Recently I was to talking to a friend who has worked his way up through the ranks of Sales from Field Rep to Director to VP.
But, like some of us who’ve worked our way up to the job we always wanted, he’s discovered that it’s not all it’s cracked up to be.
In pondering his next career move, he asked me,
“Am I crazy to be thinking about going back to being a Field Sales Rep? The money was good, my stress level was much lower and I saw my family more.”
After we talked for a while I said, “You’d be crazy not to go back to Field Sales.”
That’s probably not what you expected to hear from two ambitious, successful people who spent their entire careers working their way up to VP.
Let’s investigate why.
As reps, we wanted to become managers because:
- We wanted to make more money.
- We wanted to be in charge.
- We thought we could run the sales team better than our manager.
- We were fed up with cold calling, dealing with customers, starting each quarter at zero, and so on.
- We wanted to do higher level management work.
- We thought being in charge would make us happier.
Once we were managers, we wanted to become VPs because:
- We wanted to make more money (and get rich from stock options!)
- We wanted to be in charge.
- We thought we could do better than our VP.
- We were fed up with coaching, training and managing reps.
- We wanted to do higher level strategic work.
- We thought being in charge would make us happier.
Some of this was true. There were upsides that came from moving up the career ladder.
- Money – Our base pay went up. Total compensation did too. We never became rich.
- Stock Options – We got some. But it didn’t make us rich. These were either worthless or equivalent to a small annual bonus.
- More strategic work – It was fun and challenging to do higher level work (at first). Instead of talking to prospects about deals or reps about sales issues, we created forecasts, met with senior execs, made hiring/firing decisions, fought political battles and competed for budget.
We never considered the downsides.
- Money – Although we made more than an average reps, both of us were used to crushing it as reps. We both knew reps who made more than managers and some who made more than VPs.
- Less Chance for Upside – We were responsible for the team’s quota. When a rep wasn’t hitting his number, when someone quit, when hiring was delayed or a backfill not approved – it was too bad. We still were had to to hit the whole number.
- Control – We had more control over the sales team. But our ability to influence the company’s strategic decisions was far less than we had imagined.
- Happiness – As a rep, I loved going onsite, solving customer problems and closing deals. I ran my territory the way I wanted to with little interference. For the most part, management left me alone as long as I hit the number. My colleague had a similar experience. As executives, we spent most of our time working inside our company dealing with internal issues, politics and Corporate BS.
- Less Family Time – This is a harsh reality. VPs travel more, work more and are never really “off the clock”. When you are a VP, your work responsibilities grow exponentially and family time will suffer.
Running Inside Sales Dude helped me to realize that I won’t be returning to a VP of Sales role.
As a solo consultant, I am responsible for just myself and my work. There’s no meetings, no politics, no “make-work” and no excuses. I meet with my customers, sell, work, and get paid.
I’m not up late at night worrying reporting numbers to the board, fighting for realistic quotas or firing people.
In many ways, being a solo consultant is a lot like being a field sales rep.
It took awhile for me to adjust.

I think my ego was hardest thing to overcome (not receiving a paycheck every two weeks is a close 2nd!)
I no longer have hundreds of employees reporting to me. I’m not responsible for multi-million dollar budgets. I don’t have a fancy business card, a corporate expense account or a big title.
Would people think I was a failure? Would they think I couldn’t cut it?
More importantly, what would I think?
My friend is asking himself the same questions.
I’m not sure what he will do. But I know what I would do.
To summarize, moving up the sales career track can be a great thing.
It brings new learning experiences, money, prestige and “power”. If you have a chance to move up, it might be well worth it.
At some point, you may find that (aside from more money), you don’t want these things so much anymore. You might even realize that work was better when you were an individual contributor and begin to wonder if you should go back.
If that happens, you might want to ask yourself: “Am I crazy to not go back to field sales?”
Good luck and good selling,
Steve