Jessica Sato at a table with her chin in her palm.

Strategic Advisory For Leaders

If you want to think clearly, make grounded decisions, and design what’s next in a way that actually holds up over time, you’re in the right place.


I work with senior leaders and founders at professional inflection points, moments when what made you successful no longer fits, and the next decisions you make will shape not just your work, but your life.

This is not coaching for motivation or tactics.

It’s ongoing strategic advisory for people navigating consequential transitions where clarity, pacing, and values alignment matter because the costs of getting it wrong are real.


Most of the leaders I work with are:

- stepping into larger or more complex roles

- evolving a business or platform they’ve outgrown

- navigating growth that’s outpacing leadership infrastructure

- carrying responsibility that has quietly turned into burnout

- or realizing that continued success in the current container comes at too high a personal or organizational cost

My role is to serve as a senior strategic advisor, someone who can see the system, name what others won’t, and help you make decisions that hold up under pressure.


Together, we focus on:

  • Clarifying what no longer fits—and why

  • Identifying the real decisions beneath the surface noise

  • Pressure-testing assumptions and tradeoffs

  • Redesigning roles, businesses, or leadership containers, so they can actually support who you are now

  • And making choices that hold up over time, not just in the short term

Ongoing advisory engagements begin at $2,500 per month, with most clients working together for six to twelve months, depending on the complexity of the transition.

Hi, I’m Jess.

I bring an enterprise-level, systems-oriented lens shaped by years working inside complex organizations and advising leaders through high-stakes transitions.

I pay close attention to decision quality, downstream impact, and sustainability, because leadership that isn’t designed to last eventually costs more than it creates.

 

If you’re in a moment where staying the same is no longer sustainable, but you’re not interested in burning everything down, this kind of advisory partnership may be the right next step.

Let's Discuss Your Next Best Step