In the latest episode of the RevOpsAF podcast, James Jackson, former VP of RevOps at Snowflake, DocuSign, and Canva, argues that the single biggest challenge facing Revenue Operations today is not technical skill but the inability to say 'no' strategically. He warns against the 'curse of yes' — a doom loop where ops teams become reactive service desks, constantly fulfilling requests without driving real impact.
Jackson shares two vivid stories: a full compensation plan overhaul for a 2,700-person sales organization, and the silent creep of the 'curse of yes' that undermines operations teams everywhere. According to Jackson, the technical work is the easy part; the hard part is everything else — change management, stakeholder alignment, and prioritization.
Key takeaways from the episode:
- Total consumption comp plans can hide top performers. Jackson advocates for incremental consumption models that better reflect individual contributions.
- Comp design must serve three masters: executive leadership, go-to-market teams, and finance. Balancing these competing interests is critical.
- A listening tour can defuse politically charged rollouts. Jackson explains how gathering feedback early builds trust and reduces resistance.
- Flexibility where it matters, policy where you need scale. This principle helps ops scale without becoming rigid.
- Holdovers are largely theater. Jackson suggests limiting them carefully to avoid mutiny while still maintaining fairness.
- Break the 'doom loop' by moving from reactive request fulfillment to strategic, above-the-line prioritization.
For RevOps leaders looking to level up, the message is clear: stop being a service desk and start being a strategic partner.