Blog

From the Chief of Staff team

Thinking on personal operating systems, high performance, and the tools that help you stay sharp at the top.

SalesMay 2026·7 min read

I Walked Into a $200K Meeting With Zero Prep

Back-to-back calls since 9am. A negotiation-stage deal at 2pm. Ninety seconds of context review that never happened. The universal AE horror story.

AnalysisMay 2026·8 min read

Your Company Is Paying $85K/Year for Gong. You Open It Once a Month.

Gong costs $1,600/user/year. For a 50-person sales team, that is $85K in year one. The VP of Sales bought a dashboard. The reps got another tab to ignore.

SalesMay 2026·6 min read

The 47 Tools in Your Sales Stack and the One Question None of Them Answer

Your team spends $500 to $1,500 per rep per month on software. CRM, engagement, intelligence, enrichment, forecasting. None of it can answer: what should I say in my meeting in 3 minutes?

ProductMay 2026·7 min read

Prep for Every Meeting in 10 Seconds

You are 90 seconds from your next meeting. You have not looked at the deal in a week. Pull out your phone, ask one question, and walk in knowing everything.

AnalysisMay 2026·8 min read

What a $1,600/Year Sales Tool Does That a $15/Month One Can't

An honest comparison of Gong, Sybill, Clari, and Chief of Staff. What you get at each price point, what you give up, and who each tool is actually built for.

PrivacyMay 2026·7 min read

Your CRM Data Belongs on Your Phone, Not Someone Else's Server

Every sales AI tool takes your pipeline, your call recordings, and your contacts and puts them on their servers. We built Chief of Staff to work differently.

ProductMarch 2025·8 min read

Introducing Chief of Staff: Your AI-Powered Personal Operating System

High performers do not fail because they lack ambition. They fail because their systems cannot keep up with their pace. Chief of Staff is built to change that.