KeepSmart W⏱️rkshop
Ready, Set, Plan: Walk Into Annual Planning Already Ahead
Stop Planning From a Blank Page
August 11th, 2026, from 1:00–1:30 pm ET
Why most Annual Planning sessions start in the wrong place
Most teams walk into Annual Planning with a blank whiteboard and good intentions — then spend the first hour just trying to remember what happened this year. Nobody pulled the market data. Nobody checked how the Winning Moves actually performed. The ideas that should've been collected weeks ago show up as first-time debates in the room.
That's not a planning problem. It's a prep problem.
In 30 minutes, we'll show you how to use Rhythm's AI Connector to walk into Annual Planning already knowing where the gaps are — so the session becomes a decision meeting instead of a discovery meeting.
This session is for you if:
- You're heading into Annual Planning in the next few months and want to walk in prepared, not reactive
- You've sat through planning sessions that spent too much time re-explaining "where we are" instead of deciding "where we're going"
- You want your team contributing ideas and insight before the session, not just during it
- You're curious what the AI Connector can actually do beyond status updates and goal creation
What you'll walk away with
This isn't a product tour. It's a practical walkthrough of how to use the AI Connector to get ahead of your next Annual Planning session. Here's what we'll cover:
1. Evaluate Your Strategy Against Market Insights
See how to point the AI Connector at your current strategy and current market conditions at the same time — surfacing the gaps and open questions your team needs to work through, before planning day.
2. Assess Your Winning Moves Going Into the New Year
Get a clear, evidence-based read on how each Winning Move actually performed — using linked goals and execution history, not gut feel — so you know what to keep, kill, or reshape for next year.
3. Turn Insights Into the Right Meeting Agenda
We'll show you how to take what you've learned and immediately set the meeting agenda your team needs leading into planning, so no time in the room is wasted.
4. Build Your Pre-Planning Checklist
Leave with a clear list of what to do right now: getting your team's ideas onto an idea board, pulling together budget information, and gathering the market data you'll want on hand when planning starts.
Registration is now open. Limited space available.
About the Workshop
About the Keep Smart Webinar Series
Keep Smart is Rhythm Systems' ongoing client education series — practical, live sessions designed to help your team get more out of the Rhythm platform and the Think Rhythm® methodology. Sessions are free for all clients and always recorded.
Past sessions have covered topics like foundational goal setting, KPI setup best practices, and using AI in your weekly rhythms. This session is designed for teams starting to look ahead to their next Annual Planning cycle.
Meet Ryan Walcott
Head of Product
Ryan Walcott is Head of Product for Rhythm Systems, specializing in helping firms with over $10M in revenue focus and align their teams to accelerate their growth by establishing a healthy rhythm of strategic thinking, execution planning, and doing the work.
He leads the design, development, and implementation effort of the Rhythm software which enables clients to work on and record strategy, build effective execution plans, collaborate with their teams, and see the status of plan execution using dashboards. This is what allows clients to achieve success and grow their business.


Meet Jessica Wishart
Rhythm Product Manager
As Sr. Product Manager at Rhythm Systems, Jessica gets to collaborate with our amazing customers and internal teams to understand problems, brainstorm possibilities, and launch product solutions. Our tools help people achieve their goals through better execution habits.
Jessica's educational background in counseling helps her deeply listen and empathize with the needs of our customers and the market, and our strong execution culture helps us deliver great products with the same focus, alignment, and accountability our methodology provides for our customers.
