The purpose of this article is to outline why monolithic, all-in-one, Billing solutions and architecture for SaaS/AI are dead, and why unbundled, best-of breed, Monetization Infrastructure is an inevitable customer-centric future.
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This article is a technical deep dive into the future of the billing stack, written by our Co-founder and CEO, Dor Sasson. It explores how modern SaaS companies can rethink billing infrastructure to support more flexible, scalable monetization strategies — starting with entitlements at the core.
A huge thank you to Lotem Kaiser (Director of Product, Similarweb), Ronen Morecki (VP Payments, Monday.com), Brandon Walsh (Director of Product Monetization, Intercom), Robert Marki (Senior Billing and Monetization Engineer, Hotjar), and Alex Carrillo (Director of Product Monetization, Oyster) for their thoughtful feedback and real-world insights during the writing of this piece. 💚
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Prelude: Software GTM Purchase Models
In order to understand why monolithic all-in-one billing software is obsolete, we first need to examine where complexity and rigidity originate in the stack - and why all existing solutions and approaches have failed so far. We’ll do this by evaluating the architecture from the perspective of the end customer's purchase experience.
By large, there are three main GTM purchase models in which Software of any type and kind is sold:
- Traditional Sales (Enterprise sell)
- Self-service (eCommerce transactional sell)
- Partnerships: MSP, Resellers, OEMs
Some organizations are more likely to begin their journey with one over the other; B2C mobile apps are more likely to sell self-service first, Cyber Security Enterprise software is more likely to be sold via traditional Sales. However, 99% of organizations selling some type of digital goods will grow in revenue to a point where they’ll have to support all three models.
Organizations starting with Self-service will experience a completely different set of challenges as they grow in revenue compared to others starting with Traditional Sales, and vice versa. Their revenue anatomy (Purchase journey, ACV/TCV, Sale cycle, Pipeline generation, ROI, transaction volume, fulfillment and provisioning, billing and payment schedules and terms, taxation, collection, reconciliation, recognition and more) will look very different and will dictate different architectures and solution suites. When it comes to Self-service first environments, Product/R&D are typically the organization driving Billing solutions, but in Traditional Sales focused environments, Sales and Finance are the main drivers. These teams and GTM environments have different sets of requirements and priorities -and in many times - contradictingrequirements:
Yet, even today, so many companies continue to try to build or buy all-in-one billing solutions, with the intention to solve all use-cases altogether, at the finest grade. This double, or triple or even quadruple expectation, playing whack-a-mole to battle feature parity again and again is bound to yield poor results. No one can be everything to everyone - neither internal teams nor vendors.
The reason is because most companies do not experience any issues with their billing infra until it is too late. The conflict between Self-service and Traditional Sales billing is a snoozed time-bomb; most organizations glide past it, completely unaware to the severity and depth of the problem, sometimes getting to beyond $100m in ARR. It is only when the organization is big enough to strategically introduce a new GTM purchase experience in-order to expand further, when everything explodes.
“It is only when the organization is big enough to strategically introduce a new GTM purchase experience in-order to expand further, when everything explodes. “
The Rise and Fall of the Monolith Billing Engine
At first, most billing engines tried to do something simple; automate the entire purchase experience altogether. Built around static subscriptions and simple pricing models, they were very effective in doing so.
Today, it is clear that all-in-one simple mindset suffocated Software businesses GTM agility. Here are just a few reasons why:
- Lack of flexibility in adapting to new pricing models - Usage-based, hybrid, and now AI-powered software
- Integration headaches: forced businesses into rigid schemas, APIs and workflows, resulting in vendor lock-in
- Tried to solve everything for everyone: built for product and engineering, scaled for finance. Carrying a hammer, everything looks like a nail, the monolithic engines continued to develop more and more features in-order to stay relevant, resulting in a very mediocre piece of software. As they continued to try to maintain all of it, they started to slow down innovation.
- Couldn’t excel in both self-service and traditional sales environments resulted in being mediocre at both.
The hidden complexity and rigidity of monolithic billing architectures
But the reality is that billing is far more complex; Self-service purchase and Traditional Sales purchase are entirely different and require a completely different architecture design and approach. Engineers who face this every day know the truth about Billing.
In Self-service environments, the purchase begins with the end customer:
Note how everything is fully automated and designed to operate at high-volume and scale, and allow for seamless online transactions, around a standardized and well optimized product catalog and payment flows.
Businesses focusing on Self-service revenue are primarily concerned about:
- Transaction volume
- Conversion rates (free to paid, monthly to annually)
- Approval rates (Payment success)
- Tax and rev-share costs optimization
- Purchase UX - promotions, campaigns and buyer experience
In Traditional Sales environments, the purchases begins with a Rep (AE/AM):
Note how the architecture center of gravity is the Quote-to-Cash (aka Order to Cash, Q2C). Many of the workloads are intentionally manual, and designed to support flexible and bespoke billing and payment terms, with high focus on financial governance.
Businesses focusing on Traditional Sales revenue are primarily concerned about:
- Revenue reporting and forecasting
- Sales Capacity planning: ACVs vs Quotas and Reps OTEs
- Contract time to close optimization
- Quote generation efficiency
- Flexible terms: billing schedules, payment terms, renewal terms
Monolith billing engines always strive to stitch, solve and be competitive for all use-cases and environments. Large Software organizations result in “building around the vendor” in-order to allow their business to continue to grow and expand their GTM options, budgeting both for 3rd party costly vendor together with in-house team to build and maintain around and on-top of the vendor.
The truth is your Monetization Infrastructure should look like AWS, not Salesforce
The unbundled monetization infra revolution
If you were building software from scratch today, would you architect it like Salesforce—a rigid, one-size-fits-all system that forces you into its way of doing things? Or would you take inspiration from AWS—an infinitely flexible, modular, API-first infrastructure that lets you compose exactly what you need, when you need it?
Billing has been stuck in a Salesforce-era mindset for too long. A monolithic, all-in-one system that dictates how you sell, invoice, and fulfill—rather than adapting to your business model. But monetization infrastructure should look like AWS: a composable set of single-purpose, interoperable services that give you the agility to price, package, and sell software on your terms.
🔹 Modular, single-purpose services – The AWS approach: each service does one thing exceptionally well.
🔹 Interoperability & extensibility – Built to integrate, not lock you in.
🔹 Decoupled provisioning & billing – Just like AWS separates compute, storage, and networking, monetization should separate the packaging, the pricing, the billing schedules and the payment terms etc.
The truth is your monetization infrastructure should look like AWS, not Salesforce
Monetization is a strategic enabler. The old world of monolithic billing is about invoicing transactions; the new world of unbundled monetization is about optimizing revenue, buyer experience, and growth. The choice is clear: Do you want a rigid system that dictates how you sell—or a flexible infrastructure that empowers it?
Why now? The forces driving unbundled monetization infra.
There are multiple forces pushing the market out of monolith billing and towards a composable vision:
- AI-first software is rewriting the rules – Dynamic, usage-based, and hybrid models demand agility in pricing and packaging.
- SaaS giants must evolve or die – The pressure to innovate on GTM models is existential.
- Revenue expansion is multi-channel – Growth requires self-service, sales-led, and partner motions—no monolith can support them all without trade-offs.
- The billing market is in upheaval – Stripe is doubling down on Stripe Billing, while Zuora exits the public markets. Companies are rethinking their stacks, making bold rip-and-replace decisions at renewal.
- CPQ is back—but different – AI-powered sales tools are supercharging GTM teams, requiring structured governance for quoting, deal flow, and commissions. Manual quoting is becoming extinct.
Pioneering the Future of Unbundled Monetization Infrastructure with Stigg
The shift from monolithic billing to Unbundled Monetization Infrastructure isn’t just a theory—it’s happening now, and Stigg is leading the way. Stigg was built from the ground up to solve the monetization challenges of modern SaaS and AI-first businesses by offering a composable, API-first infrastructure that gives companies full control over how they price, package, and sell software.
Stigg introduces a new set of primitives and APIs, as well as well-thought & well-engineered flexible schema that completely decouples commercial concepts from code. With Stigg’s entitlement and provisioning layer, any pricing model, any monetization flow can be supported, via any billing platform.
Unlike legacy billing solutions that force companies into rigid structures, Stigg is setting the foundations for a unified provisioning layer, supporting all GTM purchase experiences: Self service, Traditional Sales and Channels. By doing so, Stigg enables:
- ✅ Decoupled pricing, entitlements, and billing – Allowing businesses to iterate on GTM models without backend limitations.
- ✅ Modular, plug-and-play components – Seamlessly integrating into existing finance, sales, and product workflows.
- ✅ AI-driven monetization – Powering dynamic pricing, real-time metering, and predictive revenue intelligence.
- ✅ Flexibility at every stage of growth – Supporting self-service, sales-led, and partner-driven motions without compromise.
Stigg is redefining monetization infrastructure, ensuring businesses can innovate at the speed of their market, not be held back by it.
