by Stephanie Bennett | Sep 3, 2026 | RevOps
Your AE promises a customer a Q3 feature. Product killed it in a planning meeting three weeks ago. No one told sales. It’s a revops product roadmap alignment problem, and it’s more common than most GTM leaders want to admit. The feature that got promised...
by Stephanie Bennett | Aug 27, 2026 | Operations
Your fractional CFO wraps up a nine-month engagement. She rebuilt your reporting and fixed a broken revenue recognition process. Then she leaves. Three months later, someone asks why AR write-offs get approved a certain way. No one remembers. The answer walked out the...
by Stephanie Bennett | Aug 20, 2026 | Chief of Staff
You know you need help. What you don’t know is whether that help is a chief of staff or an EA who can catch more than a calendar. Hiring a chief of staff is one of the most consequential moves a founder can make. It’s also one of the easiest to get wrong....
by Stephanie Bennett | Aug 13, 2026 | Executive Support
Chief of staff AI tools promise to save you hours every week. Some of them actually do. Most just move the busywork somewhere else, and you don’t notice until you’re re-checking everything the tool handed back. I’ve spent enough time in the role, and...
by Stephanie Bennett | Aug 6, 2026 | Operations
Someone hands you a business plan. Maybe a founder built it over a weekend with ChatGPT. It reads clean: a TAM slide, a five-year revenue model, a competitive matrix with checkmarks in all the right boxes, and a hiring plan that somehow lines up perfectly with...
