Engaging with Sales Challenges: Listener Questions Answered

Ron wants to know how to get CEOs to actually answer his cold calls (or at least respond). He runs a recruiting firm and finds that his cold calls to top executives often go unanswered, and it’s driving him nuts. He wants to know if there’s a better way to break through all the noise—or if he just needs to buckle down and make more calls. On this Ask Jeb podcast episode I give Ron specific strategies for connecting with hard-to-reach prospects like CEOs.   Why Sales Feels Harder Than Ever Let’s face it: sales is tough, and it’s not getting any easier. With an explosion of AI-driven messages and automated outreach, our prospects—especially C-suite executives—are tuning out more than ever. We call this phenomenon the “great ignore.” If you don’t stand out from the torrent of spam, you will get lost in the shuffle. Ron’s question—“Do I just need to make more calls, or is there some next-best method?”—is a dilemma many of us face. The short answer? It’s both. You do need volume, but you also have to differentiate. If you’re just another voice in the crowd, you’ll be ignored, no matter how many dials you make.   Tactic #1: Multi-Threading (Don’t Just Call the CEO) A key point I shared with Ron is the power of multi-threading. That means calling multiple people in the organization—not just the CEO. While the CEO might be the ultimate decision-maker, other stakeholders, like the COO or HR director, might be easier to reach. These people can also give you valuable intel on hiring needs, budget constraints, or timing. Call the CEO: Leave a compelling message or send a short, punchy email. Call Other Stakeholders: Dig for inside info on immediate hiring needs or open reqs. Use That Intel: Let the CEO know, “I’ve spoken with your COO; you’re looking for a VP of Sales. I have a candidate you need to meet…” This top-down, bottom-up approach helps you gather context, build rapport, and earn the right to talk to the CEO by proving you’re not just randomly dialing.   Tactic #2: Leave Voicemails—But Make Them Count Ron admitted he’s not always sure whether to leave voicemails. Most of us have left hundreds of voicemails and gotten very few callbacks, so it’s tempting to skip them. But here’s the thing: in today’s world, voicemail transcripts often end up in a prospect’s email inbox or text messages. Keep It Short: No more than 30 seconds. Make It Compelling: Name-drop a role you know they’re hiring for or highlight your unique solution in a single sentence. Use a Teaser: “I’ve got the perfect candidate for your open VP of Sales position—let’s talk.” Even if they don’t call back immediately, they’re hearing your name and your pitch. Over time, that repetition can pay off—especially if you combine voicemails with other forms of outreach.   Tactic #3: Build Sequences That Tell a Story The real magic is in creating a multichannel sequence over 30 to 60 days. It’s not just “call once and cross your fingers.” Instead, plan multiple touches that tie together: Voicemail #1 Follow-Up Email (within 24–48 hours) LinkedIn Connection Request or DM Voicemail #2 (referencing your email) A Handwritten Note or Card (really stands out) Voicemail #3 (referencing the note) Be creative. Use each step to reinforce the last, rather than just repeating the same “Hey, it’s me again!” message. Tell a story or highlight different benefits at each step. Show them you’re genuinely interested in their business—not just cold-calling from a script.   Tactic #4: Know Your Prospect’s Buying Window Sometimes the CEO won’t respond because there’s no immediate need for your product or service. For Ron, if they’re not hiring, they won’t care about a recruiter. That’s okay—it doesn’t mean you should vanish. Keep Dripping: A low-frequency sequence keeps you on their radar. Listen for Signals: Maybe they just received funding or they’re expanding into a new market.