I had a young buck reach out to me through LinkedIn a couple weeks ago.  After a bit of back and forth we set up a call.  He is considering a career move into tech sales, starting out as an SDR.  He wanted some advice.  He’s seen some of my posts and thought I might be a good person to speak with.

BTW, did you know that most people are willing to help, all you need to do is ask?

I won’t name him, but I’ll send him this post to help him remember what we talked about.  These are the things I wish I was told when I first started out.  No particular order.

1.  You should interview your boss as much as they interview you.  This might be the best piece of advice I could give someone.  A good boss can make or break a job.  Now I am am not advocating that a good boss is to blame if you don’t do well, ultimately you need to take ownership.  But a boss that is a coach and mentor and not just a manager will help you be invincible.  (This of course assumes the boss knows how to coach and mentor).  This is also probably more important early in your career.
2. It’s easier to negotiate before you take the job than after.  This should go without saying, but sometimes we think, “I’ll just prove myself in the first 90 days, then ask for higher salary, higher commission, bigger bonus, etc.”  Make sure you understand the entire comp package, ie., insurance, 401K, on target earnings, etc. so you can make the best decision.  Talk to the other reps.  Is everyone hitting goal?  What % does it increase each year?  How exactly is variable pay structured?  %?  Are you paid on meetings alone?  Are you incentivized to qualify or just get people on the phone?  Know exactly what is expected of you.
3. Protect your brand.  If you go out into the world and sell professionally, you are your own brand.  If you sell something to someone and then your company can’t execute, it’s on you.  And it can follow you.  How healthy is the company?  Are they a startup?  VC funded?  Seed or Series A,B, etc?  Profitable?  Do they have a working product?  Do you like that way it looks?  Does the industry you will be selling in sound exciting?  How do the reviews looks on Glassdoor, AngelList, Crunch base and Indeed?
4. Go for the most upside.  I’ve taken pay cuts for more upside.  Always go for upside.  If you believe in yourself and your goals are bigger than your company goals AND you have #1?  Look out.
5. If there is equity at play, get as much as you can and understand ahead of time the path to get more.  (See #2)
6. When you are young and don’t have a family, there is no such thing as risk.  It’ll work out.  So this particular gentleman is looking at two positions, one in the city he lives and the other in SF.  He is a bit hesitant about the risk.  When you get older, and have a family, then I think “risk” comes into play.  But before then? What’s the worst that can happen?  It doesn’t work out?  Who cares?

So what do you think?  Did I steer this guy in the wrong direction?  If you think so, let me know and I’ll introduce you before he follows my advice…