Last week I was on a call with a founder who said something that stopped me in my tracks:

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"I don't think we're corporate enough."

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This wasn't a company struggling to get traction. They're generating quality leads, they've got big-name customers, and their product is solid. But they're losing deals at the final hurdle with enterprise buyers.

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The problem? Their brand and messaging still screams "startup" when they need to whisper "enterprise partner".

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The enterprise perception gap

Here's what's happening: you've built momentum with early adopters and mid-market customers using messaging that emphasises innovation, agility, and disruption. That worked brilliantly for the first wave.

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But now you're talking to enterprise buyers, and they need something different. They need to know you understand compliance, security, integration complexity, and stakeholder management. They need to trust you won't disappear in six months.

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Your scrappy startup brand that got you here is now holding you back.

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Why this is harder than it seems

The challenge isn't just about looking more "professional" (whatever that means). It's about recognising that different people in the buying chain need completely different value propositions.

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Take one of our clients in the HR tech space. When we did discovery work, we found:

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• The Head of HR cares about employee experience and reducing admin burden
• The CFO cares about cost savings and ROI
• IT cares about security and integration
• Legal cares about compliance and data protection

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The startup was leading with "save money" messaging on their homepage. Good for the CFO, but it completely missed the person who was actually championing the product internally - the Head of HR.

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Real examples from our clients

‍The Value Prop Puzzle

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We recently spoke with an AI-powered research platform that's successfully moved from early adopters into conversations with major enterprises.

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Their challenge? The value proposition needs to be different depending on where you are in the organisation:

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• User-level researchers need to know it makes their day-to-day easier
• Research leads need to see how it improves quality and speed
• C-suite needs to understand the commercial impact

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Their website real estate can't accommodate all of this equally. So which personas do you prioritise? How do you create a clear path for each without diluting your message?

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This is the classic enterprise messaging challenge - and it's something we see across multiple sectors.

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Data Platform: From lead gen to demand gen

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Another client came to us generating leads, but struggling to convert them. The issue? They were optimising for volume (lead gen tactics) rather than quality (demand gen approach).

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Their content focused heavily on product features, when enterprise buyers needed to understand:

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• How this solved a strategic business problem
• Evidence of working with similar organisations
• Clear implementation and support processes

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Once we shifted their messaging to address these enterprise concerns, their conversion rates improved significantly - not because they got more leads, but because the leads that came in were far more qualified and "ready".

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SAAS: Research-backed credibility

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This SaaS client has amazing technical capabilities but were struggling to get past initial conversations with enterprise prospects.

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The breakthrough came from customer research. We discovered their prospects weren't questioning whether the partnership would work - they were questioning whether the company would still be around in two years.

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We shifted their messaging to emphasise:

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• Regulatory compliance credentials
• Enterprise-grade security
• Clear roadmap and company stability signals
• Case studies from recognised brands

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The messaging became less about "disruption" and more about "trusted partnership". That's what enterprise buyers needed to hear.

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The signs you need to enterprise up"

You probably need to evolve your messaging if:

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1. You're getting into later-stage conversations but not closing - Enterprise buyers are interested enough to talk, but something's holding them back from committing
2. You hear "we need to see more enterprise customers first" - This is code for "we don't trust you're ready for our complexity yet"
3. Your sales cycle has suddenly lengthened - More stakeholders mean more concerns to address in your messaging
4. You're competing against established players - And your "we're innovative!" pitch isn't landing like it used to
5. Your website gets traffic but low conversion - People are finding you but not feeling confident enough to reach out

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How to fix it (without losing what made you special)

The good news? You don't need to throw everything out and start over. Here's what actually works:

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1. Map your buying committee

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List out every persona involved in the buying decision:

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• Who uses the product day-to-day?
• Who champions it internally?
• Who holds budget approval?
• Who needs to sign off on security/legal/IT?

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For each persona, document:

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• What keeps them up at night?
• What does success look like for them personally?
• What concerns do they need addressed?

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2. Audit your current messaging against these personas

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Look at your:

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• Homepage
• Product pages
• Case studies
• Sales deck
• Email campaigns

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Ask: which persona is this speaking to? If the answer is "everyone" or "unclear", you've found your problem.

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3. Create a messaging hierarchy

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You can't say everything to everyone on your homepage. So prioritise:

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Top level (homepage): Your enterprise-level value prop that speaks to the economic buyer

‍Second level (product pages): Persona-specific benefits and use cases 

‍Third level (resources): Deep-dive content for specific concerns (security, compliance, integration)

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4. Add enterprise trust signals

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Without being cringey about it, make sure you're showcasing:

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• Recognisable customer logos (with permission)
• Security certifications and compliance standards
• Integration capabilities with enterprise tools
• Support and SLA information
• Implementation methodology

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5. Evolve your visual brand carefully

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This doesn't mean becoming boring. But it might mean:

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• More white space and cleaner layouts
• Professional photography over illustrations
• Case study format over blog posts
• Detailed documentation over casual guides

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Think "Stripe" or "Notion" - modern and clean, but clearly enterprise-ready.

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The transition doesnt happen overnight

One thing I always tell clients: this is an evolution, not a revolution.

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You don't flip a switch and suddenly become "enterprise". You gradually shift your positioning as you learn more about what enterprise buyers actually need from you.

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Start with small experiments:

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• A/B test different homepage headlines
• Create an "enterprise" landing page and see how it converts
• Update your most-viewed product page with enterprise messaging
• Refine your sales deck based on feedback from lost deals

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The companies that do this well maintain their startup energy and innovation whilst building in the credibility signals enterprise buyers need.

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Getting help with the transition

If this resonates and you're trying to figure out how to evolve your messaging for enterprise buyers, we can help.

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Our fresh eyes approach means we:

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• Interview your prospects and customers to understand what messaging resonates
• Audit your current positioning against enterprise buyer needs
• Map out your buying committee and their specific concerns
• Create a prioritised roadmap for evolving your messaging

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It doesn't require a huge team or months of work. Usually we can identify the biggest gaps and create a plan to address them in a matter of weeks.

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Hit reply if you want to chat about your specific situation.

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One last thought

That founder I mentioned at the start? After our conversation, they realised their challenge wasn't that they needed to be more "corporate" - they needed to speak to different people in different ways.

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Their product innovation was still their superpower. They just needed to package it in a way that made enterprise buyers feel confident saying yes.

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That's the real skill - maintaining what makes you special whilst building trust with bigger, more risk-averse buyers.

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P.S. If you missed our session on brand storytelling with Al Berry, you can catch up here. We talked about building authentic brand stories that work across different buyer types - definitely relevant to this topic.