How to Successfully Redesign Your Website When Going Upmarket

But as you set your sights on enterprise clients, there's something important staring back at you: your website. 

The same website that helped you win over those initial SMB customers might be actively working against you when courting upmarket clients.

We've worked with dozens of SaaS companies making this exact transition, and one thing is clear: the website that got you here won't get you there. 

Enterprise buyers have different expectations, concerns, and decision-making processes. Your website needs to evolve accordingly.

In this guide, we'll walk through exactly what to focus on when redesigning your website for an upmarket audience, common pitfalls to avoid, and how to execute the project effectively. 

Let's dive in.

Messaging & Positioning: Speaking Enterprise Language

The most frequent concern we hear from companies going upmarket is how to adjust their messaging. There's a delicate balance to strike: you need to appeal to enterprise decision-makers without alienating your existing SMB customers.

What Changes When You Go Upmarket

Enterprise buyers care about different things:

• Risk mitigation becomes more important than exciting features
• Security and compliance move from footnotes to headline concerns
• ROI and business impact take precedence over cool functionality
• Scalability and integration capabilities become deal-breakers

Your current messaging likely emphasizes product features, ease of use, and quick time-to-value – all great for SMBs. 

But enterprise buyers need to know you can handle complex deployments, meet stringent security requirements, and deliver measurable business outcomes.

Action Items for Your Redesign

1. Develop enterprise-specific messaging frameworks that address the concerns of more senior, risk-averse decision-makers.
2. Tone down overly casual or "hypey" language. As one founder put it: "Catchy copy with bold claims that might work in B2C would end up hurting us in an enterprise context." Aim for a more measured, credibility-focused tone.
3. Consider creating separate sections for enterprise solutions. This allows you to maintain SMB-friendly messaging in some areas while speaking directly to enterprise concerns in others.
4. Lead with outcomes, not features. Instead of "Our AI-powered dashboard shows real-time metrics," try "Reduce reporting time by 65% while improving cross-departmental visibility."
5. Align messaging with your updated ICP (Ideal Customer Profile). If you haven't revisited your ICP to reflect your upmarket ambitions, do that before touching a single line of website copy.

Trust Signals: Proving You Belong at the Enterprise Table

Enterprise buyers don't make impulsive decisions. They're methodical, risk-averse, and need abundant evidence that you're a safe bet. Your redesigned website must build trust at every turn.

Action Items for Your Redesign

1. Create a dedicated Trust Center or Security page that addresses compliance, security certifications, data handling practices, and privacy policies. Make it comprehensive – enterprise legal and security teams will comb through this.
2. Showcase detailed case studies and testimonials from your most impressive clients. One founder noted: "Our old website had zero social proof. We decided to turn this around, collecting testimonials, metrics, and case studies to back up our claims." Quantify results wherever possible.
3. Display client logos strategically (with permission, of course). If you've landed any recognizable enterprise names, feature them prominently. If not, group industry logos to create the impression of sector expertise.
4. Develop higher-level content assets like whitepapers, industry reports, and ROI calculators. Enterprise buyers expect more substantive resources than the product tutorials that might satisfy SMB users.
5. Consider your gating strategy carefully. While capturing leads is important, excessive form fields create friction. Many upmarket-focused companies now gate only their highest-value assets and leave educational content ungated to build trust first.

UX & Design for Enterprise Buyers

As you move upmarket, your design needs to evolve from "startup fresh" to "enterprise ready." This doesn't mean becoming boring – but it does mean prioritizing clarity, professionalism, and information architecture over flashy animations.

Action Items for Your Redesign

1. Simplify site structure and navigation. Enterprise buying committees often include 6-10 people with different priorities. Make it easy for each stakeholder to find what they need with intuitive information architecture and clear navigation paths.
2. Prioritize information clarity over design trends. While you want a modern look, enterprise buyers care more about finding information quickly than being wowed by parallax scrolling effects or avant-garde layouts.
3. Ensure the site feels substantial. Enterprise buyers associate depth with credibility. Your site should convey that you have comprehensive solutions, not just a single cool product. This means developing robust solutions pages, industry verticals, documentation, and resource centers.
4. Incorporate strategic social proof visually. Display customer logos, partner badges, or industry recognition prominently – these serve as instant credibility markers for enterprise visitors.
5. Pay attention to accessibility. Many enterprises have formal accessibility requirements for their vendors. Ensure your site meets WCAG standards – it's not just inclusive, it's increasingly a business requirement.
6. Maintain consistent branding throughout. Enterprise buyers associate visual consistency with professionalism and attention to detail. Ensure your color schemes, typography, button styles, and imagery follow a cohesive system across all pages. This consistency builds trust and reinforces brand recognition. Consider creating a design system or style guide that documents all visual elements and their proper usage to maintain this consistency as your site grows.

SEO & Technical Considerations: Preserving Your Digital Assets

One of the biggest risks in any website redesign is losing the SEO equity you've built. This is particularly costly when moving upmarket, as you may need to rank for new enterprise-focused keywords while maintaining existing traffic.

Action Items for Your Redesign

1. Meticulously plan URL structures and redirects. If you're changing URLs (try not to!), map out 301 redirects for every single page. As one marketer cautioned: "I didn't [hire an SEO pro] and I had a 60% drop [in traffic]. It took me about a year to get back to normal."
2. Preserve high-performing content. Identify your top-ranking pages and most-linked content. Don't remove or substantially rewrite these pages unless absolutely necessary – instead, update them to fit your new narrative.
3. Balance marketing agility with technical SEO. Many companies move to user-friendly CMS platforms like Webflow or HubSpot during upmarket redesigns for easier updates. These can be good choices, but understand any performance implications and mitigate accordingly.
4. Focus on mobile performance even if your primary audience is desktop users. Google still evaluates mobile experience for rankings, and many enterprise decision-makers review vendors on their phones during commutes or between meetings.
5. Pay attention to Core Web Vitals and speed. Enterprise users expect professionalism, and that includes a fast-loading website. Optimize images, minimize JavaScript, and use modern development practices to ensure your site performs well.

Conversion Strategy: From Self-Serve to Sales-Led

As you move upmarket, your conversion strategy needs to shift from driving immediate sign-ups to nurturing higher-value leads through a consultative sales process.

Action Items for Your Redesign

1. Reconsider your primary CTA. While "Start Free Trial" might have been your go-to button, enterprise buyers often prefer "Request a Demo" or "Contact Sales." Consider making this shift, or at least A/B testing both approaches.
2. Think carefully about pricing display. Many upmarket SaaS companies remove specific pricing for enterprise tiers, opting instead for "Contact us for enterprise pricing." As one expert notes, "If you are selling a $500k+ ACV product, there's probably no need to have transparent pricing, and plenty of downside."
3. Optimize your lead capture forms. Enterprise prospects expect to provide contact information, but don't overwhelm them. Short "Get in touch" forms generally perform better than lengthy questionnaires, which can be saved for later in the process.
4. Design for a longer sales cycle. Enterprise buying decisions take months, not minutes. Structure your site to provide resources for each stage of this extended journey – from initial research to technical validation to procurement.
5. Create content for buying committees. Different stakeholders need different information. Consider creating role-specific resources (e.g., "For CIOs," "For Security Teams") to address the varied concerns of enterprise buying groups.

Success Metrics & ROI: Measuring What Matters

How will you know if your upmarket redesign is successful? Setting clear KPIs before you start helps focus the project and demonstrates its impact afterward.

Action Items for Your Redesign

1. Set specific, measurable goals tied to business outcomes. Examples might include "increase enterprise demo requests by 30%" or "improve conversion rate from enterprise landing pages by 25%."
2. Establish baseline metrics before making changes. Capture current performance data on traffic, conversions, bounce rates, and time on site so you can measure the redesign's impact.
3. Plan to monitor both short and long-term metrics. Some impacts (like improved user engagement) might be visible immediately, while others (like SEO performance or sales pipeline influence) take time to materialize.
4. Look beyond vanity metrics. While increased traffic is nice, what really matters is whether your site is attracting the right visitors and converting them into qualified leads that your sales team can close.
5. Set up proper analytics tracking from day one of the new site. Ensure form submissions are correctly tagged, goals are properly configured, and you can track the user journey through your redesigned site.

Project Execution & Resources: Making It Happen

A website redesign is a significant undertaking, especially one that needs to appeal to enterprise clients. Here's how to approach the execution phase effectively.

Agency vs. In-House: Making the Right Choice

When moving upmarket, many companies choose to work with specialized agencies that understand enterprise B2B dynamics. This approach has several advantages:

• Expertise in enterprise UX and messaging: Agencies that focus on upmarket B2B clients bring valuable perspective on what works for this audience
• Cross-functional teams: A good agency provides strategists, UX designers, developers, and copywriters who've done this before
• Faster execution: With dedicated resources, an agency can often complete a redesign more quickly than an in-house team with competing priorities

At GRAFIT, we specialize in helping SaaS companies make this exact transition with our web design, development, and product marketing services. Having guided dozens of companies through upmarket redesigns, we've developed a streamlined process that addresses all the concerns outlined in this article.

Timeline and Budget Expectations

Be realistic about what it takes to execute an enterprise-grade website:

• Timeline: For a comprehensive B2B SaaS redesign targeting enterprise, expect at least 6 weeks from kickoff to launch when working with an agency (it might take even 3-4 months, depending on the agency). In-house projects often take longer due to competing priorities.
• Budget: While costs vary based on scope, most upmarket SaaS redesigns fall in the $20K-$50K range when working with specialized agencies. This investment typically pays for itself many times over with just a few additional enterprise deals.

Tips for a Smooth Project

• Content before design. Don't make the common mistake of designing pretty pages and then scrambling to fill them with text. Nail your messaging and site structure first, then design around that content.
• Choose the right platform. Select a CMS or web platform that balances your technical needs with marketing agility. Options like Webflow, HubSpot CMS, or headless solutions can all work well depending on your specific requirements.
• Assign a single owner. Have one person responsible for driving the project forward and making decisions when needed. Too many stakeholders with equal say can lead to analysis paralysis.
• Break the work into phases. A logical sequence is: strategy → messaging → site structure → wireframes → visual design → development → QA → launch. Each phase should have clear deliverables and approval points.
• Plan for content migration. Don't underestimate the work involved in transferring and updating content. This is often the most time-consuming part of a redesign.
• Design with scalability in mind. Your website needs to grow along with your business. Plan for future expansion by:
  
  • Creating modular page templates that can be reused for new products or solutions
  • Building a flexible navigation system that can accommodate additional sections
  • Choosing a CMS that allows easy content updates without developer involvement
  • Implementing a design system with reusable components for consistent scaling
  • Setting up information architecture that can expand to include new industries, use cases, or product lines

A scalable website architecture prevents the need for another major redesign as your enterprise business grows, saving significant time and resources down the road.

Final Words: Worth the Investment

Redesigning your website for an upmarket audience isn't just about looking more professional – it's about making your website an accurate reflection of what your company has become and where it's heading. 

While it requires significant effort, the returns can be substantial: higher-quality leads, increased credibility with enterprise prospects, and ultimately, larger deals.

The companies that succeed in this transition approach their redesigns strategically, focusing not just on aesthetics but on the specific needs and concerns of enterprise buyers. They create websites that speak the language of their target audience, build trust through comprehensive information and social proof, and guide prospects through an appropriate buying journey.

Whether you tackle this project in-house or with expert help, the principles remain the same: understand your upmarket audience deeply, address their unique concerns, and create a digital experience that positions you as a credible enterprise partner – not just another startup with a pretty website.

Ready to transform your website for upmarket success? Let's talk about how GRAFIT can help you craft a digital presence that resonates with enterprise buyers and accelerates your growth.