I’m Jess Ridge.
For nearly two decades, I’ve worked inside complex public and nonprofit systems—where decisions carry real consequences, public trust is fragile, and the pressure to deliver is constant.
The Moment That Changed My Understanding of Leadership
There was a moment, years ago at Boston City Hall, when everything felt unbearably loud.
Not just the sirens and construction outside—but the noise inside my own head. The endless to-do list. The replaying of conversations. The weight of decisions that mattered. I remember wanting to yell, “Stop!”—and realizing that the only place I could actually pause was within myself.
That moment changed how I understood leadership.
I knew how to move initiatives forward. I understood strategy, timelines, and stakeholder partnerships. What I began to see more clearly was this: the pace alone was not the only challenge.
It was the disconnection—from myself, from others, and from the deeper purpose of the work.
That realization didn’t take me away from complex systems—it shifted how I move within them.
It also clarified what meaningful work truly requires.
Alignment Requires Practice
Today, I help people and organizations strengthen how they work together so their impact is more attentive, creative, and durable.
My work brings together long-term contemplative practice, dynamic facilitation, and mission-aligned strategic advising.
I’ve spent my career working across differences in government, philanthropy, and community organizations—where outcomes matter, relationships are consequential, and the way we collaborate shapes what becomes possible.
Over time, I’ve come to understand something fundamental:
Alignment requires practice.
And tending to how we are together is not a distraction from impact—it is what unlocks energizing teamwork, more creative solutions, stronger collective momentum, and results that endure.
How I Lead
Across contexts, I center people and their strengths as core to strategy.
I bring unlikely voices into meaningful and productive conversation.
I hold complexity without losing the thread.
I help teams move from fragmentation toward collective action.
Whether at the micro level of individual awareness or the macro level of cross-sector collaboration, I work at the intersection of human capacity and collective impact.
Experience & Lineage
My work is shaped by:
12 years in government and politics, including 8 years at Boston City Hall, as Chief of Staff for then-City Councilor At-Large Ayanna Pressley
16 years leading and supporting large, multi-sector initiatives, including 8 years at the national non-profit, UpTogether
Deep experience in cross-sector partnerships, strategic facilitation, and systems-level coordination
Long-term contemplative and somatic practice that informs how I approach leadership, conflict, and change
The Evolutionary Leadership Workshop (2017 and 2018) and the Facilitators’ Coaching Cohort (2025)
Being a member of the Stewardship Team for Bent Birch Retreat Center
I’ve worked alongside elected officials, foundation leaders, agency directors, community advocates, and cross-sector coalitions—navigating public scrutiny, shifting political landscapes, and complex stakeholder dynamics.
I’ve led mindfulness and body-based practices at City Hall, boardrooms, in houses of correction, and online.
Life has also been a teacher—marriage, motherhood, pregnancy loss, and close relationships altered by addiction, mental health challenges, and uncertainty—deepening my capacity to meet intensity with greater steadiness, discernment, and care.
I believe we are capable of doing work that strengthens both outcomes and our shared humanity.
Especially now.
If something here resonates, I’d love to talk.