For sales representatives, there’s no time like the holidays. While other people start planning vacations and writing out of office emails, salespeople are in a race against the clock to close as many deals as possible before the year ends.

The flurry starts around Thanksgiving, and only ratchets up in pressure from there. With quotas to hit and fewer working days to do it in, every minute that can be used to send outreach or book a meeting is valuable. It’s not uncommon for a rep to work Christmas Eve or to the last minutes of New Year’s Eve to push every possible remaining deal through.  

After all, a successful end of year can make the difference between a rep and their team hitting their annual quota or missing it. 

Lost in the scramble, however, is what happens next. Once the clock strikes midnight, a new quarter begins and there’s a new target to hit. If you aren’t careful, you can end up with a barren pipeline and no prospects on the horizon.

3 Tips to Start the New Year Strong in Sales

  1. Start laying the groundwork for January deals in November.
  2. Territory planning can help you start the new year fast.
  3. Ease into the new year with educational outreach like webinars to connect with potential customers. 

Marcus Knight learned that lesson the hard way as a sales rep several years ago. He focused all of his efforts in December on closing every deal he had in his pipeline to reach his end-of-year targets. By all accounts, he was successful, reaching 150 percent to his quota and earning a significant holiday bonus.

But he forgot to plan for January. Without any prospects in his pipeline to start the year and a new book of business that required a longer sales cycle than he was used to, he ended up whiffing on his quota the next quarter. 

“I ended up being only 50 percent of my goal, which in sales, is not good,” said Knight, who now works as the VP of go-to-market at the e-commerce supply chain platform Shipium. “It really caused me to think about, ‘What can I do to fill my pipeline long term to make sure I hit my overall goal?’” 

While closing end-of-year deals can feel all consuming, there are steps you can take to balance your pipeline that doesn’t require stashing deals for the next quarter. It starts with careful planning and an eye toward the future. 

 

Start Laying the Groundwork for January Deals Now

If there’s one lesson Knight took away from his new-year struggles, it’s that it’s never too soon to start preparing deals for January.  

Most of the attention in November and December is spent on customers who are interested in closing before the end of the year. Those customers often have a budget to spend that doesn’t roll over to the new year, which can require extra urgency. But it’s important not to overlook the opportunities that exist in touching base with less urgent prospects before the start of a new year, Knight said.

Companies often take time at the end of the year to plan their budget for the next year. The earlier you can get on a prospect’s radar, the more likely your product will be factored into the budget plan, Knight said.

“Let’s say you didn’t have that conversation about the budget ahead of time, then you’re left out of the budget conversation for the new year,” Knight said. “Now you’re trying to figure out, ‘What can they replace? What software can they live without?’ And that’s a harder sale.”

“This should be a long-term relationship and partnership ... If [you] are upfront and honest about what [your] capabilities are and aren’t then you’re gaining and building trust for that buyer at that organization.”

Other customers operate on a fiscal calendar that ends in the spring, which means they’ll be motivated to close a deal in January or February. If you aren’t reaching out to those prospects or checking in with them in November and December to start the sales process, you may miss those opportunities.

The process starts with setting clear expectations with the buyer during the first meeting, Knight said. Ask them when they plan to implement the product and then create a clear action plan outlining when each step needs to be completed to close the deal.

Be as transparent as possible about vacation days and what you can deliver when. If you need to introduce another rep to step in for you to keep it moving forward, make sure you facilitate that transition. 

“This should be a long-term relationship and partnership,” Knight said. “If [you] are upfront and honest about what [your] capabilities are and aren’t then you’re gaining and building trust for that buyer at that organization.” 

Preparing a deal to close in January and February requires careful planning, Knight said. Vacations, sick days and the slow ramp up to normal work in January can also kill a deal’s momentum before it ever gets going.

The first meeting you schedule with the prospect in January should also advance the deal down the sales funnel. Create a shared agenda and coordinate with the prospect to make sure any stakeholders who need to be at the meeting can attend, Knight said. If the meeting is just a check in, the buyer will be more likely to either forget about it or cancel. 

As December comes to a close, you should continue checking in with the prospect, sending them valuable insights like an article relevant to their job or a white paper to stay top of mind, Knight siad.

“If I talk to a prospect in December and we schedule a meeting in January, the following week I’m sending content that is relevant to their business and the solution I’m providing,” Knight said. “As we get closer to the holiday break, I’m just confirming that the time [for the meeting] still works.” 

Of course, the burden to prepare for January shouldn’t be placed entirely on the shoulders of sales reps. Managers need to prioritize and value pipeline building at the end of the year, too, Knight said.

Knight schedules a weekly 90-minute block of time with his sales team in December to focus exclusively on January pipeline planning. During that time, reps are expected to send outreach to new prospects and follow up with existing leads. He’ll also sprinkle in incentives for the rep who has the most opportunities in their pipeline for January.  

“If we’re just spending 90 minutes per week of just carving [January opportunities] out, it makes it much more manageable for that to happen,” Knight said. 

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Territory Planning Can Help You Start the New Year Fast

Everything starts fresh in the new year. Sales leaders often use that time to announce new compensation plans, annual quotas and revenue strategies. The quota clock, however, keeps ticking.       

If you aren’t prepared for those changes, it can mean a slow start to your first quarter, which can set you behind for the rest of the year. 

The best way to set yourself up for a quick start to January is to begin territory planning in December, said Roberta Lepage, an account director for the sales development platform Rev. Territory planning is the process of reviewing your list of accounts and prioritizing them based on order of importance and when you think you can close them.

“We’ve all built a list of the top 300 accounts we’re going to go after, and you finally get them on the phone and they’re just not a good fit. Now, you and your BDR wasted so much time,” Lepage said. “It’s worth putting the time in to build that territory plan properly. It’s going to save you so much time throughout the year.”  

The first step is to review the deals you closed over the past year, Lepage said. Look at how many opportunities you created and what your conversion rate was on those opportunities. Then examine who you reached out to in those interactions and the differences between successful deals and lost ones. Doing so can help you identify areas for improvement in the new year and gives you a better sense of what your ideal customer profiles look like. 

From there, you can use that as a blueprint for targeting accounts in the next year. Identify which ones closely match your ideal customer profile and then create a list of people at those companies you can reach out to and start researching them.

“If you can start the year with a few quick wins, it helps with your attitude for the rest of the quarter and year.”

Always start with the lowest hanging fruit, Lepage said. These are customers whose deals didn’t close in time in December and existing top customers who are ripe for expansion. Then move on to customers who are showing buying signals — perhaps their fiscal year ends in the spring or they post on LinkedIn that they’re hiring marketers.

“If you can start the year with a few quick wins it helps with your attitude for the rest of the quarter and year,” Lepage said.

Of course, sometimes territories and customer priorities can shift from one year to the next. That’s why it’s important to revisit your plan at the start of the year and make any necessary changes.

Lepage experienced that first hand at a previous company. Her sales leaders gave her a new territory at the end of January rendering her previous territory plan moot. Still, she was able to rely on her knowledge of the ideal customer profile from her plan to acquaint herself with her new list of accounts. 

She then researched those new accounts, adjusted her plan priorities and earned a quick win by expanding the product within an existing customer. Taking the time to territory plan helped her stay methodical even as she faced pressure to close deals. 

“Once I got my book of business, I prioritized my accounts,” Lepage said. “One of the things I looked at was customers who spent the most money with us and were growing. ... I was able to close a substantial deal with them that made up for a slow start to my quarter.” 

The worst thing you can do at the start of the year is “spray and pray” with your outreach in the hopes of getting lucky with a deal, Lepage said. Taking the time to territory plan gives you the tools to be personalized with your outreach right away.

“If you’re stressed about creating pipeline, don’t go back to bad habits of spray and pray. That’s going to burn bridges … to get one meeting,” Lepage. “Go intentionally through your accounts and send them a personalized note.” 

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Ease Into the New Year With Educational Outreach

Knight knows how easy it is to return from the holiday break and try to hit the ground running with a big deal. But it’s important to remember that most of your buyers are just trying to get back into the swing of things. 

If you ask them for a one-on-one meeting right after vacation, they’re going to tune you out, he said. 

Instead, Knight suggests easing into those early interactions with new prospects with educational material. Record a video discussing how your product works and helps similar customers, or host a live webinar on your product and invite prospects to attend.

“I may host a webinar or something more broad … to just say, ‘If you have 30 minutes to learn how we’re helping out this market, come on in and ask any questions you want,’” Knight said. “People are going to take a week or 10 days to get back into the swing of things, so you want to meet them where they’re at.”

Hosting a webinar is also a great way to start conversations with a wider network of prospects. You can ask customers why they attended and where they’re at in the buying cycle. Even if they aren’t open to purchasing your product now, you can set follow up meetings and start slotting them into your pipeline later in the year, Knight said.   

Transitioning from the end-of-year sprint to the blank slate of January is never easy. While careful planning and strategic outreach are critical to a successful first quarter, don’t forget to be human, Knight said. 

If you take the time to connect with your buyers on a personal level and show you care, that’ll only continue to pay dividends throughout the next year.

“I’ve seen the best reps be very successful with [emails] like, ‘Hey, I remember you said your kid had a soccer game going on over the holiday break, … good luck.’ That stuff goes a long way,” Knight said. “So be human, be present. If you are true with what you’re doing, it’ll come back around, and you’ll be successful.”

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