I Asked Sales Reps How They’re Making Holiday Sales More Fun. Here’s What They S...

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Gingerbread cookies, fuzzy sweaters, lots of PTO … some folks look forward to the holiday months, while others dread it. If you work in sales, you're likely skewing one of two ways: Relish the holiday hustle and reap the rewards later, or brace yourself for a two-month marathon of nonstop, full-throttle holiday sales.

Wherever you fall on the spectrum, the truth is this: The holidays bring unique challenges and opportunities for salespeople, and navigating the pressure of year-end quotas doesn't always make reps feel the most holly and jolly.

So, what is the magic trick for keeping your sales team's spirits high during this time of year? Well, I'd say that it's less of a "trick" and more of a shift to your typical approach to sales. I spoke to a few HubSpot Business Development Representatives (BDRs) to get the full scoop, and if you want to know how they're putting a personalized spin on the holiday season, read on to find out.

Table of Contents:

• Holiday Sales Tips: How to Leverage the Holidays in Your Sales Strategy
• Holiday Sales Team Tips: How to Keep Motivation Going 'Til the Last Rep Goes on PTO
• Back To You

Holiday Sales Tips: How to Leverage the Holidays in Your Sales Strategy

1. Stage some friendly (holiday) competition.

Come December, most sales leaders tend to revisit an age-old tradition that has yet to go out of style: Holiday competitions. If you're considering this (relatively easy) route, you should definitely look for ways to bring it into the contemporary moment, especially with sales teams now embracing the hybrid/remote life. I chatted with Bri Lopez, a HubSpot Corporate Business Development Representative and BDR Culture Committee Member, to explore not only how you can achieve this but what it could look like in practice:

• Host a "Merry Blitzmas." Bri shares that "every Blitzmas, Corporate and Mid-Market BDRs engage in a cold-calling competition" that determines the winner by how many times a sales rep "uses a holiday-related word with a prospect." (Yes, that means bonus points for folks who aren't afraid to say "ugly sweater" or "season's greetings" to a prospect.)
• Utilize your work-from-home (WFH) platforms. Bri recommends bringing holiday cheer to your Slack channels and other cross-departmental communications. Don't be afraid to use those holiday-related gifs, people.
• Offer an optional "Holiday Hustle Hour." This idea is my own but it's Bri-approved. Organize an optional hour for your sales team to jump on a video call together. Encourage folks to show up in their holiday sweaters and utilize fun Zoom backgrounds. Then, have them share their best holiday-themed sales pitches in real time, awarding points for creativity and successful calls.

2. Encourage your team to get festive with their prospects.

When I asked HubSpot SMB Natalie Drevets how she maintains good vibes during the holidays, she kept her answer short 'n sweet (no Sabrina Carpenter):

"My favorite part of the holiday season is keeping things light and festive with prospects," she explained. "I've found it can be easier to build rapport and find ways to break the ice on cold calls by referencing the holidays."

And if you play your cards right, you might be able to weave in some holiday-related puns or lead-ins to your sales pitch. Here are some that I suggest using:

• For my B2C reps: "Hope I'm not catching you in the middle of decking the halls! I'll keep this quick so you can get back to the holiday spirit - but first, I wanted to share something that might add a little extra joy to your business this season."
• For my SMB reps: "I know this is the season for gifts, so here's one you don't have to wrap. Imagine if [solution or product] could help you [insert benefit] before the year ends!"
• For my B2B reps: "Just wanted to bring some holiday cheer your way - and maybe help you cross one more thing off your year-end list with a solution that's practically a gift!"

3. Emphasize any and all holiday deals your company has to offer.

When the holidays hit, it's time to bring out the big incentives: Discounts and special deals.

'Tis the season when buyers are actively searching for the best offers, so providing limited-time discounts or exclusive holiday bundles can create a sense of urgency and attract new customers. And I'll say it: Offering festive, limited-time promotions not only makes your products more appealing to consumers but also encourages quicker decision-making. Consider promoting a discount on your company's product/service in one of these ways:

• "Holiday Flash Sale"
• "Buy One, Gift One"
• "New Year Starter Pack"

4. Integrate seasonal emojis and language into your sales enablement materials.

Natalie shared that "using holiday inspired language and emojis" helps align prospects with sales efforts around the holidays. Whether you're sending an email or making a call, you and your teams' holiday cheer will translate more successfully if you choose to infuse a bit of festive spirit into your customer interactions.

Here are a couple of recommendations that'll make your holiday sales strategy shine:

• Design custom holiday personas for your customers. Tailor your customer personas to reflect holiday-specific needs, challenges, and buying motivations. Consider outlining how budget constraints, year-end deadlines, or holiday promotions could impact a prospect's decision-making.
• Create holiday-themed playbooks for your reps. Develop a few playbooks that align with the holiday season. These playbooks can give your team tailored conversation starters, holiday-related analogies, and creative ways to handle common seasonal objections (like budget freezes or end-of-year hesitations).
• Create holiday-inspired video testimonials. Video testimonials featuring satisfied customers can become even more impactful with a holiday twist. Reach out to customers to share their success stories, focusing on how your product or service helped them achieve their year-end goals.

Holiday Sales Team Tips: How to Keep Motivation Going til the Last Rep Goes on PTO

1. Consider team-specific gift-giving.

During our conversation, Bri shared that "the Mid-Market and Corporate BDR teams do an annual Secret Santa swap."

And while Secret Santa can be tricky, here's how Bri and her team have made it easy (so you can, too):

• Put Together a Price-Appropriate Gift List: Set a budget that everyone is comfortable with and create a list of ideas that fall within that range. This ensures that all gifts feel fair and no one feels pressured to overspend.
• Use a Gift Exchange App: Platforms like Elfster or DrawNames allow team members to sign up, draw names digitally, and even drop hints or add gift ideas to their wish lists. This makes the process seamless and private.
• Create a Fun, Virtual Unwrapping Event: Bri noted that once folks receive their gifts, they hop on a Zoom call where everyone can "unwrap" their gifts together, turning the exchange into a heartfelt team bonding moment.
• Encourage Personalized or Practical Gifts: Suggest salespeople purchase/ask for meaningful or useful gifts, like a cozy accessory.

2. It's the holidays! Embrace being on theme.

If your team gets excited by the possibilities of the holiday season, let them.

Allow them to embrace the festive spirit and channel that energy into their work. Outside of the suggestions I listed above, check out more opportunities that you can take advantage of to make the holiday sales season feel a little bit more festive (especially if your team is primarily WFH) down below:

• Create a team playlist filled with everyone's favorite holiday songs and share it in your Slack channel or collaboration space. Listening to holiday tunes while working can help build a sense of connection and lift spirits during the busy season.
• Hold a Virtual Holiday Baking or Cocktail Class. Host a virtual team event where everyone can learn to bake a classic holiday treat or mix a festive drink. Send out ingredient lists in advance or offer a small allowance so everyone can participate.
• Send "Holiday Care Packages": Surprise team members with small holiday care packages filled with items like hot cocoa, candles, or holiday snacks. This thoughtful touch goes a long way in showing appreciation and spreading some holiday cheer.

3. Establish a culture of understanding around the holidays. It'll go a long way.

During our conversation, Natalie expressed that "team morale" is key. Bri also agreed. "Creating a culture of understanding, being empathetic towards others … I think that's the best way sales reps can help each other out during the holidays," she noted.

Natalie and Bri's reflections are no surprise; they're indicative of how crazy the holiday sales season really get. The holidays are a sincerely hectic, high-stress time for sales teams, especially with potential customers focused on their own seasonal priorities.

Encouraging small acts of support - like checking in with teammates, celebrating small wins, or covering for one another as needed - can strengthen your sales team and make the holiday season manageable and, ultimately, rewarding.

4. Acknowledge that the holidays can be a stressful time for your team, then adapt accordingly.

Bri echoed Natalie's sentiments about the holiday sales season, citing that empathy goes a long way for salespeople during this period of time. "The holidays are always a really stressful time for most people … I always encourage being kind to one another [during this time]," she mentioned. "It's important that salespeople have space to reflect and an opportunity to [check in] with their colleagues."

All quotas aside, the holidays can be rough for folks, and anything - whether it be stress, seasonal fatigue, or even personal obligations - could impact their sales performance. During this season, go the extra mile to foster an environment that allows your team members to acknowledge these challenges without judgment.

Plus, recognizing that everyone's experience during the holidays varies does go a long way; it can lead to a more empathetic and resilient sales team that feels truly valued and understood beyond just the numbers they deliver.

Back to You

The holidays often get a bad rap among sales reps, but that shouldn't be the case. This time of year provides excellent opportunities for your team to connect more personally with prospects and capitalize on the spirit of the season.

It's also a wonderful time of the year (all puns intended) for reps to thrive and set themselves up for future success, even if prospects can't meet right away due to time or company constraints. Instead, those individuals become strong follow-ups your team can tap into right at the beginning of the new year.

One way or another, you, as a sales leader, can always find effective ways to motivate your reps and help them crush it come holiday season. Though the list of actionable tips and "tricks" I've mentioned here isn't exhaustive (as the holidays could technically bring endless cheer), they still prove incredibly useful when this time of year comes around.

Topics: Sales Management

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