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Revenue Operations

Everything you wanted to know about Billing Systems

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Contract amendments, usage-based pricing models, and self-service have made SaaS revenue more complicated than ever before. That’s why in today’s world, the integration of CPQ, usage, and billing is mission critical. 

In this webinar, Sandeep Jain, Founder and CEO at MonetizeNow, Lindsey Bailey, Finance Operations at Middesk, and Matthew Dubreuil, Revenue Ops & Strategic Alliances at DoControl, answer these key billing related questions: 

  1. What is the right architecture for billing? 
  2. When is the right time to change your tech stack? 
  3. How do you select your billing systems?
  4. What is the customer experience for billing?

“Everyone should care about billing. Whether you realize it or not, it touches every part of your business.”- Lindsey Bailey

Does your RevOps team work as closely with finance as you should? If not, it’s time to wade into the world of billing systems and bridge the gap between your two functions. As Lindsey Bailey says, “you want to be in lock step with each other.” The faster your revenue team can bill customers, the more deals you can close, and the faster you can scale. 

If your company is deciding whether to bring billing into your RevOps tech stack, it’s important to answer these 4 key billing questions:

What is the right architecture for billing?

First, you need to decide whether to buy best-of-breed tools for quoting, usage, and billing or to purchase one cohesive system to cover everything. In the era of SaaS contract amendments, Sandeep Jain, Founder and CEO of MonetizeNow, recommends having a single source of truth, especially for your product catalog. This is especially helpful for startups trying to iterate and scale fast.

When is the right time to change your stack?

If you're a Seed or Series A company, it’s easy to install a new billing system because there’s no need to migrate data. It’s especially important today since investors expect profitability from day 1. Having a pricing structure and the flexibility to iterate quickly can be a quick win. 


At Series A or Series B companies, you’ll typically deploy CPQ first. This gives you time to clean up your CRM data and center your business around contracts. Next, you can migrate your CPQ tool and replace your existing billing system. 

For Series C and later companies, you may already have a lot of processes and systems. Start a new CPQ tool on a contained business workflow for a new product, then migrate to your new billing system.

How do you select a billing system?

“If you’re a RevOps person now, you are being led into the billing conversation. You can’t ignore it anymore.” - Sandeep Jain 

Our panelists recommend these features when selecting a billing system: 

  • Native CPQ and billing
  • Robust product catalogs
  • Native usage billing 
  • Modern tools like APIs, payment processors, what-if modeling, and alerts
  • Revenue recognition 
  • Low engineering support required
  • A partner you like you and trust 

What is your customer experience in your billing system?

“RevOps has a responsibility to provide a seamless customer experience from presales to post sales. That involves not just the quoting piece but the invoicing piece.” - Matthew Dubreuil 

“It all comes down to trust,” says Matthew Dubreuil, Revenue Ops & Strategic Alliances at DoControl. Customers should be able to handle their billing, make changes to their quantities and usage, and even renew their subscriptions in your product itself. Invoicing should be easy to see and have clear pricing, prorations and more. At the end of the day, RevOps needs to care about billing; it’s all a part of the customer experience. 

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