For consumer brands, the holiday season is usually the biggest time of year for revenue, but for B2B companies it can be hard to close new deals and keep your sales pipeline healthy. This article has a few tips we've learned from 4 years of doing outbound sales during November and December.

Table of Contents:

  1. Act like a real person, timing matters
  2. Acknowledge the time of year in your scripts
  3. Create a sense of urgency
  4. Provide a promo to get started now
  5. Hail Mary! Schedule meetings in the new year

1. Act like a real person, timing matters

Always pause sales outreach (Email, phone calls) for a few days before AND after major holidays. One reason for this is that so many people will be OOO, you will essentially waste valuable contacts. Sure, they might read and respond to your email when they get back to the office, but more likely they will be busy catching up on their core tasks and just delete it.

If contacting prospects on a more personal channel, like LinkedIn or Instagram, Automatic OOO messages may not apply. This is where authenticity and acting like a real person comes in. Let's say that according to the timing and sequencing rules you created in your CRM or, you get prompted to send a connection message on Christmas Eve. Sending that request according to your automation rules puts you at risk being viewed as a bot (writing personalized outreach messages is already hard enough!), or, worse, as someone who doesn't respect your prospects' private time.

The recommended option is to "read the room", and hold off on sending that request until a few days after the holiday. You'll be more likely to get a response, and a cordial one at that.

2. Acknowledge the time of year in your scripts

Another great way to increase the authenticity and seasonality to your outreach is to mention that it is in fact, the holiday season!

Compare this to a tactic for writing effective subject lines- which is to look through your own Sent email folder. What are real subject lines that you use to communicate with coworkers and customers? Chances are, they are 2-3 words and don't look like a newsletter headline. Similarly, reflecting on emails or phone calls made to colleagues and friends during this time of year can help you come up with genuine-sounding opening and closing lines. A few examples:

"Hope you're enjoying the snowy weather in Denver, feels like the holidays!"
"How is the year wrapping up for your sales team?"
"Happy Thanksgiving, I will follow up with you next week. Enjoy your time off!"

3. Create a sense of urgency

Creating urgency in a cold outreach script is definitely an art form. In general, understanding the stage that your prospects are at, or key events that are happening in their business, can help you write better, more pointed questions.

A recently hired CMO is probably looking to refresh their brand and build out their budget:

"Hard to believe it's time to start budgeting for the new year, but are you thinking about updating your messaging or website in 2022? We put together a few ideas for you...."

A startup founder who just hired their first employees probably needs to step up their financial reporting:

"Our accounting firm is all about helping growing businesses advance to their next stage. Would you be interested in practical financial reports that highlight the information you'll need in 2022?"

These two examples have an element of urgency that comes from context + referencing the time of year and looming deadlines.

4. Provide a promo to get started now

Let's assume that a prospect has expressed some interest, maybe even had a meeting, but now they've ghosted you or their budget for the year is used up. Try coming up with a creative promotion to encourage them to talk to you, or one that will solve their budgetary constraints.

At Hello Outbound, we sell subscription packages that always include one month for onboarding. If we talk to a prospect in November who says they can't get started until the new year, we could hypothetically offer them a highly discounted or free onboarding month that's only available for December. Then, January 1st they will be ready to hit the ground running with our program.

This would incentivize them to come on as a client right away, and while we would miss out on some money from the onboarding period, our close rate would look healthier and we'd have guaranteed revenue the following month.

5. Hail Mary! Schedule meetings in the new year

Of course, one option is to not send any sales outreach during November and December. But this is a sure-fire way to end the year with no new prospects in your pipeline and no meetings to come back to in January. If you are noticing lots of folks saying they don't have time to meet, or can't prioritize new initiatives, try offering up the option to meet at a later time.

This could be built into the end of your original outbound message:

"I understand this time of year can be crazy, so please let me know if I should reach out in the new year instead."

Or, used as a follow up to prospects who reply:

"Thanks for getting back to me, I know Q4 is crazy for our industry. Would it be okay if I follow up with you mid January?"

While this doesn't help you hit end-of-year sales goals, booking a meeting for a later date is better than not booking a meeting at all, and ensuring a strong start to the new year is a huge benefit to keeping up outbound sales through November and December. Just make sure to touch base sometime between your initial contact and scheduled phone call to remind the prospect who you are, and why they should still want to talk to you!


Yes, doing outbound sales during the holiday season is worth it! Try tapping into upcoming deadlines and offering end-of-year promotions; just remember to acknowledge the season and be respectful of your prospects' vacation time.1