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.

As a coach for founding PMMs
These are the messages I live for

This week, a member of the Foundry shared a real, tangible win they owned and implemented.

A 12% increase in adoption in a couple of days, all from a small activation campaign. 💪

The best part is that this was fully aligned with her goal when joining the cohort in the first place.

How did I know?

One of the things we did at the beginning of the Fall Foundry cohort was hop on a 1:1 kick-off call with every member.

The point was getting to know each person, what motivates them, what their struggles are, and the specific nuances of their company/product.

We both are clear about their goals heading into the program and can keep those top of mind each week.

It’s something that would be impossible with a big group, which is why I intentionally keep the Foundry cohorts small.

And it’s totally worth it.


PS. Applications are open for the next Foundry cohort, starting Jan 6th. If you’re you're overwhelmed, running in circles, and feeling like nobody understands your job and the impact you can have — it could be the program you’re looking for.

If you’re interested in applying or want to learn more, drop me a quick DM.

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

Here are 13 tips for improving your interactive demos
A 45-min webinar condensed into 8 mins ⏲️

If that’s even too long, here they are:
↳ Use the data they give you
↳ Don’t leave CTAs until the end
↳ Make your AI feel real
↳ Every story needs characters
↳ Use barbeque copy
↳ Set expectations up front
↳ Build a demo center
↳ Let them build their own experience
↳ Say “hello” 👋
↳ Make your demo the logical next step
↳ End with proof, not promises
↳ Don't assume everyone knows how demos work
↳ The gate that makes you want in

If you want the full webinar and breakdown of each tip 👉 https://lnkd.in/gaUHPCEF

If you want 120+ practical demo examples 👉 https://lnkd.in/gf-C_Xwd

Buying is hard.
And your company doesn’t make it any easier.

Purchasing software is messy and uncomfortable. And most people don't choose it — they're forced into it out of necessity.

It's not like buying new clothes, although I'll be the first to admit that I got overwhelmed buying new running shoes the other day and just walked out of SportChek. 

Even as a small business owner, I hesitate over a $20/month subscription these days. I push the decision off because I don't want more tools slowly bloating my expenses. And that's in a world where I can sign up easily, see pricing, and test things out, because I'm buying simple products with freemium plans and low barriers to entry.

But imagine buying enterprise software. I'm not talking about Oracle-level stuff. I mean normal B2B SaaS. Marketing or sales tech that's even a somewhat substantial investment for a company.

We all know the buying process isn't as straightforward as we'd like to think. There are plenty of Gartner graphics out there showing just how messy the typical buying process is.

Instead of making it easy for buyers, most SaaS companies — maybe through ignorance or a "we've always done it this way" mentality — make it really hard to buy.

There's a comical gap between what buyers want and what a company's marketing and sales approach actually delivers:

A buyer asks: “Is this the right product for me?”
↳ Your marketing says: “We’re made for everyone!”
↳ Your sellers say: “What’s your job title? Budget?”

A buyer asks: “Can I see how it works?”
↳ Your marketing says: “You’ll need to book a demo.”
↳ Your sellers say: “Are you “qualified?””

A buyer asks: “How much does it cost?”
↳ Your marketing says: “Can’t tell you that.”
↳ Your sellers say: “Let’s set up a pricing call.”

A buyer asks: “Who else like me is using this?”
↳ Your marketing says: “We’re 4.8 on G2.”
↳ Your sellers say: “Here’s a case study from 2019.”

It’s a wonder anyone buys anything at all!

When buyers hit a wall, they often leave. They just stick with the pain they already know.

So if you want buyers to stick around, don’t make them jump through hoops.
Answer their questions, fast. Give them confidence that your product is for them.

An illustration of the gap between what buyers need and what your company delivers. 

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