[2] Pitch Perfect: The Art of Making Your Message Stick

Ah, January—the “Monday” of months for salespeople. Prospecting season is here, and it feels like the gym on New Year’s Day: packed, slightly chaotic, and full of ambitious resolutions. Every salesperson knows the drill: crack open last year’s “close lost” deals, whip out the trusty “new year, new budget” emails, and brace yourself for the inevitable crickets. January is officially “Prospecting for Sales Month,” but let’s be honest—it’s also “Guess How Many Calls Go Straight to Voicemail Month.”

Let me tell you about my first January in sales. I had a list of close-lost deals and a shiny new email template. Armed with optimism and caffeine, I hit send on a message that was, in retrospect, a masterpiece of mediocrity: “Hi [First Name], circling back on our conversation last year.” Spoiler alert: The only thing that circled back was my manager asking why no one was responding. Lesson learned: if you don’t stand out, you’re just background noise.

A great pitch doesn’t just check the boxes—it struts down the runway, turning heads and leaving an impression. Whether you’re following up on close-lost deals or stepping boldly into cold outreach, the goal is the same: captivate, resonate, and inspire action. Think of it like finding the perfect pair of heels—it’s not just about looking good; it’s about walking with confidence and making a statement that’s impossible to ignore. Make it creative, make it personal, and above all, make it unforgettable.

So, as we hit the ground running in 2025, let’s ditch the treadmill of tired tactics and focus on creating pitches that captivate, resonate, and inspire action. Start by checking the boxes, but don’t stop there—spice things up with a creative twist.

The Basics (With a Twist):

Let’s be honest—classic sales strategies can feel like sensible flats: reliable but lacking flair. Deals in Heels is all about taking your outreach to new heights, adding a bit of sparkle and personality to make it stand out. Here’s how to elevate the basics with creativity and intention:

1. Close-Lost Campaigns: Rekindle the Spark

• Checkbox: Revisit deals that didn’t pan out last year.

• Spice It Up: Instead of the classic “Are you ready to reconsider?” email, position yourself as a valuable resource. Share an industry insight, a new product feature that aligns with their original objections, or a trend report. Bonus points for adding a personal touch like a Loom video explaining how your solution can help them tackle 2025 challenges.

Template:
Subject: [First Name], [Industry] is Changing in 2025—Here’s How We Can Help

Hi [First Name],

When we last spoke, you were considering [specific solution] to tackle [specific challenge]. Since then, we’ve introduced [new feature or product update] that’s helped companies like [name drop competitor/similar business] achieve [measurable results].

I also came across this report on [industry trend] and thought of you—it’s packed with insights about [specific problem your product solves]. If you’re ready to revisit the conversation, I’d love to show you how we’ve evolved to meet your needs.

Here’s a quick [Loom/short description of resource] for a sneak peek: [insert link].

Best,
[Your Name]

2. Contacts That Went Silent: Ghost-Busting 101

• Checkbox: Follow up with prospects who ghosted you.

• Spice It Up: Skip the lifeless “Just checking in” email and embrace humor. A cheeky subject line like, “Did I lose you to a better offer?” or “Haunted by our last chat?” pairs well with lighthearted content, such as a GIF about ghosting or a quick, personalized note that reignites the conversation.

Template:
Subject: Is this the end of the story, [First Name]?

Hi [First Name],

I hope this doesn’t make me look like the clingy ex of sales, but I had to reach out. Last we chatted, you were interested in [specific solution], and I’m curious—did a competitor sweep you off your feet, or are you still exploring options?

If it’s the latter, I’d love to reintroduce how [your product/service] could solve [specific challenge]. Plus, we’ve made some exciting updates since we last spoke, like [feature or update].

P.S. If you’re ready to chat, here’s a quick link to my calendar: [insert link]. If not, I promise no hard feelings—but I may send a ghost meme in return. 👻

Looking forward to hearing from you!

Best,
[Your Name]

3. Accounts That Wanted You to ‘Circle Back’ in the New Year: Listen and Lead

• Checkbox: Check in with those who said, “Let’s talk in January.”

• Spice It Up: Avoid the bland follow-up and instead reference their exact words or needs from your last conversation. Incorporate something surprising, like a LinkedIn poll about their industry, or share a case study showing how you’ve helped a similar company.

Template:
Subject: Let’s pick up where we left off, [First Name]

Hi [First Name],

I hope your new year is off to a great start! When we last spoke, you mentioned revisiting [specific goal or challenge] in January. I wanted to circle back with a quick update: we recently helped [similar company] achieve [specific results] using [your solution].

I also put together a quick LinkedIn poll about [industry trend] that might interest you: [insert link]. Would love to hear your thoughts!

If now is a good time to reconnect, let’s set up a quick chat to explore how we can tackle [specific need] together. Let me know what works for you!

Cheers,
[Your Name]

[TL/DR] Each interaction should feel less like a canned email and more like a custom-crafted pair of heels—tailored, stylish, and designed to leave an impression. By infusing personality and strategy, you can take the basics to dazzling new heights.

Beyond the Basics: Creative Prospecting Ideas

When the standard playbook starts to feel like a pair of scuffed pumps, it’s time to glam it up with strategies that turn heads. It’s all about creative, high-impact tactics that leave a lasting impression—think stilettos, not sneakers. Here are some innovative approaches to elevate your January outreach:

1. Curated Company Flyers: Make It Personal

• What It Is: Design a one-page flyer tailored to your prospect’s company, highlighting specific ways your solution aligns with their goals or challenges.

• Example: For a SaaS company focused on streamlining operations, create a flyer titled, “5 Ways [Your Solution] Can Save [Prospect’s Company Name] 100 Hours in 2025.” Include a quick breakdown of features, quotes from past conversations, or even a testimonial from a similar client.

• Why It Works: It’s visually engaging, personalized, and shows you’ve invested time in understanding their needs.

2. Unique Goody Boxes: Surprise and Delight

• What It Is: Send a thoughtfully curated gift or care package inspired by your past conversations with the prospect—this doesn’t have to break the bank. A small, meaningful gesture can have a big impact.

• Example: If they mentioned a love for coffee, include a mug with a witty quote like, “Let’s espresso our options for 2025,” paired with gourmet coffee beans and a handwritten note. If they’re into books, add a bestseller about leadership with a note saying, “Here’s a chapter for every great decision we’ll make together.”

• Why It Works: It brings a personal touch and reinforces that you’re paying attention—not just pitching.

3. Crowdsourced Content: Be the Connector

• What It Is: Run a poll or survey relevant to their industry and share the results. This positions you as someone who understands their world and can provide actionable insights.

• Example: For HR leaders, create a survey asking, “What’s your #1 priority for employee engagement in 2025?” Package the results into a clean infographic titled, “What 100 HR Leaders Are Focusing on This Year.” Share it with a note: “Your peers weighed in—where does your strategy fit in?”

• Why It Works: It’s a subtle way to engage without directly selling while establishing your credibility as an industry expert.

4. Personalized Video Messages: Add a Face to the Name

• What It Is: Record a 60-second video addressing your prospect directly, using tools like Loom or Vidyard.

• Example: Start with a warm greeting like, “Hi [First Name], I just wanted to send a quick note—well, a quick video—because I’ve been thinking about [specific challenge they mentioned].” Follow up with, “Here’s how we’ve helped companies like yours tackle this in 2025.” End with a playful note like, “And hey, if nothing else, you now know what I look like when I talk too much about solutions!”

• Why It Works: Videos are personal, engaging, and hard to ignore. They show effort and personality, which is a winning combo.

5. Podcast or Book Recommendations: Share Something Valuable

• What It Is: Share a resource that aligns with their challenges, goals, or interests.

• Example: Send a message like, “I came across this episode of [Podcast Name] about [topic] and thought of our conversation about [specific challenge]. One quote that stood out: [insert quote]. Let me know what you think!” Alternatively, if they’re into self-improvement, send a book with a note: “I think this chapter is practically written for what you’re tackling this year!”

• Why It Works: It positions you as thoughtful and resourceful, which builds trust and rapport.

Creative prospecting isn’t just about standing out—it’s about showing you’ve walked a mile in your prospect’s shoes (even if they’re not designer). Whether it’s a chic flyer, a thoughtful care package, or a video that brings a smile, these approaches blend the glamor of high heels with the practicality of making meaningful connections.

Go ahead—strut your stuff and make your outreach the talk of Q1!

Now it’s your turn—what’s the most creative prospecting tactic you’ve tried? Any big wins or hilarious fails? Share your stories in the comments; let’s crowdsource some inspiration to kick off 2025 strong! 💡👠