As more B2B companies mature and scale, the natural next step is to pursue enterprise customers. Bigger accounts. Longer contracts. Higher stakes. But there’s one surprisingly common obstacle standing in the way:
The Website
Recently, I spoke with a VP of Marketing at a fast-growing B2B company. They had ambitious goals to move upmarket. Their product had evolved to meet enterprise-grade demands. Their sales team was ready for longer, more complex deal cycles.
But there was a problem.
“Our website is holding us back from landing enterprise clients,” she told me.
And she was right.
The Disconnect Between Product and Presence
The company’s platform was robust and enterprise-ready. But its website hadn’t caught up. It was still speaking to small business buyers—visually, verbally, and strategically.
This is a pattern I see often. The product matures. The strategy shifts. But the website stays stuck in startup mode.
What does that look like?
- Outdated design
- Generic messaging
- No clear enterprise positioning
- A tone that feels too casual for the boardroom
Would you show up to an enterprise pitch meeting wearing a hoodie and flip-flops? Probably not.
You’d dress the part, speak with clarity, and project confidence. Your website is no different. It’s your digital front door.
If a senior decision-maker from a Fortune 1000 company lands on your homepage, what do they see? Do they feel like they’re in the right place—or do they quietly bounce?
A clunky design or vague messaging can instantly undermine trust, no matter how good your product is. Here’s a simple comparison:
- HubSpot has a warm, friendly tone and approachable design—perfect for SMBs.
- Salesforce presents itself with polished visuals and strategic messaging—built to resonate with enterprise stakeholders.
How to Know If Your Website Is Enterprise-Ready
If you’re thinking about (or already pursuing) an upmarket strategy, take a step back and assess your site through three critical lenses:
1. Competitive Analysis
Start by reviewing the websites of your top competitors—especially those who already serve enterprise buyers. Ask yourself:
- How does our site compare in design, messaging, and overall tone?
- Do we stand out in a positive way—or for the wrong reasons?
- What common elements signal credibility and trust in this space?
Your website must answer these questions clearly and confidently. And it must do so while maintaining a smooth, intuitive experience for different types of users—new prospects, long-time customers, technical buyers, and casual browsers alike.
This is less about aesthetics and more about strategic communication and user flow.
Let’s explore how to design a website that gracefully bridges the past and future.
2. Visual Design
Enterprise buyers associate polished visuals with operational excellence. If your site feels dated or inconsistent, they may question the quality of your product (even if it’s exceptional). Consider:
- Do our visuals resonate with senior stakeholders?
- Are we using modern, consistent design elements?
- Would a visual refresh elevate how we’re perceived?
3. Messaging and Positioning
This is where many websites fall short. They continue speaking to SMBs even when the product and pricing are clearly enterprise-grade. Evaluate your content:
- Is our value proposition tailored to enterprise pain points?
- Do we clearly articulate strategic outcomes—not just features?
- Is our differentiation obvious within the first 30 seconds?
Your website is often the first and last place a prospect interacts with your brand before making a decision. If it feels small-time, they’ll assume your company is too.
But when your website mirrors the priorities, language, and expectations of enterprise buyers, trust builds faster. You move from “vendor” to “partner.” Sales cycles get shorter. And marketing spend becomes more efficient because you’re attracting the right audience—not just more noise.