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Simon
Pan
Director, Revenue Operations
Leah
Simon is a Revenue Operations and GTM Strategy leader with more than 12 years of experience building operating rhythms, planning cycles, and high performing teams at PE and VC-backed SaaS companies. Throughout his career he has managed revenue operations teams spanning deal desk, order administration, legal and contracts, and systems administration. He works directly with Sales, Finance, and executive leadership to turn forecast rigor, territory and quota planning, and CRM hygiene into growth the business can actually plan around. Most recently he built and owns the agentic AI systems running deal intelligence and CRM automation for a VC-backed SaaS organization. That work covers pipeline and forecast prediction with probabilistic win rate modeling, automated win/loss analysis across closed deals, and champion identification and testimonial extraction for marketing's customer advocacy program.
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23 September 2026 13:15 - 14:00
Fireside chat | The Forecast Is Wrong. Here's Why That's Fine.
Every RevOps leader has sat in a QBR defending a number that was already stale before the meeting started. Forecasting has become a trust exercise more than a math exercise, and the gap between what the model says and what the board believes is where careers get made or broken. This session moves past the mechanics of weighted pipeline and into the harder question: how do you build a forecasting process that survives contact with reality? We'll look at how leading RevOps teams are blending historical data, rep judgment, and macro signal into a forecast that's directionally trustworthy even when it's not perfectly precise, and how they communicate uncertainty to the board without losing credibility. Takeaways: - A framework for separating forecast confidence into commit, best case, and pipeline coverage, so leadership knows exactly what they're betting on - How to build feedback loops between forecasting accuracy and rep coaching, turning misses into a diagnostic tool rather than a blame exercise - Practical guidance on when to trust the model and when to override it, and how to document that judgment so it improves over time