Why Winning Deals Feels Harder in 2025 - And What to Do About It

The sales process has changed. Here’s how to adapt and grow smarter in 2025.

More MSP leaders are saying the same thing this year: “We're doing the work. Showing up. Delivering. But deals are stalling—or just not closing.”

You’re not imagining it. It really is harder to win new business right now. But not for the reasons you might think. If you’re struggling to get traction in the market, it’s not because your offer isn’t good. It’s because the buying process itself has changed, and many sales strategies haven’t caught up.

Let’s break down what’s actually going on—and what you can do to shift momentum back in your favor.

The Sales Environment Has Shifted

The external landscape has gotten trickier—even for firms doing all the “right” things.

• Buyers are stuck. There’s more internal hesitation. More approvals. More caution. Even small deals are being scrutinized.

• Everyone’s selling, few are trusted. The inbox is saturated. Cold outreach isn’t dead, but it’s harder to cut through the noise if your brand isn’t already known.

• Sales cycles are stretching. Where a project might have taken just weeks to close in a year or two ago, it’s now dragging to 45 or even 90+ days. Decision-making has turned into decision-deferring. As one peer recently put it:“The leads aren’t always the problem—it’s getting buyers to take the next step that’s breaking down.”

Some of the Blockage is Coming From Inside

Sometimes we’re unintentionally making it harder on ourselves. Common internal missteps we’re seeing across the ecosystem:

• Undifferentiated positioning. “Great service” isn’t a competitive advantage. If your website or proposal could belong to any other MSP, you’re relying on luck—not leverage.

• No visible proof. No fresh testimonials, no recent case studies, no story the buyer can share with their internal team. That slows trust—and trust is what shortens cycles.

• Passive follow-up. A proposal with no strategic next step is just a PDF in someone’s inbox. The best closers today? They guide the buyer, not just follow up with “Any thoughts?”

• No buyer enablement. You’ve convinced your contact. Great. But can they convince the CFO? The IT lead? Their boss? Buyers aren’t just evaluating you—they’re evaluating how easy it will be to say yes to you internally.

What’s Working in 2025 (From the Field)

Across the Teamwrkr network and beyond, here’s what’s helping real firms keep deals moving:

• Peer reputation. Buyers trust other buyers. Being known in your ecosystem—even indirectly—gives you a warm start.

• Smaller entry points. Fixed-fee assessments. Discovery sprints. Pilot projects. Small starts reduce risk—and start the trust flywheel.

• Sales support for the buyer. One-pagers. Outcome summaries. Short videos. Make it easy for your contact to pitch you inside their org.

• Real positioning, not recycled claims. Clear industry focus. A strong POV. Language that reflects your actual value, not just your service list. The firms getting traction aren’t louder. They’re clearer, faster to trust, and easier to say yes to. Sometimes you don’t need a better offer—you need to give your buyer a better story to tell.

A Smarter Sales Reset: 5 Moves That Work

You don’t need to start over. You just need to reframe how you engage. Here are five tactical shifts that can unlock real movement:

1. Tighten your Ideal Customer Profile. Generalists are struggling. Specialists are thriving. Know exactly who buys what you are selling.

2. Update your proof. Testimonials, social proof, and real client stories matter more than ever. Don’t wait to “perfect” them—just publish.

3. Shrink the first ask. Low-risk starts lead to long-term wins. Think discovery, not deployment.

4. Support the internal pitch. Ask: “Who else needs to see this?” Then give your buyer tools to advocate for you.

5. Lean on your network. The fastest path to a closed deal is a trusted intro. Be worth referring to—and ask for referrals often.

Growth Has Evolved

What we’re seeing is not a collapse. It’s a shift. The MSPs and service firms growing in 2025 aren’t doing everything differently. They’re doing a few key things smarter:

• Getting warm leads from real partners

• Supporting buyers like collaborators, not targets

• Building a reputation that compounds

This is exactly what we’re working on every day inside the Teamwrkr Community. Because:

• Better deals don’t come from louder sales—they come from higher trust.

• Stronger teams grow through the right relationships.

• Smarter growth is built through intentional systems, not hustle alone.

Summing It Up

If it feels harder to win new business this year, you’re right. But that doesn’t mean growth is off the table. It just means the playbook needs to evolve.

So ask yourself:

• Where am I still relying on tactics from 2022?

• How am I helping my buyer become my internal champion?

• Who in my network could unlock my next opportunity?

If your answers aren’t clear, it’s time for a reset.

Join the Community

At Teamwrkr, we believe trust, visibility, and community-driven growth are the new foundations of how work gets done. We're building a community where MSPs can get better deals, grow stronger teams, and grow smarter. Join us.