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How to keep your sales and marketing going when team members take personal time off

Taking regular breaks from work is crucial. But when it comes to sales and marketing, time off can feel risky for the company. Will your sales come to a grinding halt? What will happen to your revenue and cash flow? Who will manage campaigns if people are out of the office?

These fears trickle down to your reps. They hesitate to take time off or, when they do, to completely disconnect. Priceline’s Work-Life Balance Report revealed that only 21% of Americans used all of their PTO in 2020, with more than half of those regretting not taking all of it.

A previous edition of the report also showed that 29% of Americans are expected to be available on vacation, 38% feel the pressure to check email while away and 15% work for some portion of every vacation.

But it pays off to encourage employees to rest. “When the brain can think positively, productivity improves by 31%, sales increase by 37% and creativity and revenues can triple,” says Shawn Achor in his book, The Happiness Advantage.

Vacations are good for the company and your reps, but you need smart strategies in place to keep hitting your sales goals and stay productive as a team. Let’s dive into techniques and tools to keep your sales strong all year long.

Table of contents


How to make sure your sales keep going during vacation (and tools that help)

Here’s how to tackle the time before, during and after your rep takes their PTO, along with tools that will strengthen this process.

1. Encourage reps to progress every deal in their pipeline in the weeks before leaving

When reps leave the office for a week or two, they lose control over the sales pipeline.

What if leads return voicemails while they’re away? What about checking in with prospects who were close to buying? If a prospect emails the rep and doesn’t hear back, will it ruin the deal?

Reps don’t have control over what their leads and prospects do while they’re on vacation, but they have complete control over what they do before they leave. This is the foundation of activity-based selling, which is the focus on activities like calls, meetings, emails and follow-ups instead of outcomes outside of the rep’s control.

Motivate your reps to take action on as many deals in their pipeline as they can. For example:

  • For middle and bottom of the funnel prospects, they can mention their upcoming absence to offer additional support and ask for the sale

  • For top of the funnel leads, they can schedule meetings and follow-ups to answer questions that push leads further down the funnel

This way, all leads and prospects will get the information they need to complete the purchase or move into the next stage of their buying journey.

“We get our reps to review and prioritize three types of prospects and customers before their PTO,” explains Luke Genoyer, the Head of Demand Generation at Global Call Forwarding. “Important active leads, new customers (including free trial accounts) and existing customers with pending deals. Reps determine the next steps for each of those so they’re easy to pass on to the team.”

Get your reps to collaborate (a tactic that can also help improve productivity) so they can cover each other’s deals when one is away and communicate this during their pre-vacation check-ins with leads. This way, if leads choose to take action while their contact is away, they’ll know who to reach out to.

Reps can also add contact details of the rep covering their deals in their voicemail greeting and their out-of-office message. With this process in place, no deal will be lost (or accidentally fall through the cracks).

2. Use workflow automation to stay top of mind while reps are away

Salespeople can push leads through the pipeline even while away thanks to workflow automation.

Workflow automation is the process of putting important, but repetitive tasks on autopilot. You can automate different types of tasks, including deal creation, contract sending and manual admin.

Here are some processes you can put in place for your sales team to implement before their PTO starts:

  • Nurture leads. If a lead is qualified but needs more time and information before going forward, add them to a nurture campaign that automatically drips valuable content to them

  • Transfer deal ownership. If a prospect takes action while their original rep is out of office, automatically ping the rep that’s covering for them so the prospect doesn’t have to wait

  • Create follow-up tasks. If the rep checked in with a lead before leaving but hasn’t heard back while away, create a follow-up reminder for when they’re back

Automation will keep leads and prospects warm and notify the rest of the team to jump in while a rep is away to maintain momentum. Your sales pipeline will keep moving without hands-on activities or reps having to check emails from the beach.

3. Help reps set their schedules for when they return

Returning from vacation can be a dreadful experience. The change of pace and the backlog of emails and updates can overwhelm even the most organized sales reps.

With the two tactics outlined so far, your sales team will keep their deals moving even while away. To maximize those efforts, work with reps on their schedule after returning.

Here’s how to save time and what to focus on:

  • Leave the first day back free of external calls and meetings. Encourage your reps to have a buffer day and block time to catch up with email, check in with colleagues who looked after their pipeline and review notes and events in the CRM

  • Use the remaining days of the first week back for check-ins. Which deals need action because they progressed while the rep was away? What about leads that went silent? Get reps to focus the rest of the week on reaching out to active deals in the pipeline

  • Focus on hot prospects. The pressure to catch up with everything within a day is strong, so remind your salespeople to prioritize the hottest deals and take their time on those at the top of the funnel

Help your reps balance their sales time and avoid distractions so they can get back up to speed and keep on crushing their goals.

4. Use tools to stay on top of deals

Here are the tools you can implement to make collaboration, tracking, automation and planning easier for the entire sales team when a team member is away.

Customer Relationship Management (CRM)

A CRM is a central place to keep track of every lead that enters the pipeline and moves through the funnel. Pipedrive makes this process visual and intuitive with drag-and-drop features.

Using a CRM on a team level is essential as each deal gives you space for contact history, notes, calls and calendar events. This means that when a sales rep is on vacation, another one can pick up right where they left off with full context.

A meeting scheduling tool

Many meetings and follow-ups require multiple touchpoints just to schedule a meeting. When team members have to reassign deals to each other because of PTO, scheduling gets even more challenging.

Tools like Pipedrive’s Scheduler make it easy to share available time slots for a call or a meeting. With it, each team member can display their personal availability to the leads they are looking after while the sales rep in charge is out of office.

Email automation

Sending nurturing emails should be a one-off job: Writing an email template and segmenting it to suit many different prospects.

The right email automation tool seamlessly connects your sales and marketing workflows for personalized email campaigns. You can create your valuable content once and make it easy for reps to activate flows before they leave for vacation.

Sales documents

Make quotes, proposals and contracts easy to access and use for the entire team. For example, when a prospect is ready to buy, the sales rep covering for an absent team member should be able to create and send a contract in a few minutes, not hours.

You can use a tool like Smart Docs to streamline this process. It allows you to sync fields from your CRM, create quote tables, store proposals, share links and get notifications on every view and change, so reps can take action when the deal is hot.


How to manage your team’s PTO and sales quotas

With tactics and tools in place, here’s how to manage your sales team when it comes to allowing PTO and the way it affects hitting sales quotas.

Define best and worst times for vacations

Do you know how different seasons, like summer months or winter holidays, affect your sales? If there are natural peaks and dips to your sales volume throughout the year, you can map out the best and worst times for taking PTO.

“If you can quantify the effect of these seasons, you can plan for them by building up your pipeline when you know business is strong. This will allow you to let your sales team take a well-deserved break,” says Sara Archer, the Director of Sales and Marketing at Chartmogul.

When you document which weeks and months have low and high lead activity, you remove the pressure your reps may feel to be “always on” and motivate them to go all-in during naturally busy times.

Get reps to plan and book their time off early

Once you and your team know the seasonality of your sales, urge your reps to schedule their vacations as early as possible. There are many advantages to this, including:

  • It gives the whole team sufficient time to prepare for the absence of a team member

  • Other team members can plan their time off according to what’s already booked

  • You can build other plans, like offsite events or four-day workweek experiments, into the schedule based on accurate team availability

Planning PTO early benefits everyone. The team member that’s booking their vacation will get PTO approval easier and the rest of the team can prepare for the time they’ll cover their colleague’s deals.

Consider quota relief

Quota relief is an adjustment to a rep’s sales quota to match a lower number of working days in a given period. It’s an optional tactic you can use to relieve the pressure sales reps can feel while away.

For example, if a salesperson takes a week off, but their quota for the month remains the same, they’ll struggle to fully unplug from work because they have 25% less time to close the same amount of deals. Quota relief can provide that breathing room.

However, quota relief isn’t an all-size-fits-all solution:

  • If you implement tactics covered earlier, your sales might not dip at all during a rep’s vacation

  • If you have a long sales cycle, like 90 or 120 days, quota relief makes less sense than if the cycle is 30 days or shorter

  • If you use annual sales targets, you can shift quota to a busier time of the year and leave the yearly goal unchanged

A survey by the Bridge Group found that quota relief is more common in large organizations and those with a monthly sales cadence, and virtually non-existent in smaller organizations and those with a quarterly sales cadence.

Sales reps that don’t get any quota relief say they “never take any vacation” and “never completely unplug for more than two days in a row.”

Consider how much PTO your reps currently take and the impact it has on the team’s morale and motivation. Use what you learn to decide whether offering quota relief makes sense for your situation.


Should you ever refuse PTO requests from your sales reps?

In an ideal world, your reps will request time off and you’ll approve it. But what if things don’t go smoothly? When should you decline a PTO request? Here are scenarios to consider.

1. The sales rep didn’t give proper notice

If a sales rep wants to take a vacation soon—say, in a week or two—it leaves very little time for you and the rest of the team to prepare for their time away.

It also leaves very little time for the rep in question to move key deals forward before they leave, set up automations and plan their activities for their first week back. This opens the rep and the team to the risk of missing quota for that period.

2. The sales rep booked too much PTO at once and/or during a busy season

Once you’ve learned your peak and low sales seasons, motivate your reps to take breaks based on these seasons. Bake this into your team processes and reward your team for respecting this practice. Rewards you’d use for hitting quota, like vouchers, experiences, products, recognition in the company and even cash rewards, can work well in this case.

If a team member books PTO during the season of most sales opportunities (including trade shows and key events), or their long vacation trickles into this period, consider declining the request.

3. The request is against your PTO policy

Finally, if a request goes against a rule in your company’s PTO policy, you can decline it. A simple example is a rep requesting too many days off in a calendar year.

However, be sure to check in with this team member to learn the reason for their excessive PTO days. Are they dealing with a health challenge or a personal issue they can’t handle when working? Are they on the edge of burnout?

Chances are, your rep isn’t trying to game the PTO system, but needs support and wiggle room to deal with a problem. Make sure you do everything you can to offer that.

Work with your sales reps to find alternate solutions

These scenarios come down to having empathy and understanding for individual preferences, issues and needs of your sales reps.

Don’t just decline PTO requests. Create a safe space for your team members to communicate their needs and work with them to find alternate solutions if their original request doesn’t work.


Should you introduce a rota for PTO?

If you find that your reps’ requests for time off frequently overlap or seep into busy sales seasons, you might consider creating a PTO rota. This is a predefined schedule of available PTO periods.

Having a rota for PTO can remove friction from requesting PTO and waiting for approval. This is because your reps can choose from pre-approved vacation periods and reserve them on a first-come, first-serve basis.

If you’ve built a strong culture of productivity, teamwork and collaboration, your team members will care about getting work done in a way that benefits the team. They’ll care about other reps’ results as much as their own. This means they’ll be mindful of everyone’s schedules as they book their PTO, and you might not need a PTO rota.

But if you choose to implement a rota for PTO, be sure to approach it as an experiment and regularly ask for your team’s feedback.

Finally, make sure you work your PTO rota into your overall rota for shifts and schedules so it’s easy to access for everyone on the team.


Final thoughts

Taking time off in sales can be stressful, but now you know it doesn’t have to be. You can help your sales reps plan their sales activity in advance, get help from team members while they’re away and catch up quickly once they return.

When you default to teamwork and empathy, you can have it all: a hungry, productive sales team and team members who know how important it is to rest and recharge.

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