How to convince a startup to hire you

This is part of an ongoing startup advice series where I answer (anonymized!) questions from readers, like a written version of Smart Bear Live. To get your question answered, email me at asmartbear -at- shortmail -dot- com.

Ambitious Sailor writes:

How can a former navy officer with twelve solid years of overseas defense contracting experience convince a tech startup to hire him as their business guy?

I’m currently talking to [CEO] at [hot new tech company] and I have an interview coming up.

I have a love of entrepreneurship and I figured I may be able to learn a few things from smarter people than myself.

Replace your question with “why” instead of “how:”

Why should a former navy officer with overseas defense contracting experience be “the business guy” at a startup? Especially a hot tech startup?

My guess is, if you’re honest, the fact is that there is no particular reason you should be the CEO of that company. Which is why you’re asking me how to convince them otherwise.

But that’s not to say you shouldn’t be! There or somewhere. The question is not “how to convince,” the challenge is this:

Define the startup in which you would be the perfect person to be CEO or Biz Dev. Not just “OK,” not just “no reason why you couldn’t,” but perfect. No one one Earth better. Construct one startup like that — an imaginary startup.

Who would the founders be? (Probably technical with no sales or business experience, so they need someone for that role.)

What industry would it be? (Probably defense, a place where you have to “know someone” and “know how the game is played” to participate at all, where the founders aren’t those people, so they’re dead unless someone like you runs sales.)

What type of product would it be? Technical? Administrative? Mission-critical? Think hard — a startup doing something mission critical is a hard sell. What kind of product could you sell with your eyes closed

Where is the startup? (e.g. maybe it’s not near Washington, but washington is where everything goes down and you don’t mind being there, so they need you there.)

Keep going, what else? You don’t mind travel; what kind of biz dev or sales requires overseas travel that you can do cold but the founders would be bewildered?

Of course I’m ignorant of this whole industry so it’s quite likely I’m not even in the right ballpark with any of those ideas. But the mindset is right.

Now, does the startup you find have to match exactly on every point? No. But now you know what you’re looking for.

And, once you find it, you’ll get the job. If not, they’re the crazy ones.

Add your advice to the discussion section!

9 responses to “How to convince a startup to hire you”

  1. I am/ have been in the same position and I can actually tell you based on the fact that when there is a match: GO for it!

    Starting your question with a WHY always puts you in the driver seat of what you want to achieve and what makes you tick and go after a particular goal.

    WHY do you want to be in a startup?

    I believe it is awesome that someone with that much experience wants to go after their passion/ what they love so don’t settle for anything less that Jason already had you painting in your mind. Life is to short for that ;)

    All the best and looking forward to hearing about your progress!

    Great post Jason and awesome advice series!


    • Stefanos,

      I have tried to get 3 businesses off the ground with no success. Taking advice from two of Jason’s collugues  (Joshua Baer and Bill Boebe) at Capital Factory I believe I need to get some experience at a startup for a few years. ( I met them through Joshua’s office hours)
      I took Jason’s advice and targeted two startups (  and ) that I would be a good fit at.
      Fidelis helps veterans take advantage of their GI Bill benefits. I have been following up with them since the summer. I was turned down for one job but was invited to a coffee meeting  with their head of counceling in  San Francisco on March 01, 2012. ( I was going out their anyway for a military job fair, so it worked out)
      The day after that  meeting was set, a Regional Manager position  in San  Diego at the same firm became available.  I  had a couple of email exchanges  with their VP of Operations this last weekend.  He had questions on salary and if there was a similar position here in Texas would I take it. Hard to tell if I will be selected for an interview.
      I also learned about  through a couple of tweets from folks I follow. Again a couple of email exchanges with the CEO and was told no room at the inn currently but maybe when they expand here in Central Texas in Q3 or Q4.
      I also reached out to a fellow former officer who works with startups in DC in his capacity at Microsoft. He gave me additional info on TroopSwap and a link to a Qoura question that  listed several companies that look promising. That led me to finding  out about  an open Supply Chain Manager position at FitBit.

      I have been following and commenting on Brad Feld’s blog and remembered he was an investor. I sent a tweet to him and  Brad was kind enough to forward my Bio onto the CEO.

      A number of peers think I am crazy. They think I  should go into a nice safe Fortune 500, Defense sector or goverment job.  Folks don’t understand why I keep trying to get a business off the ground after 3 failures.They don’t understand why I am putting my own money on the line this week to go meet with folks in San Fransisco for jobs that are iffy at best.

      I have had an interest in entreprenuearship since the 8th grade and studied it in college. I enjoyed the military but left when it was not fun anymore. I am just  tired of not doing what I really want to do.

      If SF does not work out, you will see me at the job fair at SWXSW.

      Catch me @billmcneely

      • Nice one.

        The F500 job will always be there waiting for you, so there’s almost no opportunity cost.

        BTW we (WP Engine) will be at the job fair at SxSW, if indeed you’re in that position.  :)

  2. Awesome post. I think a lot of non-technical people, who would be good candidates for biz dev jobs at startups, have trouble positioning themselves for the jobs they want. I like the idea of envisioning the perfect job scenario for you and then going out and finding it. Good stuff. 

  3. I often got pitches by startups trying to hire me for free… Well, not really, they said “equities”, but since 99% of startups fail, naturally I’ll discount any startup equity that’s not my own by 99%. Which effectively be nearly “free”. If you’re challenged to get experienced people for your startup, here’s a few points to see what the other side of the bargaining table might think.

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