Jessica Williams of Shopify on How Culture, Community & Psychology Shape the Brands We Trust
Off Script
In this episode of Be Anomalous, Jessica Williams joins me for a grounded, wide-ranging conversation about marketing as human behavior, creator-led entrepreneurship, and what real influence looks like inside powerful systems.
Jessica has spent her career inside some of the most influential companies shaping modern culture and commerce — from Visa to Coinbase, and now Shopify, where she leads Brand Marketing for a platform powering millions of entrepreneurs globally.
She’s worked closely with creators, founders, and global icons — helping turn influence into real businesses, community into distribution, and culture into strategy.
But Jessica’s story doesn’t start in a boardroom.
She grew up in a home where her mother ran a psychology practice out of their living room — surrounded by athletes, high performers, and people navigating mental health challenges. That early exposure shaped how she understands people, behavior, ambition, and decision-making.
It’s also why she believes marketing isn’t just a business function — it’s behavioral psychology.
In this conversation, Jessica offers a rare, honest look at what it means to build influence without being the loudest voice in the room. She talks about risk in a world that moves too fast to cancel you, why “playing it safe” is often the most dangerous strategy, and how ambition evolves as life, leadership, and responsibility grow.
This episode is for founders building from scratch and for corporate leaders navigating power, culture, and decision-making from inside the system.
If you’ve ever felt caught between stability and creativity, safety and impact, or structure and self-trust — this episode is for you.
🎧 Listen to the episode:
What You’ll Learn
Why marketing is fundamentally about human behavior, not tactics
How creator-led entrepreneurship actually works behind the scenes
Why being “safe” is the fastest way to become forgettable
What community-driven brands do differently from big box companies
How to build influence without chasing visibility
Why boundaries are a leadership skill, not a weakness
How ambition changes — without disappearing — as life gets fuller
What it really takes to adapt in fast-moving industries
Favorite Quote
“A rising tide lifts all boats.”
A reflection of Jessica’s belief that influence, leadership, and success aren’t zero-sum and that the best work happens when people build together, not in competition.
Favorite Book
A book that helped Jessica reframe growth, ambition, and learning as a series of small, sustainable actions — rather than dramatic breakthroughs.
In This Episode, We Cover
(00:00) Jessica’s origin story and growing up around psychology
(03:45) Why marketing is behavior, not just business
(06:30) From Visa to Coinbase to Shopify — building brands at scale
(10:15) Leadership, mentorship, and protecting your people
(13:00) Why being “safe” is the riskiest strategy
(18:00) Creator-led brands and the power of authenticity
(24:00) Why most celebrity brands fail
(30:00) Community as the new distribution
(36:00) Confidence, networking, and finding your voice
(40:00) Boundaries, ambition, and redefining success
(43:00) Advice for founders and corporate leaders navigating change
Referenced in This Episode
Creator-led and celebrity-founded brands on Shopify
Community-driven commerce and pop-up retail
Behavioral psychology in marketing
Boundary-setting as a leadership practice
New episodes drop every Monday and Thursday.
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