5 Sales Prospecting Tips to Unblock Your Holiday Sales Funnel

Sales Development

The period from Thanksgiving to New Year’s can be a tough time in B2B sales.

You still have goals and quotas, but instead of workplaces abuzz with activity, you encounter tapped-out annual budgets, vacationing decision-makers, and an overall atmosphere of wanting to take time off.

The holiday season is huge for retailers, representing up to 30 percent of annual sales, but sales departments in B2B tend not to expect much from this time of year. It can be a self-fulfilling prophecy — some teams find that their close rates in December plummet by 10–20%.

It doesn’t have to be this way.

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Over our years of outbound selling, we have identified five quick tips that contribute to outbound prospecting success during the end of the year. As a result, our clients’ sales funnels continue to fill consistently — even while wading through an influx of out-of-office responses.

These techniques may not work for every business, but they could work out for you. Test them out and do a little bit of tweaking. See if you can customize them for your outbound prospecting.

Here they are… 5 holiday prospecting tips you can put to work today.

Tip #1: Focus more on nurturing current leads.

The holiday season is all about spending time with those who matter most. So why not extend that philosophy to your sales funnel?

Look at your sequence touchpoints and identify those who have engaged with you in the past but have fallen by the wayside in favor of higher priorities. Set a goal to identify an X number of those prospects who you would like to put into an end-of-year re-nurturing campaign.

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If possible, set up a multi-touch sequence that involves email, phone, and LinkedIn messaging. Since they have communicated with you before, these are all warm channels for you to reach out again. Connect over something that connects the holidays and your business relationship.

How to Do It

  • Bring up something that’s both timely and relevant, like end-of-year budgeting or holiday marketing.
  • Personalize your message with the recipient’s name, and reference a prior conversation.
  • Allude to something they’ve expressed interest in previously — hopefully you took some good notes during initial conversations.
  • Settle on a next-step based on their timeline, whether that’s a sale before end-of-year or a meeting in 2020.

How NOT to Do It

  • Don’t send the same message out to everyone. Not segmenting and personalizing your messaging never gets you anywhere in outbound prospecting — during the Holidays or any other time of year.
  • Don’t include language like “we know you’re probably busy” or “when you have time.” Assume they’re in business mode just like you are.

Tip #2: Emphasize End-of-Year Budgeting

We’ve mentioned end-of-year budgeting several times, and that’s not an accident. Just like the retail shoppers who are racing around town and surfing the internet to get the most gifts for the least amount of money, B2B clients are focusing on getting the most out of their remaining budget.

Let your competitors take the end-of-year slump as an excuse to knock off early. Get focused, look at those touchpoints again, and follow up with promising leads.

When you make contact, ask about the prospect’s remaining budget. Have options for different budget levels prepared, so when they give you a number, you can show them how your product or service fits perfectly.

How to Do It

  • Do your homework. Have a couple of suggestions ready so you can make your offering work with their budget.
  • Ask multiple questions. Focus on budget, but also ask what they’re hoping to accomplish in the coming year. The more you know, the more you can tailor your pitch.
  • Talk about pricing and onboarding.
  • Can you be flexible about billing so you make the sale and they get the perfect closure for their fiscal year?
  • Guide them into a purchasing mindset. Use words like “this month” and “this year.”

How NOT to Do It

  • Don’t pitch too soon. Wait until you’ve figured out the right angle.
  • Don’t pigeonhole a solution where it doesn’t belong. If your product or service would work best for them in 2020, go with that.

Tip #3: Schedule your 2020 Appointments Now

Appointment scheduling is a time-consuming part of the sales professional’s day. At times, it can cut significantly into your client contact time, which inevitably reduces your revenue.

RELATED: Your Sales Appointment Scheduling Process is Hijacking Productivity

Don’t let that happen in January. That’s when your leads are back in the office and ready to buy what they need for the new year. Take advantage of the downtime in late November and December to schedule meetings for early 2020.

Of course, between office parties and people trying to use up their expiring vacation time, it may be harder to reach your prospects during the holiday season. Instead of letting that slow you down, consider using an online scheduling tool that lets contacts choose a mutually convenient appointment when they’re at work and in that mindset.

Alternatively, think about engaging an outbound sales agency to get your early 2020 calendar booked. At Leadium, we have an expert team that not only identifies high-potential prospects but also uses the best strategies and tools for appointment setting.

How to Do It

  • Include a touchpoint in your current sequence that focuses solely on messaging for 2020 planning, identifying this might be a slow time to connect, and schedule a meeting for after the new year.
  • If you catch them on a phone call, try to schedule right away over the phone. If you can’t, arrange another way of choosing a time.
  • If you get an out-of-office message, make a note in your CRM of the date that the person will be returning. Follow up a day or two after they get back and get the ball rolling.

How NOT to Do It

  • Don’t push a meeting back into 2020 if the prospect wants to meet with you now. They might be hoping you can help them use up the rest of their 2019 budget.
  • Don’t get stuck in your process. If a client wants to set up the meeting later or use a particular tool to do it, be willing.

Tip #4: Pick up the phone.

Not all decision-makers hop on a plane out of town in December. Many are in their offices, taking advantage of the relative quiet to plan for next year.

These are the people you want to talk to. They’re thinking about how to grow their businesses, they understand the value of thinking ahead, and they’re probably considering the rest of this year as well as next.

In sales development we can become shackled to our email sequences sometimes and forget that we are all just humans who communicate best 1:1 in verbal conversations. During Holidays, there is a general feeling of openness, and you might find that a call converts quicker to a demo or sales appointment.

How to Do It

  • Approach this cold call like any other. Ask your questions, make your pitch points, and connect where your product or service meets their needs.
  • Meet them where they are. Some will be focused on their 2019 budgets; some will be thinking primarily about next year. Offer them solutions accordingly.
  • Work with their schedules. If they want you to call back after the new year, get them to suggest a particular day and time.

How NOT to Do It

  • Don’t come across like you’re interrupting someone’s holiday. You’re not. You’re helping the prospect do what they’re already doing, which is preparing for next year.
  • Don’t leave a message if your call reaches a machine. They might be on vacation and come back to so many messages that yours falls through the cracks.

Tip #5: Launch an end-of-year specific outbound sequence.

When business slows down for the holidays, decision-makers have more time to do what they couldn’t do in busier periods. That includes reading emails, and it’s particularly applicable to longer prospecting emails.

As we discussed earlier, the holidays are when many decision-makers take deep dives into how they do things. They’re already thinking about changing certain approaches, so an email could engage a prospect at just the right time.

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How to Do It

  • Use an email automation tool (our #1 pick always being Outreach.io) to create a multi-touch end-of-year sequence that incorporates themes we have already touched on: end-of-year budget, 2020 plans, and holiday-specific messaging.
  • Create a message that would be relevant to prospects spending their 2019 budgets as well as those looking ahead to 2020.
  • Create a sense of urgency. Offer a special deal for those who take action before the new year. Perhaps a free consultation?
  • Craft subject lines and pre-headers that are personable, inviting, and communicate your unique offer.

How NOT to Do It

  • Don’t send out something too general. Make it relevant to the time of year and the new fiscal year coming up.
  • Don’t be cute. People are already getting enough snowman and Santa references from B2C advertising. Avoid images or sparkly gifs — honestly, those hurt your deliverability rates anyways.
  • Don’t overdo the urgency. Everyone is asking people to “buy now” during the holidays.

Holiday Prospecting Tips: Wrapping Up

Here are your key takeaways for prospecting in the holiday season…

➜ The holidays are notorious for being slow in the B2B space. If you don’t accept this assumption as a given, you’ll have many opportunities that others miss.

➜ Take advantage of the slower holiday pace to touch base with current leads and work on lead generation by cold-calling new prospects. Not everyone is doing business, so you’ll have a captive audience.

➜ In December, B2B marketing clients are working to use up their current year’s budgets. Give them ideas.

➜ Some prospects will be making decisions for 2019, some will be thinking about 2020. Listen to where their thoughts are and pitch accordingly.

Do you rev up prospecting at year’s end? What’s your favorite holiday prospecting tip?

Kevin is the Co-founder & CEO of Leadium, the industry leader in outbound sales and lead generation. He is focused on driving affordable growth at startups and small-to-medium sized businesses (SMBs). Prior to Leadium, Kevin held several sales strategy, product marketing, and customer success positions in leading enterprise companies and startups. He was a part of the founding team that led MOKO Social Media’s NASDAQ listing and worked with Wayup as they participated in YCombinator and obtained $15m in funding.