Outbound Squad How to handle vet AEs who think they know it all
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Oct 21, 2025 Clara Johnson, Head of Training at Outbound Squad, shares her rich experience in sales to tackle the challenge of getting veteran AEs back into prospecting. She emphasizes using data to highlight the benefits of AE-sourced pipelines, making prospecting time-efficient with short daily sessions. Clara also discusses the importance of teaching AI as a skill, not a crutch, and advocates for a structured approach to AI prompts that ensures quality messaging. The episode is packed with practical tips for engaging seasoned reps.
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Veteran Rep Resistance Is Cultural, Not Just Attitudinal
- Veteran enterprise reps often resist prospecting because they feel above it or fear micromanagement.
- Sales leaders must acknowledge that experience can create entitlement and design changes accordingly.
Use Data To Sell Prospecting To AEs
- Back requests for new behaviors with data showing AE-sourced pipeline converts better than inbound or SDR funnels.
- Use that evidence to answer the rep's question: why should I prospect when my deals already close?
Make Prospecting a Small Daily Habit
- Make new prospecting behavior trivial by carving small, consistent time blocks (30–60 minutes) for it in reps' calendars.
- Reduce friction so experienced reps can adopt outbound without large schedule disruptions.