1. If you were to describe your job to a 5 year old, how would you describe it?

Great question. Simplifying is one of the most challenging and valuable skills in this industry! Having transitioned from the traditional agency world to We Are Rosie - an industry disruptor - I am regularly challenged with describing not only what I do but who we are. So here goes ... We Are Rosie is a big group of people with marketing skills (we call them Rosies), who for many reasons can’t or don’t want to have a full-time job but do still want to do marketing work. Companies can add these people onto their teams for short amounts of time to help them get their work done. My job at We Are Rosie is to make sure the world knows about us and really loves us, so we can give as much work as possible to our Rosies.


2. What is the best advice you've received in your career?

As I was giving my resignation at a job I had really loved, the head of the office said something to me that really stuck. I was leaving the company because I wanted to move to New York, and for many reasons (including general industry and work culture at the time), I hadn’t felt comfortable sharing that desire or asking whether a transfer was a possibility. So, as I resigned I shared my love for the company and regret at having to leave in order to pursue life goals. He was very gracious, and offered a sage little rhyme that really shaped who I became as a leader: “the higher you go, the less you will know.” From this bit of counsel, I have made a concerted, conscious, and continuous effort to manage up and also listen down throughout my career. I decided that I owed it to myself and to anyone I managed to open up all the possibilities. Sometimes that meant being labeled too ambitious. Sometimes that meant helping someone I really wanted to keep on my team to move on. But it always felt right, and leaves me with no regrets.


3. If you could thank someone that helped get you to where you are now, who would you thank and what would you say?

This is a really interesting question for me at this stage of my career. Had you asked me 4-5 years ago when I was a jet-setting, striving, global agency executive, I probably would’ve credited my parents for their example and drive, bosses and other leaders who noticed me and took a chance on me at pivotal moments in my career, or perhaps certain advisors who gave me critical insight and kept me steady as I navigated the corporate ladder. But today, I want to thank my 3-year-old son. I thank him for forcing me to step back and see it all more clearly. To stop accepting and rationalizing the inequity, unconscious bias, burnout, and trauma so prevalent in this industry as the price of success. Now at We Are Rosie, I am still working as hard as I ever have, but on terms that work for me, and with people on a mission to change lives. I am trusted with total flexibility, I am respected as a human with a life, and I get to do good in the world with every hour I spend at work - which is the only work worth the trade of time with my son.

*Jessie is currently the Head of Product & Strategy for We Are Rosie and lives in Hermosa Beach, CA*