The biggest mistake in monetization? Expecting too much from your billing system.

Fynn Glover

Insights on Monetizing SaaS with Rob Eanes, VP Product at WorkLeap

In a recent Monetizing SaaS episode, we sat down with Rob Eanes, VP Product at Workleap, which recently acquired the company he'd co-founded as CTO, Pingboard.

Professional Story & Career Journey

"I always enjoy the early stages of a startup."

Rob's career began during the dot-com crash, where he found a job at a small agency working on projects for both Fortune 500 companies and startups. This role exposed him to various business aspects beyond engineering, including sales and project management. After nearly a decade, he transitioned to independent consulting, which taught him the challenges of solo entrepreneurship.

Rob eventually moved to Austin, Texas, joining the startup ecosystem there. This led him to co-founding PingBoard, an organizational chart and directory tool. After ten years of leading engineering and growing the business, PingBoard was acquired by WorkLeap, where Rob is now VP Product and driving the integration of a broader suite of employee experience tools.

Lessons on Monetization, Pricing, and Packaging

"The biggest mistake? Expecting too much from your billing system."

Rob's experience with PingBoard gave him a front-row seat to the complexity B2B SaaS companies face to support monetization operations and evolve their pricing & packaging as they grow. Often, the company was faced with a hard trade-off: continue to ship new features, or divert engineering resources to support pricing & packaging changes.

This is a challenging situation to end up in, and it usually occurs because pricing is often an afterthought in the early days and then implemented over time in fragmented, homegrown systems that divert engineering resources and delay monetization initiatives. 

Here are 4 of the lessons he highlighted during our conversation:

  1. Understand Your Billing System's Limits Expecting a billing system to solve all your problems is a common mistake engineering leaders make, and they end up with full-time billing engineers as a result. Often what ends up happening is the tight coupling of your billing tool and entitlements in your application, and this forces the business to go through engineering to support monetization initiatives.

  2. Architect for Clear Data Flow Between Systems Most companies are dealing with a collection of disconnected tools and processes to support monetization operations like pricing & packaging changes, or custom configuration, or upgrade and downgrade paths. Ensuring that data flows clearly between systems like your application, CRM, CPQ, ERP, and billing system is critical.

  3. Managing Exceptions Custom pricing and exceptions can lead to a messy codebase, SKU sprawl, and a lot of varied customer state. This increases system complexity, making it harder to ensure accuracy, maintain code, and handle edge cases efficiently.

  4. The Hidden Costs of Custom Solutions

    Many engineering teams end up mired in building homegrown glue to support monetization ops. There's generally a set of familiar components: feature flags, hard-coded entitlements, admin consoles, integrations with business systems (e.g. billing & CRM), and the list goes on. Beyond the cost to build and maintain these systems, what often occurs is that pricing & packaging is tightly coupled in the codebase.

Where to Find Rob Eanes

To learn more about Rob Eanes and his work at WorkLeap, visit Rob is also available on LinkedIn for those interested in connecting with him.