Visionary leader · Strategist · Author

Visionary leadership,
made plain.

I’m Jessica Madison, a servant disruptor with more than 20 years of executive leadership across Fortune 500 companies, professional sports, healthcare, and higher education. I help leaders see the vision, say it plainly, and run with it.

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20+ years executive leadershipFortune 500Professional sportsFounder & CEO, On Your Mark EnterprisesAuthor

See It. Say It. Run It.

See It.

Look past today and name what’s next.

Say It.

Write the vision down and make it plain enough to act on.

Run It.

Move on it by serving people and breaking the norms that hold them back.

The Servant Disruptor

Many layers.
One unfolding story.

Service was modeled for me long before leadership was. Over 20+ years in business, sports, healthcare, and education, I learned that serving people well often means challenging “how it’s always been done.”

I’m a strategist, author, philanthropist, and speaker on a lifelong journey of learning and growing. I’m always writing my next chapter, making room for new ideas, mentoring, and leading. This is where I bring those parts of my life together.

01 / Strategy & leadership

The Strategist

Clarity that moves people.
Strategy that moves work forward.

I bring more than 20 years of experience across marketing, sales, and communications to help organizations see where they can grow—and build a practical path to get there.

From leading sales teams to developing partnerships and shaping marketing plans, my work brings creative thinking together with the discipline to execute. I believe lasting growth depends on developing people along the way.

Strategy in practice.

20+ years of connecting ideas, people, and execution.

Marketing

Brand positioning, integrated campaigns, and digital content strategy.
Enrollment marketing experience, with 13.6% enrollment growth reported.
Clear positioning that connects an organization’s purpose with its audience.

Sales

$5.67M+ in total revenue generated throughout my career.
$1.36M in first-season sales under my team leadership, reaching 117% of quota.
$538K in new partnership contracts secured through business development.

Communications

Executive storytelling that makes vision and priorities clear.
Stakeholder engagement and media partnerships that connect people to the mission.
Community outreach that builds relationships and strengthens engagement.

Strategies in motion