E62: CRO Life: from a $20B Exit, to a Hyper-Growth AI Org (Michelle Donnelly, CRO @ Crescendo)

Crescendo went from zero to $100M ARR in under two years. And today's guest, CRO Michelle Donnelly, is leading the revenue team.

In a market where every AI competitor claims the exact same capabilities, Michelle argues that "trust me" sales tactics don't work anymore, and what her team is doing instead. She explains why she banned traditional sales demos in favor of building functional prototypes using prospect data (sometimes within 24 hours). Michelle also breaks down the transition to outcome-based pricing and how she she's working to compress new rep ramp time.

All this, and a ton more!

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Chapters:

01:39 Introduction to Michelle Donnelly and Crescendo

04:54 Leaving Salesforce for a risky hardware startup

11:25 Leveraging your network to spot market trends

16:18 Navigating pivots and finding product-market fit

19:44 Selling amidst the noise of the AI market

25:50 The challenge of simplifying complex messaging

30:45 Strategic priorities for scaling revenue teams

33:18 Replacing standard demos with "show me" solutions

35:50 Building trust by becoming your customer's customer

40:21 Balancing high-level strategy with frontline realities

43:02 Maintaining focus with the rule of three

45:09 Using internal AI to accelerate rep onboarding

48:23 Rapid fire: Traits of great revenue leade