Jason Oakley

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.

Senior Director of Product Marketing

This is a long overdue appreciation post.

This past September, I kicked off the first cohort of the PMM Foundry, which is my group coaching program for founding PMMs. I wanted to keep it intentionally small so that everyone in the group could get to know each other, have the opportunity to get into the weeds of things they were working on, go deep on questions, and for it to feel more like a tight-knit group vs a large faceless call.

I'm very grateful that it turned out that way. And it wouldn't have been possible without the incredible group I was able to work with. Collin Mayjack, Ahmed Zain, Lysle Hood, and Zak Cherif. You guys are amazing ❤️

A few of the guiding principles we tried to bring into the cohort were:

• Show up and be present 
• Contribute generously 
• Stay curious, not judgmental 
• Keep it practical 
• Confidentiality is key 
• Progress over perfection 
• Lift each other up 
• Own your growth

Unsurprisingly, this group took that to heart and brought it, every call.

As a coach, I had a blast learning about these different companies, and getting into the weeds of real founding PMM stuff, the building from scratch, the wide variety of different challenges and projects, and the wins that come with getting product marketing right in a startup.

And I hope each member got the sounding board, the guidance, and the accountability they were looking for when they joined in the first place.

I loved it so much I'm gonna keep doing it. In fact, we're already 3 weeks into the second cohort of 6 members, which I can tell are going to be just as impressive as the first. 

If you're interested in learning more about the Foundry or want to join the next cohort, starting April 6th, drop me a DM.

An experienced product marketer with a passion for product, SaaS, and entrepreneurship. 

In over 10 years of working in small to medium-sized startups, I've had the opportunity to build two product marketing teams (working on my third), and get my hands dirty in other areas like sales, field marketing, customer marketing, and customer success. 

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.

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

For AI products, especially chat-based ones, you’re mostly demoing text. The questions being typed, the outputs being generated. 🥱

So naturally, creating an interactive demo for these types of products can be tricky. What can you show or how do you show it in a way that feels more interactive, feels more real?

Eric Holland 💀 and I have experimented with using video captures for this exact purpose, but when Navattic showed us their Animated Text feature, we knew that was it.

It lets you animate any text in your screen capture, like it's being entered or generated in the moment. It makes the interactive demo actually feel interactive, like you're using the product right now. 

If you're a Navattic customer, you need to try this feature on your next demo. 

I recorded a quick tutorial below 👇

It only takes a few seconds and makes your demos that much more engaging. It draws the attention of your audience and brings more life to an otherwise static, text-based demo.

Give it a try and let me know what you think.

I've made this messaging mistake more times than I can count.
Not having a clear picture of my ICP. That one person I'm talking to.

When I try to bundle multiple people into one message, I get vague and have to straddle different problems, use cases, benefits, etc.

But when I speak to one person, my messaging gets way more specific.

So when I’m working on a messaging document, I try to keep one single person in my head. My ideal customer. 

I try to picture them in front of me, like I'm talking to them in person.

"But Jason, what if I need to create messaging for multiple personas?"

1️⃣ Prioritize just one, OR
2️⃣ Create separate messaging for each

If that feels like too much work, ask yourself:

“Do I really need to talk to all these people? Can I prioritize one for this specific situation, launch, etc.?”

My only caveat here is that if I’m in a pinch and I find that there are a couple of different personas where their pain, their use case, and the benefits they're looking for are exactly the same, then it’s okay to write messaging for one of them knowing that it will also cover the other.

And that’s something you can look for as a way to get scrappy and not have to create a library of separate messaging documents.

The mistake is trying to cover a bunch of different buyers in one messaging framework in order save time.

Just picture that one buyer in your mind.

Need coaching or feedback on your interactive demos?
Eric Holland 💀 and I are starting a live coaching series that we're calling, "Ask the Dash Bros".

Our first session is happening this coming Wednesday, January 21st at 12PM ET. 

It's free to join and it's meant for Navattic customers (or future ones) that have questions about their demo strategy, how to build a great demo, and how to get the most out of interactive demos as part of their go-to-market.

OR if you have an interactive demo and feel comfortable with us reviewing it live on the call, we can do that too.

This is our first one of these, but what you can expect is a casual Google Meet with people who are interested in talking about interactive demos, and candid (non-judgmental) advice from two guys who have experience building these things, not only for themselves, but for some pretty impressive companies.

If you follow the link below, you can register to get added to the calendar invite, and you’ll have the option to submit a question or the link to your demo you want feedback on. 

And if you just want to join and learn from other people's questions, that's cool too.

Register here → https://lnkd.in/gCwcdQuw

Eric and I don't really offer one-on-one demo coaching (unless you're a DemoDash customer), so if you do want this type of support, this is the best way to get it.

See you on the call!

I'm seeing this more on interactive demo centers.
Adding a full “choose-your-own-adventure-style” demo right in the hero as the first call-to-action.

In Navattic, we call these multi-flow demos. Combining multiple demo flows into one mega demo. And in the case here with Notion's Demo Hub, they're combining all of their use case demos and making it easy for visitors to jump right into that experience when they hit the page.

A few reasons why I like this approach:

1️⃣ It allows people to stay in that Navattic demo experience without having to jump back and forth between a demo and your landing page.

2️⃣ It removes unnecessary steps, increasing the likelihood that you'll keep people in that demo experience for longer.

3️⃣ Because of that, there's a greater chance your buyers are going to consume multiple demos and learn more about your product.

With demos like this, you'll want to add a step (in this demo it’s step two) that gives viewers some context and tells them how to move about the demo. It sets expectations, tells the visitor what they need to do, and makes it feel more like a flexible demo environment.

This is a best practice Navattic sees across their top 1% of demos, something they talk about in their latest State of The Interactive Product Demo Report.

So if you're looking to increase engagement on your demo center, try adding a multi-flow demo that combines many (or all) of your demos and put it as that main CTA at the top of your page.


P.S. Show Don't Tell is a newsletter that Eric Holland and I put out every Tuesday. This is a new video series that spotlights one of those examples in more detail. If you want your Navattic demo featured in the newsletter or in this series, drop Eric or me a DM!

Wondering how your interactive demos stack up against the best on Navattic?

They just released their State of The Interactive Product Demo Report, which you can now see on their website — 100% ungated, I might add.

Not only can you see how you compare to the top 1%, 10%, and 25% of demos built on their platform, you can also steal their tactics.

You can learn the common best practices followed by their top-performers and apply them to your demo, so you can increase things like engagement rates, completion rates, and click-through rates.

For example, did you know that 50% of the top one percenters put their demos on multiple pages across their site? Not just their demo center, but their homepage and product pages too. Putting your demos in multiple places is one of the surest ways to increase traffic and engagement. 

If you want to be in the top 1% next year, click the link below and go check out the full report.

👉 https://lnkd.in/gGdienNQ

Unless you're already there, in which case, congrats you did it! 👏

Here's a cool framework for how to think about your learning objectives when it comes to win-loss interviews and building a win-loss program.

It comes from the brain of Ryan Sorley, who was the founder of DoubleCheck (one of the first and best win-loss consultancies out there) and now VP of Win-Loss at Klue. So he knows his stuff and he's done thousands of win-loss interviews. He also helped us write the Win-Loss Playbook that we just published in the Jetpack this month. 

Ryan has this concept of the Win-Loss Mountain Range 🏔️

It's a metaphorical roadmap of learning objectives that you need to climb throughout your different win-loss interviews.

It has four parts:

The Mountains
(a.k.a. Research Objectives)
The topics, goals, and business challenges you want to gather insights around. Some objectives are more important (bigger) than others.

The Snow Peaks
(a.k.a. Async Research)
The types of data that are easier to gather at scale, through an online questionairre.

The Mountain Base
(a.k.a. Interviews)
Richer, more specific data that can only be gathered through 1:1 interviews.

The Valley
(a.k.a. Insights)
Where all of the data comes together to create insights. Connecting the dots from data, to insight, to action.

For me, this is a helpful way to frame the outcomes I’m trying to get from doing win-loss in the first place, and it helps flip this switch in my brain so that I'm more thoughtful heading into not just win-loss interviews but customer interviews in general.

If you're a Jetpack member, go check out the new Win-Loss Playbook. And keep an eye on it because we're going to continue building on it over the year.

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