SaaStr · 2022-12-31 · 1250d

Hiring a Stretch VP of Sales: Benefits, Risks, and Practical Evaluation Framework

Brendon Cassidy argues that hiring a 'stretch VP of Sales'—typically a director-level candidate who served as a #2 to successful sales leaders—is often preferable to recruiting either perfect startup VP candidates (rare) or BigCo VPs (misaligned). The article provides specific evaluation criteria and timelines for assessing stretch VP performance, emphasizing their ability to build teams and drive revenue growth quickly.

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Metrics in this report

Ideal Revenue Range for Hiring Startup VP

1-50$ millions

range

Company stage when hiring proven startup-experienced VP of Sales

Revenue Growth Timeline for Stretch VP

3months

required

Timeframe for demonstrating upward revenue trajectory before reconsidering hire

Stretch VP Hire Assessment Timeline

30days

minimum

Time to bring first candidate/hire into sales organization

Zenefits Sales Team Scaling Speed

0-200reps

achieved by

Sam Blond's sales organization building achievement in 18 months