The holiday season should be a chance for busy founders to breathe a little, spend time with the people they love, and step away from the constant grind. But anyone who has ever run a business knows that December is never quiet. It is a storm disguised as a festive break. Clients disappear. Prospects get distracted. Pipelines stall. Deals go cold because someone stepped away for a long weekend. And CEOs are left juggling year end tasks, unfinished goals, and a nagging suspicion that revenue is leaking from places they do not have time to inspect.

This is exactly where a great Executive Assistant becomes a revenue generator instead of a cost center. During the holidays, a strong EA is not just keeping your calendar tidy or reminding you about travel plans. They are quietly capturing money you would have left on the table. They are reopening conversations that died in September. They are nudging customers who love you but forgot to reorder. They are chasing opportunities that were never lost, just ignored.

The truth is simple. The holidays are chaos for CEOs, but they are an incredible window for EAs to uncover hidden revenue. And if you train them right, or if you hire the right one, that EA can pay for themselves several times over between November and January.

Below are the clearest, simplest, and most overlooked places where an EA can unlock revenue during the holiday season.

Most CEOs know they should be reaching out to their best customers during the holidays. Almost none of them do it consistently. Not because they do not care, but because they are buried. Holiday campaigns, budgeting, travel, team issues, family logistics. Everything collides at once.

A strong EA fills the gap.

A. Personal check ins that spark reorders

Customers are humans first. During the holidays, a warm check in that is not a sales pitch lands better than any automated email sequence. A skilled EA can segment your top customers, reach out personally, and reference past conversations in a way that feels human and intentional.

That kind of touch often triggers something simple like:

Oh, I meant to order before the break. Thanks for reminding me.

Multiply that by fifty customers and you have a nice bump with very little effort.

B. Renewal reminders that do not feel robotic

Most renewal sequences break down in December. People miss emails. They forget dates. CFOs disappear. EAs can step in with more thoughtful follow ups that keep deals alive without annoying anyone.

They know how to read the room. They know when to send a short message. They know when to ask for the right point of contact. They know how to gently push things forward.

The CEO does not have the bandwidth for this level of nuance. The EA does.

C. Holiday appreciation that builds loyalty

A heartfelt message or a small gesture goes far. Not generic swag. Not automated cards. Something that actually acknowledges the relationship. Your EA can organize gifts, handwritten notes, digital cards that look personal, or even set up quick calls before the break.

People remember this. Especially during a season when inboxes feel cold and transactional.

Every founder has deals that drifted away for reasons that were not deal breakers. People got busy. Someone went on leave. Budgets paused. Leadership reshuffled. None of these prospects said no. They just did not move forward.

Your EA is your secret weapon for reviving these opportunities during the holidays.

A. Dusting off old leads with fresh context

Your EA can go through your CRM, identify deals that went quiet, and give you a short list of quick wins. Prospects who liked you, requested proposals, or asked for follow ups that never happened. December is the perfect time to reopen these conversations because decision makers suddenly get reflective. They think about next year. They want to fix old problems quickly. They assume everyone else is slow, so your outreach stands out.

While other businesses go silent, your EA makes you the one who stayed awake.

B. Reopening conversations for Q1 momentum

There is a magic phrase that works exceptionally well in December:

“I know things got busy, but I wanted to see if you wanted to revisit this ahead of Q1.”

People want to start the new year with solutions already lined up. Nobody wants to waste January sorting out loose ends. A good EA can send those messages for you, keep the tone warm and helpful, and send reminders at the exact right moments.

C. Booking January follow ups before the chaos hits

January gets crowded fast. Calendars fill up, people return from break overwhelmed, and decision makers vanish under piles of email. An EA who locks in meetings before Christmas protects your pipeline from the January traffic jam. They can handle the scheduling, confirm the calls, prepare notes, and create a tight follow up plan.

You are not scrambling in January. You are positioned.

Every business has seasonal opportunities. The holiday period is full of natural openings that most CEOs know exist but never get around to tackling. A strong EA sees these cracks and fills them.

A. The “year end catch up” everyone postpones

There are partners, vendors, teams, and customers who require periodic conversation. December is the perfect time to close the loop on these. Your EA can create the list, send the outreach, coordinate the calls, create summaries, and move next steps forward.

These conversations often reveal:

CEOs usually miss this. EAs catch it.

B. Anniversary and milestone reminders

Customers love being remembered. Whether it is a subscription anniversary, contract milestone, first-purchase anniversary, or partnership date, your EA can surface these moments and help you celebrate them. This builds customer loyalty and creates a sense of long term partnership, which directly affects retention.

C. Lapsed customers who just need one thoughtful nudge

Many customers do not stop buying because they are unhappy. They stop because they got busy or forgot. A gentle end of year message from your EA can reignite a relationship.

Something like:

“I was reviewing our records and realized we have not connected in a while. If you are planning initiatives for the new year, I would be happy to help you get started.”

That single nudge can turn a cold contact into a warm lead again.

One of the biggest hidden revenue wins from an EA during the holidays has nothing to do with outreach. It is about protecting the CEO’s time and mental bandwidth. A founder who is scattered, overcommitted, buried in logistics, and juggling year end tasks cannot sell. They cannot follow up. They cannot think clearly enough to close deals sitting right in front of them.

An EA steps in and absorbs the chaos.

A. Filtering the noise

Holiday season creates a flood of low value distractions. Invitations, emails, travel plans, administrative clutter, sales pitches, holiday requests, scheduling conflicts. A great EA filters all of this before it ever hits the CEO’s brain.

The CEO gets a clear screen. That clarity often leads directly to revenue.

B. Preparing call briefs and follow up packets

If you want to convert opportunities fast, you need to be sharp going into every call. An EA who organizes briefs, updates notes, preps materials, and manages next steps gives the CEO the mental edge needed to close late year deals.

C. Keeping the CEO consistent

Consistency is where revenue dies. Follow ups get missed. Promises get forgotten. Pipeline gets stale. An EA who tracks every touchpoint and pushes the CEO to follow through is basically printing money. The CEO becomes reliable. The deals move.

Here is the long term win. When a great EA handles these holiday tasks, they do not just get results for December. They create repeatable systems you can use every year.

A. A retention calendar that runs itself

Your EA can build a year round touchpoint plan that ensures your best customers never slip through the cracks again.

B. A revived pipeline that stays alive next year

Those old leads do not need to become cold again. Your EA can keep them moving, checking in quarterly, updating statuses, and ensuring nothing gets lost.

C. Holiday processes that improve every season

Once your EA handles one holiday cycle, they document everything. Next year becomes easier. More refined. More strategic. And more profitable.

There is something about the holiday season that makes all of this more effective than any other time of year.

People are sentimental. Personal touches hit harder.

Budgets need to be used. Departments need to spend leftover funds or lose them.

Leaders feel reflective. They think about what went wrong, what they want to fix, and who can help them.

Your competitors slow down. Your consistency becomes a competitive advantage.

People have more room for quick decisions. Half of the world is on break, which means people answer messages faster and with less friction.

A great EA knows how to leverage all of this.

Once a CEO experiences an EA who drives revenue, they never go back. Because they suddenly see all the invisible money that was slipping away. It changes the relationship. The EA stops being an assistant and becomes a force multiplier.

They help you show up as the CEO you want to be, not the one drowning in details.

They help you move into the new year with momentum instead of chaos.

They help you turn the holiday slowdown into a competitive advantage.

And they do it without needing you to lift a finger.

Most founders underestimate how much revenue an EA can unlock during the holiday season. Not because they doubt their assistant’s ability, but because they simply do not see the opportunities they are leaving untouched. A great EA sees everything. They find every abandoned opportunity, every neglected touchpoint, every lapsed relationship, every upcoming renewal, every potential upsell, and every place where a CEO’s inattention kills momentum.

The holidays are not a slowdown for a strong EA. They are an opening. A chance to clean up the mess, revive the pipeline, and set the business up for a strong start to the year.

If you do not have an EA who can do this for you, you are losing money you do not even realize is missing.

LoftyHire specializes in placing world class Executive Assistants who do more than manage calendars. They help CEOs generate revenue, protect their focus, and operate at their highest level. If you want an EA who can turn the holiday season into a growth engine, LoftyHire can match you with someone who will elevate your entire business.

If you are ready to stop leaving money on the table, start here with LoftyHire.