From CMO Perspective: The 5 Strategic Questions Your Website Should Answer (But Doesn't)

Your website cost $150,000. It looks professional.

The metrics aren't terrible. But when you ask your executive team "Is our website driving business results?" the room goes quiet.

Here's the uncomfortable truth: Most expensive websites are built around design preferences, technical capabilities, and marketing tactics, not business strategy.

As someone who spent years analyzing marketing systems for Fortune 500 companies, I've observed this pattern repeatedly. Companies invest heavily in websites that look impressive but fail at their fundamental job: supporting business objectives.

The problem isn't your agency, your budget, or your team. It's that nobody asked the right strategic questions before building.

The Strategic Alignment Gap

Research from McKinsey shows that 70% of transformations fail, with strategic misalignment being the primary cause (McKinsey, 2022). Companies implementing fragmented approaches capture only 31% of potential revenue benefits, while strategically aligned approaches capture 50% or more (BCG, 2020).

The financial impact is substantial. When your website doesn't align with business strategy, you're not just leaving money on table: you're actively working against your competitive positioning, customer journey, and revenue model.

Most CMOs inherit websites built by predecessors or agencies who never connected digital execution to business fundamentals.

The site works. It's not broken. But it's not working for the business.

Want to diagnose your website's strategic alignment? Download the free 25-Point Strategic Website Assessment to evaluate where your site fails to support business objectives: Get Free Assessment →

Question 1: Website Business Strategy - Does Your Site Support Your Actual Business Model?

This is the most critical question, and the one most commonly ignored.

Your business model determines what your website must accomplish. A transactional e-commerce model requires completely different functionality than a consultative B2B services model. Yet most websites are built using generic "best practices" that ignore these fundamental differences.

The Business Model-Website Mismatch

Transactional Models (E-commerce, SaaS self-serve):

• Need: Speed, simplicity, frictionless purchasing

• Website priority: Remove every possible barrier to transaction

• Success metric: Conversion rate, average order value

Consultative Models (B2B services, enterprise sales):

• Need: Depth, credibility, relationship building

• Website priority: Educate, demonstrate expertise, qualify leads

• Success metric: Lead quality, sales cycle length

Hybrid Models (SaaS with sales-assist, professional services with products):

• Need: Segmented paths for different buyer types

• Website priority: Route users to appropriate journey

• Success metric: Path completion rate by segment

The Strategic Misalignment Pattern

This pattern appears frequently in B2B consulting firms. Companies invest $200,000+ in "modern, fast, clean" websites and see conversion rates drop 30-40%.

The root cause? Their business model required 6-9 month sales cycles with multiple stakeholder touchpoints. Buyers needed to assess expertise depth, review case studies, understand methodology.

These new websites were optimized for speed and simplicity: appropriate for e-commerce, disastrous for consultative sales. The minimal design couldn't support the credibility signals and detailed information their buyers required.

Strategic Question to Ask: "If a qualified prospect lands on our website, does it provide everything they need to progress through OUR specific buying journey?"

Not a generic buying journey. YOUR buying journey based on YOUR business model.

Question 2: Is Your Competitive Positioning Clear to Visitors in 10 Seconds?

Boston Consulting Group research shows that digital leaders achieve earnings growth 1.8 times higher than digital laggards (BCG, 2020). A key differentiator? Clear competitive positioning that's immediately obvious.

Your competitive positioning should be evident within 10 seconds of landing on your homepage. Not buried in an "About" page. Not hidden behind corporate speak. Immediately clear.

The Three Positioning Questions

Who are you? Not your company name. Your category and what you actually do.

Who is this for? Your ideal customer profile, explicitly stated or clearly implied.

Why should they choose you instead of alternatives? Your unique value proposition that differentiates from competitors.

The Positioning Clarity Test

Most websites fail this simple test:

Show your homepage to someone unfamiliar with your company for 10 seconds. Remove it.

Ask them:

1. What does this company do?

2. Who is it for?

3. Why would someone choose them over alternatives?

If they can't answer all three clearly, your positioning isn't working.

Why This Matters Strategically

In crowded markets, lack of clear positioning creates two problems:

First: You compete on price. When visitors can't identify why you're different, they default to comparing prices. This commoditizes your offering regardless of your actual differentiation.

Second: You attract wrong-fit prospects. Unclear positioning means everyone thinks you might be for them. You waste resources on unqualified leads who were never good fits.

Strategic Question to Ask: "Can a qualified prospect land on our homepage and immediately understand how we're different from our three main competitors?"

Question 3: Does Your Customer Journey Match Your Sales Process?

Your sales team has a process. Your marketing team has a funnel. Your website has... a navigation menu that reflects your org chart rather than how customers actually buy.

Research from Forrester shows that companies with proper customer journey alignment achieve significantly higher conversion rates and customer satisfaction (Forrester, 2024). Yet most websites are organized around internal company structure, not customer behavior.

The Journey-Website Disconnect

Your sales process: Awareness → Consideration → Evaluation → Decision → Onboarding

Your website: Products | Services | About Us | Resources | Contact

See the problem? Your website structure reflects how YOUR company is organized, not how YOUR customers make decisions.

Mapping the Strategic Journey

High-performing websites align structure with actual buying behavior:

For B2B Services:

1. Problem recognition ("I need to solve X")

2. Solution exploration ("What options exist?")

3. Provider evaluation ("Who can solve this?")

4. Credibility assessment ("Can I trust them?")

5. Commercial evaluation ("What's the investment?")

6. Decision validation ("Will this work for us?")

   
   

Your website should facilitate this exact sequence.

The Multi-Stakeholder Challenge

Many B2B purchases involve multiple decision-makers with different concerns:

• Economic buyer (CFO): ROI, total cost, risk mitigation

• Technical buyer (CTO): Integration, security, scalability

• User buyer (Department head): Usability, features, support

• Coach (Internal champion): Political viability, change management

Does your website address each stakeholder's specific concerns? Or does it speak generically to "customers"?

Strategic Question to Ask: "If I traced our actual customer journey from first touch to closed deal, does our website support every critical stage and stakeholder?"

Question 4: Are You Attracting Your Ideal Customer Profile?

Traffic is vanity. Revenue is sanity. The strategic question isn't "How much traffic do we get?" but "Are we attracting the RIGHT traffic?"

Research shows that SEO leads achieve a 14.6% close rate compared to 1.7% for outbound leads (Search Engine Journal, 2018), but only when you're ranking for keywords your ideal customers actually search.

The Traffic Quality Problem

Companies frequently celebrate 200% organic traffic growth driven by impressive SEO rankings, then six months later discover revenue is flat and sales teams complain about lead quality.

The issue? SEO strategies that target volume, not buyer intent.

Common misalignments include ranking for:

• "Free project management software" when products start at $5,000/year

• "Project management for students" when selling to enterprise

• "Simple project management" when differentiation is sophisticated workflow

High traffic. Wrong audience. Zero business value.

Strategic Audience Alignment

Your ideal customer profile should drive your visibility strategy:

Define your ICP strategically:

• Company size (revenue, employees)

• Industry vertical

• Growth stage

• Technology sophistication

• Budget capacity

• Decision-making process

Then reverse-engineer visibility:

• What keywords do THEY search?

• What content do THEY consume?

• What problems are THEY trying to solve?

• What language do THEY use?

The Qualification Function

Your website should actively qualify or disqualify prospects. This seems counterintuitive, why would you want people to leave?

Because unqualified prospects waste your sales team's time, inflate your customer acquisition costs, and dilute your positioning.

Strategic websites help good-fit prospects self-identify and poor-fit prospects self-select out. This increases lead quality while reducing wasted effort.

Strategic Question to Ask: "If we analyzed our organic traffic by revenue potential, what percentage qualifies as our ideal customer profile?"

Question 5: Does Your Website Enable Your Revenue Model?

Your revenue model, how you actually make money, should dictate your website's functional priorities. Yet most websites are built with generic capabilities that don't support specific revenue requirements.

Revenue Model Types and Website Requirements

Recurring Revenue (Subscriptions, SaaS):

• Priority: Trial conversions, upgrade paths, retention signals

• Website must: Reduce friction to trial, demonstrate ongoing value, support self-service expansion

• Critical metrics: Trial signup rate, activation rate, expansion revenue

Project-Based Revenue (Consulting, Services):

• Priority: Lead qualification, expertise demonstration, project scoping

• Website must: Educate on methodology, showcase results, facilitate project discussions

• Critical metrics: Qualified lead rate, average project value, sales cycle length

Product Revenue (E-commerce, Manufacturing):

• Priority: Product discovery, purchase completion, repeat ordering

• Website must: Streamline product selection, minimize checkout friction, support reordering

• Critical metrics: Conversion rate, average order value, customer lifetime value

The Revenue Enablement Test

Ask your sales and finance teams: "What percentage of our revenue comes from website-generated leads or transactions?"

If the answer is "We don't know" or "Very little," you have a revenue model-website misalignment.

Your website should be a revenue driver, not a brochure. The specific functionality required depends entirely on how your business makes money.

Strategic Investment Alignment

Companies spend an average of $100,000-$300,000 on website development, yet often can't connect that investment to revenue impact. This happens when websites are built around aesthetics and technical capabilities rather than revenue enablement.

Strategic Question to Ask: "Can we trace a direct line from website investment to revenue impact, and if not, why not?"

The Strategic Website Audit Framework

Most website audits focus on technical issues, design problems, or SEO opportunities.

These are important, but they're tactical concerns.

Strategic website audits start with these five questions and work backward to tactical execution:

1. Business Model Alignment: Does the website support how we actually do business?

2. Competitive Positioning: Is our differentiation immediately clear?

3. Customer Journey: Does the structure match how customers buy?

4. Audience Quality: Are we attracting ideal customer profile prospects?

5. Revenue Enablement: Does the website drive our revenue model?

Only after answering these strategic questions should you worry about page speed, mobile optimization, or keyword rankings.

What CMOs Should Do Next

If you can't confidently answer all five questions, you have a strategic alignment problem that tactical improvements won't fix.

Immediate Actions:

Conduct a Strategic Audit: Evaluate your website against these five strategic questions. Document gaps between business requirements and website reality.

Align Stakeholders: Bring together your executive team, sales leadership, and marketing leadership. Ensure everyone agrees on what the website must accomplish strategically.

Prioritize Strategic Fixes: Address strategic misalignments before investing in tactical improvements. A fast, beautiful, SEO-optimized website that doesn't support your business model is still a failure.

Getting Strategic Analysis

I offer website diagnostics from a business strategy perspective, not just technical or marketing analysis:

Quick Diagnostic ($297): 25-point assessment across Strategy, Technical, Experience, Language, and Leads domains. Human analysis delivered in 1-2 business days. Book HERE.

Comprehensive Diagnostic ($997): 99-point deep analysis with strategic roadmap. Includes presentation and implementation priorities. Delivered in 5 business days. Book HERE.

These aren't only technical audits. They're strategic evaluations of whether your website actually supports your business.

Unsure of what to do next? Book a 1on1 session →

The Bottom Line

Your website should answer five strategic questions before it worries about technical performance, design trends, or marketing tactics:

1. Does it support your actual business model?

2. Is your competitive positioning immediately clear?

3. Does the customer journey match your sales process?

4. Are you attracting your ideal customer profile?

5. Does it enable your revenue model?

Most expensive websites fail at these fundamentals because they're built by people optimizing for their domain (design, development, marketing) rather than business strategy.

If your website cost six figures but can't clearly answer these five questions, you have a strategic problem that tactical fixes won't solve.

References

BCG. (2020). "Companies Can Flip the Odds of Success in Digital Transformations from 30% to 80%." Boston Consulting Group. https://www.bcg.com/publications/2020/increasing-odds-of-success-in-digital-transformation

Forrester Research. (2024). "Customer Experience Index." https://www.forrester.com/research/

McKinsey & Company. (2022). "Common pitfalls in transformations: A conversation with Jon Garcia." https://www.mckinsey.com/capabilities/transformation/our-insights/common-pitfalls-in-transformations-a-conversation-with-jon-garcia

Search Engine Journal. (2018). "Inbound vs. Outbound Marketing - What's Best?" https://www.searchenginejournal.com/inbound-vs-outbound-marketing-whats-best-2017/176422/

About the Author:

Remon Geyser brings Fortune 500 research methodology to website performance analysis. He spent years analyzing marketing systems at Kantar Millward Brown for companies like Unilever, GSK, and PepsiCo, co-founded a platform acquired by Mailchimp, and has led 250+ research and consulting projects across 48 countries. He created the STELLAR Method to diagnose website performance from a business strategy perspective, not just technical or marketing tactics. Learn more at remongeyser.com.