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 exit

• How he used LinkedIn to overcome imposter syndrome and grow his personal brand

• The most common blind spots for PMMs moving into leadership

• How he turned his expertise into a scalable business

Things 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 mindset

This 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.co

• Hire Andrew as your coach: https://deliveringvalue.co/coaching