May 2026 Summaries

The transition to a usage-based billing (UBB) model presents challenges in maintaining customer trust, primarily due to issues of clarity and communication. While the economic benefits of UBB are often clear, the real test lies in how the billing is integrated into the customer experience. Customers can become frustrated when the new billing model lacks transparency, leading to confusion about spending and the value they receive, which can result in billing disputes and operational inefficiencies. Successful UBB transitions require setting clear expectations, treating the first invoice as a trust-building moment, providing customers with visibility and control over their spending, and reinforcing the value of the new model. Companies that excel in these areas create a billing experience that aligns with customer expectations and demonstrates the value of the changes, thereby enhancing trust and satisfaction.

Lucia Zhang reflects on her experiences at Orb, a company focused on building products in the billing space, emphasizing the importance of precision and trust when every product decision affects revenue. She discusses the significance of usage-based pricing and how it shapes the next generation of technology products, highlighting the unique challenges and opportunities in this emerging field compared to more mature markets. At Orb, the product management role is deeply intertwined with engineering and design, fostering a collaborative environment where each function has distinct responsibilities. Zhang underscores the importance of understanding customer needs and maintaining domain expertise to make informed product decisions. She describes a high-trust, high-expectation culture where autonomy is earned through deep understanding, and there is an emphasis on prioritizing impactful opportunities over minor improvements. The work at Orb is characterized as greenfield, with substantial opportunities for discovery and innovation, making it an ideal fit for product managers who thrive on exploration and meaningful contributions.

AI companies are navigating complex pricing strategies amidst uncertainty, aiming to balance growth and monetization by focusing on both cost and commercial levers. A recent listening tour revealed that companies are considering pricing on multiple timelines, from initial adoption strategies like freemium models to long-term monetization goals. The challenge lies in effectively communicating value and differentiating products, with some firms finding success by separating cost discussions from value, and emphasizing differentiated features. Case studies highlight the importance of pricing strategies in managing customer perceptions, with lessons learned including the potential benefits of friction and the necessity of pricing for loyalty and differentiation. Companies are advised to use a structured approach to gather pricing signals across various dimensions, allowing for a more comprehensive understanding of the impact of pricing changes. Through nuanced pricing conversations and strategic adjustments, AI companies strive to build sustainable, value-driven partnerships with their customers.

Orb has reimagined the role of webhooks in modern billing systems, transitioning them from mere notification tools to vital activation layers that connect billing events to business operations in real time. This approach allows companies using usage-based pricing models to respond immediately to changes such as plan modifications, failed payments, and usage thresholds. Orb's webhook system is designed to ensure reliability and efficiency through at-least-once delivery, automatic retries, and configurable endpoints, while SDK helpers in various programming languages facilitate integration. To address the challenge of large webhook payloads, Orb introduces a slim webhook feature that trims unnecessary data, optimizing processing and reducing risks associated with outdated information. This streamlined method reflects a broader shift towards real-time, actionable billing, enabling businesses to run more effectively on their billing systems rather than merely managing them.

Usage-based billing (UBB) represents a strategic shift for SLG companies, aligning revenue with actual product value and fostering innovation, but it also necessitates comprehensive organizational changes. Transitioning to UBB impacts various business functions, including sales, finance, customer service, and engineering, by altering compensation structures, contract negotiations, forecasting, and billing processes. Sales teams face challenges adapting to quota pressures and pricing variability, while finance departments often rely on manual processes to accommodate complex contracts. Customer service teams may struggle with maintaining trust due to billing discrepancies, and engineering resources can become strained by the need to handle custom pricing logic. Additionally, revenue operations must adjust their forecasting models to account for the continuous and unpredictable nature of usage-based revenue. Companies that successfully implement UBB treat it as a holistic system change rather than a simple pricing adjustment, ensuring seamless integration of all business processes and maintaining accurate, real-time data across departments.