How to Build an Enterprise Sales Strategy for Startups (Ask Jeb)

Here's a problem that'll tie you in knots: You've got a killer software solution that saves companies massive amounts of money on employee benefits. You know exactly who needs it: Fortune 1000 companies with self-insured health plans. But you can't get a single meeting with the people who matter. That's the situation Peter Kleinman from Provo, Utah, finds himself in. As the sales and marketing guy for his dad's startup, he's tasked with landing enterprise clients while juggling full-time classes at BYU. He has LinkedIn, Sales Navigator, and a burning desire to make it work. He also has virtually no chance of success using his current approach. If you're nodding your head right now, keep reading. Because Peter's problem is your problem if you're trying to sell into enterprise accounts without the business acumen, social proof, or strategy to break through. The 100-Foot Wall Problem Here's the biggest issue: Fortune 1000 CHROs and C-suite executives have built a wall around themselves that's about 100 feet high. Their entire job is keeping people like you from wasting their time. And if you're young, inexperienced, or new to enterprise sales? That wall might as well be 1,000 feet high. Peter is doing everything the sales books tell you to do. He's going straight to the top. He's messaging decision makers on LinkedIn. He's targeting the right titles. He's also getting absolutely nowhere. Here's why: It has nothing to do with age and everything to do with business acumen. You can't speak the language of enterprise buyers if you've never lived in their world. You don't understand their buying process, their risk aversion, or the organizational politics that determine whether your deal lives or dies. Most critically, you're trying to sell something they don't even know they need. And you have zero social proof to back up your claims. That's not a recipe for success. That's a recipe for frustration, burnout, and a pipeline full of nothing. The Bottom-Up, Top-Down Strategy If you can't get to the top, start at the bottom. I'm not talking about giving up on enterprise accounts. I'm talking about running a multi-threading strategy that builds your business acumen while creating pathways into those massive organizations. Here's how it works: Find the amplifiers. These are the people in the trenches who actually deal with the problem your solution solves every single day. They're not directors or VPs. They're managers, analysts, and coordinators who feel the pain but lack the authority to fix it. These people are 100 times easier to talk to than C-suite executives. They'll take your call. They'll teach you. They'll tell you exactly what's broken in their organization and how decisions actually get made. Compress your experience. When you talk to these amplifiers, you're not selling. You're learning. You're asking questions like, "Help me understand how you make these decisions," and "What problems are you running into?" Every conversation compresses years of experience into hours. You learn the language. You understand the pain points. You gather insights that become ammunition for conversations with decision-makers. Surface the insights upward. Now when you finally get in front of that CHRO or VP of Benefits, you're not some kid with a PowerPoint. You're someone who understands their organization better than they do. You can tell them stories about what their own people are experiencing and how you can close the gap. That's how you get meetings. That's how you build credibility. That's how you win deals when you have no business acumen and no social proof. The Insurance Broker Shortcut Here's another path Peter needs to explore: Insurance brokers. If you can't talk to the self-insured companies directly, talk to the people who advise them. Insurance brokers work with these organizations every day. They understand the buying process. They know the pain points. They're infinitely more accessible than Fortune 1000 executives. Better yet, they can become your distribution channel. If your software helps them serve their clients better, they'll sell it for you. This is classic fanatical prospecting. When your ideal customer is hard to reach, find the people who already have relationships with them. Build those relationships first. Let them open doors you can't open on your own. Stop Playing in LinkedIn's Sandbox Peter spends a lot of time on LinkedIn. Posting to the company page. Messaging prospects. Running outreach campaigns. Here's the truth: C-suite executives aren't hanging out on LinkedIn waiting for your cold outreach. They're not there. And the few who are there ignore 99% of the messages they receive. LinkedIn is great for research and building your personal brand. But if that's your entire go-to-market strategy, you're dead in the water. You need real tools. A proper CRM like HubSpot to manage your pipeline and run marketing campaigns. A platform like ZoomInfo to identify the right people and get their actual contact information. An integrated stack that lets you execute across email, phone, and social simultaneously. Most importantly, you need to pick up the phone. Real conversations with real people will always beat automated LinkedIn messages. Always. The Real Investment Required Peter's dad hates sales. He wants to build a great product and have customers magically appear. The company is running its entire sales operation on an Excel spreadsheet. That's not going to cut it. If you want to win enterprise deals, you need to invest in the tools, training, and processes that make it possible. You're looking at $50,000 per year minimum for the tech stack alone. Plus conferences, trade shows, and face-to-face relationship building. That sounds expensive until you land your first six-figure deal. Then it looks like the smartest investment you ever made. Your Action Plan If you're in Peter's shoes, here's what you do right now: Stop going straight to the top. Identify the amplifiers at the bottom of your target organizations and start having conversations with them. Learn the language. Gather insights. Build your business acumen fast. Find adjacent markets. If decision-makers are too hard to reach, find the brokers, consultants, or advisors who already have relationships with them. Invest in real tools. Get off the Excel spreadsheet. Build a proper sales tech stack with a CRM, contact database, and marketing automation. Use AI to accelerate everything. Get face-to-face. Attend conferences. Work trade shows. Build relationships in person where trust forms faster than it ever will over LinkedIn. Enterprise sales doesn't require working harder. It requires working smarter with the right strategy, the right tools, and the relentless discipline to execute even when the path forward isn't clear. That's how you break through the wall. That's how you win deals you have no business winning. And that's how you turn yourself from a struggling startup intern into an enterprise sales machine. Ready to master LinkedIn and build a prospecting system that actually works? Grab a copy of The LinkedIn Edge for the complete handbook on leveraging LinkedIn, AI, and modern sales tools to win more deals.