Credit to Cash Leaders | Episode 01

Topic: The Billing Backbone: The Critical Connection Between Invoices and Orders

Why do so many finance teams still struggle with billing accuracy, revenue leakage, and invoice disputes—even with modern ERPs and CRMs?

In the first episode of Credit to Cash Leaders, we sit down with Brandon Polson, Director-level global Order-to-Cash leader at Insight Software, to unpack one of the most overlooked foundations of O2C success: the billing backbone.

With over a decade of hands-on experience scaling O2C operations—from high-growth internet service providers to complex, acquisition-heavy SaaS environments—Brandon shares practical, no-fluff insights on why orders are the foundation of invoices, and how weak handoffs between sales, finance, and billing quietly erode revenue.

In this episode, Brandon walks us through real transformation projects, where automation—not hype-driven AI—delivered measurable efficiency, reduced manual effort, and rebuilt trust in invoicing systems.

Here’s what we unpacked in this episode:

👉 Why orders—not invoices—are the true source of billing accuracy

👉 How weak CRM and order structures lead to invisible revenue leakage

👉 The “handshake problem” between sales and finance—and where context gets lost

👉 How rebuilding mass actions and audit trails eliminated system failures

👉 Why AI is not always the answer for invoice validation

👉 How automation using existing tools outperformed AI-based approaches

👉 Achieving 30–40% time savings in invoicing—and the roadmap to 70%+

👉 Brandon’s phased view of AI in O2C: revenue leaks → analytics → automation → security → people

👉 Leadership advice for finance professionals navigating AI, growth, and change

One insight that really stood out:

🗣️ “Orders are the foundation of invoices. Without solid orders, your invoicing leaks revenue.”

If you work in Order-to-Cash, billing, credit, AR, or finance transformation, this episode offers deeply practical lessons on building resilient billing systems, avoiding revenue leakage, and applying automation with intent.

Chapters

00:00 – Welcome to Credit to Cash Leaders

01:30 – Brandon’s O2C journey and scaling operations

04:00 – Why orders are the foundation of invoices

06:30 – CRM gaps, manual work, and revenue leakage

09:00 – Rebuilding mass actions and audit trails

12:00 – Invoice validation: AI vs automation

15:00 – Efficiency gains and human-in-the-loop design

18:00 – The future of AI in Order-to-Cash

23:00 – Leadership advice for finance professionals

26:00 – Closing thoughts

📌 Subscribe for more conversations with O2C, credit, billing, and AR leaders

📩 Follow for upcoming episodes on Credit-to-Cash transformation, automation, and AI