Cyrus Woolard

Recent Posts

Is Your Sales Comp Plan Motivating Your Team to Close?

Posted by Cyrus Woolard on October 3, 2018

In enterprise sales, not all compensation plans are created equal. When sales leaders get it wrong, they don't just risk losing their most valuable players. They're also gambling with decreased morale and additional turnover—not to mention lost revenue. The wrong comp plan can also impact your organization's ability to hire experienced sales professionals, meaning you may be setting yourself up to miss quotas for several quarters down the line. 

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Emissary of the Month: Ed Goldman

Posted by Cyrus Woolard on September 25, 2018

For more than 20 years, Ed Goldman has driven technology strategy at blue-chip enterprises like Boeing, Marriott, and, most recently, Intel, where he was Enterprise CTO of the company's Data Center Group. 

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How AI Will Change Enterprise Sales (and How it Won't)

Posted by Cyrus Woolard on August 13, 2018

It's not an exaggeration to say that artificial intelligence (AI) and automation pose existential threats to many professions—the number may be as high as 10 million, more jobs than were impacted by the Great Recession of 2008—and sales is no exception. In fact, Forrester predicts a million sales reps will be displaced by 2020.

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Three Reasons Your Buyers Are Swiping Left

Posted by Cyrus Woolard on June 25, 2018


Enterprise sales isn't Tinder. Instead of a series of short-term flings, the name of the game is building long-term relationships. And as Dr. Phil, Oprah, Delilah, and just about every other self-styled relationship guru has told us, doing so requires communication and trust. That takes time and commitment—and that doesn't happen overnight.

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Tags: Emissaries Speak, Sales Intelligence

How to Avoid Epic IT Sales Pitch Fails

Posted by Cyrus Woolard on May 14, 2018

Have you ever followed up with a prospect, only to be told that they're passing on your solution based on abstractions like "lack of cultural fit" or "lack of team alignment"? Huh? What gives?

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Tags: Information Technology, Enterprise Software, Emissaries Speak