10 Hacks for Driving Customer Success-Led Revenue and Better Margins

One of the most impactful GPs I’ve had the privilege of working with in the SuccessVP portfolio is Cassie Young—we’re both invested in Amanda Kahlow, and her incredible company 1mind.

Few investors bring the same depth of operating expertise that Cassie does—she’s successfully led marketing, sales, and Customer Success teams, giving her unparalleled lived-insights to help founders build their go-to-market strategies. Last fall, Cassie delivered an unforgettable presentation at the Customer Success Meetup in New York City. Whether you’re a founder crafting your go-to-market plan or a seasoned Customer Success leader refining your playbook, her 10 actionable hacks are truly game-changing.

1. Ask the Renewal Question Early

Don’t wait until the renewal date to ask if your customers plan to stick around. Cassie recommends popping the question early: “If your renewal were imminent, would you renew?” If the answer is no, you’ve got time to fix the issues.

💡 Pro Tip: Celebrate when a customer says they won’t renew — it gives you the chance to turn things around.

2. Make Your Pricing Work Harder

Is your pricing model built for organic expansion? An atomic unit of pricing (like Monthly Active Users) ensures contract values grow as customers use more of your product.

💡 Quick Fix: Regularly meter usage to avoid surprise billing and renegotiate when customers outgrow their contracts.

3. Aspire to Never Have a Renewal

Rip up the old contract and renegotiate when customers are pacing ahead of their usage. The catch? Add 12 months to the contract term. This “pull and push” strategy keeps your customers locked in longer.

4. Map Your Customers to Upsell Opportunities

Create a 2x2 matrix:

• Vertical Axis: Net Promoter Score (NPS).

• Horizontal Axis: White space (room to sell more).

Focus on customers in the top-right quadrant—those who love you and have room for growth.

5. Gamify Incentives with Spiffs and Lotteries

Motivate your CS team to upsell with short-term incentives. One example? Offer lotto tickets for every qualified lead they generate, with a grand prize like an all-expenses-paid trip.

6. Add Time-Sensitive Language to Contracts

Seal the upsell deal faster by incorporating urgency into contracts. Example: “This product costs $100,000 now, but if you wait longer than 90 days, the price increases by 50%.”

7. Use Benchmarking to Drive Value and Upsells

Customers love to see how they compare to peers. Show benchmarks that highlight areas where they’re underperforming—and conveniently, offer products that can fix those gaps.

8. Reallocate Work to Maximize Value

Track how your CS team spends their time. If high-cost CSMs are stuck on low-value tasks, shift those tasks to support staff or automate them.

💡 Example: One company reduced ticket support time for CSMs by hiring a dedicated CS Ops person, boosting ARR per CSM by 15%.

9. Reevaluate Low-Value Customers

Not all customers are created equal. If small accounts consume more time than they’re worth, consider restructuring:

1. Charge for premium support.

2. Limit support access.

3. Politely let them go.

10. Use Support Data to Influence Product Roadmaps

Analyze high-cost, high-volume support tickets and fix the root causes in your product. Example: Automating GDPR data deletion saved one company hundreds of thousands in support costs.

🎯 Bonus: Take Credit for Your Wins

Sales teams love to shout their victories from the rooftops. CS teams? Not so much. Cassie suggests using visual metrics like:

• Growth in average contract value (ACV) per customer.

• A margin improvement chart that highlights how CS initiatives contribute.

Cassie’s advice is clear: retention isn’t just the cheapest form of growth—it’s your secret weapon. Whether you’re popping the renewal question early or using spiffs to gamify upsells, these hacks will help you crush Q4 and beyond.

Ready to implement these tactics? Let us know which one you’re trying first and see you at the next Customer Success Meetup!