When Your Two Biggest Customers Demand 30% Cuts

Lessons from managing $500M in ARR through the 2008 crisis

This is a companion to "Winter Is Coming: A CEO and CMO Guide to Seizing Share While Others Freeze." If that piece was about playing offense with your brand, your messaging, and your partnerships, this one is about playing offense with your pricing.

What would you do if your two biggest customers called today, asking to cut their contracts by 30% each?

Depending on your size and stage, that could represent anywhere from a 5% to 30%+ hit to topline revenue. Boom. Just like that.

That's what it was starting to feel like for my $500M SaaS Subscription team at Dun & Bradstreet on October 1, 2008. The moment our 1,000-person sales force started directing their attention to Q4. It was a bloodbath. In the tsunami that was the 2008 financial crisis, my company's customers started really feeling the downturn heat in Q3. We felt it immediately after.

If a downturn arrives, this could be you. This piece is your pricing playbook for when those calls come, and how to turn them into leverage instead of losses. Because when those calls come, your answer doesn’t just reflect policy — it reflects your belief in the value your team delivers. That’s what this piece is all about.

This Only Applies If You’re in the Enterprise Game

These strategies apply to complex enterprise contracts — $250K, $500K, $1M+. Not transactional SaaS. Not $199/month subscriptions.

Enterprise deals are multi-product, multi-team engagements with flexibility in scope, structure, and value creation. That complexity is where your leverage lives. You can shift product mix, expand access, adjust terms and still hold pricing power.

If the only thing your company can “give” is more usage of a single product, this playbook doesn’t apply. These moves are about giving to get. You earn flexibility, term, and growth by delivering value across the full relationship, not by trimming line items.

And the stakes are high. If you're in a $1M+ deal and you're negotiating like it's transactional SaaS, you’re not just leaving money on the table — you're training your customer to see you as a commodity.

In these contracts, your price isn’t just revenue. It’s positioning. Cut carelessly, and you don't just lose margin, you lose your seat at the strategic table.

Move 1: Fill the Contract, Not the Discount

Usage is down and budgets are tight. But that doesn’t mean your value has dropped. Your job is to protect revenue without retreating on value. One way to do that is to keep the price and load the contract with more perceived value.

Start by identifying high-utility, low-marginal-cost levers that are underused. Then design a customer success play to bring them online over the next 30–60–90 days.

Add:

• Modules that have no marginal cost

• Reporting or analytics they haven’t turned on yet

• Benchmarking data that helps them justify spend

• Seats for adjacent teams that build cross-department visibility

You’re not lowering standards — you’re stretching the impact of their existing investment. Think of it as redistributing value, not reducing it. 

At D&B, we had near-infinite product and pricing flexibility to maintain or even increase enterprise contract value, despite real usage declines. Our team could rapidly offer alternatives, depending on the customer's product usage and trends. They all tied back to delivering more value in the face of lower usage levels. For example, richer data and access to more product modules.

Example: A customer has 100 seats on your Pro tier ($90/seat), which costs $9,000 per month. Instead of removing seats, you temporarily upgrade 60 of them to the Enterprise tier — delivering more capability, more flexibility, and more substantial ROI for the same cost. Or, if CRM seats are declining, you introduce a Marketing Automation module to fill the gap with new functionality.

This helps the customer succeed right now. It makes them feel like they’re getting more, not less. And it reinforces your position as a strategic partner who invests in shared outcomes, not a vendor trimming scope to preserve line items.

Move 2: Use Price Offensively to Expand the Obtainable Market and Take Share

This applies to companies selling usage-based products with low marginal cost, where pricing is tied to delivered value, not cost to serve. In these businesses, pricing power stems from product ROI, rather than unit economics. 

Your customer is already using your product to its fullest, up to the threshold where the ROI still holds. Beyond that point, they stop. Why?

• The marginal cost feels too high.

• They use a workaround or a cheaper vendor.

• Or they simply leave it undone.

Your Serviceable Obtainable Market (SOM) stops cold at that value threshold, not because of product fit, but because of price. That’s your opportunity. You can offer to take over the “long tail” — the lower-value, lower-sensitivity, harder-to-justify transactions — and bring them under your umbrella.

The move: “We’ll give you all of that for 20% more.”

You’re not charging more for the same value. You’re absorbing adjacent spend that they were never going to consolidate on their own.

Your current contract covers the high-value slice (above the transaction value threshold, $T). Everything to the right of that curve — the unmonetized long tail — is the competitor’s territory. You’re about to take it.

Example: A $750K contract supports 30,000 high-value transactions. You offer 3x the transaction volume for just 25% more, and now you’ve unlocked the full curve. The incremental cost per unit drops from $24 to $3.64. But the customer’s perception? “We centralized all of it with one provider.”

This isn’t a discount. It’s matching price-to-value proposition that wins market share.  Done right, the customer feels like they eliminated noise.

Move 3: Make Concessions Reversible, Not Permanent

If you have to cut prices, do it with guardrails. Time-box it. Tie it to volume or behavior. And always trade it for a longer-term commitment.

Think like a phone company. Better rates are available when you lock in for 24 months.

The principle is simple: you never right-size a contract without increasing the term. But you don’t lead with that. You lead with outcomes.

Talk ROI and impact. The conversation is never about how much less they’ll pay; it’s about how much more they’ll achieve, with your help.

You’re not trimming costs. You’re re-engineering success. When they win now, they grow with you later.

Examples:

• Reduce the price only if the term extends.

• Shift to a lower tier, but bundle it with high-value features that support their new goals.

• If budget is truly constrained, structure pricing to step back up over time, with the reset committed in writing.

Script: “We’ll structure this to give relief now, and ensure we’re set to restore full value on the other side. This isn’t a concession — it’s a plan.

Navigate the Risks

These moves aren’t without risk. Aggressive contract restructuring can trigger procurement scrutiny or internal reviews, potentially delaying deals. Value-loading can create unrealistic expectations that increase friction during renewal later. Share-grab pricing can provoke competitive responses that lead to a race to the bottom, or signal desperation if not positioned correctly.

Mitigate by:

• Documenting all value additions to prevent scope creep

• Setting clear rules of engagement for discounts and term extensions

• Running scenarios where usage doesn’t recover, and planning the commercial recovery path

• Training the deal desk and finance to review pricing moves based on long-term customer potential, not just short-term pressure

Acknowledging risk doesn't strengthens the strategy. Executives don’t want perfect ideas. They want proven strategies with guardrails.

Price for the Market You Want to Lead

The downturn may change how much your customer uses, but it doesn’t change the value you deliver per unit. You can acknowledge they need less, while still affirming what you’re worth.

The goal is to do everything possible to preserve and grow total contract value. And if you must shrink, you shrink with a plan to grow again.

Codify the value and set the conditions. Protect the return path, so every dollar you concede now has a roadmap back to full value, by:

• protecting margin in the near term

• preserving your pricing power for future cycles

• reframing your relationship as strategic, not transactional

• building leverage for competitive displacement

Pricing is your product’s self-esteem. It signals how much conviction you have in the value you deliver, even when usage dips, and pressure rises.

Get it right, and you don’t just survive the downturn. You walk out of it with more share than you had going in.

If You’re a CEO, CMO, CRO, or Pricing Leader, Start Here. Plan ahead, so you're prepared for rapid response if Winter washes over your client base:

• Identify which enterprise accounts are under volume pressure.

• Audit your pricing plays against these 3 moves.

• Set clear enablement, discount, and CS handoff rules.

• Codify your path back to full contract value on every concession.