Setting Yourself Up for a Successful Year-End

When should Year-End planning start? Based on my experience in mid-market SaaS sales, it needs to start 6 weeks out from 12/31.

I run a large group of ERP-focused solutions engineers. Here is what we consistently observe in the last 2 weeks of the year:
• Deals sliding to next year
• Opportunities stalling with no timeline
• Increase in “Closed Lost” opportunities
• Semi-reckless discounts to finish deals
• AEs scrambling to prep resources

Big Question For Sellers: Do your clients have the same perspective on Year-End as you do?
Unless they are publicly traded or funded by an outside source, the likely answer is “no”. You’re the one under pressure, not them. You need to facilitate the timeline!

How To Do It:
Here are 3 ways to manage your Q4 timeline well. These should start immediately (mid-November). Don’t settle for price concessions and artificial dates in the waning hours of 2025.

1. Be realistic with your expectations: If you haven’t completed a discovery before Thanksgiving, why do you think a purchase decision will be made by EOY? Benchmark Year-End deal timelines across other (mid-year) opportunities you’ve closed. Don’t sandbag opportunities for no reason, but be realistic! Unrealistic expectations will send you chasing deals that won’t close this year, and ignoring opportunities that could. Don’t be the fool who, in the final week of the year, updates a dozen Opps in CRM to a close date of March 2026!

2. Communicate well with your client: Is there a difference to your client if they purchase in December vs January? If you’ve used a joint evaluation plan from the beginning, you’ve already roughly planned the timeline, from the intro call to the “go live”. A joint evaluation plan lets you be consultative, without being pushy.

How can you incentivize clients to sign before Christmas? Here are a few lines I’ve used :
a. We can commit resources faster since the client signed before a swath of others at Year-End.
b. We won’t have to jump on calls between Christmas and New Year’s to wrap up this deal!
c. The client's resources get a break after a sometimes lengthy selection process. New year, new project – and we get to ride the momentum with fresh eyes in January.

3. Understand your client's realities: It shocks me how often sellers are surprised that key stakeholders can't review pricing/ legal can't redline a contract between Thanksgiving and EOY. The average employee is out 7 to 10 business days during this window. Questions you should be asking now:
a. What is your contract review process?
b. Who will be the ultimate signer? (and what is their availability)
c. What company events should we work around?

This list is relevant at any time of year, but during crunch time, margin for error decreases. To get it done by 12/31, you must plan deliberately and communicate thoughtfully. ‘Tis the season to close deals, not make concessions and push Opps to 2026.