Cross-sell is the single biggest revenue multiplier after retention, but it rarely behaves like a flywheel at scale. I’ve long been a skeptic of cross-selling because few companies actually get it right. Klaviyo’s Q4 numbers (110% NRR, 60%+ ARR multi-product, 15%+ three-product adoption) are a rare example.
Twilio isn’t there yet. Its multi-product trend is moving in the right direction, but cross-sell still sits in my “Unknown” bucket.
In past posts, I’ve argued that’s because cross-selling has three hard requirements:
- It needs a forcing function: a product or use case that naturally pulls multiple SKUs into the same workflow. Without that, everything beyond messaging behaves like a sidecar.
- It demands simplicity for sales and customers: unified pricing, clear packaging, and low-friction handoffs. If it isn’t easy for your salespeople, it will never be the main deal.
- It requires aligned incentives at scale: shared quotas, comp plans that pay for cross-sell, and specialist overlays that actually get used—without blowing up ISV and channel relationships.
On that third point, Twilio’s Thomas Wyatt is trying to move the ball. Twilio has updated 2026 compensation to explicitly incent cross-sell and upsell and has added a specialist function to support the global sales team with more advanced products. The open question is whether that’s enough to reach the long tail of self-serve customers or if product-led growth still has to do most of the heavy lifting.