The sad truth is, I printed out this applicant’s resume to get an official count. Yes, it was true. This rep had 20 jobs in 20 years, they were all sales jobs, and not a single one lasted more than 13 months.
Amazingly, he was hired even on the 19th job. He must have been a great interviewer. Nineteen separate employers had enough hope to give this guy another sales job, thinking it’d be different this time.
After looking at his resume, I decided I wouldn’t ever encourage someone to go to a sales job that didn’t feel right to them, even if I felt they were passing up a high-potential career move.
So how does a talented rep rack up 20 jobs in 20 years? By following a playbook. And in his honor, here it is: the ten career-killing mistakes, presented exactly as the voice in his head must have presented them.
#1. Show Me the Base
Focus on the money. Have you seen the cost of housing these days? I’m sure you live in a VERY expensive city. Have you seen the price of strawberries? Your base salary is super important. In fact, it might be the most important thing for picking your next job. NEVER undervalue yourself!
#2. Self-Awareness?!
Self-reflection is a waste of time. You already know what you’re good at. You know what matters to you, for crying out loud, you’ve taken all those sales assessments. You’d rather go to the party than sit at home and read!
#3. Follow Your Old Sales Manager
People who know you give you the best packages, territories, and roles. You’ll be taken care of and won’t have to worry so much, because you have cover.
#4. Don’t Bother to Investigate the Leadership Team
I mean, they’re all practically the same, right? If they made it to CEO, they must know what they’re doing. You aren’t the CEO, so don’t think about it too much.
#5. Every Time You Close a Deal, Relax
At the bare minimum, go out for a few drinks and take some time off. I hear tickets to Europe are cheap right now! After all, you’ve worked so hard for all that PTO. Sales is so stressful, seriously!
#6. Don’t Worry About Using That Cumbersome CRM
If they want you on the phone and in front of clients, it’s impossible to log everything, isn’t it? Just skip it. It’s so administrative. Next time around, find a company where you get more administrative support.
#7. Never Be Afraid to Share Your Opinions, Especially with Executives
When your territory, comp plan, or boss changes, make sure your executives know how unfair it is. Go ahead and announce your dissatisfaction on social media. I mean, squeaky wheels get fixed, right? Changes wreck your productivity, so you can’t be expected to deal with too much chaos. Maybe take a few days off for your mental health.
#8. Focus Only on Selling
Don’t worry about building internal relationships at your company. You’re a salesperson, so bringing in business should be good enough. No need to go out of your way to attend company events. They’re optional!
#9. Your Personal Life Should Be Fascinating
Keep your personal life chaotic because, after all, you only live once. A chaotic home life keeps things interesting and gives you something to focus on besides the monotony of the daily grind.
#10. Rely on SDRs and Marketing for Leads
Your SDR should be able to generate all your leads. Wasn’t that promised in the interview? Unfortunately, you’re too experienced to make cold calls now! That’s what Predictable Revenue says, and I’m sure your CEO has read it. You’ve come way too far in your career for cold-calling grunt work.
Now, About That 21st Job
You’ve probably noticed the advice above is exactly upside down.
Chase only the base, skip the self-reflection, follow your old boss anywhere, ignore the leadership team, coast after every win, fight every change in public, and you too can be explaining twenty jobs on one resume to a recruiter who’s counting.
The reps who build long, lucrative careers do the opposite. They know what they’re good at before they pick the seat, they investigate the company and the leadership before they say yes, and they treat every move as a strategic decision instead of an escape.
Twenty jobs in twenty years is a resume. Three or four great ones is a career. Choose accordingly.
