Don’t let the 90 degree days fool you: the holidays are upon us!

Well, at least they are for retailers. As Q3 comes to a close, the most savvy retail brands are already planning for Black Friday and beyond. We’re talking peppermint mochas, Mariah Carey defrosting on Spotify, and store associates trying to figure out if “free gift wrapping” is a perk or a logistical nightmare.

In truth for retailers, this isn’t just another quarter. It’s the quarter. And the Director of Retail who oversees multiple stores, sales performance, and customer experience; it’s both the most wonderful and the most stressful time of the year.

The Director of Retail’s job is to make sure stores aren’t just riding the holiday wave but surfing it, balancing as the store traffic crests through December and beyond. That means hitting sales targets, keeping AOV high, and making sure her teams aren’t drowning in Google Sheets when they should be delighting customers with clienteling.

So how does she set her brand up for holiday success? Let’s unwrap some strategies.

The best gift you can give your stores this year? An appointment book that’s packed tighter than Santa’s to-do list.

A good Director of Retail has probably already experimented with appointment selling, but now’s the time to double down. Think of it as holiday shopping with FastPass. Customers get one-on-one time with a stylist or associate, no fighting through crowds, no waiting in line. The associate, armed with CRM data, knows what they like before they even step inside.

Here’s an idea: encourage your stores to run themed appointments such as “Holiday Party Ready,” “Gifts for Him (That He’ll Actually Use),” or “Secret Santa Gifts Under $50.” Customers love a hook, and associates love having a reason to pull curated product stories together.

The Director of Retail knows her teams are great with people but not with spreadsheets. Fortunately, spreadsheets don’t follow up with customers, people do. However, unfortunately, people are humans and human associates often forget to follow up. Maybe texts get lost, or follow-up becomes inconsistent, or some shoppers just fall through the cracks.

Here’s where a good retail CRM can swoop in like Rudolph on Christmas Eve to save the day. With unified data from sources such as Shopify, Klaviyo, and Gorgias, associates can send personalized follow-ups that actually sound human. (“Hey Sarah, remember that sequin top you loved last week? We just got it in your size. Want me to hold it for you?”)

Holiday shoppers are overwhelmed. They need nudges. They need reminders. They need elves (aka your associates) who seem to magically remember what they liked. Your retail CRM makes that possible without associates scrolling through old texts like they’re looking for their ex’s number at 2 AM.

If Black Friday is the Super Bowl, then our Director of Retail is the head coach. She can’t just throw her associates onto the sales floor and yell, “Sell harder!”

Instead, she needs to equip them with tools and training. That means:

• Clienteling basics: How to log notes in the CRM, how to send outreach that feels personal, not spammy.
• Role-playing: Give associates holiday shopping scenarios. (“A dad walks in five days before Christmas and says, ‘I need something for my wife.’ GO!”)
• Upselling practice: Encourage teams to create full “holiday looks” or “gift bundles” they can pitch instead of one-off items.

Above all, place an emphasis on customer service. What differentiates brands today is the level of personalization and “good vibes” that store associates can bring to their customers. When all else fails, establishing a great relationship with the shopper can cover over a myriad of mistakes.

Waiting for customers to wander in is so 2015. Today’s Director of Retail knows foot traffic alone won’t cut it. She needs a holiday playbook that combines:

• Targeted outreach: Using CRM segmentation to reach local shoppers with “in-store only” perks.
• Appointment selling: See point #1, because it’s that important.
• In-store events: Ugly sweater parties, influencer takeovers, or holiday sip-and-shops. Anything to turn a store visit into an Instagram moment.
• BOPIS incentives: Buy online, pick up in-store; but sweeten it with a freebie or in-store discount.
  

This way, stores aren’t waiting around like Kevin McCallister hoping shoppers show up. They’re proactively inviting them, engaging them, and giving them reasons to return.

One of every Director of Retail’s biggest holiday headaches? Leadership asking for ROI and visibility when she doesn’t have the data. Associates might be texting customers, but unless it’s logged, it’s invisible.

Here’s where a solid retail CRM is like the famed Santa Tracker for retail. Every outreach, every appointment, every conversion gets tracked and logged. This way, she can see which associates are crushing it and where opportunities are being missed.

Better yet, she can roll up all that data into reports that leadership loves. “Yes, boss, our stores increased AOV by 18% thanks to curated gift bundles suggested through Endear’s CRM.” Mic drop.

Remember when you got a gift that clearly had no thought behind it? (Looking at you, yet another Amazon Echo from Aunt Carol.) That’s how customers feel when they get yet another generic email blast.

Our Director’s brand can stand out by personalizing outreach at scale. Leveraging the customer data in your retail CRM, sales associates can pull from shopper-specific data to craft relevant, thoughtful messages.

• Bought a cocktail dress last year? Send them a digital lookbook of matching accessories (links included, of course).
• Always shops for gifts in December? Nudge them early this year, then hit them with a January blow-out sale coupon and reminder in the first week of 2026.
• Has a loyalty birthday coming up? Add a little perk. Perhaps a freebie eyeliner that the CRM already showed that they had purchased last year.
  

Holiday shoppers want to feel like their favorite associate is like Santa, someone who makes every interaction feel special… even if deep down they know he’s seeing a few billion other people.

A good Director of Retail knows her store associates are the unsung heroes of the holiday season. They’re gift-wrapping at lightning speed, dealing with last-minute shoppers, and
answering “Do you have this in a medium?” approximately 3,000 times a day.

So give them some holiday cheer, too. Create contests for most successful follow-ups, best appointment sales, or highest AOV. Your retail CRM should be able to show you this type of reporting to track it fairly. Then celebrate the wins via shoutouts in team meetings, gift cards, or even a holiday bonus.

Because happy associates = happy customers = holiday sales magic.

Let’s face it: the holiday season isn’t over when the last gift is sold. Sometimes, the relationship is just getting started. After all, there may be a slew of new shoppers coming into a brand’s store. Not only is that first experience crucial to the lifetime of their patronage, but it’s the jumping off point to start clienteling. So, January is when the Director of Retail can turn one-time holiday shoppers into repeat customers.

That means following up with new buyers, inviting them back for styling appointments, or nudging them to join the loyalty program. Endear’s engagement recipes make it easy to schedule those post-holiday touchpoints so the relationship doesn’t fizzle like a leftover bottle of champagne.

For our tired but successful Director, the holiday season isn’t just about hitting December numbers; it’s about setting her brand up for long-term success. By leaning into appointments, training, personalization, and data-backed clienteling; she can empower her associates, delight her customers, and impress the grumpy execs upstairs.

Because when she wins the holidays, so does her entire brand.