Selling Season: Why September to December is the Most Critical Window of the Year

Every September, the rhythm of business changes. Summer fades, kids return to school, and leaders turn their attention to closing the year strong. For MSPs, this period marks selling season, which is the most important four months of the calendar year.

Why Selling Season Matters

From September through December, business decision-makers are in action mode. They are:

• Finalizing their 2025 numbers

• Evaluating people and processes

• Planning ahead for 2026

This urgency creates the most favorable climate for MSP agreements to be signed. What you close during this period has an outsized effect not just on your 2025 performance, but also on your 2026 recurring revenue base.

Four Keys to Success in Selling Season

1. Review and Reset Goals: Assess your current MRR and activity targets. Adjust upward if you’re on pace, or diagnose root causes if you’re not, whether it's activity, FTAs, or close rate.

2. Prioritize Warm Leads: Double down on LinkedIn outreach, Warm 250 activity, and COI meetings. Review past FTAs from the last 12–18 months for deals that may now be ready to close.

3. Increase Sales Discipline: Ensure weekly sales meetings are structured and consistent. Discipline becomes even more critical as the year winds down.

4. Double the Recipe: Boost activity levels across the board. In sales, the difference between incremental and exponential results often comes down to simply doing more of the right things.

Looking Ahead

Most leaders spend the bulk of their time dealing with day-to-day issues rather than executing on solutions. The MSPs that win selling season are those that focus on the right priorities and consistently take action.

At TruMethods, we’ve seen that every successful transformation includes one constant: new MRR at the right price.

The clock is ticking. Use the next four months to shape your results for 2025 and set the foundation for 2026 growth.