You can be on Entrepreneur’s cover!

How to Keep Your Customer Success Teams Organized and Prepared Throughout the Holiday Season The holiday season can be stressful for your customer success team. Here are a few tips to get them prepared for the frenzy.

By Hila Levy-Loya

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

The holiday season is here, and while that might mean family gatherings and hot chocolate for some, for those of us in customer success, it can mean high-intensity and understaffed teams. The last two months of the year tend to be frenzied. Leading up to holiday vacations, clients are rushing to wrap up projects before they're out of the office, organizations want to utilize the remaining budget for the year, and even those who aren't taking vacations are rushing to wrap up projects because they know that so many others will be unavailable.

This can create a lot of pressure for your customer experience teams that these employees turn to during this season — not only because your teams will have to deftly help clients under stress, but because your teams might also be trying to prep for their own holiday vacations or working with a smaller headcount than usual if holidays have already begun. This means both clients and employees can end up unhappy.

But it's not too late to be proactive and ensure that your customer success team has a great holiday season. Here are some best practices to help you succeed:

Related: 6 Ways to Keep Employees Engaged During the Holiday Season

Before the season begins

Start early: While talking about the holidays in September might feel silly, at my company, we start talking about them long before they arrive. This is part of our strategy to go into the season with our eyes wide open at every level of the organization. We learned this the hard way two years ago when we underprepared, and our customer success team ended up with a large backlog and frustrated customers.

When we bring it up early, it gives us time to think through the challenges of the previous year, brainstorm solutions and then actually build the systems needed to implement them. Employees and managers get the chance to share what went right and what didn't so they can prep on both team and individual levels.

Talking openly about anticipated staffing needs also gives team members the opportunity to share their vacation plans early. This then helps us anticipate our workforce size more accurately and plan accordingly.

Use data to plan: Two years ago, we didn't have solid data from this time period, making it challenging to be prepared both in the moment and the following year. This led to poor staffing, which resulted in poor customer experience. Since then, we have put a lot of effort into creating data analytics and gathering and utilizing data from previous years to understand peak and down times, which in turn helps us optimize staffing.

Related: Prepare Now So Your Team Can Enjoy the Holidays and Still Be Productive

During the season

Within the organization: Once the holidays start, no matter how much you've prepped plans and people, the rush can still be overwhelming. We focus on staying in tune with our employees' sentiments and morale to make sure that we can step in if someone needs a boost or a break.

On top of that, we try to be proactive in not only fairly compensating people who work special hours, but also in giving everyone recognition for their hard work. It's true that this is always a priority for us — but especially during the holiday season, it goes an extra-long way.

To ensure the support team has the resources they need, we have on-call contacts in other key teams so that even when people are out of the office, there's always someone to turn to, whether it's IT issues, sales questions or development emergencies. This helps things run smoothly when the support team is dependent on other departments in the organization.

Outside the organization: During the holidays, we're open with clients about the fact that responses might be slower than usual between specific dates. Typically, we display banners on our site with this notification. Letting clients and users know what to expect over the course of a few weeks helps them plan their own work and minimizes frustration down the line.

Related: The Best Leadership Skills for the Holidays

After the season

Immediately after the season ends, it's time to start prepping for the next year. This means taking notes on everything that went right and everything that went wrong while it's still fresh in our minds. Employees might have had a different experience than our leadership, so we debrief with the teams to get their input on how things went and include that information in our notes, too. If there is any feedback that's immediately relevant, we work to implement it right away. Otherwise, we store our notes somewhere that will be easy to find next year.

The holidays can be a challenge, but if you and your team are prepared before, during and after the season, they can also be a tremendous opportunity to delight both customers and staff. So, use these tips to set your team up for success this year.

Hila Levy-Loya

VP of Customer Success & Experience at

Hila Levy-Loya is the VP of customer success and experience at with over 20 years of experience in tech. She oversees everything customers experience, from speedy responses to their inquiries to education on the product and continually supporting teams of all sizes using

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Resumes & Interviewing

Build a Better Resume with This $35 Subscription

AI Resume Builder promises to help you apply to jobs twice as fast.

Side Hustle

He Took His Side Hustle Full-Time After Being Laid Off From Meta in 2023 — Now He Earns About $200,000 a Year: 'Sweet, Sweet Irony'

When Scott Goodfriend moved from Los Angeles to New York City, he became "obsessed" with the city's culinary offerings — and saw a business opportunity.


I Got Over 225,000 Views in Just 3 Months With Short-Form Video — Here's Why It's the New Era of Marketing

Thanks to our new short-form video content strategy, we've amassed over 225,000 video views in just three months. Learn how to increase brand awareness through short-form video content.

Business News

Samsung Makes 6 Day Workweeks Mandatory for Executives as the Company Enters 'Emergency Mode'

Samsung said its performance "fell short of expectations" last year. Now executives are required to work weekends.


6 Habits That Help Successful People Maximize Their Time

There aren't enough hours in the day, but these tips will make them feel slightly more productive.


You Won't Have a Strong Leadership Presence Until You Master These 5 Attributes

If you are a poor leader internally, you will be a poor leader externally.