DON’T CALL THE BABY UGLY

Here’s the problem with sending this message to a CRO:

“Noticed your reps have missed quota by 12%. I can help you upskill their sales skills to close the gap. Worth a conversation?”

Unintentionally Offensive: 

Suggesting the reps need upskilling without context might imply the CRO has failed to train their team. This can put them on the defensive and close off the conversation. It’s like calling someone’s baby ugly. 

Assumptions Without Understanding: 

The message assumes the quota gap is due to a skills issue, but the real cause could be lead quality, pricing, market conditions, internal processes, or misaligned quotas. 

Jumping to conclusions without understanding the root cause makes you seem presumptive.

Generic and Lacking Insight: 

CROs handle complex revenue strategies, and offering a vague solution like “upskilling” doesn’t show deep understanding of their specific challenges. 

It feels superficial and disengaging, lacking personalized insight.

Here’s my revision: 

“Hi [CRO’s Name] - Seeing that SaaS sales teams targeting finance and operations leaders have been struggling with quota attainment. Largely due to increased CFO scrutiny and longer approval cycles.

Since your team missed quota by 12%, I’m curious if you’re experiencing the same challenges.

If so, happy to share some ideas that are helping teams navigate these hurdles.”

The second message, acknowledges a broader trend that SaaS sales teams are facing (CFO scrutiny and longer approval cycles), which positions the sender as more informed and empathetic. 

It then asks the CRO if they’re experiencing the same challenges, creating space for dialogue and discovery, rather than jumping to conclusions or pushing a solution upfront.