Allison Metcalfe's path to CRO was built on systems thinking, multiplier leadership, and a journalist's instinct for "why." In this episode, Kyle and Allison talk through what separates good revenue leaders from great ones, and how to actually lead peers and execs, not just manage them. And maybe we shouldn't tell you this, but… Allison even reveals her hardcore alter-ego that helps her better ride the highs and lows in the CRO role. Thanks for tuning in! Catch new episodes every Wednesday. Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters: 01:47 Allison Metcalfe's Career Journey 03:41 Non-Traditional Path to CRO 05:16 Architecture Thinking and the AI Era 07:25 Systems Thinking and Curiosity in Revenue Leadership 09:01 Managing Executive Relationships 10:56 Discovering Multiplier Leadership 18:44 Decision-Making Without Consensus Paralysis 24:30 Building Healthy Executive Relationships 30:11 Authenticity and Connection in Remote Work 33:09 Using Enneagram for Team Understanding 38:00 Radical Empathy Across Departments 46:27 Collaborating Effectively with Finance 53:21 Navigating 2026 Planning Conflicts 58:26 Data-Driven Decision Making and Change Management 01:03:32 Quick Fire: Career Lessons, Alter Egos, and Book Recommendations

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“What did the council decide on item 42?” — answered with the speaker and the moment.

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