Jessie Young, Uber's Global Head of Restricted Verticals and Founder of halo, has navigated a career driven by a bold curiosity and talent for solving challenging problems.
Jessie’s unconventional yet purposeful journey has touched upon law, corporate finance, strategy, and successful startups. Soon after Uber’s inception, she joined the team, spearheading impactful initiatives in the launch of UberEats in Australia and New Zealand and leading finance readiness for Asia–Pacific through Uber’s IPO. Since then, Jessie has assumed a leadership style revolving around self-understanding and empowering her teams to excel. Her resilience among adversity and genuine understanding of people demonstrate the importance of empathy in fostering exceptional teams.
We asked Jessie about how her career background has led her to where she is today, what she finds most challenging about hiring, and the advice she would give someone starting on a similar journey.
Tell us about your career background. How has it led you to where you are today?
Hindsight suggests my career plan has a cogency that is really no deeper than insatiable curiosity. I have always followed my nose to problems that both fascinate me and are begging for a new solution. I am currently the Global Head of Restricted Verticals at Uber, but I began my career as a lawyer in Australia. When Uber launched, I joined in a strategy and corporate finance role through IPO before moving into general management. I have had a few failed and flourishing startups, including my own yoga business. Today, I work alongside my day job as a venture partner, board director, and startup advisor, as well as the founder of advisory consulting, mentoring, and community: halo.
My career is catalyzed by hypergrowth moments: launching UberEats in Australia and New Zealand in a nascent team of less than 10; stewarding Uber Asia–Pacific through IPO; co-building a team that grew from five to 3,500 to deliver on-demand groceries; integrating an alcohol delivery company into a billion dollar business; and being the first in the world to launch cannabis delivery on a third-party marketplace.
What’s the most impactful career experience you’ve ever had and how does it impact your work to date?
In early March 2020, I was leading retail categories on Uber in Australia. It was a brand new offering, and we were on the precipice of rolling out nationwide. Within two weeks, I was on government calls about how we could deliver food to vulnerable Australians if Covid-19 lockdowns persisted. My job was then launching grocery delivery around the world, growing 45 times in less than nine months. I learned that perfect is the enemy of good; perfect is not a position to defend. In hyper-growth environments, you must be ruthless on the priorities that matter most. Fail fast, fail forward. That means you are adapting, learning, and surviving.
There are very few one-way doors. Strategy is what happens in the gaps, in what you choose not to do just as much as what you choose to do. Therefore, step willingly, but mindfully, into new opportunities.
What, in the earlier parts of your career, best prepared you for this particular role?
Careers are modular. The best creators are often the best curators, taking pieces of their lives and threading those inputs in new and novel ways. My background in law gave me an understanding of the regulatory sandbox and how to play within it. My background building new businesses gave me the courage to follow my instincts, listen to the customer, and make decisions on imperfect information. My work as a venture partner enables me to balance growth and value. I do not just read—but now interrogate—commercial performance. The unique sum of these parts makes my capacity greater than the whole.
How have you grown as a leader since you started this role?
Integrity is a superpower. Understand what makes you you, know yourself intimately, and raise the floor of your team by doing so. I am more comfortable saying no, and I know why I say yes. Moreover, I know better when to say nothing at all.
What piece of advice has played the biggest role in your career so far?
There are very few one-way doors. Strategy is what happens in the gaps, in what you choose not to do just as much as what you choose to do. Therefore, step willingly, but mindfully, into new opportunities. You can nearly always go back to where you started. You will nearly always neither want to, nor need to.
Looking back, is there anything that you would change or do differently within your career journey?
I did not access nor try to build a traditional pedigree—be that the “right” internships, brands, or degrees. I cannot A/B test the results of following the head or the heart. I observe that growth is predicated on confidence. Pedigree definitely plays a role in shoring up the foundations that enable you to step into new, bigger, and bolder opportunities. At times, I’ve lacked that confidence, largely because I felt too different. I might focus on pedigree, or at least, focus on the sources of my confidence, earlier in my career.
Which books have been most helpful to you?
Usually, I’m reading a few books at once. My favorite resources are those that stretch me to the edges of my thinking. They aren’t necessarily the characters or messages I like the most. The most recent resources to rotate through my nightstand are Sapiens: A Brief History of Humankind by Yuval Noah Harari, Meditations by Marcus Aurelius, and Legacy by James Kerr. Don’t underestimate the pedagogical value of fiction. A few of my favorites in the past month are Moby Dick, To Paradise, (I’m a bit late!) and Three Women.
What’s something you do outside of work that makes you a better leader?
Listen. Be an empathetic friend, partner, and family member. Learn from others. Ask questions. Then use those inputs as building blocks in how you show up for your team, your customers, and yourself.
What do you look for when hiring someone on your team?
I seek to understand their character in the face of adversity. Intelligence quotient, empathy quotient, and adversity quotient are a holy trinity you want to set high. If I had to take a bet on one, I’d pick a high adversity quotient. The wisdom to dance with, rather than fight, life’s inevitable challenges is often unteachable. It’s also the parapet of resilience that makes a team extraordinary.
What do you find most challenging about hiring?
How do you understand who someone is, aside from what they do? How do you step outside your biases or the neurological laziness to group someone into a pattern you’ve seen before? Moreover, how do you do all that in a series of 30- to 60-minute phone calls?
What advice would you give someone starting out on the journey you’re on?
In a speech at my law school graduation, I repeated a quote from Archilocus: “We do not rise to the level of our aspiration, we fall to the level of our training.” At the time, I was referring to the foundations of a legal education. Today, I realize that is true also of our human experiences. Do not underestimate the importance of your life and living it. Invariably, that means failing, growing, changing, and adapting. You do not have the answers, and you likely never will. You do have your own unique perspective and your capacity to create based on who you are alone is powerful beyond measure.
