A Roadmap for Cross-Sell and Upsell Success
The Untapped Potential of Pricing Strategy
Growth targets are aggressive. Margins must be preserved. And capital efficiency is a driver. Fortunately one high-impact lever remains surprisingly overlooked: pricing.
We’re not referring to traditional pricing exercises focused on squeezing margin or tracking competitor benchmarks. Instead, focus on pricing as a commercial growth enabler. Pricing can be a strategic tool that unlocks expansion revenue from your existing customer base.
Among recent conversations with CFOs, CROs, and Operating Partners, one thing has become clear: pricing is being recast. It’s a go-to-market priority for cross-sell/up-sell into the base.
If you’re not using pricing to fuel cross-sell and upsell, you’re missing out on a low-risk, high-return growth strategy. Consider this:
- Pricing misalignment may be stalling your expansion playbook, even when customer success and sales execution is world-class.
- Customers don’t understand pricing bundles and add-ons,so they don’t buy more.
- Your team lacks the tools and authority to design for buyer expansion journeys.
Pricing touches every team: sales, marketing, product, and customer success. And when it’s misaligned, everyone loses. But when designed for simplicity, clarity, and growth, it becomes the fastest way to boost revenue per logo.
This article walks you through how leading PE firms and their portfolio companies are rewriting the rules. You’ll get a step-by-step roadmap to reframe pricing as a lever for expansion—not just extraction.
If you’re still treating pricing like a back-office function, you’re behind. Read on before your competitors do.
Pricing as a Growth Enabler (and Retention Boost)
The role of pricing is about monetizing growth. Getting more revenue from the same customers with greater predictability and less acquisition cost.
In addition, fuller adoption across product lines increases customer satisfaction. Those companies offering a true platform solution have the ability to maximize stickiness through platform adoption. By increasing platform adoption, cross/up-sell impacts both growth and retention KPIs.
1. The New Mandate from the C-Suite and PE Sponsors
Private equity sponsors and portfolio company ELT leaders are asking a new question: How can pricing unlock expansion?
They aren’t looking for clever discounts. They want system-level pricing changes that promote adoption across product lines. This new mandate reframes pricing as a go-to-market lever, not a finance control.
That shift is overdue. Most portfolio companies leave money on the table through disjointed pricing models. Cross-sell and upsell potential is buried under complex SKUs, unclear value ladders, or sales team misalignment.
To respond, CEOs and CROs need pricing architectures built for growth moments:
- Add-on product launches
- Customer renewals and upgrades
- Account-based expansion motions
2. Why Go-to-Market AI and Sales Enablement are Not Enough
It should be a top priority to adopt AI tools and capabilities into your go-to-market motions. While these tools will give you a significant boost, they don’t fix the core underlying issue. If your pricing doesn’t make upselling easy to sell and easy to buy, your growth model breaks.
Here’s what too many companies miss:
- CSMs and/or Sales reps struggle to articulate upgrade value.
- Buyers can’t navigate confusing pricing options (especially when there are groups within a customer business that require customers to split out amounts for internal reporting).
- The existing pricing approach imposes rigid structures that restrict flexibility.
The result? Strong products underperform and fail to capture the true value of the investment. Instead of hitting goals for revenue expansion, you see stalled growth and renewal fatigue.
3. Pricing as the Hidden GTM Gap
This disconnect often goes unnoticed. Companies invest in sales training, messaging, AI innovations and digital journeys but pricing remains static. That’s the hidden gap. Sales motions evolve. Products evolve. But pricing? It lags.
Especially in PE-backed companies, pricing strategy is often inherited from founders or legacy systems. It doesn’t reflect new commercial priorities or expansion goals. It doesn’t evolve fast enough.
Symptoms of misaligned pricing:
- Sales can’t explain “why now” or “why this add-on.”
- Cross-functional teams debate instead of align.
- Customers get inconsistent offers across divisions.
Fixing this means treating pricing as part of go-to-market, in both expansion and new logo.
Strategic Cross-Sell Pricing: A Playbook for Portfolio Companies
1. Aligning Pricing with Customer Expansion Journeys
Not every customer is ready to buy everything on day one. But most want to grow with you. A modern pricing strategy reflects that. It meets buyers where they are and walks them forward.
Three approaches that work:
- Tiered pricing that supports different usage levels
- Bundles that introduce related products gradually
- Consumption-based models that scale with use
The key is to price for commitment, and also for access. This may involve letting customers test, learn, and grow without jumping into a massive contract. Make expansion low-risk and high-reward.
2. Designing for Simplicity and Clarity
Confusing pricing is the fastest way to stall customer growth. If your buyer needs a spreadsheet to understand the offer, you’ve already lost.
Take a real-world example. One Cortado client was struggling to launch a new platform. The product was strong, but adoption was weak. Why? Their pricing required buyers to switch plans completely.
We helped them reframe the model:
- Unbundled key features
- Introduced a “modular add-on” tier
- Priced it for ease of experimentation
The result? A 40% increase in multi-product deals within two quarters. Simplicity created movement.
3. Building Internal Cohesion Across Commercial Teams
Your pricing strategy must be understood and championed by more than just finance. Sales needs to sell it. Marketing needs to message it. Product builds a roadmap tied into the pricing strategy.
That requires cohesion. You can’t let each function interpret pricing their own way.
Start with shared ownership. Build a pricing committee that includes:
- Sales leaders
- Marketing leaders (including product marketing)
- Product managers
- Finance partners
Then close the loop. Create feedback channels where field teams report what’s working and what’s not. Use that data to refine offers. Treat pricing as dynamic not one-and-done.
Equip teams with tools to help:
- One-pagers for add-ons
- ROI calculators tied to usage
- Playbooks with upsell language
When internal teams align, the customer experience follows.
Execution: Where to Start and How to Drive Change
1. Conduct a Pricing Diagnostic
Before you fix pricing, you need to understand what’s broken. A diagnostic reveals where friction lives. Look at:
- Deal win/loss reasons
- Renewal conversations
- Discounting patterns
Are reps negotiating around pricing? Are customers confused at renewal time? Is your pricing aligned with product usage? These signals point to strategic misalignment.
Evaluate sales incentives, too. If reps focus too little or too much on expansion deals, that can be unhealthy to the blend of GTM bookings. Your compensation model should reinforce pricing architecture.
2. Build an Iterative Strategy
Don’t try to overhaul everything at once. Start with the areas where impact is most visible:
- Products with higher churn
- Customers with unbought add-ons
- Segments with high CAC and low expansion
Test new pricing structures with small groups. Track how often customers choose upgrades. Watch revenue per deal. Analyze sales team feedback.
Then adjust. Pricing isn’t static. Iteration is what drives improvement.
3. Get PE Involved Early in Pricing Strategy
When PE gets involved early, two things happen:
- Pricing strategy gets political capital to succeed.
- Portco teams see pricing as a priority.
That unlocks faster alignment and better execution.
Use your PE firm’s muscle to:
- Set pricing governance expectations
- Share cross-portfolio learnings
- Provide budget or resources to bring in pricing experts
Conclusion: Pricing Strategy as the Cross-Sell Accelerator
Pricing isn’t just a number. It’s a narrative. It tells your customers how they can grow with you. It shows your team where value lives. And it gives investors the leverage they need to scale without chasing unsustainable growth.
For PE-backed companies, pricing is no longer optional. It’s fundamental to the investment thesis. Without a scalable, expansion-friendly pricing model, every dollar of ARR is harder to earn.
The best companies treat pricing like a product. They design it. Test it. Iterate it. Align it. And they turn it into a growth lever that drives up enterprise value.
Ask yourself:
- Is your pricing making it easier to sell?
- Easier to buy?
- And easier to grow?
If the answer isn’t a clear yes, it’s time to act.
We help PE-backed companies design pricing that drives cross-sell, upsell, and retention fast. Schedule a meeting to explore your pricing growth opportunities.
