Why This Product Marketing Expert Walked Away From a $2B Exit—With No Regrets (Jason Oakley)

What makes someone leave a high-paying product marketing role just before a massive acquisition?In this episode, I sit down with Jason Oakley—founder of Productive PMM and co-founder of Demo Dash—to unpack the bold career decisions that shaped his journey in tech. From leading product marketing at a hypergrowth startup to becoming a full-time creator and consultant, Jason shares the systems, mindset shifts, and lessons that helped him bet on himself.We talk about what it really takes to succeed in product marketing today—and why your biggest edge might come from making uncomfortable moves.If you're a product marketer, startup operator, or aspiring solopreneur, this one's for you.In this conversation, you'll learn:Why Jason left a senior product marketing role before a $2B exitHow he used LinkedIn to overcome imposter syndrome and grow his personal brandThe most common blind spots for PMMs moving into leadershipHow he turned his expertise into a scalable businessThings to listen for:(00:00) Intro(08:54) Jason's early life and entrepreneurial spirit(09:55) Thank you to our sponsors, Navattic & Appcues(12:40) Making hard career decisions as a product marketer(22:10) Real talk for young professionals in tech(28:24) Becoming a product marketing thought leader(30:23) Overcoming imposter syndrome on LinkedIn(32:39) Launching digital products as a PMM(38:29) Why practice beats perfection(43:39) Lessons from managing a team(55:13) Work-life balance and founder mindsetThis episode is presented by:Navattic: Interactive Product Demo Software - https://navattic.com/value Appcues: User Engagement for SaaS - https://appcues.com/value Resources:Connect with Jason:LinkedIn: https://www.linkedin.com/in/oakleyjason/ Productive PMM official website: https://www.productivepmm.com PMM Files Newsletter: https://productivepmm.com/newsletter Connect with Andrew:LinkedIn: https://www.linkedin.com/in/andrewcapland/ Substack: https://media.deliveringvalue.coHire Andrew as your coach: https://deliveringvalue.co/coaching

There are no comments yet.

Please log in to write the first comment.