Pricing & packaging decisions don’t just impact sales—they shape a company’s entire product & operational structure.

When Ryan Burke joined Pagos, he saw firsthand how early commercial decisions create long-term technical & business complexity.

This episode of Monetizing SaaS is packed with insights for founders, product leaders, and pricing strategists—especially those navigating multi-product SaaS growth.

Key Takeaways:

🔹 Early pricing & packaging decisions create long-term challenges.Pagos started with bespoke enterprise sales, leading to inconsistencies in how pricing & entitlements were enforced. As the company scaled, cleaning up the debt became a major project.

🔹 Multi-product SaaS requires a clear strategy for cross-selling.Pagos originally had separate products with different websites and UX, making cross-sells difficult. Unifying the experience improved usability and helped drive expansion revenue.

🔹 Pricing and packaging should be treated as a product decision, not just a sales decision.Ryan highlights how pricing, like product documentation, should be a test of clarity. If you can’t explain it well, your customers won’t understand its value.

🔹 Entitlements & metering must be structured early.Pagos initially enforced pricing entitlements in multiple ways—metadata, feature flags, custom logic. Standardizing this earlier would have prevented major tech & commercial debt.

🔹 Self-service isn’t just for SMBs—it’s an enterprise growth lever.Many enterprise deals start with frustrated analysts signing up for a self-serve demo, then advocating for the product internally. Underinvesting in self-service can slow down enterprise adoption.

What We Cover in This Episode:

🛠️ How Pagos evolved from separate products into a unified SaaS platform

💰 Why pricing and packaging should be a product decision, not just a sales decision

📊 How self-service can drive enterprise adoption

🚀 The challenges of enforcing entitlements and metering in SaaS pricing

🔍 Why early commercial decisions create pricing & packaging debt

⏳Chapters

00:00 – Intro & Welcome

01:10 – Ryan’s background: Braintree, High Note, and joining Pagos

03:00 – What drew Ryan to interactive media & product design

06:30 – Lessons from 8 years at Braintree: scaling, management, & velocity

09:45 – The move to High Note: Going from PayPal to a startup

12:10 – Why fast iteration speed matters in early-stage startups

15:30 – Joining Pagos: Why payments analytics is such a huge gap

18:20 – The complexity of enterprise payments & multi-processor setups

20:50 – Pricing & packaging challenges in SaaS

22:30 – Why early-stage pricing decisions create long-term tech & commercial debt

25:10 – The challenges of multi-product SaaS pricing

27:15 – Standardizing entitlements & enforcing pricing across multiple products

30:00 – Why self-service isn’t just for SMBs—it’s an enterprise growth lever

32:00 – The similarities between documentation & pricing pages in product clarity

34:15 – How AI is lowering the knowledge barrier in payments analytics

37:00 – What Ryan has learned about scaling multi-product SaaS pricing

40:00 – Closing thoughts: What’s next for Pagos & where to learn more