck!

If you’ve made it this far, I sincerely hope this article was helpful.

Please feel free to reach out on LinkedIn if you have any questions!

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