Jason Oakley: Founder of Productive PMM & DemoDash on Lean PMM Teams, The Rise of Interactive Demos, and How to Scale Impact Without Burning Out

On this episode of Embracing Erosion, Devon sits down with Jason Oakley. Jason is an experienced product marketer, coach, and entrepreneur, recently recognized as a top 100 product marketing influencer. He’s the founder of Productive PMM, where he provides tools, coaching, and inspiration to help founding and solo PMMs deliver meaningful impact without burning out. He’s also the cofounder of DemoDash, an interactive demo agency focused exclusively on Navattic customers, helping SaaS companies turn product demos into one of their most effective go-to-market assets.

In their conversation, they discussed what Jason is hearing from PMMs navigating leaner teams and tighter budgets, how interactive demos are evolving as a GTM advantage, the systems and frameworks he’s built through Productive PMM to help solo PMMs scale without burning out, and much more. Enjoy the conversation!

Key Takeaways

Interactive demos are high-intent content. Buyers exploring a demo are already deep in the evaluation journey — making them one of the most valuable GTM assets when done right.
Story beats features. Great demos tell a narrative through personas and scenarios rather than a simple feature tour, helping buyers visualize real-world use cases.
Keep demos fresh. Interactive demos aren’t “set and forget.” The best teams track engagement data, refine messaging, and update stories regularly.
Founding PMMs wear every hat. Today’s PMMs are expected to handle positioning, segmentation, and pricing and execution — demanding strong systems and boundaries.
Confidence compounds speed. When PMMs trust their instincts and have leadership support, they move faster and make better strategic calls.
Build systems before automation. Repeatable playbooks, workflows, and light automation come before layering in AI — structure drives sustainability.