Episode 37: The One Question That Drove a 200x Increase in Client Revenue

2025-05-16

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Asking one bold question turned a $50K client into a $10M account and reshaped how account managers think about trust, strategy and growth. Account management leader Joanna Hagelberger joins Alex Raymond to talk about what account management looks like when it’s done right, from building the function from scratch at high-growth InsurTech companies to leading with curiosity instead of a script. What happens when you stop asking surface-level questions and start inviting your clients to think bigger? Joanna shares how one conversation sparked a 20...

Asking one bold question turned a $50K client into a $10M account and reshaped how account managers think about trust, strategy and growth.

Account management leader Joanna Hagelberger joins Alex Raymond to talk about what account management looks like when it’s done right, from building the function from scratch at high-growth InsurTech companies to leading with curiosity instead of a script. What happens when you stop asking surface-level questions and start inviting your clients to think bigger? Joanna shares how one conversation sparked a 200x expansion and why most account managers don’t realize they have permission to ask the hard questions.

This episode also gets into the realities of scaling an account management team, how to avoid segmentation mistakes, and why internal alignment matters just as much as client relationships. What do you do when your executive team has no idea what’s happening with your top accounts? How do you keep account managers from working in silos? Joanna brings clear, grounded answers from the field, along with a mindset shift that every account manager needs to hear.

Episode Breakdown:

00:00 Intro and Meet Joanna Hagelberger

02:04 Building Account Management from Scratch

06:57 Customer Support vs. Customer Success vs. Account Management

09:27 No Surprises: The Role of Internal Account Reviews

15:52 The Five-Year Question That Led to 200x Growth

20:17 Curiosity as a Core Account Management Skill

26:28 Taking Ownership and Leading Accounts

31:12 Segmenting Accounts the Smart Way

36:28 How to Think About Portfolio Size

40:04 Becoming a Strategic Account Manager

41:35 Why Finance and Product Should Be Your Best Friends