About
Confidence is the first product every founder builds.
Winnovation Agency began in Hilton Head, supporting founders and entrepreneurs across the Charleston to Jacksonville corridor, a region full of talent, creativity, and underdeveloped entrepreneurial infrastructure.
What started as hands-on support for founders navigating early ideas, pitch rooms, and uncertainty quickly revealed a pattern:
Founders weren’t struggling because they lacked ideas.
They were struggling because they lacked confidence, clarity, and belief.
That insight shaped everything that followed.
Mission
To build confident founders and strengthen entrepreneurial ecosystems by developing clarity, conviction, and presence in the people leading ideas forward.
We support founders, students, startups, and organizations at the moment ideas are evaluated, helping them show up with confidence, communicate clearly, and lead with belief in themselves and their work.
Vision
We help founders trust themselves as leaders before they’re evaluated in high-stakes rooms.
We envision entrepreneurial ecosystems where founders are prepared not only to build ideas, but to carry them, with confidence, clarity, and conviction.
Our vision is a future where:
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confidence is recognized as a strategic advantage
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pitch rooms reward clarity and belief, not just polish
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ecosystems grow stronger by investing in the people behind the ideas
We prepare founders to own the room
not just explain the slide deck.
TAKE IT TO THE NEXT LEVEL
Strategic But Human
At Winnovation Agency, we are committed to providing the best consulting services in the industry. Our team of experts is here to help you develop and execute the most effective marketing strategies for your business, taking into account all the latest trends and best practices.
Our Founder
Meet Sierra Pollard, Ph.D.
Sierra Pollard, Ph.D., is one of the world’s leading experts in design thinking, entrepreneurial networking, and ecosystem development. An award-winning strategist, author, professor, and philanthropist, Sierra is known for building powerful connections between people, ideas, and opportunity at scale.
She is the founder of Winnovation Agency, a coaching and consulting firm dedicated to developing confident founders and strengthening entrepreneurial ecosystems. Sierra works globally with students, founders, startups, institutions, and innovation communities to help leaders build clarity, conviction, and presence in high-stakes environments where ideas are evaluated, funded, and scaled.
Sierra serves as a professional pitch competition judge multiple times each week, evaluating founders across universities, accelerators, startup programs, and innovation ecosystems. Through this work, she has reviewed hundreds of founder teams across industries and stages, giving her rare, real-time insight into what judges, investors, and accelerators are actually looking for. Her expertise extends far beyond slide decks and frameworks and centers on founder readiness, confidence under pressure, and the ability to lead decisively through uncertainty.
In academia, Sierra is a professor of innovation and design thinking, recognized for creating experiential, cross-disciplinary programs that connect business, engineering, and creative disciplines. She is the author of multiple books and educational resources on innovation, ideation, and entrepreneurial mindset, widely used by students, educators, and founders.
Beyond her professional work, Sierra is a committed philanthropist and ecosystem builder. She has founded and supported initiatives that expand access to entrepreneurship, education, and innovation, particularly for women, students, and nontraditional founders. Her community-driven work has strengthened regional ecosystems from Hilton Head and Charleston to Jacksonville, with impact extending nationally and internationally.
Sierra is also a sought-after keynote speaker, regularly invited to speak at startup events, pitch competitions, universities, leadership programs, and innovation conferences. Her talks combine strategic insight, real evaluation experience, and confidence-building frameworks that leave audiences clearer, more connected, and ready to act.
Sierra's life mission is to build up communities and inspire the creators to achieve greatness where opportunity moves.
Our Expertise
Design Thinking
and Innovation
Entrepreneurship and
Product Strategy
Career Development
and Coaching
Experiential Learning
Facilitation
Certifications and Professional Credentials
Certifications are not the foundation of Winnovation Agency’s work.
They are the tools.
These certifications reflect deep, applied training in design thinking, innovation strategy, facilitation, and entrepreneurial development. More importantly, they represent methodologies that have been tested, refined, and applied across real founders, startups, classrooms, pitch competitions, and innovation ecosystems.
Each certification informs how we coach founders, evaluates pitches, designs programs, and builds ecosystems. They are not theoretical frameworks. They are operational systems used in live environments where ideas are challenged, funded, or dismissed.
This combination of formal training and real-world application allows Sierra to translate complex methodologies into practical, confidence-building tools founders can actually use.
