Product Marketing Life 1 PMM, 3 layoffs, and a whole lot of learning, with Shawn Dye, Calendly
Nov 28, 2025
Shawn Dye, a Product Marketing Manager with experience across startups, shares intriguing insights from his unconventional career journey. He discusses the emotional toll of facing three layoffs in one year and how that shaped his views on stability. Shawn emphasizes the importance of building strong relationships within teams, adapting quickly, and documenting work to enhance customer empathy. He also critiques the polished images often found on LinkedIn, urging for more authentic narratives about the challenges of being a solo PMM.
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Customer Proximity Drives PMM Value
- Centering customers and direct conversations keeps PMM work grounded and impactful.
- Shawn values roles that let him speak to customers and pull actionable insights into product strategy.
Embrace Nonlinear Career Progression
- Accept non-linear career paths and expect zigzags rather than straight ladders.
- Stop overproducing to prove worth; take smarter risks and surface insights sooner.
Always Record And Save Decisions
- Record everything and save meeting notes to protect yourself and build credibility.
- Use records to synthesize decisions and resolve cross-functional disputes quickly.