#VillageTalks: Jose Santiago — Building Systems Where Students Feel Seen

Some leaders do more than manage systems.

They transform them.

That is exactly what stood out in this powerful #VillageTalks conversation with Jose Santiago.

Jose currently serves as an assistant principal in Chicago, leads work around culture, belonging, attendance, discipline, and student services, and is actively pursuing his doctorate in educational leadership.

But what makes this conversation so powerful is that Jose’s leadership is not rooted in title.

It is rooted in lived experience.

He shared something that stayed with me:

he grew up navigating systems in Chicago that did not always fully see him.

That reality has now become part of his mission.

To build schools and systems where students feel seen, supported, and still held to high expectations.

That combination matters.

Support and accountability.

Belonging and excellence.

Jose also spoke powerfully about what drives him to continue pursuing his doctorate while leading, parenting, and building at a high level.

At the center of that journey is family.

His wife.
His children.
His mother’s sacrifice.
And the desire to model possibility for the next generation.

This conversation was especially meaningful as Jose unpacked the beauty and brilliance of Latino students and families in Chicago.

He reminded us that excellence is not something schools “give” students.

It is something students already bring with them.

Culture.
Language.
Storytelling.
Music.
Food.
Leadership.
Resilience.

As Jose said so clearly, students come in as the cultural experts of their own lives.

That framing is powerful.

Because too often systems begin from deficit.

What students lack.
What families don’t know.
What communities supposedly need fixed.

Jose challenges that entirely.

Instead, he invites us to start from asset.

From brilliance.

From voice.

From history.

One of the most compelling parts of this conversation was the emphasis on village and collective impact.

Jose shared how schools often say “it takes a village,” yet too often still operate in silos.

Teachers here.
Counselors there.
Administrators in another lane.
Community partners disconnected.

But when the village is activated, everything changes.

Housing support.
Violence interruption.
Scholarships.
Social services.
Tutoring.
SEL supports.

All aligned around the whole child.

That is the future of education leadership.

Not isolated excellence.

But coordinated care.

Jose represents a new generation of leadership in Chicago:

culturally grounded,
systems-minded,
community-connected,
and deeply committed to ensuring Black and Brown students are seen not through deficit, but through possibility.

This conversation is a reminder that real leadership is not about position.

It is about building systems where young people can thrive.