The Best and Worst Times for Inside Sales Reps to Take Vacations

In today’s competitive environment, hitting quota often demands working long hours. The best sales reps work hard because they have a competitive drive that compels them to win. But that doesn’t mean that you don’t deserve to take some time off to relax on a tropical beach, explore the Roman Colosseum or simply disconnect from the immense pressures of your sales job.

Here are some tips for when and when not to use that PTO you’ve been accruing.

When Are the Worst Times to Take Vacations?

1. During The First Six Months You’re Hired

As a general rule, unless you’re ill, don’t miss a single day of work during your first three months in a sales position. In fact, try to avoid taking vacations during your first 6 months on a job. You want to send the message that you’re dependable, dedicated and driven. Nothing can undermine this faster than going on an extended vacation too soon. 

2. Around Annual Reviews

Looking for a raise or promotion? A good annual review can go a long way to helping you advance in your career. Many companies hold annual performance reviews at the same time each year. During and leading up to your review, you should not only avoid taking PTO, but you should also be pulling longer hours than ever to crush those quotas.

3. During Peak Seasons

No matter what you’re selling, chances are that there is a certain time of the year where customers are just simply more likely to buy. If you can identify when those times are, then you should make sure you’re on the job in order to maximize the revenue that you close.

4. During Key Trade Shows/Conventions

When I was an inside sales rep, there were still in-person events I was expected to attend. While almost all of inside sales reps time is spent selling remotely, the reality is that more and more companies are taking an all-hands-on-deck approach to key conferences and trade shows. This is especially true in startup environments. For example, since Revenue.io was built especially for Salesforce customers, Salesforce’s Dreamforce convention is especially important to us. Even our remote sales reps frequently take key roles at this event.

As a general rule, most companies don’t want you to take more than 10 days of PTO at a time. Take this as a compliment since, if you’re a great sales rep, being gone for too long can have a strong negative impact on your company’s bottom line.

When Are the Best Times to Take Vacations?

1. Around the Holidays

There are probably some industries that do their best business in late December. But unless you’re selling toys or egg nog, chances are that the late holidays are a dead spot. This is especially true in B2B sales, when key decision makers are routinely out of town. Chances are your company is already giving you some holidays off. I always like using my PTO to extend those breaks. Consider taking the entire Thanksgiving week off, as I did last year, or perhaps the time between Christmas and New Years Day.

2. After Winning a Big Deal

Sales, by its very nature, is precarious. As a sales rep, more often than not, you’re only as good as the last deal you closed. If you just closed a big deal, your boss will probably be far more happy to approve a PTO request.

3. After Having a Great Quarter or Year

In sales, the times that we really need the breaks the most (when we’re in a slump or stressed about hitting goals) are actually the worst times to take off. It’s far better to take PTO when things are going well. After all, the last thing you want is to return to find a pink slip to go with that sun tan.

That being said, if you are overly stressed to the point that it’s affecting your performance, try taking a long weekend. Taking a Friday off won’t likely make or break your quarter. And the short break might be enough to let you reset your game, and crush it when you come back on Monday.