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Opportunity Starts With Me: Sheila Wakida

Published on May 18, 2023

In my almost five years at Dropbox, I’ve been awarded increasingly more responsibility in my roles. And while my career progression is a reflection of Dropbox’s focus on internal advancement, it’s also the result of my ownership and awareness of creating opportunities. 


My Dropbox story begins when I was recruited for a Technical Program Manager (TPM) role. As a Product Manager for most of my career, I was not sure what my career trajectory would look like if I made this shift. But after speaking with the phenomenal recruiter about the anticipated job and the supportive culture at Dropbox, I quickly understood this role would yield countless opportunities and open many new doors for me. Right away, I was tasked with various challenging residency projects and with much dedication, I was able to successfully complete them all within a surprisingly efficient timeframe.


Following this success, our CTO offered me an opportunity to be the Execution Lead for our new product strategy. At the same time I also received an opportunity to be the Group Product Manager for Platform. Ultimately, I chose the option totally out of my comfort zone. This work culminated in the Dropbox Work In Progress conference with Michelle Obama as our keynote speaker. It was a truly amazing experience, and one that I look back on in awe and amazement because of the sheer size and complexity of the project. It brought us together as an organization driving towards a common purpose, and is certainly a highlight of my career.


I was then promoted to an engineering leadership role, which provided the opportunity to go from leading a small team of specialized TPMs to a Group Lead with a team of over 50, across multiple functions and programs. With every new role comes challenges, and this was no exception. There were many hard decisions involved in leading critical initiatives and my TPM teams took on more and more strategic projects. The experience I gained in this role contributed to my advancement to Director of Engineering for Core Systems, and a seat on the Technology Leadership Team.


I attribute my career growth to the unique ways in which Dropbox recognizes impact and hard work, and I’ve learned to focus on creating the most impact out of the opportunities in front of you. I strive towards doing the best possible work and at the highest level of quality that I can deliver, no matter how big or small the task. For me failure is not an option, it’s owning the solution and making no excuses. The ability to instill passion, excitement and pride in the work at hand is also an essential element in leading successful teams. 


Today, I’m the proud Senior Director of Engineering, Developer Productivity - a role I achieved while also attending graduate school at Northwestern University to earn a Masters of Science in data and analytics. My teams continue to drive execution for some of the most technically challenging and high risk projects at Dropbox to date. Dropbox’s engineering talent is top notch and that’s because the company rewards those that strive to do their very best, embrace those that own their failures, and recognize those brave enough to take on the toughest challenges to transform them into opportunities.


Bring on even more opportunities in 2023!