SaaS Entitlements - A roundup of some of the best thinking & writing on the internet about a critical & misunderstood architectural layer

Every SaaS company has entitlements. They're the rules that define what a customer can access based on their plan, subscription, or contract.

Almost no one talks about them. Yet nearly everyone builds them in-house — even though they’re not core to product value.

That decision leads to real problems:

• Entitlements get hardcoded into app logic

• Developers get pulled into billing work they don’t want to do

• Monetization gets slower and harder to evolve

In a world where small teams are shipping faster with AI tools, hardcoding entitlements is a liability. You’re locking your business into:

1. An infinite roadmap of plan logic and exceptions

2. Developer resentment and burnout

3. A lack of pricing and packaging agility — which kills GTM velocity

We’ve been pushing hard to help teams understand why entitlements matter — and we’re not alone. Here’s a roundup of some of the best writing and conversation on this topic.

🧠 Best Thinking on Entitlements

• Shar Dara (ex-Stripe, Vercel) How do you know what features your users should access?

• Fynn Glover (Schematic) Why every SaaS app needs an entitlement layer

• Arnon Shimoni (Paid) Why you should separate billing from entitlements

• Sandeep Jain (MonetizeNow) Entitlements, Part 1 Entitlements, Part 2

• AWS SaaS Factory + LocalStack Simple and flexible SaaS entitlement management

🎙️ Engineer & Operator Perspectives — Real-World Lessons on Entitlements & Monetization

Calendly / Mailchimp

• Justin Gagnon — Make Monetization a First-Class Citizen

• Aubrey Rhodes — Lessons from Mailchimp & Workful

Expo / LaunchDarkly

• Joe Ryan — From Seat-Based to Usage-Based Pricing

Supabase

• Kevin Gruneberg — Building Billing & Monetization at Supabase

Localstack

• Alexa Gjonca — Why Great Pricing Strategies Don’t Get Implemented

Salesloft

• Scott Mitchell — Turning Pricing Into a Metadata Exercise

Saleo

• Dan Hellerman — Getting New Features in Customer Hands

Koala / Segment

• Tido Carriero — Segment’s Pricing Journey & Building Koala

Pagos

• Ryan Burke — Monetization as Infrastructure

Pangea

• Rob Truesdell — Building Monetization Infrastructure

Logik.ai

• Fazal Gupta — Evolving Enterprise SaaS

Crossbeam / HubSpot

• Harker Roslin — Asking the Hard Questions About Pricing

Firetiger / Cloudflare

• Rustam Lalkaka — GTM Strategy & Product Velocity

💼 RevOps, Finance, and Monetization Strategy

• Thomas Sellers (UiPath, Citrix) — Leading Monetization at Scale

• David Caughman (Docker, Stripe, Simon-Kucher) — Pricing as Product

• Kayvan Dastgheib — Enterprise Monetization in Practice

If you’re building entitlements in-house in 2025, make sure you’ve thought through the real cost — in developer time, monetization agility, and GTM speed.

If you want to talk entitlements or share your setup, drop us a note or get started today.