How to Make Your Sales Job More Attractive to Reps
Updated July 2, 2026
A few years ago, a CRO sat down with a candidate I was placing. The role was new. The vertical was new. The path forward was uncertain.
Most CROs would have led with the pitch: growth trajectory, big TAM, hot product, generous OTE. He led with the current reality instead.
He told the candidate exactly what they were trying to build. He explained why they were hiring this specific person. He named the obstacles ahead, and laid out the changes that would have to happen for any of it to work.
The candidate took the job. He went on to land the first several enterprise clients in that new vertical. The transparency wasn’t a recruiting risk. It was the reason the candidate said yes.
The Top 10% Are Skeptical for a Reason
Top sales reps have been promised the moon before. The growth that didn’t materialize. The OTE nobody on the team was hitting. The product that wasn’t as differentiated as the demo made it look. They’ve heard the pitch enough times to know what’s missing.
They’re scarce now too. Companies can’t afford an average rep in one of their limited seats, and the hiring stakes are higher than they’ve been in years. That combination of skeptical candidates, scarce talent, and high stakes punishes the polished pitch. It rewards the hiring manager who tells the truth.
Transparency Filters In the Right Candidate and Filters Out the Wrong One
Most hiring managers hide the problems because they think the problems will scare candidates away. The opposite is true.
Real obstacles filter the candidate pool. The reps who get scared off by a tough quota, an unfinished product, or a hard market were going to use those same things as excuses six months in. The reps who lean in and ask “what would I need to do to win here?” are the ones you want. Sales is tough by nature, and obstacles are inherent in the role. Being direct about what they are makes the accept-or-decline decision a real decision instead of a coin flip.
What to Be Transparent About
A few specifics hiring managers most often try to hide, and that always come out anyway.
1. Quota attainment. If only 30% of the team is hitting quota, say so, then explain why. Maybe the territory was over-promised. Maybe the comp plan was built around an old motion. Maybe the previous reps didn’t have the right skill set. Whatever the actual reason, name it. We’ve seen candidates join teams where nobody was hitting quota and do 3x quota themselves, because they understood what wasn’t working and had the skills to fix it. That’s the candidate you want, and you only get them by being transparent about the situation they’re walking into.
2. The CEO or leadership reality. If the CEO is demanding, name it. If the CRO just left, say so. If the leadership team is in flux, the candidate will find out in the first 30 days regardless. Better they hear it from you in week one than from a colleague in week five.
3. Product or market challenges. If the product is still being built, the market is still being defined, or the ideal customer profile (ICP) is still being figured out, those are real opportunities for the right rep. They’re also disqualifiers for the wrong one. Either way, the candidate needs to know.
4. Recent disruption. Layoffs, comp plan cuts, quota raises, a reorg. Name them. The candidate will read about them on Glassdoor or hear about them from a former employee. Going first means you control the framing.
The Cost of Working Around the Problem Instead of Through It
Whatever the obstacle is, you won’t fix it by hiding it from the people you’re hiring to help solve it.
Working around the problem in the interview means you hire someone who doesn’t know the problem exists. They start. The problem hits them in week three. Now you have a frustrated new hire who feels misled and an unsolved problem that just got worse.
Working through the problem means you hire someone who walked in with full knowledge. They came specifically because the challenge interested them. When the obstacle hits, they’re not surprised. They’re prepared. The more a new rep or leader knows going in, the more they can be part of the solution instead of adding to the problem.
The candidates who take the job after hearing the bad news are the ones you want. The ones who walk away after hearing it were going to walk away in 90 days anyway. You just saved yourself the second search.
If you’re starting a search and the role has obstacles you’re not sure how to talk about with candidates, that’s the conversation worth having before the first interview.
