Here is a question that comes up more than you might think: What do you do when your company is pushing you to have bigger, more strategic conversations with C-suite executives, but every relationship you already have is two or three levels below that?

That is exactly where Jeremiah Wren found himself. He is an account manager in the architecture, engineering, and construction technology space. His company has roughly 270 accounts and about 75 percent of them do not yet have a C-suite relationship in place. The push from leadership is to get in front of CEOs, CIOs, and other senior executives to have conversations about how AI is going to reshape the industry. Jeremiah’s challenge was not the message. It was the fear that going over someone’s head would damage the relationship he had already spent time building.

If you have ever felt that same hesitation, keep reading.

Your Contact Is Not a Wall. They Are a Bridge.

The biggest mistake account managers make when they want to move up the chain is treating their current contact as an obstacle to get around. That mindset will get you in trouble every single time.

Here is the reality: the person you are dealing with at the purchasing or mid-level has their own concerns. They do not want to look bad in front of their boss. They do not want their vendor going rogue and wasting executive time, which reflects on them. And in some cases, they want to protect their own sphere of influence. That is just human nature.

So when Jeremiah said he was worried about signaling to his contact that the contact was not “qualified” for the conversation, I told him he had it backwards. The goal is not to replace that relationship. The goal is to expand it by building multiple threads through the organization simultaneously.

When you position the C-suite conversation correctly, your existing contact becomes your entry point, not your competition. You sit down with them and say something like: “We are doing an educational initiative to help our clients understand what is coming with AI in your industry. We want to make sure every level of your organization, including your leadership team, has the insights they need. Can you help me figure out where to start?” That person may say to start with them. Great, tell the story. When they are impressed, they will bring you upstairs themselves.

That is how you get multithreaded without burning anyone.

The Message Has to Match the Audience

Here is where Jeremiah needed the most work, and honestly, it is where most salespeople struggle.

When I asked him to pitch me his C-suite message on the spot, he gave me something that sounded like it was written for a project manager. Not bad. Just wrong for the room. His message talked about data structure and being “prepared for the shift.” A CEO hearing that is not going to feel urgency. They are going to feel like this is an IT conversation they can delegate.

C-suite officers are not wired to think about data architecture. They are wired to think about three things: how do I grow revenue, how do I reduce cost, and how do I stay ahead of my competitors. That is it. If your message does not connect directly to one of those three things, you have already lost them.

Understanding what actually motivates decision-makers at the executive level is one of the most important skills you can develop as an account manager or enterprise seller. You have to step into their shoes completely before you open your mouth.

Here is an example of what I walked Jeremiah through on the spot:

“The reason I want to spend time with you is because there are three trends in AI that are going to reshape your industry in the next three years, and the CEOs and CIOs I am talking to are paying very close attention because the last thing they want is to be caught flat-footed while their competitors leapfrog them. What I want to do is give you key insights that will help you look strategically at where you can lower expenses, increase sales, and become more competitive. So rather than playing catch-up, you are already ahead of the curve when these changes hit. All I need is thirty minutes.”

Notice what that does. It leads with the outcome. It creates urgency without panic. It names the exact concerns a senior executive carries and promises a specific, time-bounded solution. That is the difference between a message that gets a meeting and one that gets delegated back to your buyer.

Use AI to Sharpen the Message

One thing I told Jeremiah that surprised him: use your AI tools to workshop this. He mentioned he has been using Claude lately, and honestly, for this kind of work, it is one of the better options available.

Here is how I would do it. Take a rough draft of your executive message, feed it into your AI with full context about your industry, your company, the specific roles you are targeting, and what keeps those people up at night. Ask for a few different versions. Then read them out loud. You will immediately hear what sounds like you and what sounds like a robot. And cut everything that sounds like a robot, because C-suite executives have heard every version of that language and it will kill your credibility fast.

The goal is not to generate a script and read from it. The goal is to sharpen your thinking so that when you are actually in front of that executive, you sound like someone who belongs in the room.

Practicing and refining your prospecting messages before you make the call is one of the most overlooked disciplines in sales, and it is what separates the reps who get meetings from the ones who keep getting voicemail.

The Long Game Always Wins

Here is what I told Jeremiah at the end: the more you have these conversations, the better you get at them. And the more you are inside these organizations, talking at every level, the more they start to see you as the expert. Not the vendor. Not the account rep. The trusted authority.

That positioning is everything when it comes time to actually sell the implementation. You do not want to walk into a room and be a stranger. You want to walk into a room where everyone already trusts you because you have been showing up with valuable insights for months.

That is not a flash-in-the-pan sale. That is a relationship that compounds over time. And for an account manager holding 270 accounts with 75 percent still untapped at the C-suite level, the opportunity in front of Jeremiah is enormous if he plays it right.

Stop trying to skip steps. Build the wall layer by layer. Get multithreaded. Lead with what the executive cares about. And treat every conversation, at every level, as a chance to become the person this company cannot afford to buy from anyone else.

FAQ

Q: What if my contact actively blocks me from reaching the C-suite?

A: First, figure out why. Are they protecting their power? Are they worried you will embarrass them? In most cases, repositioning your ask as a C-suite-specific initiative that benefits the whole company will open the door. If they are unreasonably blocking you and you risk losing the account by going around them, have your manager or a senior leader in your organization make the call to the executive directly. That gives you plausible deniability while still getting you into the room.

Q: How do I know when my message is ready to take to the C-suite?

A: Test it on someone who will give you honest feedback. Run it by a colleague, a manager, or even your AI tool. If you cannot land the value in under thirty seconds and make the other person say “I want to know more,” keep working on it. The message should connect immediately to revenue, cost, or competitive position.

Q: Should I always ask my existing contact for an introduction, or can I reach out to the C-suite directly?

A: Both approaches can work depending on the relationship. If you have a solid relationship with your contact and they are not blocking you, asking for an introduction is almost always the better move. It warms the call and protects the existing relationship. If your contact is disengaged, passive, or the account is already lukewarm, going direct to the executive is a reasonable play, especially when you are sharing insights rather than selling.

Q: How long does it take to get multithreaded inside an account? A: There is no formula, but if you are consistently having conversations with new people in the organization and delivering value at each level, most account managers can build meaningful multithreading over six to twelve months in a complex account. Start with your current contact, get introduced up one level, and then another. Let the organization pull you through.

Got a sales or business challenge you want Jeb to tackle? Submit your question and you could be featured on a future episode of the Sales Gravy Podcast.