Jenny Liang

Jenny Liang coaches innovation leaders and strategic operators who thrive in ambiguity but struggle to articulate their unique value or navigate complex career transitions.Drawing on 15+ years building ventures at the intersection of design, technology, and social impact, Jenny brings first-principles thinking from her science background and pattern recognition from scaling organizations like Sostento (480% revenue growth) and launching products serving 2M+ users at BCG X. She’s designed ethical AI frameworks, led civic innovation for 8,500+ city employees, and taught design strategy and ethical strategic foresight for several years at Otis College of Art and Design. As a Sidebar facilitator and executive coach for over 2 years, she’s guided dozens of senior leaders through career pivots, team challenges, and strategic decisions. Her 4+ years as a suicide prevention crisis counselor means she can hear anything without judgment and collaboratively drive behavior change.

Jenny’s coaching style is direct, structured, and practical. She helps clients translate accomplishments into powerful and relevant stories, build frameworks that cut through complexity, identify what’s actually blocking progress (hint: it’s often not what you think), and make decisions aligned with their values—not just market pressure. Her superpower is seeing the capabilities you take for granted and helping you leverage them strategically.Clients leave sessions with concrete next steps, renewed clarity, and permission to be as ambitious about their life as their career.

I joined Sidebar as both a member and a facilitator because I believe collective learning and leadership are critical to navigate the complex global challenges we face today. Facilitating teaches me new modes of engaging and empowering groups across space and time, while also accompanying individual leaders in their learning journeys.

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