Run the Numbers

An Operationally-Focused CFO’s Guide to Scaling From SMB to Enterprise: Lessons From ServiceNow

29 snips
May 26, 2025
Andrew Casey, CFO of Amplitude and former key player in scaling ServiceNow, shares insights from his impressive career. He highlights the monumental shift in strategy needed when moving from SMBs to enterprise sales. Casey emphasizes the importance of understanding customer value, effective deal structuring, and transparent pricing. He also discusses the challenges of multi-year contracts and the pitfalls of auto-renewals. With a focus on empathy-driven leadership, he reflects on how understanding customer perspectives shapes operational success.
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ANECDOTE

Early Tough Enterprise Negotiation

  • Andrew Casey shared how he helped HP escape a $40 million losing contract by enforcing payment terms strictly.
  • This experience sharpened his negotiation skills with large enterprises early in his career.
ADVICE

Keys to Structuring Win-Win Deals

  • Structure deals to incentivize customer adoption and ensure both sides feel a fair value exchange.
  • Maintain transparency in pricing and align deals tightly to your customer's value proposition.
ADVICE

Transparent Usage-Based Pricing

  • Build usage-based pricing models on transparent, easily validated metrics your customers can relate to.
  • Simplify pricing to avoid nickel-and-diming, which enterprise customers strongly dislike and hinder adoption.
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