Guest: Judy Abad, Chief of Staff, CFOO, Freshworks

Host: Scott Amenta, Founder, Chief of Staff Network

Judy Abad has oscillated between Chief of Staff and functional leadership roles at some of tech's most iconic companies, including Facebook, Instagram, Slack, WhatsApp, and Freshworks. In this conversation, she unpacks the key differences between owning metrics as a functional leader versus synthesizing priorities as a Chief of Staff, and why both paths build the skills you need for the C-suite.

You'll learn how to build credibility by running toward the hardest problems, why you should stop asking for permission and start apologizing later, and how to evaluate Chief of Staff opportunities with pointed questions that reveal whether the role is set up for success.

Judy's advice: think in decades, but act now, and know when to walk away from losing hands.

Learn more about Chief of Staff Network's upcoming events, courses, and membership on our website: https://www.chiefofstaff.network/

About Judy Abad

Judy began her career in tech at Facebook when the company had around 500 employees, starting in sales before becoming one of the first Chiefs of Staff to the CRO. From there, she helped launch Instagram's first ad products, ran product marketing at Slack as employee 100, and led business product launches at WhatsApp. She's also been an early-stage startup operator and investor. Today she's Chief of Staff to the CFOO at Freshworks, where she focuses on connecting cross-functional work and driving execution at scale.

Key Takeaways

- The CoS role and functional leadership are not rungs on a ladder, they are different lenses. Functional leaders own a domain and make decisions with imperfect information. Chiefs of Staff synthesize across all domains and know when to escalate. Both skills compound into each other over time.

- "No one knows what they're doing" is not an excuse. It's permission. Stewart Butterfield told Judy this before a major enterprise launch at Slack, and the point was that the person closest to the work, the person who lives and breathes it every day, is exactly who should be making the call.

- P&L ownership and team size are proxies for seniority, not guarantees of it. What actually matters for getting to C-suite level: the ability to learn quickly, high EQ, intense curiosity, and a strong sense of ownership. Chiefs of Staff can build all of these without ever carrying a functional title.

- Career decisions are two-way doors. Almost every move is reversible. The pressure to find the perfect forever role before you make a change leads people to stay stuck. Meeting yourself where you are in this moment is not a compromise, it is a strategy.

- Know when to walk away from losing hands and when to double down on winning ones. Thinking in decades means you are not just optimizing for the next role. You are building toward what will still feel meaningful when you are mid-career or beyond.