Blog - Steve Bussey

Flexibility in Billing Systems Is Crucial for Adapting to Market Changes: Conversation with Steve Bussey

Fynn Glover

Having built a couple of different billing systems for Salesloft as they were scaling, and now having co-founded Supered which us growing quickly, Steve Bussey has learned a ton about monetization operations in high growth SaaS businesses.

Steve recently sat down with Schematic on the Monetizing SaaS podcast, where he shared his journey, his insights on current trends, and the critical lessons he's learned about pricing, packaging, and monetizing B2B SaaS.

From software developer on a rocketship to founding CTO

An internship at a web agency led Steve to develop a successful software product, sparking his interest in SaaS. He joined SalesLoft early in their journey and spent seven years helping the company grow from ~$1M to nearly $100 million in revenue.

Along the way, he knew his goal was to become a startup CTO, so he leaned into learning as much as possible about various technical and leadership skills. After Salesloft, Steve co-founded Supered, which he's currently building, and which has grown super quickly in the Hubspot ecosystem.

Trends in B2B SaaS

“I think companies now prefer comprehensive solutions that consolidate multiple functionalities.”

Steve identified a couple of trends he's thinking about in B2B SaaS:

  1. Broader offerings vs. Point solutions: Contrary to past advice of focusing on a niche, companies need SaaS vendors to do more than a single job and so will start to prefer broader suites that consolidate multiple functionalities.

  2. Efficiency with Less Funding: The trend towards achieving more growth with less funding is becoming more prevalent. We're going to see a lot of companies grow to significant revenue with far fewer employees and far less funding.

Lessons in Pricing, Packaging, and Monetization

“Changing pricing models is painful and should not be done lightly....If I wanted to flip to a usage model instead of a flat model, how difficult is that going to be?”

Steve's extensive experience with pricing and monetization in SaaS offers valuable insights for product & engineering leaders about why monetization operations is so complex and also highlights the inflexibility around pricing & packaging that hamstrings most B2B SaaS companies:

  1. Approach Pricing Changes with Caution: Pricing changes impact the entire product and can be complex. Frequent changes can lead to significant pain points for engineers, as well as GTM, so it’s essential to thoughtfully design and test pricing models before implementation.

  2. Involve Revenue Leaders in Development: Steve advises having a revenue leader involved in the development process to ensure the system meets business needs. Misalignment can result in building systems that fail to support sales effectively. “There has to be some type of revenue leader there... Otherwise it doesn't matter how good your architecture is.”

  3. Build Flexible Systems: Avoid overly rigid systems that limit the ability to adapt to new pricing models or customer demands. Flexibility is crucial for evolving with the company’s growth and market changes. “If I wanted to flip to a usage model instead of a flat model, how difficult is that going to be?”

  4. Consider Buy vs. Build: Evaluate whether to build homegrown monetization infrastructure, or buy an off-the-shelf product. Steve learned this lesson after investing significant time in a custom billing solution at Salesloft that became obsolete due to a shift in sales strategy. “Ask yourself if homegrown monetization infrastructure is something we should really be building."

Where to Find Steve and Learn More About Supered

Steve can be found on LinkedIn for business-related updates and on X for engineering discussions. To learn more about Supered, visit their website at