8 minutes
December 3, 2022

7 tips for prospecting during the holidays

The holiday season can be one of the most challenging times of the year for sales teams. Here are our tips to help your team reach their prospecting goals during the holiday season.
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Prospecting during the holidays is one of the hardest things for B2B sales representatives. We are about to enter the apex of Christmas cheer, the out-of-office Kwanza bonanza, the 'Let's connect in the New Year' phenomenon, or, as some call it, the holidays! Do you know what stinks, though? We still have sales quotas!

We want to help you get through one of the most challenging times of the year for sales teams. Here are some tips to help you reach your prospecting goals during the holiday season.

7 tips to prospect during the holidays

  1. Be patient
  2. Send calendar invites for January
  3. Send reminders via text message
  4. Build reminders in your sales sequences/cadences
  5. Use the 'send later' function
  6. Avoid 'Happy Holidays' email subject line
  7. Produce an interesting prospecting campaign

Be patient

Having patience with your prospects is essential to keep you and your prospects stress-free. We're not asking you to be bursting with holiday cheer (although that's welcomed). We're just asking you to be patient. Deals will take a bit longer to close during this time.

If you are a sales manager planning the month of December, most companies are about to make a big push to close out Q4 strong. Your SDR team will set meetings, but most of them, if not all of them, are not going to close before the end of the year. This doesn't mean you stop trying in December; you must be patient and not force urgency on your prospects or customers.

Remember, sometimes, when an SDR qualifies a lead/deal, it'll take more than one decision-maker to sign on to a qualified meeting. Locking DMs down at the end of the year when every department juggles different days and times for PTO can be difficult when it's a brand new deal.

One of our former outbound reps gave this example of how busy the Holidays can be at a company:

"When I was running some of the conferences and events at Dyn, I remember getting pressure to take a meeting before Christmas with prospective clients. At the time, events were decided by our BDR team, our Director of Marketing, and our Director of Demand Generation. We all had various times off during December and focused on finishing up hiring for the following year. It gave me a negative outlook when sales reps kept pushing me to meet before January. I ultimately didn't respond, and the meetings never happened."

Your prospects don't care about your end-of-the-year goals. They don't care about your Q4 sales quota, and they definitely don't care about being rushed in a decision because it fits well with your fiscal year agenda.

Put your prospects first, and loosen the qualification standards in December. You don't want to have December hurt the morale of your prospectors. While it's nice to end the prospecting year off strong, you must be patient and put your buyers first, and being too pushy around the holidays could hurt your deals in Q1. Prospecting during the holidays takes serious work, but patience is genuinely crucial.  

Send calendar invites for January

We've seen many reps get a typical holiday objection and be told to reach back out in the new year. What do a lot of sales reps do? Thank the prospect for their time, create a task to reach back out later, and move on to the next lead. Don't do this.

If you wrote an excellent personalized email or had a great call and got a response, book something on the calendar in January now!

Here's a great example of a calendar invite to send:

Screenshot of a calendar invite for a sales meeting in January with notifications set for 1 day prior & 10 minutes prior

We'd recommend setting up an extra notification in your calendar invite 24 hours out so your prospect remembers the meeting. Most calendars only default to set a reminder for a meeting 10-15 minutes before, so you may have to tweak your invite by adding an extra notification.

It's also important to remind the prospect of what happened with your conversation in December. As a decision-maker, it becomes difficult to remember every conversation while balancing many other tasks. Nothing is worse than the prospect not being prepared to discuss the topic of your first touch in your sales process because you failed to remind them. Add the details of your conversation to your meeting invite, and don't be afraid to shoot them an additional manual reminder via email.

Send reminders via text message

Many sales professionals argue that text messages are the best way to remind a prospect about a sales meeting. They're not wrong. 98% of all text messages are opened compared to 22% of emails, according to Mobile Marketing Watch.

Calling is too intrusive since they already agreed to a meeting. It also seems overly 'salesy' to redo a cold call. Suppose your prospect is like us and has many unread emails in their inbox; seeing another meeting notification will only remind them how busy they are. Texting is a great happy medium and also a lot more personal.

Remember, if you want to be friendly with your prospects, put some personality into your text and keep it casual. For example:

"Hey Tom, this is {Your Name} over at {Your Company}. We talked back in December about the podcast you were on with Sales Hacker. I have us on the calendar tomorrow for 2 pm. Is that still good for you?"

Build reminders in your sales sequences or cadences

If you are using a cadence or sequence software like Outreach or Salesloft, we recommend building a series of reminders for all the prospects the second they say they are down to talk in the upcoming year.

You can boilerplate about 60% of your email and make the other 40% reference what you discussed with the prospect in December. A 2 or 3-step sequence or cadence should suffice with the following steps.

  1. Step 1: Text
  2. Step 2: An email
  3. Step 3: A call if the prospect does not show up to the meeting

Do steps 1 and 2 within 24 hours of each other to do what people call "the double tap." Research indicates that the most successful sales interactions that resulted in a close within a reasonable amount of time started with a phone call and included an email that same day.

Use the 'send later' function

If you are using a cadence or sequence software like Outreach or working the week between Christmas and New Year, use the 'send later' function with your personalized cold email. As a prospector, you can probably count on one hand the number of deals that have actually closed in less than 30 days.

Think of the outcome of your prospect for a second. Even if you or your team members have an extraordinary meeting in the second or third week of December, a lot of the deal momentum can die because of the holidays. It's essential to try and close someone when their interest is highest. How much will their interest drop if they disappear from the office for a week?

If you have a short sales cycle, you can ignore this tip, but generally speaking, most companies we talk with have at least a two or three-month sales cycle on outbound deals. As a result, spend the latter half of December writing personalized emails that will go out the first few weeks in January.

Pro Tip: When you set the send later time, make sure it's not set to the exact hour or half-hour. This will make your email look less scheduled and pre-programmed.

Avoid 'Happy Holidays' in your email subject line

As a rep, you have to be a peacock. What does that mean? You have to find a way to stand out when you prospect. Let us tell you what doesn't stand out—using the subject "Happy Holidays" anytime between Thanksgiving and New Year.

Do a subject search in your inbox and count how many emails use that subject.

A prospect's email inbox flooded 20 messages in a two-week span that contain Happy Holidays in the subject line

Instead, you need to ensure a subject line that will stand out. In our own rep's experience, you'll get a better open rate using a different, more personalized subject line with your cold outreach.

Produce an interesting prospecting campaign

When LeadIQ was starting and had a tiny office, we tried to find a way to do something nice for our customers for the holidays. Our team was kicking around a couple of ideas and our CTO at the time ended up buying a bunch of portable phone chargers with our logo on them with the intent of using them with gifts. After some debate, we ended up mailing some to select prospects instead.

Logistically, while the gifts were practical, we as a company would only have a little use for them after the holidays. There was also a limit on how many we could purchase, given the costs. But this got us thinking, with so much of our prospecting efforts going unanswered this time of year, what if we did something with our time that made the outreach better once they returned to work in January?

The plan was simple. We'd hire a string quartet and ask them to learn a few classic rock and pop songs. Based on our prospect's interest, we paired a song with their musical tastes.

Using only a simple webcam, we would record a personalized video introduction in the backroom of our office... then turn on the lights to reveal the quartet who'd play the song. We were able to crank out about 30 of these in an 8-hour session with the quarter and could have done more with some additional planning.

Think of how unique the follow-up could be for a campaign like this.

"Hey {Prospect Name}, did you see that video we sent you the song? What did you think?" certainly beats out, "Hey {Prospect Name}, do you have a few minutes to talk? Blah blah blah..."

Screenshot of a tweet where a LeadIQ seller posted a personalized prospecting video for a target account & got a response

When we ran this campaign, it yielded LeadIQ a 44% opportunity rate throughout Q1 the following year, generating 13 opportunities for one day of work with a total cost of $300 + our time.

To wrap it up (you see what we did there 🎁)

Even though the holidays pose as one of the most challenging times for B2B sales reps, you should still be pursuing your prospecting. It's an excellent time to put your head down, get creative, and experiment. These tips should help your prospecting go smoothly through the holidays and into Q1 of the New Year.