When you’re landing your first enterprise deals, the process often feels a little like trying to nail jelly to a wall. There’s no fixed playbook, but you need structure. I’ve closed hundreds of deals at Pearl Lemon, but the first ten taught me everything. They’re different. You’re learning on the fly, managing imposter syndrome, and building trust with people who have seen a thousand pitches before yours.
Here’s how I structured mine and what I wish someone had told me earlier.
1. Don’t Overbuild Your Offer. Sell the Outcome
One of the most common mistakes I see early founders make is trying to win enterprise deals by packing their proposals with too much stuff. Features, extras, long decks, and fancy presentations. It’s overkill.
At Pearl Lemon, when we closed our first big SEO client, we didn’t pitch 40-page strategy documents or shiny dashboards. We sent over a simple Google Sheet, a Loom video, and proof that we could rank pages and drive leads. That was it. And it worked.
Enterprise clients don’t care how busy you are. They care about the outcome you can deliver. Instead of promising 20 blog posts or 10 deliverables a month, explain how what you do moves the needle. Focus on revenue, reach, or reputation. Clarity builds trust. Complexity kills it. The key is building just enough to prove you’re legit. Scale from there once the deal is in.
2. Get scrappy with procurement but play by the rules
Enterprise deals come with red tape. Vendor forms. NDAs. Insurance. Compliance hoops. It’s enough to kill momentum before you start. Early on at Pearl Lemon, I got tired of scrambling. So I built plug-and-play templates for everything: proposals, contracts, and onboarding docs. That way, when a client said, “We need paperwork,” I could say, “It’ll be in your inbox in 20 minutes.” And actually mean it.
We supported VistaJet with PR and cold email outreach. During onboarding, when they requested compliance documentation such as a GDPR policy, proof of insurance, and NDAs, we had the required templates ready and provided them immediately. This enabled a smooth vendor approval process and a timely project launch.
It wasn’t about looking slick. It was about showing them we weren’t some flaky startup winging it. We could move fast and stay compliant. That’s what got us in and kept us there. If you’re trying to land enterprise clients, be the vendor who makes their lives easier. That’s how you get remembered.
3. Underpromise. Slightly overdeliver.
Your first instinct might be to promise everything to win the deal, but enterprise clients value consistency over hype. At Pearl Lemon, some of our most tangible successes came when we quietly exceeded expectations, no gloss, just substance.
Our catering arm, Pearl Lemon Catering, secured a 65k contract with Adidas by delivering on-time meals and high-quality menus under tight corporate protocols. We handled logistics and communication with professionalism and flexibility, real-world proof that underpromising and overdelivering builds credibility.
Enterprise buyers remember vendors who do more than they say, not those who overpromise and fade. Set clear, realistic expectations, then exceed them in thoughtful, dependable ways. That’s what earns trust and long-term renewal.
4. Relationship > contract. Always
Contracts are important, but they’re not what seals the deal. In enterprise sales, the real work happens in the small moments on late-night Slack chats, quick video calls, or when you take five minutes to explain something that isn’t your job.
At Pearl Lemon, one of our most memorable enterprise wins wasn’t because of a flawless pitch deck or perfect proposal. It was because I took the time to walk a VP through an SEO report she felt overwhelmed by. No jargon. No pressure. Just clarity. Three weeks later, she pushed our proposal through procurement and became our internal advocate. That deal turned into a six-figure contract.
Enterprise buyers don’t just buy your service; they buy your judgment, your reliability, and the way you make them feel in high-stakes environments. Build the relationship before you push the paperwork. That’s where real trust begins.
Your first ten enterprise deals will feel messy. They won’t all go perfectly. But that’s the point. Each one teaches you how to sell, how to listen, and how to navigate an ecosystem that isn’t built for speed. Structure them with care, stay honest when things go wrong, and focus more on becoming enterprise-ready than pretending you already are. That mindset shift is what makes deal eleven come faster.
About the Author
Deepak Shukla is the founder and CEO of Pearl Lemon, a multi-award-winning growth and SEO agency with a global team and clients spanning 15+ countries. With hundreds of enterprise deals closed across verticals like PR, lead generation, and digital marketing, Deepak has built Pearl Lemon into a remote-first, bootstrapped powerhouse. He’s passionate about scrappy execution, systems thinking, and helping early-stage founders learn how to scale with substance over flash. When he’s not building businesses, Deepak runs ultramarathons and shares his lessons on startup life through speaking and writing.
Photo by David Trinks; Unsplash
