Guests: Tyler Denk, Co-founder & CEO, beehiiv | Brian Schneider, Chief of Staff, beehiiv
Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

Most conversations about the Chief of Staff role happen with only one side of the table in the room. This one has both. Tyler Denk has never viewed any of his three Chiefs of Staff as an assistant, and the bar he holds Brian Schneider to is specific: carry enough context to sub into any meeting Tyler is running and make any call he'd make if he isn't there. What follows is a working picture of that model, including what happens to the job when the CEO shares the board deck company-wide and there's nothing left to translate.

About Tyler Denk

Tyler joined Morning Brew as employee number two in 2017 and built most of the infrastructure behind it, the content management system, the ad platform, the growth mechanics, carrying the newsletter from 100,000 subscribers to four million before the Insider acquisition. The thousands of weekly reader replies asking how it all worked convinced him the gap in the market was the tooling itself, not another newsletter. After a year at YouTube he co-founded beehiiv, first pitched as Morning Brew in a box and now an all-in-one platform for newsletters, podcasts, websites and communities. He runs the company with unusual transparency, publishing revenue, costs and the ten things keeping him up at night to the whole team every quarter, and writes Big Desk Energy, a newsletter that started with no strategy behind it and produced one of beehiiv's largest enterprise deals.

About Brian Schneider

Brian's path started as a Morning Brew college ambassador at UConn, where he pulled a thousand referrals a semester by walking into lecture halls with a pen and paper. He was working nine to five at Prudential at the time and spending his evenings at the Morning Brew WeWork before he had a job there, which is what got Tyler to bet on him for a sales seat he had no background for. He climbed from sales into revenue strategy over five years, then followed Tyler to beehiiv into a rev ops role while the Chief of Staff seat was already filled. He did that work for three years and moved into the seat when it opened, which is a longer game than most people in this role are willing to play.

Key Takeaways

• The split that matters isn't seniority, it's how the principal frames the job. Tyler puts his Chiefs of Staff in the "second CEO" bucket rather than the glorified EA bucket, and everything downstream, authority, context, delegation, follows from that single decision.

• Deployability is the sharpest frame in the episode. Brian gets dropped into whichever part of the business needs him most, currently a six to eight week turnaround on the ad network team where he operates as if he's running it, then returns to the Chief of Staff seat when the next problem surfaces.

• Radical transparency deletes a chunk of the traditional job. When anyone can see KPIs and rocks at any time, Brian doesn't spend his days interpreting what the CEO meant. He reiterates and clarifies instead, which frees him for the harder work.

• Refusing a room is a red flag. Tyler has no patience for "I don't have engineering experience" or "I'm not interested in finance." The job isn't domain expertise, it's getting to the root problem and pulling the levers to fix it.

• Trust gets built by showing up when you say you will. Brian's been at beehiiv three years and still treats relationship-building with team leads as the prerequisite to solving anything. It's also what killed the internal pushback beehiiv got for creating a role that reports to no one and moves through every team.

• Fifteen minutes, five days a week, beats an hour on a Wednesday. Tyler calls Brian every weekday morning on his ten to fifteen minute drive to the gym to level-set priorities. Most Chief of Staff pairs settle for the weekly, and it's almost never enough.

COSN runs this podcast and its newsletters on beehiiv. If you're in the role now, PRO membership is where Chiefs of Staff operating at this level connect, and if you're working toward your first seat, the Chief of Staff Launchpad is the on-ramp.