This week on the First Round Review, we’ve got a seriously detailed guide to help you tackle one of the most dreaded organizational rituals: annual planning.
Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better
Annual planning has always been painful, with many viewing it as tons of paperwork and processes that don't ultimately add up to impact.
But as teams across the tech landscape have embarked on the process this fall, we’ve observed that planning in this era is particularly challenging. Every new LLM rollout now risks upending your plans, whether it’s scrambling your product roadmap, changing your headcount calculus or ballooning your budget for new tooling.
That’s why we’re especially grateful that Jiaona Zhang came to us earlier this year to team up on a focused mission: Put together a detailed resource that helps execs put together pain-free, actually useful annual plans.
You might recognize Zhang from her two previous Review articles on building minimum lovable products and climbing the product career ladder. She’s built up a stacked resume, leading products teams at Airbnb, WeWork, Webflow, and now, as CPO at Linktree.
“What I’ve learned in the last decade is that while there are some important universal principles — like constraining the timeline — you need to commit to thoughtfully tailoring the process to your company,” she says. “‘I’ll just do what I did at my last startup’ or ‘Let's figure out what X company did and copy it’ sets you up for a lot of heartache. You shouldn’t copy-paste processes without a lot of introspection. Every company’s planning process needs to be optimized for what their problems are, the market they’re in, and the team they have to execute the planning.”
To help founders and startup execs do just that, Zhang brought in an annual planning brain trust of sorts, tapping her network to find sharp execs across different companies and organizational functions. In addition to Zhang, you’ll hear from:
- Cristina Cordova, COO at Linear, formerly Head of Platform & Partnerships at Notion and Business Lead at Stripe (where she joined as the 28th hire).
- Stevie Case, CRO at Vanta, formerly VP of Enterprise and Mid-Market Sales at Twilio.
- Rama Katkar, CFO at Notion, formerly VP of Finance at Instacart and SVP of Corporate Development & Strategic Finance at Credit Karma
This piece is detailed and long (even by our standards) but it’s worth diving into (or at least bookmarking for later). There are templates. Stories from stellar companies. Tactical examples. Previews of how they’re incorporating AI into their 2025 annual plans.
Here’s a sampling of what you’ll learn:
- How to put together your strategy doc, working with founders to channel their vision.
- Tips on avoiding the usual pain around headcount and forecasting.
- Why you should time-box the time you spend planning, and instead invest it into designing the right org chart.
- Crafting the right check-in cadence, with a scorecard template and pre-mortem question to set you on the right foot for 2025.
Thanks, as always, for reading and sharing.
-The Review Editors
P.S. If you prefer to listen, like many of you, we’ve been playing around with the incredible NotebookLM. Listen to this “conversation” here.
Recommended resources:
-Lenny Rachitsky walked us through his terrific annual planning process from Eventbrite and Airbnb on the Review several years ago. We recommend reading it if you missed it.
-Marketers: Check out this annual planning template from Emily Kramer.
-If you're anything like us, and can't stop playing around with NotebookLM, this podcast episode with Raiza Martin (the PM behind the product) is a delightful listen.