Sales for Nerds

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When I started CrowdFlower, I really, really sucked at sales.  Most people said I shouldn’t even try – that I should find a VP of Sales right away.  Five years later I have an awesome VP of Sales that might be able to outsell me.  I’m not sure.  But I am damn sure that if I brought in a new CEO and picked up a quota as a sales rep, I could easily outsell any of the other VPs of Sales that we’ve had – guys with successful track-records.

How did I get good?  I read a lot of sales books and practiced a lot.  A lot of best practices and gimmicky closing techniques don’t work for me, and frankly I haven’t seem them work my sales guys either.  Here’s some specific advice for people like me with an engineering background selling a technical product.


I aspire to be 100% honest with people when I sell to them.  When I’m late for a stupid reason (and I’m often late) I don’t make an excuse, I tell them that stupid reason.  When a customer is trying something new with some risk, I tell them exactly what their in for.  I generally don’t think customers can tell when they’re being lied to, but they definitely can tell when someone is being honest with them.  Instead of exaggerating the size of your business, tell the customer that you have two employees, that you desperately need them, and that they are the first company in their space to use you.  For those reasons, you’re about to give them a huge advantage over their competitors.


Someone once told me that for every day that goes by, a deal is ten percent less likely to close.  I am totally disorganized, so I am obsessive about following up with a customer immediately after I meet with them.  I try to get the next meeting on the calendar as quickly as possible.  I keep relearning the importance of this.


People walk out of a meeting remember your cadence much more than what you actually said.  I think it’s more important to look excited about your product than to make any particular point.  If you sell with more than one person, it’s most important that you look like you are in sync and like each other. It’s almost never worth it to contradict or interrupt someone that you’re selling with.


It used to be really hard for me to email people more than once.  In fact, sometimes it was hard for me to email people the first time.  But it’s so important.  Keep following up if you don’t hear back right away.


When I ask my best sales guys what makes them excellent, they always say that they are really good at qualifying customers out.  This runs counter to many founder’s instincts to be aggressive and persistent and pursue every possible lead.  But it’s so important.  I have no idea why but many potential customers will drag you on and on and waste endless amounts of your time when they are never going to buy.  Learn to identify these guys and hand them off to your competitors.


Like most nerds, conflict makes me uncomfortable.  I am not a natural negotiator.  I love my customers and I want them to get a great deal, sometimes such a great deal that it’s actually bad for my company.  So I make someone else the bad guy.  Sometimes it’s my board.  Sometimes it’s my cofounder.  As in, I want to give you a lower price but my cofounder would freak out – luckily in my case I can do this honestly, because my cofounder freaks out all the time.  Even when someone recognizes the tactic, it sets up a nice dynamic where you are working together to find a mutually beneficial solution rather than an adversarial negotiation.

As another nice non-confrontational negotiation hack, remind a potential customer that, when customers have negotiated too aggressively in the past, they ended up getting bad service.  Fortunately, it also turns out to be true.  The more a customer pays the more they get taken care of.