How Smart MSPs Stop Chasing the Win and Start Creating It

Many MSPs want to grow recurring revenue, close bigger deals, and spend less time chasing tire-kickers. Here's the catch: chasing "the win" isn't a strategy. The MSPs that grow consistently don't wait for luck or perfect timing. They build the systems, habits, and insights that make success more likely to show up on schedule.

This mindset came out of a conversation with Jonathan Vaudreuil, Director of Business Growth at RingLogix and a longtime student of how people actually buy. His take: "The goal isn't to win the game. The goal is to create more and better chances to win."

Below are three principles worth adopting, and how to apply them directly to your business.

Jonathan Vaudreuil leads go-to-market strategy and sales enablement at RingLogix, with a background building sales development programs at InvoiceCloud. His approach blends behavioral psychology and systems thinking to help companies build repeatable, scalable growth.

Key Takeaways

Not all wins are created equal, and the MSPs that grow fastest aren't chasing leads, they're creating opportunities. Three concepts worth applying to your business:

• More at-bats mean more revenue. Stop relying on big swings and focus on showing up every day. Growth comes from creating consistent, repeatable chances to win.

• People buy when something changes. Learn to recognize the three types of change that open the door to new deals, and how to act on them.

• The cost of winning is overpaying. The MSPs who scale aren't cutting corners. They're investing in the tools, systems, and strategies that give them control and long-term success.

Focus on Better At-Bats, Not Just Big Hits

MSPs often get stuck in a familiar loop: build a landing page, run some ads, wait for leads, then wonder why nothing closed. It's a strategy built on hoping for the perfect pitch.

"So many of the things we're trying to do as a business are about improving our at-bats—not just trying to get hits. Because if we improve our at-bats, we'll eventually get more hits."

You don't control when a whale-sized deal will appear, but you control how many good-fit conversations your team has this month. MSPs who win consistently don't rely on Hail Marys. They build repeatable paths to get in front of customers.

What this looks like for MSPs:

• Reaching out to closed-lost deals when you launch something new
• Automating your quoting and billing so nothing falls through the cracks
• Running monthly webinars or live demos to generate interest and re-engagement
• Building SEO content to attract high-intent prospects over time

It's not about the one big hit. It's about getting more swings with the right prospects.

People Buy When Something Changes

You could have the best pricing, best support, and cleanest pitch, and still not close the deal. Why? Timing.

"People buy when something changes. The times people are most likely to buy are when you change your product offering, the person making the decision changes, or their situation changes enough that they need to take action."

People don't buy because you're ready. They buy because they're ready. The best sales and marketing teams don't just shout offers into the void, they watch for signals of change and build campaigns around them.

How to use this as an MSP:

• You change: Launch a new service line, roll out a new integration, or start offering co-managed services, then use it as a reason to reconnect with prospects.
• They change: Watch for org changes on LinkedIn, like a new CTO or ops lead, and use that to reach out with a fresh perspective.
• Their situation changes: They're scaling, downsizing, struggling with compliance, their current provider is falling short, or they've seen a competitor already offering AI-powered service and now expect it. These are windows where they're open to a switch.

Your job is to be present when that change happens, and to have a reason to re-engage. Generic follow-ups don't work. Context-driven outreach does.

The Cost of Winning Is Overpaying, and That's OK

This one hits hard, especially for MSPs used to being scrappy. It's tempting to look for the cheapest, easiest path to growth. Real wins often require up-front investment of time, effort, or budget.

"The cost of winning is overpaying. You're not paying to win. You've decided to win because of what winning means, how it changes your life or your business."

When you make decisions purely to minimize short-term cost, you often miss long-term opportunity. The MSPs who win are the ones who:

• Pay for systems that give them control over the customer relationship
• Invest in tools that eliminate revenue leakage and manual reconciliation
• Spend time improving sales collateral, email cadences, and onboarding
• Upgrade their team or process before the pain point becomes visible

It costs more to do it right. But you're not just buying a result, you're buying the freedom and confidence that come with knowing your system works.

Consistent Growth Beats Chasing the Big Win

If you want to grow your MSP, don't chase every shiny tactic or wait for a perfect lead to show up. Growth doesn't come from guesswork. It comes from building systems that give you more chances to win: the right timing, acting when something changes, and being willing to invest in what actually moves the needle.

More at-bats mean more opportunities to close. More control means you're not relying on someone else's roadmap. More investment, done right, means you're setting up long-term wins instead of quick fixes. The MSPs who grow consistently aren't waiting for a lucky break. They're creating the conditions that make growth likely.

FAQ content 

What does it mean for an MSP to create wins instead of chasing them?
It means building repeatable systems, like consistent outreach, automated quoting, and regular re-engagement, so that growth comes from volume and process rather than betting everything on any single deal.

What are the three principles for consistent MSP growth?
More consistent "at-bats" instead of chasing single big deals, recognizing the moments when a prospect's situation changes and is ready to buy, and being willing to invest in systems and tools rather than always choosing the cheapest option.

Why do people buy at certain times and not others?
People tend to buy when something changes, either the vendor changes what it offers, the buyer's decision-maker changes, or the buyer's own situation changes enough that they need to act. Recognizing which of these is happening determines whether outreach lands or falls flat.

What does "the cost of winning is overpaying" mean for an MSP?
It means the MSPs that scale successfully aren't the ones cutting costs to the bone, they're the ones willing to invest up front in systems, tools, and process improvements, even when a cheaper shortcut is available.

How can MSPs get more sales opportunities without more leads?
By improving the consistency of what they already do: following up on closed-lost deals, automating quoting and billing, running regular webinars or demos, and building SEO content that keeps working over time.