Summary

The most effective sales compensation strategy for getting a small team focused on high-value complex deals is to layer a significantly higher reward on those deals without reducing incentives on transactional ones. Pair that with product knowledge training, targeted prospect lists, and the sales skills longer cycle deals require. When the risk reward math favors complex deals and salespeople feel confident pursuing them, behavior follows.

Salespeople Always Take the Path of Least Resistance

I had Doug on the show recently with a challenge I see constantly in small sales organizations. He’s running a small team across multiple product lines, the offerings are not tightly related, and his people keep gravitating toward the products that are easiest to understand and easiest to sell. The high-value complex deals are getting ignored, and the transactional volume is not generating enough revenue to move the business forward.

Salespeople, as a rule, are going to take the path of least resistance to a commission check. If something is easy to understand and easy to sell, that’s where they’re going to spend their time.

The complex deals take longer, require more skill, carry more competition, and come with a real risk of spending weeks on something that doesn’t close. Meanwhile, the transactional deal closes fast and puts money in their pocket. Until you change the math on that equation, you’re not going to change the behavior.

Start With the Compensation Structure

The first thing I would do in Doug’s situation is create a better risk reward opportunity for the high-value deals. If closing a bigger, more complex deal puts significantly more money in a salesperson’s pocket, your argument for why they should be working those deals gains real validity. You can sit down and say, here is what closing this type of deal means for you, and the numbers back you up.

You do not want to disincentivize your transactional deals in the process. Those deals are your bread and butter. They keep revenue coming in and they keep your team winning. Pull that incentive and you’ll get less of it. Keep it intact, layer a substantially higher reward on top for the complex deals, and now you have a compensation structure that points people in the right direction without punishing them for closing business.

Build Confidence With the Complex Product

The second thing I would do is figure out why your salespeople are uncomfortable with the complex offerings and fix it. In software and technology especially, salespeople often avoid complex product lines because they do not feel like they know enough. They’re going into conversations with CIOs and technical buyers who know far more about the product than they do, and that gap makes them feel insecure. When salespeople feel insecure about a product, they avoid it.

What can you do to give them the product knowledge and the conversational confidence to stand toe to toe with a sophisticated buyer? They do not need to know everything, but they need to know enough to ask the right questions, hold a credible conversation, and move the deal forward.

Pair that product knowledge with the sales skills a longer cycle deal actually requires. Complex deals demand real discovery, a step-by-step process, and the ability to handle objections from multiple stakeholders. Give your people the tools to feel capable with these deals, and they will be far more likely to pursue them.

Point Them at the Right Prospects

The third piece is targeting. Are you handing your salespeople a specific list of companies and contacts to go after for the complex deals, or are you turning them loose to find the opportunities on their own? There is a significant difference between the two.

Your job as a sales leader is to put your people in a position to win. That means doing the work of identifying where the right opportunities are and giving your team a clear starting point. Here are the accounts. Here are the contacts. Here is where I want you focused. The more precisely you can point them, the less friction there is between them and the activity you want.

Use Success Stories to Shift the Mindset

The last thing I would do is make success stories a regular part of how you run your team. Every time someone closes a complex, high-value deal, talk about it. Sit down with your team, walk through what happened, and let that win live in the room for a minute.

Salespeople will not always admit it, but when they hear a teammate close a big deal, something shifts internally. They start thinking, I want that. I want that story to be mine. It changes the mindset in a way that a directive from a manager never fully can.

Fix the compensation. Build confidence. Point them at the right prospects. Then let your own success stories do the selling for you.

If your compensation structure is not aligned with the deals you want your team closing, nothing else you do will move the needle. The Sales Gravy Ultimate Sales Compensation Guide gives you the framework to build a structure that rewards the right behavior without breaking what’s already working. Download it free now: salesgravy.com/ultimate-sales-compensation-guide

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