Most companies assume adding headcount will fix a growth problem. The real issue is usually what those salespeople actually want from the role. As specialized software sales recruiters, we hear it directly from the candidates we place, and after enough placements a clear pattern shows up. The thing that finally wins a top rep isn’t the thing most companies think it is.
There’s a set of criteria every strong candidate checks before they’ll take you seriously. Get these wrong and you’re out before the real evaluation starts.
Compensation leads. Strong sellers want to win and they’ll put in the effort, but that effort has to pay. They look beyond the base salary to whether people on the team are actually earning their OTE (on-target earnings). If nobody’s hitting it, the plan loses credibility no matter what it says on paper. They want quotas that are realistically attainable, real support when deals get complex (access to leadership, solutions engineers, a path to move deals forward), and enough consistency in comp and territories that they can trust the ground won’t shift under them.
All of that matters. But here’s what most companies miss: these are the price of entry, not the reason a top rep says yes. Once the money is competitive and the product is something they can believe in, the rational evaluation is basically over. What comes next is emotional, and for good reason.
Salespeople are emotional. Once the numbers work, the decision comes down to how they feel about the person they’ll be working for and the team they’ll be joining. And in my experience, that emotional decision splits along one line: whether the company is still growing or already established.
A growth-stage company doesn’t always have the formula figured out yet. The playbook is still being written, the motion still shifting. There’s no long track record to point to, because there hasn’t been time to build one.
So the rep bets on something else: a manager who believes in them. When the path to winning isn’t fully mapped, the emotional pull is toward a leader who sees what the rep is capable of and will go to bat for them while everyone figures it out together. The connection is personal, because at that stage, belief is most of what there is to offer. A rep will take a growth-stage role, sometimes over a safer one, for a manager who clearly wants them to succeed and will invest in making it happen.
At an established company, the calculation changes, and it’s more self-interested than it looks. The rep wants a strong leader with a track record, not for the prestige, but because a winning leader is proof of a formula that works. The logic is simple: if you can win, I can win, all I have to do is run your play.
There’s a second, more practical layer. A leader with results commands resources. Executive sponsorship on a big deal. Budget to fly out and entertain a client. The pull to move a commission around when it matters. A proven leader can get their reps what they need to close, and reps know it. Following a winner isn’t starry-eyed. It’s the smartest way for a rep to get the support that helps them hit their number.
I watch this play out regularly. One of our large clients has two sales teams selling the same solution in different regions. One is run by a senior leader who’s been in the seat five years and taken most of his team to President’s Club. The other is run by a newer leader whose team does fine, but who doesn’t have much experience selling herself or her results.
Comp is identical across both teams. Yet the veteran gets strong candidates interested almost instantly, on his track record alone, while the newer leader struggles to attract the same talent. Same company, same product, same pay. The difference is who the rep believes gives them the best shot at winning.
Get the rational factors right first. Competitive comp, attainable quotas, a plan where reps earn their OTE, real support, and consistency. Without those, nothing else matters, because you won’t make it past the filter.
But don’t mistake the filter for the finish line. Once the numbers work, you’re competing on emotion, and the shape of that competition depends on your stage. If you’re growing, your edge is a leader who genuinely believes in the people they hire.
If you’re established, your edge is a leader whose track record tells a candidate, without a word, that this is a place where sellers win. You can get the spreadsheet perfect and still lose a top rep to the team they’d rather follow.
