1 PMM, 3 layoffs, and a whole lot of learning, with Shawn Dye, Calendly
Update: 2025-11-28
Description
In this episode, we sit down with Shawn Dye, a product marketing manager who shares a candid look at his unconventional career path – from starting in HR to pivoting into product marketing after earning his MBA.
Shawn discusses his experiences at Zola and at various growth-stage startups across e-commerce, tech, and SaaS, highlighting the importance of building strong cross-functional relationships, especially with product managers.
He also opens up about facing three layoffs in a single year and how market volatility has shaped his perspective on career stability. Throughout the conversation, Shawn emphasizes the value of documenting your work, adapting quickly to new environments, and staying committed to lifelong learning.
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