Scaling As A Chief of Staff and AI Policy with Stephania Greco
Stephania Greco, Chief of Staff and Chief Compliance Officer at a Growth Fund, joins David Nebinski to unpack what the Chief of Staff role really is, scaling as a Chief of Staff, why EQ and care matter as much as initiative, and how she's navigating AI with a cautious eye on data security. You will also learn about coaching vs. managing, defining your values every five years, and why consistency is a superpower. Enjoy!
You can connect with Stephania on LinkedIn here!
FULL VIDEO
You can watch the full video of this A Chief of Staff podcast episode here
Episode highlights:
0:01: From EA to CoS & What Changes
0:05: Different Chief of Staff Styles & Relationship with the Executive
0:07: Conflict, Repair, and EQ in Practice
0:12: Care, Relationships & the “Wheel of Life”
0:17: Being human in an AI-Focused World & Event Design
0:19: Scaling via People: Hiring & Coaching an EA
0:25: Scaling via Technology: AI, Risk, and Policy
0:33: Overwhelm, Late Adoption & Playing the Right Games
0:37: Values, Consistency & Redefining What Matters
Episode overview:
This A Chief of Staff podcast episode explores what it really means to scale yourself as a Chief of Staff, weaving together role design, emotional intelligence, AI, and personal values.
Chief of Staff Stephania Greco and David Nebinski start with the core premise: a CoS exists to provide leverage and scale for an executive and team, but to do that well you first have to scale yourself. Stephania traces her path from executive assistant for a 70-person team to Chief of Staff at a venture fund, highlighting the shift from task execution to autonomy, initiative, and discovering what’s missing without being told. She frames the role as deeply contextual: it changes based on the executive, industry, and stage of the company, more like a relationship and less like a static job description.
A big throughline is EQ as a non‑negotiable CoS skill. Stephania shares a vulnerable story about a conflict with her managing partner, how her radical transparency can be a blessing and a curse, and how repair, apology, and emotional regulation build a healthier long-term working relationship. Stephania and David both talk about bringing care to work, checking in on people as humans, not just as resources, especially in a world increasingly shaped by AI.
From there, the conversation zooms into scaling via people and technology. Stephania describes hiring and “coaching, not managing” an EA who eventually owns ESG for the fund, and how letting go of control (“let the lady cook”) is key to real leverage. On the tech side, she walks through a love–hate relationship with AI, the overwhelm of rapid change, and the importance of AI policy, security, and data loss prevention especially in regulated environments.
The episode closes on values, consistency, and the “pizza” or wheel of life: how redefining your values every few years, honoring consistency, and remembering “we’re not synthetic” keeps both you and the CoS role sustainable and human.