Harker Roslin shares his career journey from teaching philosophy to working in tech and product leadership roles. He discusses his current role at HubSpot and the focus on ease of use and time to value. Harker also talks about the importance of pricing and packaging in B2B SaaS and the need for intentional decision-making and trade-offs. He emphasizes the alignment between the pricing roadmap and the product roadmap and the impact of pricing changes on the product development process. The conversation explores the challenges of implementing and managing monetization in B2B SaaS companies. The main theme revolves around the concept of rigid infrastructure and the impact it has on pricing and packaging. The conversation highlights the importance of choosing flexible tools and making foundational decisions that allow for future scalability. It also emphasizes the need for clear communication and documentation in order to effectively manage pricing and packaging. The conversation provides insights into the complexities of handling customer exceptions, dealing with legacy customer sets, and the potential technical debt that can arise from pricing decisions.