Outsider Insights | The Comp Plan Is Quietly Telling Your Sales Team Not to Hunt

Outsider Insights

Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.

The Comp Plan Is Quietly Telling Your Sales Team Not to Hunt

A CEO recently asked us why his sales team wasn't bringing in new logos, despite a healthy quota and regular reminders to his team that new business was the priority. The answer had nothing to do with effort. It was sitting in the comp plan, the account list, and the org chart -three documents nobody had touched in years, all quietly instructing the team to do the opposite of what leadership was asking for out loud.

He isn’t alone. In recent months, we’ve seen a surge of CEOs asking us to help diagnose and fix issues around their sales team not chasing new business.

What We're Hearing from CEOs

The frustration usually shows up the same way, even across very different industries:

• Leadership sets a new business target, but nothing else about the team's day-to-day changes.

• Reps are described as reactive, order-taking, or overly focused on the accounts they already have.

• A push for more prospecting produces more activity, but not more qualified pipeline.

• The same handful of people (often including the CEO) keep closing the deals that actually move revenue.

None of this is really about effort or attitude. It's a design problem hiding behind a performance conversation.

Why the System Points the Other Way

Take a typical account executive at a mid-market company. Their commission is weighted toward total book of business – and the easiest way to grow that is renewals and expansion within an existing book of business. Their account list was built years ago around whoever the company happened to land, not around where new growth actually lives. Their manager reviews call volume and customer satisfaction, not new-logo pipeline. Every incentive in that setup rewards protecting what's already there.

Ask that same person to also go hunt for net-new business, and you're asking them to spend unpaid time and unmeasured effort on something riskier than what already pays them reliably. And, most likely, you’re not rewarding them appropriately for that risk.

This is easy to miss because nothing about it looks broken from the outside. Activity is happening. Customers are being served well. Revenue isn't collapsing. It's simply flat in exactly the place growth is supposed to come from, and the people closest to the problem have no real reason to fix it on their own.

What Actually Needs to Change

Before adding headcount, targets, or another round of sales training, a few questions tend to surface where the real gap is:

• Does anyone's paycheck actually substantively increase when they land a new customer versus managing existing ones?

• Are accounts assigned by history, or by where the best new opportunity actually sits today?

• Is anyone measured on pipeline created, or only on revenue and account retention?

• Is the team’s activity the right activity to generate new business – and would more of the same activity change anything?

Most of the time, the honest answers point to a comp plan and account structure built for a different phase of the business, one where retention was the priority and new logos took care of themselves through referrals or a founder's own network. Neither is a mistake. It's just a design that has not scaled and no longer reflects what the business needs next.

Where This Leads

Realigning comp plans, account ownership, and what gets measured is a smaller, more surgical fix than most CEOs expect. It doesn't usually require replacing people. It requires being honest about what the current system is actually optimized to produce, and then intentionally changing that instead of hoping effort will override it.

This is often where a fresh, outside perspective helps most. It's hard to see where your own comp plan or account structure is a constraint when you it is what you have known for years, and it can be hard to know how to change it without creating chaos in the organization. We're increasingly brought in for exactly this kind of challenge, mapping where the current structure is quietly rewarding the wrong behavior and helping CEOs redesign compensation, account ownership, and pipeline accountability before assuming the team itself needs to change.

If new logos have gone quiet and the team looks busy anyway, the question worth asking isn't why they aren't hunting. It's what they're actually being paid and measured to do instead.