Why AI Can't Be a Chief of Staff with Sawyer Middeleer

Guest: Sawyer Middeleer, Founder, Revi Systems (former Chief of Staff, Aomni)

Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

Every company has bought the AI seats. Very few have changed how they work. Sawyer Middeleer argues the gap closes when someone maps how work actually gets done before automating it, and that the Chief of Staff is usually the person with the view to do it.

Scott and Sawyer get into building tools you'll throw away in twelve months, the difference between what AI can do and what it can do well, and why AI Chief of Staff products can triage an inbox but can't do the job.

About Sawyer Middeleer

Sawyer came up through strategy and ops at a large e-commerce company and BizOps at scaling startups. In 2023 he joined Aomni, an AI sales research startup, as its first employee and Chief of Staff, and stayed the only non-engineer through its pre-seed and seed rounds.

Because he was closest to customers, he ended up shipping front-end features to production with Claude Code, straight from customer conversations and reviewed by the engineering team. Today he runs Revi Systems, helping Chiefs of Staff and other operators bring AI into their organizations without drowning in slop.

Key Takeaways

• It's easy to automate and hard to automate well. The five-cent bot replacing the five-dollar human fails when nobody captured the context and judgment that lived in the person's head.

• Map the process and the value it creates before choosing a tool. Where AI output and human output look the same, use AI. Where the human has "that special something," keep the person.

• Assume the way you work changes every six to twelve months. The value you deliver to customers is durable; the rhythm you use to deliver it isn't.

• Every role is becoming engineering. Chiefs of Staff don't need to become engineers, but they need to think in systems, architecture and build-versus-buy tradeoffs.

• AI should add capacity, not justify cuts. An account manager who goes from 10 accounts to 15 is a reason to grow faster.

Sawyer leads the "Building the AI Flywheel" workshop at Chief of Staff Connect New York, October 22 to 23. Connect with him on LinkedIn: https://www.linkedin.com/in/sawyer-middeleer

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/