In her almost five years at Dropbox, Sheila Wakida has been promoted four times. And while her trajectory is a testament to the company’s focus on internal advancement, it’s also the result of her work ethic.
As she puts it, “I strive to do the best possible work that I can at the highest level of quality that I can deliver no matter how small the task,” she says. “For me, failure is not an option.”
Today, she’s the Senior Director of Engineering, Developer Productivity—a role she achieved while also attending graduate school at Northwestern University to earn a masters of science in data and analytics.
Here, Wakida shares the job offer at Dropbox she couldn’t refuse, the biggest highlight of her career at the company, and why you shouldn’t focus too much on your job title.
Tell us about your career path. What inspired you to pursue a career in product management, specifically in tech?
My career path started out in finance as a management trainee and I found myself gravitating towards the technology areas within the company rather than finance and marketing. I was in awe of the technology and applications that enabled trading, supported the customer, and carried the business. Becoming a product manager was a natural transition melding my finance and business acumen to the tech space. My career made yet another shift from product management to technical program management, with a focus on execution and product delivery. All of the elements and skills obtained in business, finance, product, and engineering have now landed me where I am today. Having the experience in understanding customer needs, building a business around it, and knowing how to deliver solutions have opened up opportunities that I would never have dreamed possible.
What led to your role at Dropbox, and how did you know it would be a good fit?
My story begins when I was recruited for a technical program manager (TPM) role for the Dropbox Paper team. I’m a career product manager with experience in collaboration products and platform services but had never been a TPM. I wasn’t sure what that crossover would look like and what trajectory my career would take if I made this shift. I had a phenomenal recruiter who sold me on the culture, but also on the opportunity.
How did your early work at Dropbox lead to more opportunities within the company?
As a TPM, I was given three residency projects to tackle, which were among the toughest problems that the organization had been trying to solve for some time. One project was to define, establish, and roll out the position of a technical lead (TL) for engineering. The TL designation is not a role change nor a promotion, but rather a tool to recognize high-potential engineers and help them provide greater impact. That project exposed me to different senior engineering leaders across the organization. I was able to successfully complete all of my residency projects within a quarter, which surprised my manager and other leaders. This is when opportunities began to open up.
What is one highlight of your career thus far at Dropbox?
In 2019, our Chief Technical Officer at the time offered me the opportunity to become the execution lead for a new product offering. I accepted the role because I was intrigued with doing something totally out of my comfort zone. Also, when you’re offered this type of opportunity by your CTO, you take it.
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 really brought us together as an organization driving towards a common purpose and is certainly a highlight of my career.
What have been the keys to your success as a team leader?
The ability to instill passion, excitement, and pride in the work at hand is an essential element in leading successful teams. Having to tirelessly influence without authority requires you to be a positive force to mobilize and inspire others to do their very best work.
How does Dropbox encourage career growth and development?
Dropbox is one of those truly special places that rewards those who strive to do their best, embraces those who own their failures, and recognizes those who are brave enough to take on the toughest challenges to transform them into opportunities.
What advice would you give someone just starting out in their career?
I’m often asked if there is a formula or a set of steps that have led to my fast career trajectory. My response is that there really isn’t a formula, and everyone’s path is different. I’ve learned that you should not fixate on a job title, but rather on the opportunity and impact you can make. In addition, don’t focus only on work that you’re given, but also on areas where you can make a difference.