Get the Sales Job You Want by Understanding What You’re Good At

I had a candidate who loved sales. He was talented, driven, and he could sell. But he needed a bullpen to be at his best. The energy of a sales floor, the banter between calls, someone to turn to and say, “You won’t believe what this prospect just told me.”

Time and time again, he tried remote roles, and every time, he’d fizzle out. The talent didn’t change. The environment did. Today he’s happily working in an office and performing at his best. And it took him ten years of going back and forth to figure that out.

Ten years. That’s the cost of not knowing what you’re good at, and what you need, before you pick your next sales job. 

Most salespeople evaluate opportunities by looking at the company: the product, the OTE, the funding. But the first thing to evaluate is you. Here are five questions worth answering honestly before your next move.

1. Are You a Self-Starter, or Do You Do Your Best Work with Support?

Be honest, because there’s no wrong answer, only wrong fits. Some reps thrive with nothing but a laptop, a territory, and silence. Others, like my bullpen candidate, need structure, energy, and people around them to perform.

Startups and remote-first companies reward the first type and quietly grind down the second. Established companies with real offices, ramp programs, and managers who coach reward the second type. 

Neither environment is better. But one of them is better for you, and if you’ve fizzled somewhere before, the environment is the first place to look for the reason.

2. Are You Good at Prospecting, and Do You Actually Like It?

Some salespeople can build pipeline out of thin air, and some are at their best working what comes to them. If prospecting isn’t your strength, that doesn’t disqualify you from a great career. It tells you where to have it.

Go to a larger, bigger-brand company, where marketing generates demand, SDR teams set meetings, and the brand opens doors cold outreach never will. Whatever you do, don’t take a role where the whole job is outbound and hope you’ll become a different person. 

You won’t, and your pipeline will tell on you by the second quarter.

3. Does the Money Carry You Through the Hard Parts?

Some reps love the game itself. Others are honest enough to admit the commission check is what keeps them going when the job gets exhausting, and the job does get exhausting.

If a big earning year energizes you enough to carry the grind, the rejection, and the pressure, you might be a hunter for life, and you should pick roles with uncapped upside, aggressive accelerators, and new business to chase. 

If the money alone doesn’t sustain you, you’ll need to weigh the other parts more heavily: the product, the team, the customers. Know which one you are before a comp plan seduces you into the wrong seat.

4. Do You Want Fast Deals or Big Deals?

Transactional sales gives you volume, quick wins, and a scoreboard that resets weekly. Enterprise sales gives you six-figure deals, six-month cycles, and buying committees to navigate. Some reps go crazy waiting half a year for a signature, and others find forty small deals a month soul-flattening.

Your energy has a natural rhythm. Match the sales cycle to it, and work stops feeling like a fight against your own wiring.

5. Which Buyers Do You Enjoy Selling To?

This one compounds over your whole career. The buyers you know, the domain you speak, and the deals you’ve closed with a specific type of customer are your career capital, and employers pay a premium for reps who already know their buyer.

So notice which customers you enjoy, because you’ll naturally get better with the buyers you like talking to. Pick a lane you can stand to stay in, and every year in it raises your value.

Now Put Your Answers to Work

Once you know what you’re good at and what you need, the search gets much simpler:

• Tap your network. Tell former colleagues and managers what you’re looking for, specifically. “I’m looking for an in-office enterprise role selling to finance buyers” gets you referrals; “I’m looking for something new” gets you sympathy.
• Make a list of companies you admire. Then check them against your answers. A company can be admirable and still be wrong for how you work.
• Write down your requirements. Get clear on what your next sales job needs to have before the interviews start shaping your answer for you, and know how to spot a bad fit before you take it.

My bullpen candidate lost ten years to trial and error. You don’t have to. Answer the five questions honestly, aim your search at the environments where your answers say you’ll win, and go get the sales job you actually want.