Diary of an IT Sales Expert · 2026-06-17 · 35 min
Many MSP and IT service business owners find themselves in a cycle of hiring a salesperson only for the role to fail within months. In this episode, we dig into the eight critical reasons why these hires don't work out from expecting a new hire to have a founder's drive to failing to provide a documented sales blueprint. Chapters 00:00 - Introduction: Why your new sales hire didn't work out 01:17 - The "25K Experiment": The true cost of a failed hire 03:27 - Reason 1: Expecting them to be exactly like the founder 07:16 - Reason 2: Ignoring personality differences and DISC profiles 10:52 - Reason 3: Not giving the new hire enough time (4-6 month minimum) 14:07 - Reason 4: Failing to provide a documented sales blueprint 16:52 - Reason 5: Poor alignment between sales and marketing 18:37 - Reason 6: Lack of training, mentoring, and support 21:59 - Reason 7: Weak or uninspiring incentive and commission plans 27:06 - Reason 8: No clear, consistent technical stack or offering 28:16 - How to fix it: Focusing on your "sweet spot" audience 29:26 - Building a plan for growth and a sales engine 31:48 - Inspirational Story: Aron Ralston's survival CTA Sales shouldn't feel like guesswork.
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