It’s the Holiday Season! Sales Strategies to Win 2026

We’re in the final stretch of 2025!

This time of year, between Thanksgiving and New Year's, is a period where a lot of reps start focusing on all the fun and excitement of the holidays and mentally check out from work. 

Lots of prospects are taking PTO for holiday breaks, and a lot of people aren’t thinking about buying software (that’s a 2026 problem), right? WRONG! Companies don’t stop buying. In fact, this can be a lucrative time of year when teams are looking to get ahead of 2026 tech stack-building or using up the last of their 2025 budget. 

So while your peers are finalizing their Christmas wish lists and putting together party plans for New Year’s Eve, these last weeks are your secret competitive advantage if you play your cards right. 

This article is a complete roadmap that shows you what to do, who to target, and when to reach them to stack your January pipeline and start 2026 way ahead of everyone else.

Understanding Holiday Buying Cycles

One of the first tips for crushing holiday selling is knowing when it’s the right time to reach out. You don’t want to waste time running outbound when the chances are high that people are spending time with family. Because if that’s the case, you could be cleaning your lists or looking for new accounts to break into. 

Here’s a breakdown of the best times to reach out to prospects in November and December before they dip out for the holidays.

November:

• Early November → The Friday Before Thanksgiving
  It might be all about football, turkey and gravy on the holiday, but the week before Thanksgiving is one of the BEST times of year for outbound. The decision-makers are not just focused on wrapping up the year, but also budgeting for the next one, which means replacing tools that didn’t work out with new ones before the new sales year starts.  Effective sales prospecting can start during this time with the hopes of wrapping up the sale post-holiday.

Run your best Black Friday deals and try to get your brand in front of as many eyes as possible. 

• Monday–The Tuesday Before Thanksgiving
  The week of Thanksgiving is iffy as far as getting a response. There are a lot of people who will still be working, so your best bet for outreach is the Monday and Tuesday beforehand.  The best time to get SaaS sales deals out is before the holiday week starts for the best chance to of getting more coverage and mentions about it.

Keep it light: write short emails (people are more mentally checked out now than ever, so no one wants essay-length emails), drop some voicemails for when they get back, and make some social touches.

December:

• Dec 1–15
  Just like the week before Thanksgiving, December 1-15 is an AMAZING window for outbound. Budgets are being finalized. Teams are planning Q1. And execs are more responsive now because their calendars are much lighter.
• Dec 18–22
  The week of Christmas is a pretty silent window when most buyers disappear.
  Use this time wisely to clean your pipeline, put together sequences, and run account mapping. This way, when people come back up for air from the gift wrapping, you’re ready to connect.
• Dec 26–30
  The week between Christmas and New Year’s Eve is somewhat of a ghost town. But believe it or not, there are some hidden buyers out there still working. And the best part is they’re relaxed because they’re not getting 300 emails a day, and their schedule is pretty open.

Catch their attention with a “Just checking in before the year ends” message. Get those January meetings booked (“Let’s get 15 minutes on the books for early January before calendars fill up.”). And run some campaigns that get those small deals with leftover budget closed (a lot of teams have use-it-or-lose-it budgets).

What Salespeople Should Do Between Now and January 1st

1. Identify Q1 Buyers Now. Don’t Wait Until January. 

Most teams will wait until January to start prospecting, which means they likely won’t close anything until March.

So instead of prospecting hard, now is the perfect time to identify your Q1 pipeline, so you can hit the ground running: 

• Build lists of 2026 ICP accounts.
• Use Seamless.AI Org Charts to map decision-makers and influencers.
• Add them to outbound sequences before Dec 10.
• Start connecting with them on social throughout December.

2. Hone In On Those Sobering End-of-Year Pains

I know in sales, we’re always talking about pain points. But the end of the year is when companies can feel those pains the most. You could be their holiday miracle.

Think about it, the year is nearly over. You realize that the odds of you hitting those revenue goals aren’t going to happen. That flashy tech you invested in isn’t delivering like you hoped it would. 

Beyond the tech stack, there might be new problems (broken processes, database issues, staffing gaps, etc.) that have cropped up, and it’s clear you need to add new solutions to resolve them. 

This is the perfect time for you to come in with your solution and save the day (“What do you need fixed before Q1 hits?,” “What’s the one problem you don’t want to drag into 2026?”).

3. Hit High-Usage & High-Interest Customers for Upsells

Power-users always want more and wouldn't mind a savings. Your warmest deals all year are:

• Customers who use your product a lot
• Accounts with license gaps
• Anyone visiting your pricing page or requesting more info

So in December, hone in on these high-intent prospects and run upsells with teams that already love your product because they already trust your brand and will be your fastest closes for the month. 

4. Clean and Strengthen Your Lists

At Seamless.AI we know data hygiene, and clean data is a game-changer. The math is simple… A clean lead list = A fast Q1.  Bad data = A dead Q1.

So, during those quiet spells in December, take the time to do some of that busy work so you can focus on driving deals in 2026: 

• Update account notes. 
• Use Seamless AI to get real-time validated mobile numbers and emails. Plus, use Data Enrichment to refresh outdated records and get rid of those dead leads.
• Rebuild sequences with finalized 2026 messaging.

5. Take Advantage of the Holidays & Personalize Your Outreach

People respond to messaging that’s human and relatable. In fact, people spend 38% more when their buying experience is tailored to their needs. 

When December rolls around, we all start feeling the pressure to hit quota or at least get close. So instead of sending out generic, robotic messaging, tap into these anxieties and make your prospects feel seen. 

Here are some additional outreach angles that convert well in December:

• End-of-year wrap-ups
• Industry predictions for 2026. Offer industry insights to help them hit January goals early. 

6. Build Your January Follow-Up Engine

Only 2% of deals are closed on the first contact. You know what that means? You have to follow up more than once if you want to get a closed won. While you have some downtime, prepare:

• Follow-up templates
• Objection-handling scripts
• Video messages (a great way to set yourself apart) 
• January kickoff email campaigns

Wrap-Up 

In addition to the six plays I dropped, one more task you can complete between now and the moment the Times Square ball drops on 2026 is this: Reflect on the year you had and fix what didn’t work.

Take a mental inventory of your wins and losses, identify your weaknesses, study the top performers on your team, and if you have time, maybe squeeze in a training or two to practice demos and calls. 

Reps who win aren’t always the loudest, the most charming, or the ones posting screenshots of their quota bars. They’re the ones who stay just a little bit more consistent than everyone else when everyone else checks out.

These final weeks aren’t about grinding yourself into the ground and burning yourself out. They’re about being intentional and working smarter not harder. 

So use this guide. Work the timeframes where buyers are active to your best advantage. Nurture when they’re offline. And set January up for the kind of start that changes your year. Here’s to ending 2025 with momentum—and walking into 2026 ready to make everyone else wonder how you got so far ahead.

Cheers to finishing strong.

If you are looking for a sales outreach solution that can deliver high-quality contact data along with AI-powered percision, then checkout Seamless.AI today for free and start building your pipeline stronger.