Jessica Klein · Program Builder, Educator, Connection Strategist

For 15 years, I've built programs and spaces that help people feel like they belong.

My work has taken shape in middle school hallways, counseling support settings, Jewish educational spaces, medical environments, community initiatives, and nonprofit leadership. Across each of those environments, the work has remained the same: listen closely, build trust, and create the structure, support, and opportunities that help people grow.

My strengths live at the intersection of relationship-building, program strategy, crisis steadiness, creative communication, and practical systems thinking. I do my best work where people, ideas, and needs have to be translated into support, structure, and solutions that actually work.

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Keepin' It Positive, a schoolwide culture shift

What began as a PBIS-aligned shout-out video series celebrating positive moments across the building became one of the most visible and well-received pieces of our climate work. The videos were featured at district meetings, became the most-played content on the Schoology portal, and were strong enough that other team members began creating their own versions. It started as a program I created. It became part of the school’s personality.

Watch the shout-outs →

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AI in education, built with purpose

Whether I’m working with spreadsheets, data systems, AI tools, or creative content platforms, I use tech to strengthen planning, communication, and engagement. That has included building reflection and planning workflows, helping teammates navigate new systems, creating a digital Keepin’ It P Coach, and producing videos and music that makes content more engaging for students. For me, the value of technology is not the tool itself. It’s what the tool makes possible when it helps people connect, communicate, and move good ideas into practice.

Stuck in a conflict? The coach is in.
🤝 Try the Keepin' It P' Coach →

A laptop showing Keepin' It P' and a data dashboard

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The behavior work itself

Hundreds of mediations a year taught me that students need more than a quick “talk it out” action. I built systems that hold both accountability and repair: SEL groups, peer mediation, behavior tracking, and intervention structures that gave students real chances to reflect, repair harm, and build better habits. The work helped reduce suspensions and create stronger alternatives to exclusionary discipline. To build skills, I used student voices to create plans that speak to them.

Accountability and repair. Not one without the other.
✌️ See the Keepin' It Peaceful lesson samples →

Hi, I'm Jess.

For 15 years, I've built programs and spaces that help people feel like they belong.

How I work.

The highlight reel

Three things I built that I'm proud of.

Keepin' It Positive, a schoolwide culture shift

AI in education, built with purpose

The behavior work itself

Restorative Accountability builds stronger students.

The sample library.

Let’s build something Positive!