Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better

Four top execs reveal their annual planning secrets from Notion, Stripe, Vanta, Linear, Linktree and more. From addressing AI to adjusting org charts, this COO, CFO, CPO & CRO share insights so startups at any stage can build effective, realistic plans.

Cristina Cordova

When adding a new team or role, take the time to clarify a few things: What a role is, what it’s meant to serve, how existing people have been making up for the lack of that role, and how their lives are going to be changed by new people coming in — in positive and potentially negative ways.

Cristina Cordova

Don’t start with the most important partners that you could potentially work with, but at the fourth or fifth down on your list. That way you can learn exactly what the objections from a big partner might be and start solving them. If you pitch that big company five or six months from now, you’ll be in a much stronger position.

Cristina Cordova

A big mistake early-stage companies make around launch is focusing too much on sign-ups. It’s great to have 10,000 sign-ups in one day — but are they paying you? Are they actively using your product? Are they adopting new features? Those are the things that you really need to care about.