Chief of Staff

We're hiring a Chief of Staff to pair closely with Portola's founder/CEO Quinten on strategy, growth, and monetization. You'll have a front-row seat to how a fast-scaling AI company operates and makes decisions. As part of this role, you'll work directly with the entire Portola founding team (who previously built a $300M exit together), and with Portola's board and investors (including Keith Rabois of Khosla Ventures).

Why you should be interested

This is for someone who wants to be a founder or investor in 2-3 years and wants intense, up-close operating experience first. You'll be in the room for every major decision and learn what great execution looks like from the inside.

What you'll do

You'll operate as an extension of the CEO, taking on strategy, growth, monetization, and product experiments. The specifics shift based on what the company needs most. Flexibility and ownership matter more than fixed scope.

Who we're looking for

You might be a founder, or coming from product, growth, investing, consulting, or something else entirely. What matters:

• Extremely high slope. At every job you've quickly been given more responsibility and autonomy. You can point to specific outcomes you drove personally.

• Curious and quantitative. You like understanding how things work. SQL and Excel required.

• AI-native. You use AI tools constantly to move faster.

• Scrappy. You don't need guardrails.

You’re likely 4 to 6 years into your career, although an extraordinary candidate might be even earlier. Consumer product experience (mobile, gaming, freemium) is a plus.