At Stripe Sessions 2025, Utkarsh Sengar, VP of Engineering at Webflow, and Dor Sasson, Co-founder and CEO at Stigg, took the stage to share how Webflow replatformed its monetization infrastructure to unlock flexibility and scale. Their theater session drew a packed room of leaders from across the SaaS ecosystem and sparked meaningful conversations about the future of monetization.
The response was so strong, we decided to turn their talk into a blog post — so if you couldn’t make it to Stripe Sessions this year, here’s your chance to catch up on one of the event’s most talked-about sessions.
The Challenge: A Monetization Stack Under Pressure
Webflow has long empowered designers and businesses to build for the web without code. But as the business scaled toward $100M ARR, their monetization infrastructure began to strain under new demands.
"This might feel like a therapy session to some of you," said Utkarsh Sengar, VP of Engineering at Webflow.
Engineering teams were overloaded. Every pricing change meant a long list of updates: new config entries, Stripe SKU syncs, UI updates, entitlement logic rewrites, even migration scripts. Simple questions like "Why doesn’t this customer have access to X?" required digging through multiple systems — and sync issues between Webflow’s database and Stripe made it worse.
"We’d hear: ‘Please don’t touch the billing code.’"
The numbers told the story:
- 8+ weeks to make pricing and entitlement changes
- 500+ engineering hours/year lost to billing-related work
- Rigid pricing models that couldn’t adapt fast enough to business needs
These challenges created deep operational pain:
- Inflexibility — “Every new SKU meant manually updating our code's SKU/entitlement config mapping, sync logic, some feature flags, and UI.”
- Error-prone and opaque — “Logic lived everywhere — Stripe, sync service, Mongo, and if-else trees.”
- Slow execution — "A single add‑on took weeks of schema migrations."
Webflow’s inability to quickly launch add-ons or reshuffle entitlements meant missed opportunities and revenue.
The Turning Point: From Bottleneck to Builder
What would it take to make billing a competitive advantage — not just back-office tooling?
Webflow’s engineering team knew building a homegrown system would be expensive, slow, and not core to their mission. So after conversations with peers and evaluating the landscape, they turned to Stigg.
"We realized this is important, but it’s not Webflow’s core competency," Utkarsh shared. "We needed flexibility, enterprise readiness, and support for our marketplace model — and that’s what led us to Stigg."
The Solution: Stigg’s MonetizationOS
Stigg is a developer-first monetization infrastructure built for engineering teams. With it, Webflow:
- Centralized and simplified entitlement management
- Enabled usage-based billing natively
- Empowered PMs to configure pricing changes without engineering bottlenecks
- Supported co-managed subscriptions in their marketplace product
- Integrated seamlessly with their architecture while keeping full control over checkout and tax UX
Stigg delivered the control, flexibility, and developer experience Webflow needed to modernize pricing operations — from UI to APIs to core infrastructure.
The Architecture: Before & After
Old Architecture:
Webflow's architecture prior to Stigg, Billing 2.0:
- Manual config updates across multiple services
- Stripe sync logic prone to errors
- Feature flags and migration scripts
- Billing tightly coupled to entitlements and UI
New Architecture with Stigg:
The new architecture built with Stigg, Billing 3.0, includes
- Centralized entitlement logic via Stigg
- Decoupled pricing and plan versions
- Clean API-first model with UI support for GTM
- Native add-ons, usage tracking, and co-managed subscriptions
- Rollout of pricing changes to millions of customers within a single click
Billing 3.0 is a unified, programmable billing platform that decouples monetization strategy from infrastructure constraints for PLG and SLG.
The Impact: Flexibility and Future-Proofing
"The results? Besides my promotion to VP of Engineering?" Utkarsh jokes.
Webflow’s monetization speed and scalability improved dramatically:
- Addon rollout: From months → 4 hours (PM config in Stigg + minor code + testing)
- Usage-based pricing: From quarters → a few weeks
- Marketplace rollout: From blocked → shipped
- Shared subscriptions: Enabled seamlessly with Stigg’s infrastructure
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Beyond faster launches, Stigg enabled Webflow to ship several high-impact revenue-generating features:
- Localization Add-ons
- Webflow Optimize
- Bandwidth Add-ons
- Webflow Analyze
"It’s honestly empowering for everyone. The business teams love that they can move on strategy without worrying about months of dev work. And engineering doesn’t feel like the bottleneck anymore — we’re actually enabling pricing and packaging to move faster."
The Takeaway: Buy Leverage, Build What’s Unique
Stigg gave Webflow the agility to modernize their monetization infrastructure without having to reinvent the wheel.
- Developer-first, production-grade entitlements
- Native support for any pricing model or packaging flow
- Strong support for enterprise use cases and marketplace complexity
"Stigg became the monetization platform we could build on — while still focusing on what makes Webflow unique."
What’s Next for Webflow + Stigg
Webflow is continuing to deepen their use of Stigg to:
- Give customers more flexibility with usage-based pricing and tiered overages
- Streamline provisioning and order-to-cash flows to deliver a smoother enterprise buying experience
- Quickly roll out and test packaging and pricing updates that better serve user needs
- Make it easier for customers to unlock add-ons and new products through seamless upgrade flows
“If you’re building at scale and your monetization stack hasn’t caught up — you need Stigg.”
