Most SaaS companies focus on landing new logos. Fewer capitalize on the customers they already have.

The ones that scale fastest do both.

They turn small entry deals into large, recurring revenue. And they do it by treating expansion as a strategic motion, not an afterthought.

Here’s how to make upsell and cross-sell your most reliable source of ARR.

1. Upsell vs. Cross-Sell: Know the Difference

You can’t expand accounts without knowing what kind of expansion you’re driving.

• Upsell: Selling more of what the customer already usesExample: Upgrading from Pro to Enterprise

• Cross-Sell: Selling adjacent products or featuresExample: A CRM platform offering a marketing automation add-on

2. Why Expansion Beats Acquisition

Acquiring new customers is expensive. Expanding existing ones is efficient.

• Expansion deals cost five times less than new logos

• They close faster because trust is already built

• They drive Net Revenue Retention past 120 percent

If you want predictable ARR without bloated acquisition costs, this is your best lever.

3. The Expansion Playbook

Step 1: Spot Accounts Ready to Grow

Not every customer is expansion-ready. Look for signals that show value and momentum.

Watch for:

• High product usage and feature adoption

• Company growth indicators like headcount or new funding

• NPS scores of 9 or 10

Step 2: Choose the Right Moment

Timing is everything. Expansion conversations should feel like support, not a pitch.

Ideal moments to engage:

• During onboarding: If they are already stretching limits

• In QBRs: After demonstrating clear ROI

• After usage spikes: Rapid growth signals unmet needs

Example pitch:“I noticed your team is hitting usage thresholds. Other customers at this stage find [upgrade] helps them scale more smoothly. Want to explore options?”

Step 3: Make Your Pricing Work for You

Your pricing should guide customers toward growth—not block it.

Tactics that support expansion:

• Usage-based pricing that scales with value

• Tiered packaging with feature unlocks at each level

• Seat-based or consumption pricing that grows with adoption

Reminder: Good pricing encourages growth. Great pricing makes it automatic.

Final Thought: Expansion Shouldn’t Be Optional

If upsell is still a secondary priority in your go-to-market, you’re leaving money on the table.

Here’s how to change that:

• Identify customers showing signs of growth

• Start conversations when it feels like help, not sales

• Align pricing so that growth is the natural path forward

Let’s Build Your Expansion Engine

If your current land-and-expand motion is mostly “land,” it’s time to close the loop.

On our first strategy call, we will:

1. Audit your expansion pipeline and surface missed revenue

2. Map product usage signals and timing triggers

3. Build a cross-functional playbook your teams can run next quarter

Reach out or book time. Let’s turn your customer base into your fastest-growing revenue stream.

👉 [Book a strategy call]