Jillian Di Benedetto
Jillian Di Benedetto is a Creative Director, strategist, and founder of Untethered Creative, known for translating high-level strategy into meticulously crafted, pixel-perfect design. With a background spanning advertising, branding, and digital innovation, she leads cross-functional teams to deliver award-winning work across web, user experience, and integrated creative campaigns.
Her work has earned 17 Gold ADDYs, 18 Silver ADDYs, and multiple Midas, Summit, Effie, and Webby Awards, reflecting her ability to merge aesthetic excellence with measurable business impact. Jillian’s approach blends rigorous systems thinking with bold storytelling, helping brands build clarity, consistency, and connection at scale.
Beyond client work, Jillian is an active voice shaping conversations about the future of advertising and branding, exploring topics such as creator-first platforms, the evolving role of women in tech, and what it means to build an authentic personal brand in an AI-driven market. In discussions and interviews, she often reflects on her journey from agency leadership to entrepreneurship, emphasizing resilience, balance, and designing a career on your own terms.
She is also the founder of makecence.com, a community-driven micro-giving platform that empowers people to support one another through small acts of generosity. Since launch, the platform has connected 200+ users and raised hundreds of dollars to help individuals in need, an extension of Jillian’s belief that creativity should serve people, not just brands.
A mentor, collaborator, and sought-after thought leader, Jillian is known for her distinctive voice, equal parts strategic rigor and sharp, satirical insight. Through podcasts, writing, and side projects, she inspires creatives to push beyond deliverables and see design as a strategic engine for growth, trust, and impact.
At her core, Jillian champions originality, meaningful collaboration, and ethical leadership, guided by a belief in the power of creativity to drive both cultural relevance and commercial success.
• Designlab
Figma Certification
• University of Florida - Advertising
• 17 Gold Addys
What do you attribute your success to?
I attribute much of my success to the work ethic and guidance instilled in me by my mother, a renowned child psychologist, which shaped my dedication, resilience, and people-first leadership style. As a creative leader, I bridge big-picture strategy with pixel-level execution, aligning teams and narratives to deliver cohesive, high-impact work, right down to passionately defending proper spacing in Figma.
What’s the best career advice you’ve ever received?
“Don’t build your career to be chosen. Build it so you can choose.”
What advice would you give to young women entering your industry?
Learn the tools, but master the rooms.
Keep receipts.
Ask for money.
Trust your gut.
Build work they can’t take from you.
And never make yourself smaller to fit a system that profits from your silence.
What are the biggest challenges or opportunities in your field right now?
I think the biggest challenge right is that clients and companies too often treat design as a deliverable, not a strategic engine. They want fast, cheap, templated work. But real impact requires investment, time, and strategic thinking.
Turning this into an opportunity means being a designer who can translate craft into business language. Outcomes, retention, conversions, brand equity. Stop being “order takers” and start being growth partners.
What values are most important to you in your work and personal life?
I don’t sugarcoat. I don’t perform. I value calling things what they are, even if it costs comfort. I’d rather be real and disliked than polished and hollow.
In work: honest strategy, no BS decks.
In life: saying the hard thing, protecting my boundaries.
Locations
Untethered Creative
Hollywood, FL 33021