For most of the year, sales reps control their own destinies. Make enough cold calls, send enough personalized emails and build enough connections on social media, and quota will be within reach.

Then, the holidays roll around.

It’s the season of good cheer and out-of-office replies. A time when meetings get postponed and contacts disappear for the remainder of the year. All the while there’s a quota to hit and fewer working days to do it in.

All is not lost, however. Starting after Thanksgiving, reps have a little more than two weeks to squeeze in as many meetings and outreach opportunities as possible.

“It’s important to check in with yourself and be realistic about where you stand and what it’s going to take to win.”

During that time, people may be checking their email less often, but they’re still picking up their phones and staying active on social media. Where some prospects take off for the end of the year, others have an expiring budget to spend and are more open to taking a meeting. Meanwhile, the holiday season comes ready-made with opportunities to personalize outreach messages.

Prospecting during the holidays isn’t easy, but there’s plenty of opportunity, said Ernest Owusu, senior BDR manager at 6sense. It just requires coming in with a plan and taking what the season gives you.

“It’s important to check in with yourself and be realistic about where you stand and what it’s going to take to win,” Owusu said. “It doesn’t mean you can’t win or do well, but it’s important to be aware of the environment and give yourself breaks instead of just burning out.”

Holiday Prospecting Guide

  • Cold calling and call blitzes can be a useful way to reach prospects faster. 
  • Target accounts that have shown interest in your product or who you’ve had previous contact with. Those prospects may be ready for deals at the end of the year.
  • Save OOO emails. They often include valuable customer information like new contacts or cell phone numbers.
  • Use the holidays for outreach inspiration. The more relatable the message is to the customer, the more likely they are to respond.
  • Use the days before Thanksgiving and Christmas to work ahead. That preparation can set you up for success this year or in the following quarter.


Unwrapping Out-of-Office Replies

For Owusu, one of the hallmarks of the holiday season is the flurry of out-of-office replies that pile up in the sales rep’s inbox.

The replies often trickle in during Thanksgiving week, and then pick up toward the end of December as people decide to take off for the rest of the year. For reps who are scrambling to hit quota, watching those messages accumulate can be discouraging.

“I remember getting excited about the fact that calling this time of year can be an effective [strategy] if you do it at the right times.”

Owusu still remembers the panic he felt during his first holiday season (and first quarter) in sales five years ago. Staring at 54 percent to quota and an inbox full of OOO replies, he began to wonder how he would even make a career in sales work.

Then his manager organized a call blitz.

“I remember getting excited about the fact that calling this time of year can be an effective [strategy] if you do it at the right times,” Owusu said. “It’s the easiest way to get your foot in the door.”

Now, as a manager of a BDR team, Owusu organizes call blitzes for his team the week prior to Thanksgiving and in early December.

Holiday call blitzes offer two advantages. First, reps can set up meetings faster if they reach someone by phone, which is crucial during the shortened months. Second, it allows them to sidestep the inbox black hole. People are more likely to listen to a voicemail than read an email when they come back from vacation, Owusu said.

In order to pull off a successful blitz, Owusu suggests identifying target accounts and planning a few personalized nuggets for each one to kick off the conversation. His team focuses on prospects who have shown an interest in 6sense or who it’s reached out to in the past. Those customers offer the highest chances at converting.

If a prospect is on vacation, however, it’s important to respect their boundaries. Although it can help to message them on the appropriate social media channel in the hopes that they’re checking their accounts, you should wait to call them until after they return from vacation.

And there is a silver lining to OOO replies: They often come with phone numbers and other employee contacts. Sorting through those emails and combing them for information can give a rep a valuable edge in future outreach.

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‘Tis the Season for Creative Outreach

Taking the time to personalize outreach is important any time of year, but it carries even more weight during the holidays.

At LeadIQ, SDR Manager Jamison Pence urges his team to use the holiday season as inspiration for their outreach. In one message, a sales rep tied the experience of returning a gift to bounce-back emails: “Although my uncle might be taking back the holiday sweater this year, at least I know LeadIQ’s verified email addresses won’t bounce back.”

“Personalization is successful anytime of year, but especially now because it’s more relatable. Everybody is going through a lot of the same stuff.”

In another, team members created a caroling video where the lyrics to “The 12 Days of Christmas” were changed to match the outreach process. Even though prospects are typically busier toward the end of the year, the personal touch and effort that goes into the messages often compel them to respond, Pence said.

“Personalization is successful any time of year, but especially now because it’s more relatable. Everybody is going through a lot of the same stuff,” Pence said. “If somebody sees you put in the effort and took the time, they’ll respect that and it’ll warrant some sort of reply.”

It can also help to send gifts. Last year, Owusu’s reps sent gift cards and notes to prospects at the start of December. In the messages, they wrote that they hoped the card could be used to help them buy a gift for a family member, and then asked if they had time to meet.

The key to any outreach strategy this time of year — whether it’s a sales carol or a gift card — is that it’s personal and is based around providing the customer value, Owusu said. Resist the temptation to play the numbers game to make up for lost time.

“It’s important to start early with what works really well as opposed to hitting play and doing a batch-and-blast,” Owusu said. “The minute you play the numbers game, the quality goes down.”

It also doesn’t hurt if it’s fun, added Pence.


Take Advantage of the Silent Nights

As important as it is for sales reps to make the most of their outreach opportunities during the holiday season, it’s also important to be conscious of the days when people are going to be less responsive.

The Wednesday before Thanksgiving and the night before Christmas Eve are two of the slowest days of the year. Most people aren’t going to be working, and those who are are likely not looking to schedule any meetings.

Those days aren’t a total wash, though. Instead of trying to pull all-nighters to schedule a last-minute meeting, Owusu recommends SDRs use that time to do research and take care of their administrative duties. That includes researching, sifting through notes to find priority accounts to reach out to or scheduling cadences.

Using that time wisely can give a rep a head start on their prospecting in December or January, allowing them to schedule more outreach messages or add more creativity. That boost can be the difference between meeting quota and missing the mark.

“I did everything I needed to do within a quarter for preparation over a three-day period. The following month, I just crushed my numbers.”

By the end of December, however, there’s not much a rep can do to change their fate. It can be easy to overwork during those final days, thinking that working late will get you to your quota like previous quarters. Instead, it just leads to burnout, Owusu said.

The best thing a rep can do at the end of the holiday season is set their sights on the next year and start preparing.

“I did everything I needed to do within a quarter for preparation over a three-day period,” Owusu said. “The following month, I just crushed my numbers.”

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