Welcome to a new segment of the Sales Gravy Podcast called Ask Jeb!

I believe sales professionals are the heartbeat of the economy. You’re the ones generating revenue for your organization and fueling innovations that keep businesses thriving. Without your hustle, your company doesn’t move forward—and, frankly, neither does the global economy. You’re the elite athletes of the business world.

Ask Jeb is about you and your real world challenges. It’s your agenda and you are in control.

On this Sales Gravy Podcast segment, I answer your burning questions on driving revenue, growing your pipeline, leading your teams, and staying ahead of the competition. If you want to get on the show with me and ask your question, sign up HERE

Question One: Cutting Through the Noise When Prospecting 

Bob from Tullahoma, Tennessee (whom we affectionately call “Outbound Bob” because he’s been to our Outbound Conference so many times!) asked a critical question:

“Moving into next year, what prospecting advice, piece of technology, or technique would you offer that could apply across all sales organizations and industries? What’s our ‘silver bullet’—even if it doesn’t really exist?”

No Silver Bullet, But…

I’m the first to say there’s no magic wand in sales—no easy button that instantly books appointments or closes deals. What we do have is the reality of AI-generated “crap” flooding our inboxes and social feeds. This onslaught of automated noise means salespeople must stand out more than ever.

Embrace Deep, Differentiated Sequences

My top recommendation is to lean heavily into deep, multichannel prospecting sequences. Use everything at your disposal:

• Telephone (still the fastest way to close deals)
• In-person visits (yes, face-to-face still works—and people love seeing a real human)
• Email (but make it personal and relevant)
• Direct Messaging (LinkedIn, Messenger—wherever your prospect is, be there)
• Snail Mail (because physical mailboxes are shockingly empty)
• Networking & Referrals (the original social media)

It’s not just about persistence; it’s about persistence plus differentiation. If you’re simply bombarding prospects with a bunch of generic touches, you’re just adding to the noise. Instead, craft messaging that proves you understand their world.

Messaging That Speaks to Them

Good news: the tsunami of poorly written AI outreach actually helps you stand out if your message is empathetic, clear, and focused on the prospect’s key interests. Take the time to truly step into their shoes. Know their persona, their industry, and how you solve their burning issues. Show them you’ve done your homework.

Think of It as One Extended Conversation

Each touch—voicemail, email, text, or social message—should flow logically from the last. You don’t want to leave the same voicemail three times in a row or send “Just bumping this to the top of your inbox” emails day after day. Instead, let your communication build a case for why a conversation is worthwhile. And remember: the number of touches needed to break through keeps rising (15+ touches for warm prospects, 50+ for cold). So, buckle up, play the long game, and keep your messaging sharp.

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Question Two: Targeted vs. Personalized Messaging

After Bob’s question, we tackled another big one from a Sales Gravy Coaching client who wished to remain anonymous:

How to handle short-burst prospecting and whether it helps to call businesses that share something in common, like location.

Short-Burst Sprints

I’m a fan of high-intensity prospecting sprints. Carve out 10–15 minutes, chop wood as fast as you can, then take a break. This approach keeps your energy up and your head in the game.

Narrow Your Lists

Whenever possible, focus on a list of prospects that have something in common—same industry, similar role, or even the same town. That way, your messaging can be targeted, speaking directly to a collective pain point or shared experience.

• Targeted Messaging: Useful for a homogenous group (e.g., a batch of CFOs). It may not be perfect for everyone, but it keeps you efficient.
• Personalized Messaging: Time-consuming, but worth it for your highest-value prospects (C-suite, board-level, or highly specialized buyers). Craft these messages uniquely for that individual or account.

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More Resources to Up Your Prospecting Game

Ready to dive deeper? Head over to salesgravy.com/resources to download our free guide: “The 7 Steps to Building Effective Prospecting Sequences.” You can also pick up my new book, The AI Edge, available on Amazon, Barnes & Noble, or wherever you get your books. It’s packed with actionable strategies for prospecting in the age of AI.

And if you want to sharpen your skills or ask follow-up questions, check out our coaching programs at salesgravy.com/coach. My team and I work directly with sales pros at every level, helping them craft winning sequences and hit new performance highs.

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