Key Takeaways from SaaS Pricing Panel: Avoiding the Mistakes That Stifle Growth

Recently, our CMO, Guy Marion, joined a panel of pricing experts, including Sara Archer, VP of Sales at ChartMogul, Kyle Poyar, Co-founder and Operating Partner at Tremont, and Rob Litterst, Co-founder at PricingSaaS. Together, they brought decades of experience in pricing strategy together to discuss a critical topic for recurring revenue businesses: the pricing mistakes that hamper growth. The conversation revealed real-world insights about how smart pricing strategies can transform your business.

For those who couldn’t attend the session, here are some of the key takeaways you can learn from:

The Free Plan Dilemma

A clear trend emerged early in the discussion: companies are rethinking their generous free plans.

This pullback goes beyond economic reactions. It reflects a better understanding of how free offerings should work as part of the broader revenue strategy. Companies now see that overly generous free tiers can make the conversion to paid plans harder.

Understanding What Your Buyers Actually Value

The panel emphasized that most pricing challenges stem from a gap between how companies think about their product’s value and how customers see it. Rob noted that many companies create pricing packages that “look good” without truly understanding what drives customer willingness to pay.

Kyle Poyar expanded on this idea, explaining that effective pricing requires more than just a traditional buyer persona. It needs a deeper understanding of economic value creation and customer psychology. He described how product-market-pricing fit must include pricing as a core component, not an afterthought.

The Value Metric Question: Choose Wisely

A powerful insight came when Kyle discussed value metrics – the primary unit around which you charge customers.

This observation led to a discussion about the dangers of simply copying competitors’ pricing models. The panel shared examples of companies that gained market advantage by breaking from industry norms, like an RFP tool that disrupted competitors by charging based on concurrent RFPs rather than seat licenses.

HubSpot’s Pricing Evolution

Drawing from his experience at HubSpot, Rob shared how the company transformed its retention rates from a concerning 70-75% to nearly 100% by adjusting its pricing model. Initially using standard “good, better, best” packages, HubSpot introduced contacts as a value metric while maintaining subscription tiers.

This dual-axis approach allowed customers to naturally spend more as they got more value from the platform. It ultimately put HubSpot on track for a successful IPO, showing how pricing can dramatically change business outcomes.

The Testing Imperative

Guy Marion emphasized that testing is crucial for pricing success. At Brightback (now Chargebee Retention), his team conducted hypothetical pricing discussions and implemented usage- and outcome-based pricing agreements. They maintained the right to bill for overages, allowing them to measure what companies would actually pay without prematurely committing to inflexible structures.

This provides valuable insights into customer reactions without implementing complex pricing structures.

New Pricing Models and What They Mean

The panel noted that we’re entering what Guy called a “golden age” of pricing approaches. As Guy explained, while some might view the market through the lens of “subscription fatigue,” he sees it instead as “the golden age of models that people can use now to best align” their pricing with customer value. This shift from pure subscriptions to hybrid models that incorporate usage and outcomes gives businesses more tools to create pricing that actually reflects the value, for example, based on user access to the software, agentic outcomes, or multiple product lines.

This becomes especially relevant for AI products, where Kyle pointed out most companies have approached pricing “technology first as opposed to customer first.” The panel referenced a Wall Street Journal article stating, “Nobody knows how to price AI,” though they disagreed with this premise. Guy added that Chargebee is seeing many “very fast-growing AI-adjacent businesses” still figuring out their pricing, creating excitement but also questions about long-term growth.

Freemium vs. Trial: Context Matters

When discussing acquisition models, Rob provided a practical view of when different approaches work best. Free trials shine in sales-led motions where customers feel they’re losing something valuable after the trial ends. Freemium models work better with product-led growth strategies focused on expanding users and learning from how they use the product.

Future-Proofing Your Pricing

The conversation closed with thoughts on how pricing strategy must evolve with your business. What works when you’re starting out likely won’t serve you at scale. The panel agreed that companies need a thoughtful, testing-based pricing strategy that grows as both the market and their products mature.

What became clear throughout the discussion is that pricing serves as a strategic lever that significantly impacts growth, retention, and business health, moving well beyond a simple tactical decision. The right approach connects customer value with revenue, creating a model that grows naturally with your company. Watch the full panel discussion here and reserve your copy of the 2025 State of Recurring Revenue and Monetization—a deep-dive report on the emerging pricing strategies, AI adoption challenges, and organizational best practices defining the future of B2B subscription success.