The Secret to Finding Closers who Sell Recurring Revenue Services like Pros

When I began writing this article, the question I asked myself was, "Is teaching a hockey player to play basketball easier than making your existing sellers successful with recurring revenue?" This is a topic that is dear to me, and perhaps a bit sensitive. I’ve been leading companies selling recurring revenue services for more than three decades now. In that time, I’ve learned that it’s really challenging to find people who know how to sell recurring revenue services, and even more so, those who have a passion for it!

As most Microsoft partners transition to selling recurring revenue services, many face a dilemma: whether to hire new salespeople with the desired experience and mindset, or to train and motivate their existing sellers to move from selling products, hours and projects. In my experience, it’s often a bit difficult to get people to make this transition, but that doesn’t mean you should give up.

A step in the right direction starts with plotting the course of your company and making sure that your employees are with you for the ride during that transitional journey. Everyone needs to see it as important. It’s easy to find evidence of the importance of such a shift. Both Microsoft distributors and analysts can help you decide and explain why you should do it.

Once you have set the right course towards a more successful future, you’ll need to make sure that your salespeople are on board. The easy part is to make them emotionally motivated. The harder part is to make sure that their compensation packages serve the shift towards recurring revenue.

You will, of course, need to renegotiate these packages and ensure you pay a commission for new contracts and a small amount for renewals. Many companies pay a percentage of the contract value, which motivates a salesperson to write long contracts. To me, that’s old-fashioned as we’re moving to a world of pay-as-you-go subscriptions and perhaps one-year max contracts.

Regardless of your philosophy, it’s important to pay your salespeople the bulk of the compensation up-front. It can be at contract signing, or when the customer starts the service after some kind of deployment, onboarding, implementation or whatever you call it. It’s also essential to make sure that you pay the bulk of the commission up-front if that’s a substantial part of the total compensation package.

The transitional phase can be financially challenging for salespeople accustomed to large commissions from selling traditional hourly or project-based offerings. You should consider assisting them with this transition and perhaps offer support for the first 3 to 6 months so that your salespeople become comfortable and can learn to succeed in selling recurring revenue services. Having great compensation packages and a solid services portfolio is essential regardless of whether you’re repurposing your existing salespeople or hiring new ones.

The big issue, however, is that selling recurring revenue services is very different from selling people’s hours. When you’re in the professional services business, it’s often a specific individual you’re offering to, which makes the selling more personal. When you’re selling a portfolio of recurring revenue services, you’re selling a service and not a person, which is a totally different game, and you’ll need to talk more about business outcomes than a particular individual’s qualities. In my experience, it’s a tough job for a salesperson to make this transition successfully.

The other type of salesperson is the one who is used to sell hardware and add some services on top of that. It’s a big leap to move from selling hardware to selling recurring revenue services that are less about features and more about business outcomes. I’ve seen salespeople struggling with this transition way too many times, and often they fall back into the comfort of selling what they know best. Perhaps it’s like teaching a hockey player to play basketball; it might work, but it’s not a given.

However, selling recurring revenue services is not only about your salespeople; it’s about your company’s abilities, too. Your salespeople must have complete trust in your company's ability to deliver those recurring revenue offerings successfully. They should also embrace the concept that these services are standardized and not customized to each customer’s desires.

If you’re offerings are too fluffy, open to customer-specific alterations, and your pilot customers are unhappy, it’s a hard sell internally to convince your salespeople to sell something that they fear will come back and bite them. Make sure that your recurring revenue services portfolio is modern, highly relevant, delivered with flying colors and is competitively priced.

You’ll need to be the internal gatekeeper and ensure that your salespeople are not tasked with selling something unlikely to be successful. If they hear too many complaints from their customers, they might give up. You only get one chance to persuade your salespeople. Don’t count on a second chance, as they’ll be gone to your competition in a jiffy if your offerings are unsellable or hated by your customers.

Too often, I see ambitious service catalogues that are ancient, complicated and very technical. The best place for them would be the trash bin. It’s to your own detriment if you’re insistent on keeping a services portfolio that is not up to par and that your salespeople dislike.

Truly, I think everyone deserves a chance, and sometimes you’ll find that an existing salesperson successfully transitions to a new business model based on recurring revenue. However, in all honesty, the best success I’ve had over the past decades has been hiring new people who can hit the ground running because they already have successful experience in selling recurring revenue services and the right mindset. These people will also contribute more to the development and adjustments of your services portfolio than traditional salespeople without this experience. And in my experience, it creates less friction and a happier workplace environment.

Another thing is, age doesn’t matter as much as talent does.  I’ve seen both young, talented workers and senior account managers achieve great success. I think a mix of ages, genders and backgrounds builds better teams.  Being an attractive employer to these people will ensure success in finding and keeping them. When they’re successful, your company will be successful. That’s how to build a sustainable future, whether you’re lucky enough to make your existing salespeople successful or if you find new,  talented people, either way it’s a win-win!

Good luck, and share your experiences on how it goes!

Posted by Per Werngren on March 10, 2026