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Jason Oakley

Building Productive PMM - I share practical advice, templates, and inspiration for founding product marketers.

Jason Oakley is a product marketing coach, consultant, and creator with over 10 years of experience building product marketing (PMM) functions from scratch.2 He is currently the founder of Productive PMM, a venture he started in January 2023.2 Oakley serves as a Marketing Advisor at UserEvidence, where he provides expertise on customer evidence and product marketing strategies.13

Previously, Oakley held senior positions in product marketing at several companies:

  • Senior Director of Product Marketing at Klue (December 2021 - March 2023)
  • Director of Product Marketing at Chili Piper (February 2020 - December 2021)
  • Director of Product Marketing at Uberflip (September 2019 - February 2020)2

Oakley is known for his expertise in customer evidence, product marketing, and go-to-market strategies. He emphasizes the importance of capturing customer and buyer insights to enable companies to use them effectively in marketing.1 He also advocates for the proactive collection of customer proof points throughout the customer lifecycle.1

In addition to his role at UserEvidence, Oakley is also a GTM Advisor for Navattic and has been involved in creating interactive demos for B2B SaaS companies.3 He is based in Toronto, Ontario, Canada, and describes himself as a proud father, Newfoundlander, Raptors fan, and lover of dad jokes.2

Highlights

Sep 4 · linkedin

This has happened to me more times than I can count. You spend hours drafting something — maybe a one pager. But it’s just not feeling “perfect.”

So, you delay sharing it internally.

Maybe you circulate it with a couple of people for vague “feedback.” But you never really push to get it out there. Ship a good enough version that people can actually use. You never say “it’s done for now” — use it.

So it sits.

And eventually a designer picks it up. Or your boss asks about it. Or sales comes looking for it.

But by then it’s outdated ⌛️

❌ New or changed features ❌ That customer is no longer with us ❌ That’s not the messaging we use anymore ❌ Our competitor is now saying the same thing ❌ Our branding has changed

So it's back to the drawing board. And all your time time wasted.

STOP 🛑 So much time is wasted on half-finished projects that never see the light of day.

For the majority of assets and content we take on as PMMs, there's a V0 you can ship in a few days. A version people can start testing, validating, and giving feedback on right away.

So the next time you’re working on something. Push to get a version out quickly. Something you can consider “done for now.”

It’s a way better way to validate what you have. Plus it’s wayyy more motivating to actually ship stuff.

You'll stop being the one that has to adjust to constant changes. And be the one who makes some change.

Jul 31 · linkedin

If you want to be a founding PMM Embrace being a product marketing generalist

There is just no way you’re going to be able to specialize in a startup with one or two PMMs.

🗓️ On Monday you might work on positioning 🗓️ Tuesday a new web page 🗓️ Wednesday a pitch deck 🗓️ Thursday market research 🗓️ Friday a product launch

Sprinkled in there you may have enablement requests, discussions about pricing, or a new competitor to investigate.

It’s not to say you can’t be stronger in one area coming into the role. It's important to know your strengths and your own personal positioning. You just can’t expect that to be the primary thing you work on.

Ever if your founder says it’ll be. Chances are that will change.

The founding role requires a founder mentality and that means adapting and learning whatever it takes to get the job done.

One day you may have the chance to grow the team and specialize, but for now, embrace the variety.

#foundingpmm

Related Questions

What inspired Jason Oakley to start Productive PMM?
How has Jason Oakley's experience at Uberflip influenced his approach to product marketing?
What are some key strategies Jason Oakley recommends for collecting customer evidence?
How does Jason Oakley's background in customer success shape his marketing advice?
What challenges does Jason Oakley face in his role at UserEvidence?
Jason Oakley
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Location

Toronto, Ontario, Canada