Episode Details

Most new account executives stare at their territory list and feel the weight of it immediately. Fifty accounts. A hundred accounts. Sometimes more. Each one needs research, a plan, and outreach that doesn’t sound like every other cold email clogging their prospect’s inbox. 

Jake McOsker, an account executive at Forrester Research, found himself facing exactly this problem when he moved from BDR to AE. He cracked it by changing how he used AI for account planning. 

“Rather than taking 10 to 15 minutes to get an account plan out or understand who the notable stakeholders and the decision makers that I need to go with,” he explained, “it’s a 2 to 3 minute process to go through each one of these accounts.”

The traditional approach to AI account planning doesn’t solve the territory problem. You ask ChatGPT or Claude for company information, and you get Wikipedia summaries. Founded in 1987. Headquartered in Dallas. 15,000 employees. The chief sales officer you’re calling doesn’t care about any of that, and showing up with generic facts makes you look lazy, not prepared.

When you’re new to the role, you don’t have years of pattern recognition to fall back on. You don’t know what good account planning looks like yet. You just know you need to get meetings with people who have better things to do than talk to a rep they’ve never heard of.

The solution isn’t using AI as a search engine. It’s using it as a sales assistant with a specific job to do.

The Problem With How Most Reps Use AI for Account Planning

Here’s what usually happens. A rep needs to prepare for a call with a VP of Marketing at a healthcare company. They open their AI tool of choice and type: “Tell me about [Company Name].”

The AI spits back:

• Company history
• Product offerings
• Recent press releases
• Maybe some executive names

The rep skims it, copies a few bullet points into their CRM, and calls it account planning. Then they get on the call and realize they have no idea what this VP is actually trying to accomplish this quarter. They ask surface-level questions. The prospect checks out. The meeting goes nowhere.

This happens because most reps are using AI like a faster Google. They’re asking for information instead of asking for intelligence.

AI account planning only works when you give the AI a role and a specific outcome to deliver. Not “tell me about this company.” Instead, “You’re an account executive trying to book a meeting with this company’s CMO in the next two weeks. Based on their recent announcements and what their executives are posting on LinkedIn, what initiatives are they likely prioritizing right now?”

How to Set Up AI Agents for Account Planning

The difference between a basic AI chat and an AI agent is memory and context. When you create an agent, you’re teaching it what kind of output you need every single time. You’re not starting from scratch with every account.

Here’s the framework that works:

Step 1: Give Your AI Agent a Clear Role

Don’t just ask questions. Set up the scenario with urgency and context. For example:

“You are an account executive at [Your Company]. You’ve been tasked with bringing in [Target Company] as a new customer within the next 90 days. Your first call is with their [specific role, like Chief Sales Officer]. Ba