Charly Johnson here, taking over the 30MPC noozy this week! If we haven’t met before, I’m a 30MPC Club Member, multiple-time guest, and top account executive at Salesloft.
Booking meetings in December can be really, really tricky.
Prospects are knee-deep in end-of-year planning—financial reviews, performance assessments, territory realignments, kick-off preparations—you name it.
There's a tonne going on (just ask a leader internally what they have to complete before year-end, and you’ll soon understand what I mean by "tonne going on" haha). On top of all that, many people are already off for the holidays.
So yeah, it’s tough for us poor souls trying to squeeze in some pipeline gen before logging off... but not impossible.
Here are three strategies I focus on during December period:
- Start with Low-Hanging Fruit
- Tailor Messaging for December Realities
- Prep for a Strong New Year
Let’s dive in.
1. Start with Low-Hanging Fruit
When you’re prospecting around the holidays, you want to focus on opportunities that are closer to conversion or require less effort to warm up:
- Closed Lost Opportunities: Revisit deals that fell through earlier in the year. No matter what time of the year, CL opps are the easiest way to book meetings (and typically have faster sales cycles = win win!)
- Sales Navigator Filters: Key filters to snap up some quick wins (see above):
- Exec intros / TeamLink (allows you to see the connections of other people who work at your company if they have a Sales Nav license)
- People who follow your company
- Past colleagues
- Prospects who’ve recently changed jobs
- Warm Leads: Check in on event attendees, content downloaders, and those neglected MQLs sitting in your CRM. Don’t let them gather dust.
- Intent Signals: If you have them, leverage tools like 6sense, Drift, UserGems, etc to identify accounts showing buying signals right now.
These people are far more likely to agree to a meeting around the holidays when there’s way more friction for a less interested buyer who’s knee-deep in planning (or gingerbread cookies).
2. Tailor Messaging for December Realities
You can’t pretend like the holidays don’t exist when you’re doing your outreach – it comes off as tone deaf. Instead, lean into it and have some fun with holiday messaging:
- Highlight Key Priorities: Your prospects aren’t just busy; they’re focused on specific tasks tied to their roles or industries. Use this to highlight relevant priorities they may be working on based on their function, such as financial planning, performance reviews, or territory planning. Tailor your message to show how you can help them address these needs or challenges. P.S. not sure what they’re focused on? Ask your persona internally, externally, or use tools like ChatGPT to get insight into specific projects/tasks.
- Appropriate CTAs: Acknowledge the time crunch with light, empathetic asks. For example: “Appreciate it’s a busy time, but if this is remotely interesting, happy to chat over a virtual gingerbread latte on me.”
- Stay Human: The holidays are a time for connection, so don’t shy away from warmth and a touch of humour in your outreach.
Here's an example email for inspiration using some holiday cheer:
Hi Gandalf,
Spoke with Frodo, and he mentioned the team will be implementing pods next year to align SDRs and AEs for breaking into larger enterprise accounts.
Betting with this, you’re likely focused on wrapping up end of year activities like territory plans and ensuring systems are ready to support the shift.
The common sticking point for teams in this position is tracking the effectiveness of new processes and knowing when to adjust course.
If this is on your radar, let’s swap a few messages to see if it’s worth a conversation.
Best, CJ
3. Prep for a Strong New Year
December isn’t just about short-term wins; it’s also the perfect time to set yourself up for January success.
The reality is that you're unlikely to create and close an opportunity in December, but you can absolutely prepare for the January pipeline slowdown:
- Tier Your Accounts: Segment your list to identify your top-priority prospects for Q1.
- Research Top 10 Companies: Deep dive into your highest-value targets and prep personalised outreach strategies.
- Schedule Emails: Draft and schedule emails to go out the first week of January, so you’re hitting the ground running when you return.
- Refine Messaging: Use the quieter moments to review your templates, get feedback, and sharpen your approach.
Bonus points if you use this time to chat with your prospects and gather insights for better positioning. Here's an example of how you might reach out:
Hey [name], Great to see [insert personalisation]. Honestly, I’m hoping you can help me out. I’m new to my role at Salesloft and trying to better understand the people and industries I’m working with.
Would you be open to answering a few quick questions via email or, if you’re feeling generous, a 10-min chat? I promise no pitches - just looking to learn.
No worries at all if not - great to connect either way!
**Note - DO NOT PITCH!**
Try & remove your product/service & understand their role outside of what you solve for by asking about the areas below:
- Day to day responsibilities (is there a specific area they spend a lot of time on?)
- Who they report to & who report to them
- Metrics they're measured on & metrics they report on
- Projects they focus on and why?
- Challenges they have
Write down THEIR exact language and use it in your messaging.
Final Thoughts Going Into 2025
December prospecting is tough, but it’s not impossible. By focusing on low-hanging fruit, tailoring your messaging, and prepping for the new year, you can create momentum that carries into Q1.
Use this time wisely, and who knows? You might just start 2025 not just with a bigger christmas belly but also a bigger pipeline.
Now, go grab that gingerbread latte and get to work. Happy prospecting!
