Melissa Perri sat down with Christopher Li, SVP of Product at Xactly on this episode of the Product Thinking podcast. In this enthralling episode, Christopher shares his journey from engineering to product management and the challenges his company faced in adopting the Scaled Agile Framework.

Christopher has spent the past 15 years in product management, working through different functions and eventually becoming the SVP of Product at Xactly, an enterprise software provider. Christopher explains that when he joined the company, it lacked maturity in terms of roadmap and product management practices. To address this, they instituted the Scaled Agile Framework (SAFe) to complement their annual roadmap planning process, which allowed them to balance predictability and innovation.

If you're interested in learning about navigating enterprise software and finding the right balance between planning and execution, this is the episode for you.

Christopher discusses the approach he took to balance predictability and innovation at Xactly by phasing in an agile methodology alongside the Scaled Agile Framework (SAFe). Recognizing the limitations of an annual roadmap in maintaining both long-term vision and day-to-day execution, Chris and his team introduced a quarterly discipline through SAFe. This method allowed them to complement their existing roadmap with a more adaptable and dynamic approach. However, Chris also acknowledges the challenges that came with adopting SAFe, particularly in terms of change management and process fatigue. Despite widespread buy-in, the sheer number of moving parts within SAFe necessitated a gradual integration rather than a wholesale adoption, which ultimately allowed for more tailored and effective process improvements.

Christopher discusses the transition from having distinct roles for Product Owners (POs) and Product Managers (PMs) to a more integrated approach. Historically, these roles were segregated, with POs focused internally on the R&D organization, while PMs were more market and customer-facing. However, Li's team found more long-term benefits in merging these roles into a hierarchical structure. As POs gain experience in implementing and shipping products, they naturally transition to PM roles, taking on market-facing responsibilities while delegating internal tasks to incoming POs. This shift not only enhances collaboration but also boosts morale by offering a clearer path for career progression, allowing individuals to explore various facets of product management based on their interests and strengths.

Li highlights the value of cross-functional experience in developing strong leadership within product management. He notes that many of the best leaders he has worked with have experience in various roles beyond product management, such as sales or engineering. This diverse experience gives them a well-rounded perspective on the business, enabling them to better understand how different teams and functions operate and how they can work together effectively. Li mentions that when he started his career, product management was not as well-defined, and people often found their way into the field through other roles. This organic approach helped build a broader business understanding, which is now more structured due to the growing allure of product management as a career path.

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Previous guests include: Shruti Patel of US Bank, Steve Wilson of Contrast Security, Bethany Lyons of KAWA Analytics, Tanya Johnson Chief Product Officer at Auror, Tom Eisenmann of Harvard Business School, Stephanie Leue of Doodle, Jason Fried of 37signals, Hubert Palan of Productboard, Blake Samic of Stripe and Uber, Quincy Hunte of Amazon Web Services

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