The Playbook | Issue No.

The $10B Content Revolution isn’t just about AI, it’s about execution. From the cockpit at Jasper, I helped turn early adopters into power users, scaling a category from zero to unicorn.

Now I’m applying those same lessons to 10x golf startups and reimagine growth.

The Playbook | Editor’s Note

The $10B Content Revolution

In 2022, I joined Jasper when it was still a rocket on the launch pad. Within a year, we raised $125 million at a $1.5 billion valuation, became one of the fastest-growing SaaS platforms globally, and helped define the generative AI category.

I wasn’t just there for the ride.

I was in the cockpit. Coaching customers, solving friction points, collecting user insights, and driving retention at scale.

This shares how I helped turn early adopters into power users and how the lessons from Jasper are helping me 10x golf startups today.

The Opportunity

The AI Content Boom Was Coming. Jasper Lit the Match.

In early 2022, most people still thought AI-generated content was a gimmick. Jasper proved otherwise.

The product helped businesses write blog posts, sales emails, social media captions, and website copy in seconds, with brand voice, tone, and structure baked in.

But the tech alone wasn’t enough. People needed education, onboarding, and a sense of belief. That’s where I stepped in.

My Role at Jasper

Title: Customer Success Manager

Focus: Onboarding → Activation → Retention → Advocacy

Team: Part of the early CS org scaling with product and GTM teams

Customers Supported: SMBs, content teams, agencies

My role spanned across:

• Live onboarding calls and workshops to help users launch content pipelines

• Strategic success plans for content marketers scaling from 1 → 100 assets/month

• Proactive outreach for stalled users or use-case blockers

• Feature feedback collection that influenced roadmap decisions

Big Wins + Strategic Leverage

Many Customer Coaching

I piloted and scaled a live group coaching program that improved activation rates by 26%. By mixing product demos with content best practices, we built momentum that stuck.

Customer Journey Automation

Collaborated with marketing ops to design a segmented success flow aligned with the customer’s role (founder, marketer, agency lead). Open rates exceeded 50%, and time-to-value dropped by 3 days.

“Brand Voice” Feature Launch Feedback

Helped collect and synthesize early feedback from 100+ users testing Jasper’s brand voice features. Created the internal playbook for rollout and implementation support.

Community-to-Product Loop

Worked with the community team to identify super users in Jasper’s Facebook Group. Funneled their feature suggestions directly into product sprints. Those same users became our first case study features.

Key Results

What I Learned at a $1B Startup

Content Isn’t King, Distribution + Data Are

Everyone had AI. Few knew how to use it strategically. The best customers weren’t just creating content. They tracked conversion rates, conducted A/B testing, and repurposed content across channels.

Coaching Is Scalable (When Done Right)

You don’t need 1:1 calls to make a CX impact. To drive tangible outcomes, I learned to blend async support, workshops, and community feedback.

The Category Wasn’t Built. It Was Erupted.

I didn’t just watch a category form at Jasper; I helped facilitate it. AI-powered content is now a multi-trillion-dollar wave, and I was there for the first ripple.

Why This Matters for Golf Startups Today

Golf tech is where AI content was in 2020: underrated, misunderstood, and poised for explosive growth.

• Startups need onboarding that drives activation, not just downloads.

• They need segmentation that speaks to the weekend warrior and the club fitter.

• And they need content marketing that doesn’t just inform, but converts.

I’ve taken the playbooks from Jasper and applied them to golf.

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Tess Szymanski is a proven operator in golf and sports tech. As COO of Random Golf Club, she scaled one of the game’s most influential communities, bringing fresh energy and cultural relevance to golf.

Her leadership continues to shape how players connect, experience, and grow the game.

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