E53: Sales Capacity Planning That Doesn't Suck (Jenny Dingus, SVP Global Sales @ Clio)

Clio's SVP of Global Sales, Jenny Dingus, joins Kyle Norton to talk about why the "people × quota" revenue planning model is terrible, and what they're using instead. Jenny shares how Clio's $1B acquisition flipped their planning model, how they forecast in high-uncertainty markets, and what "drawing the owl" looks like in real life. If you run revenue and you're tired of spreadsheet fantasy planning (or just want to know what two senior GTM leaders are thinking about these days), worth a listen! 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:   02:15 Jenny's Career Journey from RingCentral to Clio   04:00 Vertical SaaS and Expanding Market Opportunity   06:10 Disruption, AI, and Modernizing Legal Tech   08:00 Educating a Skeptical Market on AI Adoption   10:15 The Myth of the "People x Quota" Growth Model   12:05 Why Linear Capacity Planning Still Persists   14:45 The Integrated Planning Alternative   17:10 Planning Amid Product Launches and Acquisitions   20:15 Quotas, Motivation, and Momentum in Sales Teams   23:00 Multi-Factor Revenue Planning and Emerging Markets   27:05 Managing Speculative Growth Bets and Reforecasting   31:10 Balancing Capacity and Demand in High-Growth Environments   34:40 Strategic Congruence: Playing the Right Company Game   38:30 Communication, Change Management, and Leadership Alignment   43:45 Inside Clio's Acquisition and GTM Integration Process   48:40 Leadership Communication Principles and "Feeling" the Message   52:00 Frontline Enablement During Massive Change   56:45 Building Continuous Feedback Loops and AI-Enabled Training   01:00:30 Quickfire: Lessons in Leadership, Humility, and Focus   01:04:00 Favorite Reads and Closing Reflections