Prospecting During Holidays: Grinch Level Threat or Christmas Opportunity?

prospecting during holidays cloudlead

With holidays around the corner, the world typically goes slightly mad. Last minute shopping, eye popping deals, carols and Christmas trees all around – how can one not? But you know who dreads holidays? Salespeople. B2B marketers. For us, prospecting during holidays can become positively nightmare-ish!

For those working in the B2C world, this time is a gold mine for meeting sales and marketing quotas. But for the often forgotten heroes (B2B salespeople and marketers), we struggle to relate our campaigns to the holiday spirit.

We often think to ourselves – who wants to hear about an innovative and time saving software? The next question is – how do we spin it so this product, which has nothing to do with the holidays, resounds with our audience (who themselves are gearing up for the upcoming long weekend?)

Hence – Grinch Level Threat!

While these are real life struggles not to be scoffed at, I’ve put together a few tips and tricks that will allow you to not only achieve your current quota but also make a lasting impression on prospects and clients. So much so that they’ll help you achieve your sales quotas for the next year too, which means – making prospecting during holidays a real Christmas opportunity!


1- UPSELL – In December, focus on upselling activities

Let’s face it, prospecting during holidays or specifically starting a brand new campaign in December (especially without the right data – more on this later) might not yield the best results. So what should you do instead?

Run campaigns to nurture your actual clients and focus on upselling activities. While finding new clients to close the fourth and last quarter is equally important, what will provide faster results is concentrating on the clients you do have.

From ideas like sending $5 gift cards of Starbucks (who doesn’t like some holiday coffee) to your clients to simply sending an e-card with a 10% discount on your pro subscription plan, when prospecting during holidays, the field is open to you. Decide on a budget, brainstorm with your team and come up with unique ideas which will make your clients appreciate you.

Read: How To Integrate Lead Nurturing Into Your Sales Process


2- BE ORIGINAL – Give new prospects a reason to get back to you, despite all the holiday madness in their lives

Think about it. Would you want to respond to a generic, ‘hey, buy from us because we’re blah blah blah’?

Nope, I know I wouldn’t. Especially not when I’m prospecting during holidays and scrambling to ensure that my company finishes strong in the last quarter.

So what do you do?

Reach out not to sell, but to build a real connection with the prospect. While this is true for anytime of the year, it is something you really have to focus on at this time. Personalized outreach campaigns are successful for a reason – they don’t reach out to title Z at company X, but to Jack, the successful career driven guy in his early 30’s with a passion for baseball who was recently promoted.

So how do you access this information? It’s not practical to sit down and try to track down what Jack, David, Alisha, Lisa, Reynold etc have been up to, making prospecting during holidays a doubly difficult task.

Without blowing our own trumpet so to speak, this is where Cloudlead helps salespeople and marketers like us. From searching the depths of the internet to mine fresh, verified and up-to-date sales intelligence, Cloudlead helps ensure our clients have access to analytics and information which helps in personalizing cold outreach.

Imagine knowing which baseball team Jack roots for or what he wrote on Twitter about the last game. Or if you want to aim for a more professional approach to personalization, then having information regarding his recent promotion to the Head of Partnerships in November could really help kick off the conversation (or email) on a positive note. Having actionable sales intelligence on your prospect will also save you from using the dreaded “Happy Christmas“ schmuck as your subject line – really, we know it’s the holidays, say something original already!

Read: 5 Cold Email Templates For Personalizing Outreach And Generating Warm Leads


3- DON’T STOP – Contracts with competitors are usually ending at this time, tap into this opportunity

While it’s tempting to just give up on new sales at this time, remember that this is also the time when contracts with your competitors are ending. While companies scramble to ensure their clients will stay with them, this is the time to come up with a better offering.

If you can tap into your competitor’s clients, you can probably close a number of deals or even THE DEAL. There are a number of sources you can use to gauge your competitors clients (depending on your product) like LinkedIn and other such social networks, the tech stack on the prospect site, on product reviews on platforms like G2Crowd etc. Or you can ask us to compile such a list based on specific requirements like the ones mentioned above – just saying!


4- BE PROACTIVE – Set up something now instead of falling for the ‘get back to us in next quarter’ business

If you got a prospect to respond to your cold email, but the reply is something along the lines of ‘get back to us in February,’ don’t falter. Send him an invite for February right then and there. Fine, you won’t be able to log a new sale this month, but at least you’ll have something lined up for February (you’ll still have sales quotas and goals to meet then).

By sending the prospect an invitation ASAP, you’ll be tapping into a warm-ish lead come February and won’t have to reintroduce yourself from scratch. You’ll also not come across as pushy or too salesly.


These are just a few ways to ensure that you don’t crash and burn in your last quarter – AND start off with a strong first quarter!

For salespeople, holiday madness doesn’t have to be a Grinch level threat to their quotas – with hard work and determination, you can turn prospecting during holidays into a real Christmas opportunity!

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