[Template] Annual Planning Calendar

New template to plan your enterprise expansion strategy

Tyler Pleiss
March 30, 2025

In partnership with

It's important to understand that company initiatives like enterprise expansion are annual GTM goals, not quarterly.

Because creating enterprise stability isn’t done in three months. It takes years to create a consistent revenue stream within enterprise accounts.

So how do you actually coordinate a plan of attack?

Well the good news is that there are ways you can segment your enterprise accounts using first party data to make this more feasible.

You mean you don't need to purchase a $150k platform? You betcha!

Below is a screenshot of how I coordinate efforts on a quarterly basis.

So why do I organize my accounts this way?

You’re able to focus on prospects that have a previous relationship with you and potentially identified pain points. This makes it more likely to create new conversations, book meetings, drive qualified pipeline and revenue.

This narrowed focus will also allow you to better refine your messaging, content and outbound conversations.

And I’m excited to share that you can grab your own quarterly template.

You can use this to plan your own annual strategy for enterprise expansion.

For a more in-depth view for how this comes together, the Expanding Upmarket with Account-Based GTM Strategy guide will give you a breakdown of this calendar and which data points to use to segment your accounts.

Here’s what’s coming in April:

Step-by-Step Guide for Expanding into New Verticals: Coming in April I’ll be releasing my new guide focused on how you can build a vertical expansion strategy that drives pipeline and revenue.
An Update on 2025 Strategies: Q1 is wrapping up tomorrow so I’ll have a full breakdown of how things went and what we’re looking forward to launching in Q2.
Free consulting calls: Want to chat? No problem! You’ll get access to schedule a free call with me to talk shop.

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