Jason Oakley

Productive PMM

Founder 

Navattic

Navattic empowers prospects to get hands-on with your product earlier in the buying journey through no-code interactive demos.

GTM Advisor

UserEvidence

UserEvidence automates social proof for GTM teams. Generate verified customer evidence, product stats, and ROI data in minutes. Game-changing B2B companies like Pendo, Workato, Gong, Jasper.ai, and Ramp rely on UserEvidence to boost buyer confidence, shorten sales cycles, and increase win rates.

Marketing Advisor

Klue

Senior Director of Product Marketing

Chili Piper

Chili Piper is the most advanced routing and scheduling software for B2B revenue teams. 
We solve interesting problems, live and breathe our core value of “help,” and have a ton of fun doing it while fully distributed around the world — powered by espresso and hot sauce.

Director of Product Marketing

Hey Rocco 

The relationships we have with young loved ones are some of the most extraordinary. But, they can often be difficult to maintain, especially if you live far apart. Hey Rocco is a unique gift that creates a lasting connection between children and far away family members. 

• Self-published a children's book focused on connecting distant family members.
• Launched and promoted a successfully funded Kickstarter campaign. 
• Created a monthly pen pal subscription for kids.
• Drive customer growth and retention, product development, and content creation.

Author and Co-Founder

Uberflip

• Lead a team of two product marketers, covering all areas of customer and product marketing.
• Manage multiple analyst relationships, briefings, and market research.
• Create and deliver product-focused event presentations and webinars. 
• Develop and evangelize company-wide product positioning and messaging.
• Strategize on go-to-market, pipeline, retention, and expansion initiatives with company leadership

Senior Product Marketing Manager

• Developed positioning and messaging around the impact of exceptional content experiences.
• Planned and executed the go-to-market strategy for all product and feature releases. 
• Built training and educational resources that drove product adoption, upsell, and retention.. 
• Enabled our sales and success teams with collateral, messaging, and competitive intelligence.

Product Marketing Manager

• Managed a portfolio of strategic customers including: SAP, 3M, and GE totalling $1M+ ARR.
• Conducted monthly and quarterly business reviews to measure and prove business impact.
• Educated and onboarded new customers to ensure their success.
• Fostered strong customer relationships across all levels of the org, from champions to executives.

Customer Success Manager

Houston

• Co-founded an app to help startups grow and get feedback from their pre-launch email list. 
• Worked closely with customers to fuel product growth, positioning and messaging. 
• Created all marketing materials and educational collateral for prospects and customers. 
• Managed our go-to-market strategy and growth initiatives. 
• Houston was sold in June 2017.

Co-Founder, Product and Customer Marketing Lead

Brownie Points Inc.

• Coached merchants in launching mobile customer loyalty programs
• Supported day-to-day success and strategy of customers and mobile app users
• Worked with sales managers on generating leads and on-boarding new customers

Director, Customer Success

Verafin

• Developed programs to drive customer advocacy, references, referrals, and customer stories. 
• Consistently achieved monthly referral and reference targets, including 114 referrals in one month.

Customer Advocate Marketing Manager

• Strategic rep for a FinTech platform helping banks and credit unions fight financial crime.
• Diagnosed problems and presented solutions to assist with fraud and anti-money-laundering. 
• Navigated sales cycles with executive buyers, procurement, and complex negotiations.
• Ranked among the top five highest selling sales reps in 2013.

Account Executive

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

I’m a product marketing coach, consultant, and creator with 10+ years experience building PMM functions from scratch.

I’ve built product marketing teams at three different companies (Klue, Chili Piper, and Uberflip) — each time starting as a founding PMM.

Now, I’m on a mission to help founding product marketers and early-stage PMM teams scale faster, focus on the right work, and drive real impact within their organization.

Also a proud father, Newfoundlander, Raptors fan, morning person, and lover of dad jokes. I once wrote a children’s book about a fox named Rocco.

It’s been 3 years since I started coaching founding PMMs.
I made a sales page in Notion, got one client, and the rest was history.
I’ve taken the next step in that journey...

It's the same focus, helping founding PMMs build their function, confidence, and careers.

But the format is different.

I just launched the first cohort of The Foundry 🔥 — a new group coaching program created specifically for founding and solo PMMs.

We're already a couple of sessions into the first cohort and I'm loving the format. This is work I was meant to do and I'm stoked to be doing it. 

If you're a founding PMM, or know one that's ready for something like this, keep reading. 

👉 The Foundry is not another course. It’s an intentionally small group coaching program built just for founding product marketers.

👉 Instead of high-level curriculum that doesn’t match reality, it's 5–8 peers who are in the same boat: building product marketing from scratch. They learn together, swap stories, and tackle real challenges they're facing right now.

👉 The program is flexible and built around the group. We’ll cover topics that matter most to everyone's situation, dive into live working sessions, and keep the conversation going between calls in a private chat.

If you're overwhelmed, running in circles, and feeling like nobody understands your job and the impact you can have — I think this program is for you.

I’m only doing one cohort per quarter, and the first one is already underway. But applications are now open for the next cohort, starting Jan 6th.

If you want to apply or learn more, drop me a quick DM.

And if you know (or manage) a founding PMM that could benefit from the program, please consider shooting them this post. It would mean a lot!

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

To all future founding PMMs...
Don’t miss this opportunity to work with one of the best.

My friend Alex Eaton, the founding PMM at UserEvidence, is looking to make his first product marketing hire.

This is a major hire for Alex. And the dream role for the right person. One that will require a founding PMM mindset. 

For that reason, it's the perfect place to get the founding PMM experience, while still having the direct support of a great mentor. 

And trust me, Alex is awesome. 

Not to mention:

👉 This will be a definitive year for UserEvidence, and the space they operate in.

👉 Their leadership trusts us and gets marketing.

👉 You’ll get to work closely with amazing marketers like Mark Huber and Jillian Hoefer.

If you think like a founding PMM, this could be your dream role. You'll get to solve problems in all areas of the business, work with an incredible team, and make a real impact at a company doing great things. 

If you’re interested, shoot Alex a DM, but make sure you apply first!

👉 https://lnkd.in/gXqvH4B6

Product Marketing Job opportunity at UserEvidence 

There are a few tools I couldn’t live without.
Notion is one of them.
So getting to visit their SF office was a massive treat.

But I wasn't just there as a fan. 
I was there as a partner, getting to work with them on their interactive demos. 

Since starting DemoDash, it’s been a journey of small milestones.

• Signing my first client
• Partnering with Navattic
• Teaming up with friend Eric Holland 💀
• Launching our managed service
• And now, getting to work with my favorite company

It’s been a series of small wins that add up to something pretty special.

A huge thanks to Tiffany Hsia for being such an awesome customer and making me feel like a part of the Notion team for a day.

Not to mention, getting to share the stage with her at a Navattic user event that evening, talking about their playbook for building, distributing, and measuring their interactive demos. 

Excited for what's to come!

We’ve reviewed hundreds of interactive demos. 
Not all of them were great. 
The difference? It wasn't rocket science. 

Just some simple best practices. 
Smart storytelling. 
Small details that kept us engaged. 
The stuff that makes you go "huh, that was smart"

For six months, Eric Holland 💀 and I have been writing Show Don't Tell, our weekly newsletter at DemoDash where we share three standout demos (and the little tricks they use to win attention). 

On Thursday, we’re sitting down with the team at Navattic to share our top 10 favorite demos and the best practices that made them stand out.

For each, we’ll break down a practical tip you can use in your demos immediately. Not a long-winded lecture or fluff — just solid examples and useful takeaways. 

👀 We’ve even got a surprise gift to make building your next demo easier. 

So click the link below to grab a spot, and we'll see you Thursday!

https://lnkd.in/gTXcGpPy

An image for an upcoming webinar with Jason Oakley and Eric Holland featuring 10 practical interactive demo examples and tips. 

Turns out, buying software is easier now than it’s been in years.
 Didn’t have that on my 2025 bingo card.

I just went through the new Evidence Gap Report 2025 from UserEvidence and you know what really jumped out?

Sure, AI is shaking up how people research and buy software. But here's what never changes: Buyers still care most about real, relatable proof.

And the data backs it up. When asked what matters MOST in evaluating new software, 78% of buyers said:

“Can you prove you’ve delivered success for someone like me?”

Your product + someone like me + proof of success
Those are the three key ingredients.

It’s not enough to show off a big-name logo or an impressive stat. Buyers want to see themselves reflected in your customer stories. Same industry. Similar role. Comparable challenges.

It’s easy to forget this in the rush to optimize some new trend or channel. 

But customer evidence that hits home? That classic never gets old.

---

If you want more definitive answers on where, how, and why buyers buy from 800+ B2B marketers, sellers, and buyers, go check out The Evidence Gap Report.

👉 https://lnkd.in/gTZTFRCB

An image showing stats from The Evidence Gap Report from UserEvidence. 78% of buyers care most that a vendor can prove they've delivered success for similar customers. 

The older I get, the more I appreciate simplicity
Less really is more in most cases

My friend Natalie Marcotullio knows what I’m saying.

A year into adding their freemium plan, the Navattic team learned something that flipped their thinking on PLG.

When they first launched, they assumed users wanted to build robust, intricate demos in order to see value.

So they offered lots of features, customizable options, and advanced templates.

Turns out, all those options just overwhelmed people.

Too many paths, too many choices, and the “aha moment” got buried.

So they made a change.

They stripped back the free plan so users could build ONE simple demo, quickly.

HTML captures, an AI copilot, simple editing and publishing.

Enough for a win, to see how it all works, but not enough to get lost.

And it worked!

Users saw value faster.

And sales got to have more meaningful conversations when teams hit real limits and wanted more.

The lesson here?

Users don’t need some incredible first experience. They just need to see how the product actually works. 

Sometimes, less actually is more.

Natalie shared this (and a bunch of other practical takeaways) in her one-year PLG lookback article.

If you want the full breakdown, let me know and I’ll send you the link. 👀

Been waiting for a reason to finally build that interactive demo?
Here it is 👇

Navattic just rolled out a pretty sweet offer to mark the 1-year anniversary of launching their freemium plan 🥳

Sign up before October 10th, and instead of the usual one, you’ll get TWO free demos on their Starter plan.

That means more room for experimentation and the ability to create demos for different buyer personas, product lines, or use cases.

So if you've been on the fence or just dragging your feet on signing up for their free plan, just go do it. I mean, whether you decide to start building them now, or next month, you'll at least have two demos in your pocket to work with.

And if you want any ideas or feedback on your demos as you start building them, just drop myself or Eric Holland a note and will be happy to take a look 👀

Navattic offers 2 free demos with their starter plan

120+ interactive demo examples and best practices
From 37 weeks of writing our newsletter
All in a nice tidy swipe file 🗂️

About 9 months ago, Eric Holland and I started our agency, DemoDash, where we build interactive demos for Navattic users who have big ideas, but no time to execute. 

A big part of our creative process is looking at examples of our favorite demos. And we started a newsletter called Show, Don't Tell to build our own collection in public. Every week, we write about and share 3 new examples of real demos that are doing something right. 

It turns out other demo builders read it for that same reason — to get inspired and find ideas every time they sit down to work on a demo. 

So we wanted to make that easier. 

We packaged all of our 120+ examples up into a simple swipe file you can use to inspire your work. 

Inside, you’ll find every demo we’ve collected, each with the “why” behind its inclusion and the tip that stood out. 

Use it when you’re stuck. 
Use it to spark ideas. 
Use it to build better demos. 

And if you know someone who could use it, we'd really appreciate if you could send it their way 🙏

https://lnkd.in/gf-C_Xwd

A gif of the DemoDash Swipe File. A collection of over 120 interactive demo examples and best practices. 

You can describe how great your product is all day long.
But people want to actually see it 👀

This month in the PMM Jetpack, Logan Hendrickson broke down each section of the blueprint he uses when creating product pages for his clients.

I’ve been sharing it out, piece by piece over the last couple of weeks. Today, we’re talking about: 👇

The Show Me Section 🎥

Your Goal: Let the product speak for itself.

What You’re Solving For: You can talk about features all day, but people want to see it. This is where you build confidence and show how your product delivers on the promises you make elsewhere on the page.

What to Include:
• Interactive tour ❤️, demo video, gif
• Narrative-style walk-through (“You’re a ___, trying to do ___”)
• Highlights of the most valuable or differentiated parts of the product

Your “Show Me” Checklist:
✅ Demo or video is present
✅ Storyline shows product solving a job
✅ Focus on use cases, not just clicking through the UI
✅ Real product visuals are used
✅ Builds confidence and momentum to act

Up next? Help visitors see themselves using the product for their specific USE CASE.

Or you can jump into the Jetpack now to check out the whole playbook!

An infographic breaking down what to include in the Show Me section of your product page. From the "How to Make Great Product Pages Playbook" in the PMM Jetpack. 

Trying to measure the impact of your enablement work
The stuff that takes a HUGE amount of your time
Can feel like beating your head against a wall 🤦‍♂️

I get it. You spend a massive chunk of your time enabling frontline teams.

👉 Training them on your product
👉 Helping them deliver the right message
👉 Giving them the content they need
👉 Answering allll of their questions

But actually measuring the impact of that? It’s tough.
There’s not a lot of obvious metrics to parade around at the end of the quarter.

If you’re feeling this, here’s something you can try:
It’s called a PMM Confidence Survey

A simple way to keep your finger on the pulse of the frontline teams you support. How supported and confident they feel around the key areas you influence.

You’ll not only have some solid metrics you can own, but real feedback, too. What’s working. Where they’re stuck. What would actually help.

How do you do it?

I actually covered it all in this month’s PMM Jetpack Playbook, but here’s a quick summary of the 5-step process:

1️⃣ Define your audience

Who you’re going to survey. Sales is usually the core, but you can expand to CS, product, marketing, really any team you “enable”.

Tip: In your survey, always ask “What team are you on?” so you can segment later.


2️⃣ Create your survey

This is the consistent set of qualitative and quantitative questions that you ask.

Tip: Make sure you include open-ended prompts for qualitative feedback. This is your blueprint for how to improve your scores.


3️⃣ Distribute your survey

The cadence you decide on, announcement channel, deadlines for responses, and follow up plan.


4️⃣ Analyze the results

How you calculate and visualize your results. Focus on two key metrics: Confidence Score and Enablement Score, but don’t sleep on all of the qualitative feedback you get. Look for common themes.


5️⃣ Present your insights

How you share results and next steps with leadership, and circle back to the teams who responded.

Tip: This step gets skipped a lot. Don’t make that mistake. This is a chance to prove your impact and surface valuable insights that many parts of the org never see.


So here's my challenge to you...

If you haven’t tried a PMM Confidence Survey yet, do it in Q4. 

And for my Jetpack members, go check out the new Playbook!

It includes:
• A ready-to-use survey template
• A custom dashboard you can use to analyze your results
• A deck template to help present your insights across your org



P.S. When you're done, DM me and tell me how it went!

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