Smarter Upselling & Cross-Selling in PE Equity: A 10-Step Framework for Expansion Revenue

It’s no secret that organic growth is getting harder to come by In today’s private equity landscape, especially in the lower middle market. Customer acquisition costs (CAC) are rising. Channels are noisier. Sales cycles are lengthening. And when you have a finite hold period, waiting for growth isn’t really an option.

Over time, it’s become clear that the real opportunity for many portfolio companies isn’t outside the customer base but within it.

Upselling and cross-selling aren’t just smart levers; they’re necessary ones. Expansion revenue is becoming not just efficient but essential, especially as hold periods compress and CAC continues to rise.

Here’s the 10-step framework for smarter upselling and cross-selling I’ve seen deliver outsized results when teams take it seriously.

1. Define Success Clearly

This might sound obvious, but without alignment on the right metrics, it’s nearly impossible to scale an expansion motion. Whether the target is higher revenue per customer, a faster CAC payback, or stronger LTV, the team needs clarity.

At several companies I’ve supported, expansion didn’t get traction until the KPIs changed, literally. The moment “expansion revenue” or “attach rate” showed up in dashboards, the shift in behavior followed fast.

2. Map the Customer Base

Before launching any play, the groundwork has to be solid. That means pulling real customer data (across CRM, ERP, CS tools, billing platforms) and actually analyzing it.

The aha moments usually live here: discovering segments of customers with high tenure and low product usage, or high NPS but limited product adoption. Those signals point directly to where expansion potential is hiding.

3. Run a Gap Analysis

One of the most powerful exercises is comparing actual customer spend to potential wallet share. The numbers often tell a more compelling story than expected.

For instance, it’s not unusual to find that even large enterprise accounts are using just a slice of the available offering. When companies stop guessing and start quantifying, it becomes much easier to build meaningful expansion targets.

4. Segment Accounts Strategically

Not every customer deserves the same approach. Trying to treat them all equally is a fast path to wasted effort. Breaking the base into logical groups helps focus teams where the upside is greatest:

• Strategic – Long-term, high potential accounts
• Growth – Mid-tier accounts ready for more
• Dormant – At-risk or under-engaged
• Negative – Low-margin, support-heavy

Creating segments like these brings structure to what is often a reactive, scattered effort.

5. Identify Natural Product Pairs

This part is more pattern recognition than rocket science. Every company has its “peanut butter & jelly” pairings, which are products or services that naturally go together.

The challenge is many teams don’t step back to map those out. When that work is done, bundling becomes easier, customer conversations are smoother, and close rates increase. All without adding complexity to the sales cycle.

6. Ask Sales and CS What’s Really Going On

Sometimes the best insights come from the simplest question: “What are customers asking for that we’re not offering, or not offering well?”

Conversations with AEs and CSMs consistently surface hidden friction, missed opportunities, and customer wants that never made it into the roadmap or pricing strategy. That front-line feedback becomes fuel for smarter plays.

7. Score Opportunities Objectively

The most effective teams use a basic 2×2 model: Revenue Potential vs. Ease of Execution. Then they map plays accordingly.

This helps prevent one of the biggest traps in expansion: chasing big wins that require big lifts before you’ve earned small, fast ones. Once you’ve got wins in that top-right quadrant, it builds both confidence and momentum.

8. Build the Plays

This is where expansion becomes operational. Plays need clear packaging, simple scripting, and trigger-based timing, especially around renewals, onboarding, or product milestones.

Training the team is critical. A good playbook not only includes the “what to sell,” but also the when, why, and how. When that’s in place, sales execution gets sharper almost overnight.

9. Pilot, Learn, Repeat

No need to roll everything out at once. In fact, starting small is usually better. Focus on a segment, assign it to a few reps, and track metrics ruthlessly.

Open rates. Response rates. Conversion rates. Uplift per account. This step isn’t just about testing. It’s also about learning fast and refining the motion so it scales cleanly.

10. Scale and Monitor

Once the model works, expansion becomes a system, not a project. That means consistent dashboards, regular reporting, and portfolio-wide visibility on:

• Expansion revenue
• Attach rates
• Average deal size
• Account penetration

In firms that have institutionalized this rigor, cross-sell and upsell become second nature, while adding significant multiple uplift at exit.

Final Thought: The Growth Is Already There

Most portfolio companies aren’t underperforming on expansion because of apathy. They’re underperforming because the strategy has never been clearly defined, operationalized, and resourced.

But once it is? Teams get sharper. Revenue grows faster. And the PE firm captures value that would’ve otherwise been left untouched.

Expansion isn’t a “bonus” anymore. It’s the growth tailwind sitting right inside the customer base, ready to be activated.

Want help bringing this 10-step expansion framework for smarter upselling and cross-selling to life inside your portcos? We’ve guided teams through every phase, from mapping customer data to building high-impact plays. Let’s talk.

Craig Group Partner Brian Gustason writes about PE revenue growth on LinkedIn.