Why I Chose to Co-Found Payloop

The most enduring value is found in building the infrastructure that enables transformation.

AI is everywhere…it’s changed everything. Like many, I’ve embraced it and wanted to keep learning more. The more I dug into it, the more it felt like deja vu.  

It reminds me of the 90s in the Bay Area, when I first set out in my career. The internet was exploding and everyone was chasing their version of the dot-com dream. Up and down the 101, were new dot-com companies, many becoming unicorns overnight. Some of my friends picked jobs at the right ones, but most weren’t so lucky.  

Back then it reminded me of the original gold rush…where a few struck gold, but the real winners were the ones like Levis, who sold goods and tools to all of these prospectors. I remember asking myself: “What do all of these dot-coms need?”  

So I joined a company selling colocation, managed servers, private networks: the plumbing of the internet itself. Every company needed it. And it taught me a valuable valuable lesson: the most enduring value is found in building the infrastructure that enables transformation.

From Quote-to-Cash to Outcome-to-Value

Over the next 2 decades, I moved into software, then jumped onto the next transformation when it moved to the cloud.  I built and led teams at companies like BigMachines (acquired by Oracle), then Steelbrick (acquired by Salesforce), and then Threekit, all focused on helping businesses sell more and price better, at higher margins, while reducing the time and cost to do it.

I spent decades leading workshops for companies to refine their go-to-market processes, pricing strategies, and their customer acquisition motions, both in the one-time era of software, and within the subscription economy that emerged. These experiences gave me a unique perspective on the evolution we’re seeing again now – the rise of the Outcome-Based Economy.  

And the deja-vu continues.  Many of the challenges we’re facing today to support this rise aren’t new.

When I was working with telecom companies around the world, delivering Billing Support Systems (BSS) and Operational Support Systems (OSS), concepts like recurring charges, credits, usage, consumption, hybrid models, bundles…were already being solved. Remember 1000 min per month, with free nights & weekend plans? International long-distance, per minute, per destination pricing?  These were hybrid and usage based models, with a static monthly fee, additional usage based charges, sometimes pre-paid, sometimes post-paid.  

Burstable data lines? Similar to today’s pay-for-what-you-use models.  

Cost based and ASR [Quality] based routing?  That’s early AI Workload Optimization.  

The parallels are striking: telecom had to figure out cost allocation, quality measurement, subscription based, usage based and hybrid pricing at scale, first for the legacy LAN businesses, but then again with new infrastructure when mobile became prevalent. Today, AI companies are grappling with the same thing, just in a new domain.

The Moment It Clicked

When I met with Struck Studio, their thesis immediately resonated. Their research across their portfolio, as well as companies pitching to them for investment, showed a consistent pattern:  no one had clear visibility into their AI costs or margin profiles, not per customer, per agent, nor per action. 

Sitting there, I asked them, “So what? Once companies have this knowledge, what can they do with it?”

That question sparked an “ah-ha” moment.  

Sitting there together in Santa Monica, we realized the real opportunity wasn’t just visibility but optimization. Knowing their granular costs is powerful, but acting upon them is transformative.  

From that moment forward, we set out to build Payloop, a platform that not only surfaces granular AI costs in real time, but helps companies reduce them, manage them, and ultimately profit from the intelligence behind them.  

With these building blocks in place: tracking costs, identifying wasted spend, and understanding usage in real time, new possibilities emerge:

• Finance teams can see margin profiles and profitability by customer or feature.

• Product teams can experiment with  pricing models and forecast profitability for new features.

• Sales and Success teams can get real time usage data;  when customers are ready to upgrade — or at risk of churn.

• Executives can finally connect cost to value and align their business around outcomes

It’s a feedback loop of insight and action.  That’s the foundation of Payloop.

The Infrastructure for the AI & Outcome Based Economy

AI has launched the next great platform shift, but just like the dot-com and SaaS eras before it, next-gen infrastructure is also needed for it to mature.  

The dot-coms needed hosting and bandwidth.
SaaS needed CSPs and subscription support systems.
AI needs consumption based and Cost to Value Infrastructure.

That is what we’re building at Payloop – the infrastructure layer for intelligent cost optimization, powering the AI and Outcome based era.

Looking Ahead

We’re still early, but the pattern is clear:  AI has and will reshape how software is built, sold, priced, consumed. The companies that will thrive will be those who deeply understand their costs, align them with value of their products, and deliver measurable outcomes for customers.

If you’re building or deploying AI and care about visibility, predictability, reducing costs or outcome based pricing, we’d love to talk. Happy to offer up a free healthcheck to show you if you’re wasting spend or where to optimize, or even to just nerd out with you on what we’re both seeing in this latest digital evolution.  

John Kim, CEO
john@trypayloop.com