The bench Leadership & Team Coach

Jessy Grossman

Helping leaders find out who they are when the scoreboard goes dark.

JGJessy Grossman

    At a glance

  • 80+ leaders coached, 400+ hours
  • Built Splunk’s team effectiveness program
  • Co-taught Team Dynamics, Northwestern
  • MS, Learning & Organizational Change (Northwestern)
  • Team Coaching Certification (Brown)
Summary

Jessy combines years in high-pressure environments with deep expertise in performance psychology and team dynamics, bringing both warmth and directness to every conversation.

Coaching Approach

Working with Jessy means having a thinking partner who won’t let you off easy. She’s equal parts warm and direct, challenging you to look at your patterns honestly and connect the big picture to your day-to-day. Her philosophy is simple — strategically balance short-term momentum with your team’s long-term development.

Background & Experience

Jessy started her career as a proprietary trader, where performance lives on a screen and mistakes cost real money. That experience taught her what actually holds up under pressure — and led her to focus on building it in other people instead. She later built Splunk’s team effectiveness program from scratch, designing a working framework with practical tools, playbooks, and training products that managers genuinely used.

She’s coached 80+ leaders across 400+ hours, including long-term engagements with construction leaders across departments. She also co-teaches Team Dynamics at Northwestern University, translating current research into tools leaders can actually apply.

Credentials

Master’s in Learning & Organizational Change, Northwestern University; Bachelor’s in Government, Hamilton College. Organizational and Leadership Coaching Certification (Northwestern University), Team Coaching Certification (Brown University), Perceptive Communication Certified.

Personal

When she’s not coaching, Jessy fosters dogs, coaches her kids’ soccer team, and hosts a podcast on leadership.