The bench Leadership & Team Coach

Jessy Grossman

Helping leaders understand what they’re doing — and why — so they can lead with clarity and intention.

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 helps leaders understand what they’re actually doing — and why — so they can lead with more clarity and intention. She combines years of high-pressure environments with deep expertise in 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 what’s happening in your day-to-day. Sessions stay practical: how you’re spending your time, when to step in and when to step back, and what your team needs from you that they’re not getting. Her philosophy is simple — she helps leaders find out who they are when the scoreboard goes dark.

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 through her own practice, including long-term engagements with construction leaders, and co-taught 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.