Category Archives: Sales

The World’s Shortest Sales Career

It was 1999 and I was home after my freshman year at college.  I needed to raise money for a month-long trip to Bosnia later that summer (that’s a story for another time).  Looking through the classified ads (remember those?), I found a position in “Sales”.  That’s what it said.  I had no idea what it was.

I went to a strip-mall office park for my interview, resume in hand (I somehow managed to make it a page long), and sat in the waiting room with a bunch of other clueless job seekers.  I guess the interview went well because they “hired” me on the spot, though I still hadn’t figured out what I was supposed to do.  My new boss took me in his car for training and we drove out to a nearby residential neighborhood.

Suddenly, I realized what this was – door-to-door sales!  For those who have done this, I have a real respect for you. You get the door slammed in your face again and again and again and need to just keep smiling. It’s very, very hard.  We were selling some kind of golf coupon, and to my surprise a couple people actually seemed interested (who knew door-to-door still worked).

But the more my boss talked about the job, the crazier it started to sound.  I mean, this guy was absolutely convinced he would make his millions this way.  All he had to do (so he told me) was get X number of people working for him, and then those people would go and recruit X number of underlings, and so on, while he got a cut.  This was pre-Madoff, remember.  He said his boss’s boss’s boss had this huge mansion that he’d been to, and that someday that was going to be him.

Well, as I was pondering this, I had a more immediate realization – I hated it.  It combined several things I didn’t like: (i) I’m shy around strangers, (ii) I felt guilty trying to get them to buy this coupon (I’ve never golfed a day in my life) and (iii) I felt like I was invading their privacy.  Hell, when door-to-door salesmen came to my house, I got pissed off (I’ve since become much more polite)!

I quit after lunch.  I’d lasted 4 hours.  My dreams of Sarajevo were slipping through my fingers…

In retrospect, I think this experience may have contributed to my lack of sales mojo.  As an entrepreneur, you’re salesman-in-chief.  It doesn’t matter if you’re a genius coder or have zeroed in on the perfect market opportunity – if you can’t sell it, you fail.  And you can’t delegate this either – you need to be learning yourself why people buy and don’t buy your product.

I think part of the problem is the Technologist’s Handicap: as the creator of the product, you see all its limitations, all the bugs, all the places where you know it will get better with time.  Also, you have a rationalist, logical mindset, you want to give people all the data and let them come, through a process of careful analysis, to the inevitable conclusion that your widget is worth its price.  And technologists notoriously under-price.  You don’t present hype, you present an argument. Sure, you can talk passionately about all the technological mountains you’ve summited, but your customers won’t care.

What I’ve been told (and am continuously working on) is that sales is really about listening.  You listen to your customer’s problems, sympathize with them, feel their pain, and only then humbly suggest your wonderful widget as a solution.  All easier said than done – and this presupposes you’re actually able to get in front of them in the first place.

Have other technologically-oriented founders experienced this?  I’d love to hear.

Anyway, the story actually has a happy ending.  I tried another job (“Political Activists Wanted!”) – they’d pay you to collect signatures for ballot initiatives in Safeway parking lots.  I don’t think this was quite what the Progressive Movement had in mind when they created the initiative and referendum system…  Well, that job didn’t last either.  I ended up installing a drip sprinkler system in my neighbor’s yard with a friend, and loved it.  We were outside, figuring out how to make this thing work without flooding the kitchen and getting paid for it.  By August, I was happily Balkanized.