A candidate of mine spent 14 years at the same software company. He was a strong rep, well-liked, and had outlasted three managers. He thought he was safe.
One Tuesday morning he joined a 10 a.m. call with HR. Seven minutes later he was off the call without a job. His employer had acquired another company and didn’t need him or 25 other reps anymore.
He was three weeks from closing on a new house. He had to walk into the kitchen and tell his wife.
He found another role. He had to. With a mortgage closing and no income, leverage isn’t something a salesperson has.
The offer he accepted was a lateral move at a company he wouldn’t have considered six months earlier when he had a job. The strong market he could have used to trade up was over by the time he needed it.
After 22 years of recruiting software sales talent and more than 12,000 interviews, I can tell you that strong job markets are windows.
They open, they stay open for a while, and they close. The reps who use them well change companies during the window. The reps who don’t are the ones I meet after the window closes, taking lateral offers because they ran out of time.
What a Strong Market Looks Like for Software Sales Reps
You can usually tell a strong job market by what’s happening to base salaries.
During the last one, enterprise reps were seeing $10K to $25K bumps on their base, which on a $120K to $150K salary is an 11% to 15% raise just for changing companies.
Strong commercial reps saw $20K to $30K base increases, and AEs jumping from $75K to $95K were getting 30% base bumps. None of that is a commission story. That’s guaranteed money.
When a market is strong, companies interview candidates without domain or vertical experience. They hire AEs with three to seven years of quota-carrying time even when they’d previously required ten. The pool of jobs widens and the required match narrows.
When the market cools, both reverse. Companies tighten the profile, demand exact-stage and exact-buyer experience, and slow the process down. The reps who waited to move are now competing with each other for fewer roles.
And whenever you find yourself seeing companies negotiate against themselves on your offers, the market is telling you something.
What to Do When You’re in One
The mistake most reps make in a strong market is assuming it will last. The mistake the 14-year loyalist made is assuming his company would protect him because he had protected them. Neither assumption holds up.
Here’s what tends to separate the reps who use a strong market well from the reps who watch it pass.
Look at the people, not just the comp. It’s easy to chase a base bump. The bigger question is whether the team around you will make you better, because if you’re already the strongest rep in the room, your skills will plateau. The companies worth joining have at least a few people you’d want to learn from.
Use the market to switch industries or verticals if you’ve been wanting to. The longer you sell into one space, the harder it is to leave it. Hiring managers type-cast reps based on what they’ve sold most recently. A strong market is the rare moment when companies will take a chance on a rep crossing over from EdTech to corporate, or from MarTech to FinTech. In a cool market they won’t.
Pressure-test the sales culture before you accept. Ask to speak with a current rep on the team. Ask how often the comp plan changes. Ask whether the last person in the role hit quota, and what happened to them. Salespeople in healthy cultures will tell you the truth. Salespeople in unhealthy ones will give you a script.
Move before you have to. This is the lesson the 14-year loyalist learned the hard way. A salesperson with a job has leverage, and a salesperson without one is taking what’s available. The time to make a move is when you don’t need to, because that’s when you can be choosy about base, equity, manager, and team.
Why Loyalty Past a Certain Point Becomes a Trap
Most reps think of loyalty as a virtue. From my seat, loyalty past year seven is the biggest reason talented salespeople end up stuck.
The math isn’t complicated. The longer you stay at one company, the more your skills calibrate to that company’s product, buyer, and motion. Hiring managers see that and assume you’ll struggle to adapt.
They’re often wrong, but the bias is real, and it gets stronger every additional year you stay.
The reps who change companies every three to five years tend to keep their skills broad and their market value high. The reps who stay for ten or fifteen tend to find the market has moved on without them.
The 14-year loyalist did everything right by the standards he was raised on. He showed up, hit his number, and stayed put. His company rewarded him with a seven-minute call and 25 other people getting the same news the same morning. The loyalty went one direction.
That doesn’t mean every long tenure is a mistake. It means loyalty past year seven needs a reason beyond inertia. If you’re learning, advancing, and earning, stay. If you’re none of those, the door has been open longer than you think.
If You Make a Mistake, You Can Try Again
One of the reasons reps don’t move in strong markets is fear of choosing wrong. But during a strong market, the cost of a wrong move is lower than at any other time. If you accept an offer and it doesn’t work out, the same market that produced the first offer will produce a second one.
The reps I see making two moves in 18 months during a strong market usually end up better off than the ones who stayed and watched it close.
The loyalist didn’t have that option. By the time he was looking, the market had cooled and his only realistic offer was a lateral. The window had closed. (If a seven-minute call ever comes for you, here are eight ways back after losing a sales job.)
Strong job markets cycle. The next one will come, and cautious markets have their own playbook in the meantime.
When the window opens, the question worth asking isn’t whether to move. It’s whether you can afford not to.
