There’s an old adage “you don’t really understand something until you can teach it” or, “…until you can explain it to your grandparents.” I agree and would take it one step further: “you don’t really understand something until you can sell it.” I learned this lesson selling enterprise software. 

I joined Oracle in 2009 as an inside sales rep, selling Oracle database software to major accounts like Intuit and Chevron in the Bay Area. Having received an undergraduate degree in history, I joined Oracle with little functional technology knowledge. As evidence, I might have told you a database was a piece of hardware. But as the first few weeks turned into months, I learned what it was I was selling and more importantly I realized what made the great sales reps great was how they mapped their customer’s needs to Oracle products. They spoke to customers on the customers’ terms. In order to do this, each rep had to truly understand not just the features of the product, but the needs of the customer. 

I later learned that this has a name – “solution selling”– which is second nature to great sales leaders (and great CEOs). The other party may be a potential customer, or when I am on the other side from a CEO it’s as a venture investor keen to invest in a subsequent funding round. By understanding the other party’s needs, the chances of a match greatly increase. 

As an investor, I am no longer in a traditional sales role, but I try to remember to orient toward solution selling when interacting with my customers: entrepreneurs. I ask myself: Am I giving a spiel, which is something you reel off or recite? Am I talking more than I am listening? 

In sales, the goal of a meeting is to build a relationship in order to get the next meeting. Very often, I’ll meet with an entrepreneur, even one who’s currently in the middle of a fundraise, and as the meeting draws to a close both sides engage in a series of pleasantries, with vague indications that one side might follow-up in the future on a generally unspecified timeline. Each time it surprises me. It seems like a missed opportunity. 

A well-run fundraise follows a process, with an intended end-date and milestones along the way to keep the investors either moving along or falling away. Getting to ‘no’ can be as valuable as getting to ‘yes’ to ensure the remaining parties are in fact interested. Fundraising is an art; sales is an art (a solution selling art); but the process part is mostly science. Thinking like you’re in sales — understanding your product, the needs of whomever is on the other side, and your own need to earn the next meeting — is worth remembering.

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