Creating Safe Spaces and Confident Voices at Lead the Way

Staff Spotlight: Wailly Tamayo

At Lead the Way success isn’t just measured by certifications or job placements, it’s built on confidence, connection, and consistency. Wailly Tamayo, our Senior Post-Secondary Advisor, brings all three to every student interaction, helping young people find their voice and feel seen.

For Wailly, youth development isn’t just a job—it’s a mission. With over a decade of experience supporting youth and families in both New York City and Columbus, he leads with empathy, emotional intelligence, and a commitment to building trust.

A Path Rooted in Service

Wailly launched his career in 2013 after graduating from Syracuse University. Born and raised in the Bronx, his early work spanned school-based support, intake casework, internship coordination, and in-home intervention services for families facing hardship. After moving to Columbus in 2019, Wailly transitioned into AMP services, assisting youth aging out of foster care. He joined Lead the Way in December 2024.

“I saw the structure, the culture, and the impact LTW was having in the community, and I knew I wanted to be part of it,” he says. “It was different. It was mission-driven and student-centered.”

Leading Through Listening

In his role at LTW, Wailly works directly with students across multiple schools and neighborhoods with a focus on building relationships. “A lot of students just need someone they can count on consistently,” he explains. “When they know you’re not just checking a box but actually showing up, that’s when the real work begins.”

One early example stands out: a Latina student who had been underpaid at her job felt afraid to speak up. Wailly coached her through how to address the issue assertively. She returned not only with her missing pay, but with a new sense of confidence in her ability to advocate for herself.

“That’s when I knew this work was making a real difference,” he says.

Coaching with Patience and Purpose

One of Wailly’s greatest challenges is learning to support without “fixing.” “As a support staff member, it’s natural to want to steer students away from making mistakes. But sometimes, the most powerful lessons come from figuring things out for themselves. We’re here to support the recovery, not prevent every stumble.”

As a senior post-secondary advisor, Wailly also plays a leadership role within the LTW team. He mentors new staff, offering guidance on student engagement and emotional regulation in high-pressure moments.

“Not everyone enters this work knowing how to lead with empathy. I try to model what it looks like to be firm, supportive, and present all at once.” He emphasizes that effective youth engagement is always relational first, procedural second. That perspective is shaping how newer team members approach their work—and helping the entire organization grow stronger.

Wisdom for Youth and Youth Advocates

Wailly’s advice to students navigating school, work, and life? “Ask questions. Stay curious. Don’t be afraid to try new things professionally. You never know what will spark the light of change within you.”

And to fellow educators and youth advocates? “Don’t underestimate the power of being consistent. A calm, reliable presence can do more for a student than any single program.”

At LTW, success comes in many forms—academic milestones, job training, program participation. But for Wailly, impact is felt in the moments when a student feels heard, empowered, and seen.

“Seeing students recognize me as a safe space... that’s the most rewarding part,” he says.

Wailly Tamayo doesn’t just lead the way. He creates the kind of space where students can begin to lead themselves—and that’s where transformation begins.