Why Expensive Pricing Strategy Divided A Company

And What To Do To Avoid It Happening To You.

Your leadership team has repositioned your value proposition to the market. You’ve moved from promising “operational efficiency” to “strategic competitive advantage.”

The insight is sound.

The opportunity is real (in the right situations).

But your teams aren’t aligned (they may be nodding their heads though).

The muscle memory of the company you’ve built for years is hard to change. Sales are most likely to sell the new dream. But marketing need to flip the script from convincing operational buyers to the new vision. And customer success – always the afterthought in business reliant on renewals – is working on onboarding, revising scores and thinking about new things – while dealing with customers who bought and used it to do what they’ve always done.

Fast forward and leadership is frustrated. Relationships went from senior people sold the dream to operational people speaking with customer success. The ROI for renewing is weak. Customers internal team are grumbling. Teams feel left behind. And revenue isn’t transforming.

You hired a strategy consultancy. They threw firepower at this. They interviewed leadership. They did extensive market research. Due Diligence on steroids. Their findings were clear: “Pivot and reposition to strategic leaders. They expand 2-3x more. There’s significant upside.”

The report is right. But the people part was messy.

Telling teams to change without taking them on the journey creates a divided company.

Customer Friction

When you are trying to change, you might hear a customer (end user) ask:

“I hear what you’re saying about your new AI model and strategic value. But honestly? Right now I’ve got this in Excel. I’ve built my formulas. I know how it works. I can do it in five minutes. How is your tool actually better than what I have?”

It’s an honest question and it cuts to the centre of the problem.

Assuming an organisation is just one customer.

Even if your strategy is to serve a leader – their challenge is they have different stakeholders.

People Behind A Question

Person 1: The Operator

This is the person who’s been running the status quo (e.g. Excel process) for years. They’re efficient at it. They know every twist, turn and formula. It works fine for what they do. If it goes wrong, they know how to fix it.

What they’re really asking: “Why should I break something that works?”

What they need: Integration, not replacement. They don’t need to abandon the status quo right now. They need your system to work alongside it, not force them to change their workflow.

Your risk: If you don’t serve this person, you diminish your installed base. They become at-risk renewals. They look for competitors who respect their workflow. Their feedback up to the decision makers isn’t “I don’t want to change” – it’s “This is not fit for purpose.”

Your opportunity: Make it frictionless for them to coexist with your system. They’re not your growth driver, but they’re your foundation.

Person 2: The Change Champion

This is the person who was hired (or promoted) specifically to modernise the function. They see status quo (e.g. Excel) as a symptom of the problem, not a solution. They’re trying to build something bigger.

What they’re really asking: “Will this help me prove we need to modernise and get better results?”

What they actually need: A partner in transformation. Not just a tool. A way to demonstrate that moving away from old school processes unlocks competitive advantage. Help to make the shift and make it stick.

Your risk: Your new value proposition promises them nirvana. But the way your established teams deal with change, you end up in the same old narrative you sold the Operator. Your ROI goes back to “we saved you time” not “we made you results you care about.” Internally, they’ll hear the operator repeatedly – this isn’t any better. The Operator doesn’t want to change their habit because it’s a habit.

Your opportunity: Help them build the case internally. “Here’s what modernisation enables. Here’s how we prove it works. Here’s how we scale it. Here’s how it goes wrong and what to do about it.”

Person 3: The Executive Sponsor

This is the person who controls the budget and strategy for the function. They don’t care about the status quo, Excel or your tool. They care about competitive advantage.

What they’re really asking: “Does this investment actually move the needle on what matters to the business?”

What they need: Evidence of business impact. Not tool adoption. Not efficiency. Proof that modernising the function creates measurable advantage. Because they sold that to the board – based on what your value proposition and sales team promised.

Your risk: If after the initial sale happens you’re only talking to the Operator and Change Champion, the Executive Sponsor doesn’t know their expectations have hit the skids until it’s too late. The deal stalls. The transformation stalls.

Your opportunity: This person controls expansion budget. They’re the lever for premium growth. But you have to speak their language beyond selling the promise and get on with delivering it: competitive advantage, business impact, strategic positioning.

This needs to be done against a backdrop of their teams running interference to avoid change – as well as your own teams who have established comfortable ways of working too.

Answering Status Quo Questions

When you hear “How is this better than my existing approach?” ask yourself: Where is this customer in their transformation journey?

Stage 1: The Operators Are Efficient

Existing process works. It is stable. There’s no crisis driving change. This is your installed base.

Your job here: Don’t force transformation. Offer integration. Respect their workflow. Make adoption optional and beneficial, not mandatory and disruptive.

Stage 2: The Change Champions Are Frustrated

Excel is now a bottleneck. Manual processes can’t scale. The function can’t respond fast enough to business changes. The bosses have mandated change.

Your job here: Help them build the case that modernisation unlocks competitive advantage. Show them how to prove it works. Help them get budget and sponsorship.

Stage 3: The Executive Sponsors Are Convinced

Modernisation is approved. Budget is allocated. The transformation is happening. This is your premium customer. Begin with the end in mind. How will they be a renewing customer?

Your job here: Deliver on the transformation promise. Measure business impact. Help them scale the change across the organisation.

The problem: Most organisations try to move everyone from Stage 1 to Stage 3 simultaneously. You can’t. And if you push too hard, you lose the installed user base without gaining the premium opportunity.

Serving Without Losing

This is the complex part. And it’s exactly why collaborative work with your teams is essential.

You need:

1. A strategy that respects the installed base

Operators ask “How is this better than Excel?” and you need to be honest: “For you, Excel might be fine. Here’s how we work alongside it. Here’s what’s optional. Here’s what’s automatic. And here’s what might happen when you outgrow it and what might happen if you miss the external inputs we provide.”

They feel respected. They stay. They watch. And when they see what the Change Champions are building, some of them become curious.

This requires your customer success team to understand: Not every customer needs to transform. Some just need stability for now.

2. A strategy that enables transformation

Change Champions ask “How do I prove this works?” and you need to answer: “Here’s the journey. Here’s how we measure impact. Here’s how we build the case internally. Here’s how we scale it. Here’s how other people are doing it – here’s how to meet them to get help.”

They feel supported. They expand. They become your advocates.

This requires your sales team to understand: This is a longer conversation. This is a partnership. This is about helping them lead transformation, not just selling them a business result from a sales script.

3. A strategy that speaks to executive value

Executive Sponsors ask “What’s the business impact?” and you need to have data: “Organisations that modernised this function saw X% improvement in competitive responsiveness. Based on your situation here’s a possible range. Here’s how we measure it. Here’s how we help you achieve it. This is how you need to commit to change.”

Complexity Requires Systematic Thinking

After working on more than 50 brands and speaking directly with teams and their customers, here’s what I know.

You can’t design this strategy in a board room. Or in the rooms of expensive strategy consultants. You have to discover it with your teams and customers together.

When your sales team has conversations with all three types of customers, they realise: “Oh, the status quo ‘Excel’ question means completely different things depending on who’s asking and where they are.”

When your marketing team hears these conversations, they realise: “We need two (or three) different narratives. One respects the base. One enables transformation. One speaks to strategic value.”

When your customer success team participates, they realise: “Success looks different for each type of customer. I’m measuring the wrong things for the Change Champions. My customer health score is set up for a different time – and even then it was struggling to tell me if someone would renew or churn.”

That’s when the organisation can:

• Keep the base happy (respect their workflow, make adoption optional)
• Enable the transformation (help Change Champions build the case and prove value)
• Grow premium revenue (speak to Executive Sponsors about strategic competitive advantage)

Your teams need to help to understand and navigate complexity.

Interpreting The Signal

When a customer asks “How is this better than my status quo?” the honest answer depends entirely on:

1. Who’s asking? (Operator, Change Champion, or Executive Sponsor)
2. Where are they in their journey? (Efficient, Frustrated, or Convinced)
3. What do they actually need? (Integration, Transformation Support, or Strategic Partnership)

If your team can answer that question with clarity, you’ve got the right approach. You’re not forcing everyone into the same mold. You’re serving people where they are while creating a pathway for them to evolve.

Does your team have confidence and belief in this new vision?

Value Capture Opportunity

The organisations that nail this are the ones to grow sustainably without cannibalising the base.

They keep the Operators happy and stable.

They support the Change Champions through transformation. Their expansion revenue accelerates.

They speak to Executive Sponsors about strategic value. Their premium growth becomes significant.

And all three groups feel served, because the organisation understands where they are and what they need.

That’s the difference between “we repositioned” and “we moved markets while protecting our foundation.”

Different Approach

I work differently. I don’t make change happen to your teams. It’s with your teams.

Step 1: Teams Discover the Insight Directly

Instead of me telling your sales team “You need to reposition to strategic leaders,” I bring your sales team into conversations with strategic leaders.

Not sales calls. Real conversations where we’re listening, not selling.

“What would it actually mean if you could use this to transform your function?” “How is your CEO measuring your success?” “What would it take for you to become the strategic partner instead of the cost centre?”

Your team hears directly from customers why the new positioning matters. It’s no longer a strategy deck. It’s customer truth.

Something shifts when a sales rep hears a customer say “If you could help me position this as a competitive advantage instead of a compliance cost, you’d transform my standing in the organisation.” That’s when they get it. Not because I told them. Because the customer showed them.

Step 2: Teams Apply Frameworks to Their Own Situation

I bring diagnostic frameworks and tools. How do you identify the different types of strategic leaders? How do you discover what actually drives their decision-making? How do you position differently to someone who’s aspirational versus someone who needs to start with small wins?

But your teams don’t just learn the framework. They apply it to their own situation.

Sales figures out: “Here’s how we discover if a customer is ready for the strategic conversation or if they need small wins first.”

Marketing figures out: “Here’s what content actually resonates with strategic leaders versus aspirational ones.”

Customer success figures out: “Here’s what business outcomes we should measure, and here’s how we help customers achieve them.”

Your teams own this. They designed it. So they believe it.

Step 3: The Company Moves Together

Leadership doesn’t push the new strategy down. The strategy emerges from what the teams discovered with customers.

Sales says: “We talked to functional leaders. Here’s what they actually value. Here’s why our current approach misses it. Here’s what we need to change.”

Marketing says: “We heard this theme repeatedly. Here’s what content and positioning will resonate.”

Customer success says: “We measured this, and here’s what drives expansion with strategic customers.”

Now everyone is aligned because they’ve all discovered the same thing. Not through a mandate. Through customer discovery they participated in.

That’s building a unified company.

3 Differences This Makes

1: Teams Believe Because They’ve Heard It From Customers

Strategy memo: “Reposition to strategic leaders.” Team response: “OK, we’ll add that to the deck.”

Direct customer conversation: Functional leader says “What would change everything is if you helped me position this as competitive advantage.” Team response: “Oh. That’s completely different from what we’ve been saying. We need to change how we sell.”

The second creates genuine behaviour change. The first creates compliance.

2: Adaptive Frameworks Designed To Optimise Subscriptions

I don’t just give you frameworks. I help you adapt them to your specific situation. Based on the collective experience of my network of B2B leaders who are doing the do.

Your teams have access to tools they use, not frameworks they study then struggle to apply to your situation.

3: You End Up With Institutional Knowledge, Not a Report

A strategy consultant delivers a report. When they leave, the knowledge leaves with them.

I work with your teams to build their capability. They learn to think this way. They learn to diagnose. They learn to adapt.

Your team is still having customer conversations guided by the insights we discovered together. They’re still making decisions through the lens of strategic value, not just operational efficiency.

The capability builds.

Successful Repositioning

When you’re repositioning, you’re asking your teams to think differently about what customers value. That’s not a one-time instruction. It’s a fundamental shift in how they approach their work.

Tightening ICP is not a one stop journey.

But making the shift needs careful support and understanding. It only happens when teams experience discovery through customer conversations, and then have frameworks to help navigate the complexity of implementing it.

Strategy consultants can diagnose the opportunity.

But only collaborative diagnostic work with your teams can make change stick.

What This Looks Like in Practice

Here’s how the approach works:

Week 1: Team Workshop + Customer Discovery Planning

Your cross-functional team (sales lead, marketing lead, customer success lead, product and more) defines what you’re trying to understand. Not what you already believe. What you need to learn.

We identify the tight ICP you want to reposition toward. We design conversations that will actually reveal what this customer type values.

Week 2: Customer Conversations

Your team feels part of the conversations when they hear them.

Aspirational leaders: “What would it mean if you could lead the charge in your function?”

Pragmatic leaders: “How do you think about proving value before investing bigger?”

Constrained leaders: “What’s holding you back from investing in something strategic?”

Week 3-4: Team Applies Insights

We work through what the team heard. What surprised them? What changes how they think? What do they need to do differently in product design, sales, marketing, customer success?

We adapt frameworks to fit their specific situation. How do you discover customer readiness? How do you position differently? How do you measure success differently?

Week 4+: Implementation Planning

Your team designs how this changes their operations. Not “follow this framework.” But “Here’s how we change our discovery questions based on what we learned. Here’s what content we need. Here’s how we measure customer success.”

Ongoing: Quarterly Check-ins

We review what’s working. What’s not. Other levers to pull. When results are expected. What happened.

Cost of Taking Teams on the Journey versus Leaving It To Strategy

If you don’t take your teams through this discovery process:

• You’ll have a divided company. Leadership believes in the new positioning. Teams are executing the old one.
• You’ll see slow adoption. Teams execute what they were told, not what they believe in.
• You’ll miss the opportunity. Strategic customers should expand 2-3x more. If they’re not, it’s because your teams don’t yet think like strategic sellers.
• You’ll get frustrated. “We got the positioning right. Why isn’t it working?” Because the teams weren’t part of getting to the positioning.
• You’ll be vulnerable to turnover. Teams who feel left behind or blamed for not executing someone else’s vision often leave. Then you’re building new teams around a strategy they don’t understand.

The Opportunity

A company that’s genuinely repositioned – where leadership and teams are aligned because they discovered the insight together – is powerful.

Your teams are naturally strategic solution experts because they’ve heard directly from customers why strategic positioning matters.

Your marketing speaks to the right audience with the right message because your marketing lead was in the conversations.

Your customer success measures and optimises for the right outcomes because they participated in understanding what actually drives strategic customer value.

That alignment is powerful. But only if your entire company is moving together.

— Andy

Seeing this pattern in your business?

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