Strategic Advisory to Accelerate Your Next Level of Growth
Jessica works with solopreneurs and mission-driven organizations to bring clarity, confident decisions, and intentional momentum to your most important priorities.
“Jessica is a powerful leader, able to see new, better, improved, and more efficient ways of facilitating learning and growth for the leaders of our future”
— Jennifer Walker @diveheartfirst
About Jessica
Jessica Flynn is a strategic advisor, award-winning educator, best-selling author, and speaker dedicated to empowering mission-driven leaders and organizations.
With an unyielding commitment to empowerment, quality education, and community, her work blends strategy, systems thinking, and human-centered leadership — helping leaders find clarity, create alignment, and unlock momentum. Jessica’s experience spans education innovation, leadership development, and advising founders with purpose and scale.
Strategic Advisory for Next-Level Growth
Jessica works with founders and leaders in mission-driven organizations through focused one-hour advisory sessions that help you:
Get unstuck
Clarify what matters most
Make confident decisions
Move forward with momentum
These sessions are flexible, strategic, and tailored to your stage and priorities.
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For solo entrepreneurs and early-stage founders building clarity, strategy, and systems — often while carrying many roles at once.
This work is for you if you are:
Shaping or refining your strategic foundation
Clarifying your vision, positioning, or business model
Creating offers, systems, or structure for the first time
Growing into leadership alongside your business
Moving from reactive decisions to intentional direction
Mission-driven, and seeking structure without losing creativity or soul
Common areas of focus include:
Strategic planning and prioritization, market positioning, offer clarity and pricing, lightweight systems and SOPs, and leadership confidence. -
For mission-centered organizations with teams, traction, and increasing complexity — ready to strengthen alignment, execution, and long-term impact.
This work is for you if:
You already have a strategy and want to refine or activate it
You are leading a team through growth or change
You are aligning leadership, operations, and mission
You are navigating a significant initiative or transition
You value trusted strategic partnership over task-based consulting
You want clearer decisions, not more activity
Common areas of focus include:
Strategic plan refinement and implementation, leadership and team dynamics, operational flow, special initiatives, and change management.
Client Outcomes
Working with Jessica means more than receiving advice — it means clarity, momentum, and impact. You’ll walk away with:
A clearer view of what matters most
Practical next steps you can act on
Confidence in your decisions
Alignment with your goals and values
“I just don’t talk about it…”
An Empowerment Professional, here to Multiply Momentum and Unleash Potential
The Next Generation of Change-Makers
As the Founder and CEO of The YOU Power Project, Jessica and her team offers Empowerment Education, Consulting & Custom Program Builds. YPP is committed to unlocking potential and inspiring change. What began with a mission to empower youth to discover their passions, develop essential skills, and create positive change in their communities has grown into services that support an entire community of lifelong learners.
Redefining Education for a New Direction
As the Co-Visionary of The Academy, Jessica spearheads a transformative initiative opening new doors in education. This innovative high school aims to redefine the educational landscape by nurturing critical thinking, creativity, and personal growth. It's an embodiment of Jessica’s values: empowerment, quality education, community, and a commitment to doing it all better.
Book Jessica to speak at your next live or virtual event, or to be a guest on your podcast or tv show
Speaking topics include:
For Business
Empower Your People: A Playbook for Cultivating Highly Engaged and Winning Teams by Unleashing Their Unique Genius
What’s Your Triple Bottom Line? Aligning with the Sustainable Development Goals (SDGs)
For Education/Youth
Discovering Your YOU Power: A Young Person’s Intro to Social Entrepreneurship for Change-Making
Dream School: How to Create Learning Environments that Foster Personal Growth for ALL!
As seen on
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Honored with Second Place in CanWCC's "Flip the Script" Pitch Competition
As the CEO and Founder of The YOU Power Project, Jessica is incredibly honored to have secured second place nationwide in CanWCC's "Flip the Script" pitch competition. This recognition is a testament to the innovative and transformative work she and her team are doing at The YOU Power Project, empowering young people to unlock their potential through entrepreneurship and creativity.
This prestigious competition was made possible through the generous sponsorship of Meridian Bank, the Government of Canada, and the City of Toronto, and Jessica is grateful for their commitment to fostering innovation and supporting Canadian entrepreneurs.
Recent Awards
In the realm of transformative, economic-impact education, Jessica Flynn is not just making waves; she's steering the ship toward a transformative future. Her unwavering commitment to quality education, empowerment, and innovation has garnered recognition from prestigious platforms, solidifying her role as a trailblazer in reshaping the landscape of learning and teaching.
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Honored with Third Place in Canada, the Capital Elle Business Impact Award is here to flip the script on who gets funded in Canada — and why.
Jessica is an award-winning educator and the founder of The YOU Power Project, a social enterprise that helps youth ages 10 to 18 develop real-world skills, build confidence, and launch operational businesses or community projects. Through experiential programs like Passion to Purpose and Student Ventures, she teaches young people how to turn their ideas into action and become leaders in their communities. The YOU Power Project partners with schools, municipalities, and nonprofits to deliver entrepreneurship and leadership training that consistently produces high venture launch rates and prepares youth for future-ready pathways.
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Honored with the City of Barrie’s Community Impact Award in Education
Jessica Flynn has dedicated her career to reimagining what education can look like and how it can truly empower young people.
Flynn is the founder of The YOU Power Project, a social enterprise that helps youth discover their potential through entrepreneurship and changemaking.
The initiative engages young people between the ages of 10 and 18 in programs like Student Ventures and Passion to Purpose, guiding them to identify their strengths and identify meaningful problems to solve.
The YOU Power Project was built around the idea that young people don’t have to wait until adulthood to make an impact. If they already have creativity, insight and drive, all they need is the right tools and support.
Flynn’s mission is to help youth build confidence, leadership and real-world skills.
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Gathering the most renowned educationists, EdTech innovators, policymakers, and researchers, the Education 2.0 Conference reimagines the education space and seeks innovative solutions to the most pressing problems impacting learning and teaching globally. Jessica Flynn was honored in an exclusive recognition session, spotlighting her incredible contributions to reforming and improving global education. Her dedication aligns seamlessly with the conference's mission of uplifting lives and building a better, more sustainable future through quality education.
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Recognized as a Top 100 Finalist in Canada's Total Mom Pitch, sponsored by TD and Bell Canada, Jessica Flynn stands out among the country's innovative and dynamic entrepreneurs. Her vision for education and commitment to community resonate with the ethos of the competition, showcasing her as a leader driving positive change. This accolade underscores her impact not only in education but also in the broader entrepreneurial landscape..
“Passion drives excellence, and it could not be more true when working with Jessica Flynn!”
Lindsay Earle, @mountainmoviefest
The Best-Selling Book
