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I once sold more deals than anyone on my team and still missed my number. That year I finished at 95% of quota at Salesforce. And I still missed, because every deal I sold was a department-level deal. Small, tactical, easy to approve and easy to forget. So what is enterprise tech sales, and why…
One of the biggest mistakes tech sellers make is confusing interest with intent. A prospect can like your product, attend a demo, and ask for pricing without having a real reason to buy. Great sellers qualify ruthlessly. They want to understand whether the customer has a meaningful problem, whether they want to solve it now,…
Nine years ago, a guy I just met at a mastermind was in the middle of a strange challenge. He was handwriting five thank you cards a day every day for a full year. This challenge eventually led to a book “The Mr. Thank You Project,” Ted Talk, and professional speaking business. Not long afterwards,…
There’s a lot of garbage online about what it takes to become successful. Make millions by 30, retire early, follow this blueprint, use this hack, build an app that prints money….blah blah blah! That might work for a select few people, but that’s not how it works for 99% of people. There is one step…
On paper, Ed Wakefield was successful by every measure. Successful career in B2B sales.President’s Club winner at Salesforce.Happily married with two young boys. But behind the scenes, Ed was secretly struggling with alcohol. 18 months ago, he decided to get sober completely on his own. No rehab, AA, or sponsor. Instead of following conventional paths…
Selling enterprise deals is a completely different game from selling transactional ones, and it calls for a different set of skills. What works when you’re closing fast, smaller deals simply doesn’t transfer to enterprise software. At its core, enterprise sales is about earning trust. Executives don’t buy software because you delivered a polished presentation. They…
Everyone wants to blame their territory, the timing, or a lack of natural talent when they’re not hitting quota. But that’s not really why tech sellers fall short, and I know because I’ve been there myself. I missed quota three years running before I turned things around and became the #1 Enterprise AE at Salesforce,…
Imagine working an 8.5M deal for an entire year, and still having the paperwork unsigned going into the last day of the fiscal year! That would rattle anybody, but Rob O’Keefe fully trusted that the deal would close on Friday January 30th, and that’s exactly what happened. He knew this because he had personally brokered…
The biggest lie in tech sales is that more activity equals more success. After coaching more than 1,000 tech sellers, I have seen the same pattern repeatedly. The reps struggling most often say, “I’m working my hardest, but I’m not getting results.” Then we look at their calendars. Most of their time is spent on…
$200,000,000. That’s how much Crystal Ives has sold in her career against all odds. Her mother was diagnosed with schizophrenia and spent 7 years in and out of mental hospitals starting when she was 5 years old. Her father murdered two people and served time in prison. At 7, her grandfather went bankrupt and gave…
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