The Professional Journey of Elyssa Gray, VP Brand | Betterment

Elyssa Gray, VP Brand, Betterment


If you had to choose one specific creative piece (can be a song, photo, artwork, movie, play, etc.) that best reflects your professional journey, what would that be and why?

There’s no easy, winning ticket to professional success in advertising: no one skill or experience has made my career. So, I think about how a convergence of factors have enabled my trajectory. The network of champions in my life. Living by the golden rule (as corny as that may sound). Setting up my team to work in harmony. Maintaining a strong eye for quality. Demonstrating my gratitude and appreciation for others’ contributions. These are the deeply interconnected elements of my career journey. Some may feel lucky in their careers, but for me, it was more like ​Sliding Doors, a movie where day-to-day decisions—even small ones—become critical in the story.

What was the turning point, or most important moment, in your career? How has this moment led you to the leader you are today?

There are many points throughout my career that have been pivotal. Decisions that I made to change roles, quit my job and move across the country, leave a job without a new job waiting. These were all conscious decisions that surprise me when I think back to them about how calm I was with each of these changes. I am a ​planner, not having a plan is just not something I do. And yet, when I have faced situations without an actual plan—forced to become comfortable with the uncomfortable—I find I thrive. I recall when I left Visa after 13 years, and was ​freaking out about what I was going to do and how I had no plan, a wise woman said to me, “Maybe your plan is not having a plan.” With that one sentence, I was completely at ease and able to just be in the moment and not stress about what was to come and the things that I could not control.  

Tell us about a female figure who’s had a major impact in your life/professional journey.

It’s been my good fortune to know so many women who’ve inspired me—some of who even scared the shit out of me but they still inspired me to be better, work harder, and be more empathetic. One woman who will always influence me is my mother. My mom is a hard worker, and she always has been. As an adult, she earned her Master’s degree. She was a teacher for many years and eventually became the head of the science department at a NYC private school. I attribute my good work ethic to her. She also is a very thoughtful person and has an insane attention to detail. Every present she gives is wrapped with such care—ribbon that matches the paper and is curled perfectly with scissors. Now retired, she tutors my son every week and creates handwritten (​very neatly  handwritten) tests for him to study from on his own. Quality matters. Presentation matters.

What is the bravest thing you’ve done in your career so far?

One thing that I continue to work on is how to advocate for myself or give constructive feedback to someone more senior than myself. When I have challenged a problem I see that’s affecting me, I feel empowered and brave because I’m making my way myself. I was talking with a friend about this piece and when I was sharing my answer to this question, I explained it this way:

“I have no problem advocating for others, but for myself—yikes!”  

He had an interesting take on this: ‘Advocating for others is brave, if not more so and more impactful. Think about the impact you have on the larger team when you advocate for them, and you don’t really have anything to gain.’ That thought resonated with me, because the idea of a team being successful versus me being successful on my own is how I lead.