Selling Season refers to the annual 4–5 month window—typically October 1 through February 1—when most employers are actively evaluating and switching their payroll provider. During this time, the urgency to upgrade systems, consolidate vendors, and improve compliance makes prospects far more open to new solutions.

This document will empower your GTM team to plan accordingly for Selling Season as it has been shown that Check partners that have a GTM plan ready by September 1st achieve 155% of their target forecast while those that do not only attain 62%.

Next Steps:

Here are the most common “employer buying triggers” between October and February:

If you're in sales, marketing, partnerships, or product at a payroll platform—this is your Super Bowl.

Selling Season is when:

Your job is to show up early, provide value before they ask, and offer a seamless path to start Jan 1.

Below are two graphs, the first one shows an actual legacy payroll’s sales rep quota expectations for submitting closed-won deals to implementation. The second graph shows when new employees went live on Check’s system.

It is important to note that your payroll GTM team will be having employers who will be closed-won to submit to implementation in early Q4 but will not run payroll until January 2026. It is critical that your GTM team coordinates with yours and Check’s implementation teams regularly about this timeline gap.

Selling Season 2025 is your opportunity to capture outsized growth, and the Check Selling Season Playbook is built to help you do exactly that. Whether you’re launching payroll for the first time or scaling an established program, this guide outlines how to use each resource effectively, who on your team to involve, and how to stay ahead of the curve in Q4 and Q1.

This is your strategic command center—the document that brings it all together. It outlines key Selling Season phases, provides timelines, and links to every tactical resource you’ll need to plan, execute, and adapt. All GTM teams should read this document cover to cover:

Who should own this:

ICP drift happens—especially after product changes. This workshop helps you re-evaluate your highest-potential segments heading into Selling Season. Use it to clarify where to double down and where to pull back.

Best for: Emerging and mature partners

Invite: Marketing, product, GTM leads

Link: Segmentation Reset Workshop

If your reps don’t have updated scripts and persona-driven demo guidance, they’ll struggle to compete. This toolkit gives your team the confidence to sell payroll in any conversation.

Best for: Launch-stage and emerging partners

Invite: Sales enablement, revenue leaders, AEs

Link: Sales Enablement Toolkit

You can’t scale what you can’t measure. This worksheet shows where leads are dropping, which channels are converting, and where your biggest untapped opportunities lie.

Best for: All partners

Invite: RevOps, marketing, GTM strategy leads

Link: Funnel Analysis Worksheet

For teams ready to level up, these tools offer strategic leverage:

Your Selling Season Prep Checklist is now live. It’s structured by section—ICP & Forecast, Sales & Marketing Materials, In-Product Strategy, Internal Readiness, and Channel Planning—with space to assign ownership, track status, and add notes.

Best for: All partners

Invite: RevOps, GTM owners, Check Strategy lead

(If your team doesn’t have one yet, your Check contact can help you build it.)

Link: Selling Season Prep Checklist

Use these battle cards to prepare your reps to win against ADP, Gusto, Paychex, and other top players. Keep them handy during Q&A-heavy demos and competitive calls.

Best for: All partners

Invite: Sales reps, AEs, enablement leads

Link: Competitive Comparison Matrix

Get a month-by-month plan for your Selling Season campaigns, plus tactical tips for execution. This resource helps you go from ideas to consistent activity.

Best for: All partners

Invite: Demand gen, marketing, sales leaders

Link: 📅 Campaign Planner & Execution Calendar

This internal tool is for you—the Check partner lead. Use it to run structured monthly (or bi-weekly) reviews with your team and Check to assess progress, surface blockers, and adjust strategy. Focus more time on Enterprise, stay lightly engaged with Accelerate, and touch base quarterly with Quickstart.

Best for: You and your Check team

Use with: Leadership reviews, executive check-ins, quarterly retros

Link: Partner Selling Season Progress Tracker

From email templates to product training decks, the resource library makes execution easier. Pair that with targeted Sales Rep Training to make sure your reps can confidently talk about payroll—no matter their background.

Best for: All partners

Invite: Reps, marketers, onboarding teams

Available on-demand, please let your Check team know if you would like to coordinate a sales rep training.

Every partner has different strengths and gaps. Don’t go it alone—your Check team is here to help you build, customize, and execute your Selling Season strategy. Bring us in early so we can support your team before it’s too late to course-correct.