I'll start:
Lesson 1: You learn more in the losses than the wins
--I had a trash quarter, but it forced me to scrutinize my process closer than ever before. Even with the pain of missing quota, I can say I'm a better rep than ever before
Lesson 2: Good relationships drive better business
--two of my biggest deals happened over the course of 3 months. The clients started small because implementation was a concern, then grew with their comfort level. Because I wasn't greedy in the beginning, the customer is much happier, and I got more total contract value from the account
Lesson 3: I suck at end of quarter incentives
--I had four accounts that were SURE to close in Q2 and put me on top of the team. I thought the old "EOQ discount" pressure would be the compelling even the client needed. However, one DM went on an unexpected vacation (his wife was complaining about work-life balance), one champion got in a car accident, I pissed off another DM who didn't appreciate how pushy I was, and I skipped an internal approval with another client and failed to truly learn their timeline.
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