When I sat down with Jordan Nemrow, Co-Founder and CTO of Woflow, I knew we’d be talking about structured data and automation. What I didn’t expect was to hear one of the most candid and insightful breakdowns of how AI is quietly reshaping engineering culture, leadership, and workflows—from someone building at the bleeding edge.
Here’s what stood out.
From Facebook Post to Chrome Extension
Woflow didn’t begin with a pitch deck—it started with a Facebook post. Jordan posted: “If you copy and paste at work, I want to buy you a beer.” That Facebook post led to a coffee with Will Ley, who became the first user of Jordan’s automation tool… and later his co-founder.
From there, Woflow evolved from a browser-based macro recorder into a platform that helps companies structure merchant data at massive scale—powering food delivery, e-commerce, and more. “Six months later, we were profitable.”
The Hidden Complexity of Structuring Data at Scale
Anyone can structure data. The hard part? Doing it 10,000 times an hour.
Jordan emphasized that it’s not the AI or the ML models that are the hardest part—it’s the operational architecture. From customer ingestion to QA and delivery, the end-to-end system must be airtight.
And to do that, Woflow uses a human-in-the-loop model—a strategy that gives their AI workflows an edge in both accuracy and scale.
How Generative AI Quietly Changed Everything
One of the biggest takeaways from the conversation: AI didn’t make a loud entrance at Woflow—it just started working. “The first time I plugged an LLM into our product, I knew everything had changed.”
By offloading first drafts to LLMs and applying humans as QA layers, Jordan’s team cut down manual labor, increased quality, and boosted margins—even if the LLM costs haven't dropped yet.
More importantly, he predicts that AI-native workflows and infrastructure will reshape how we build and connect systems.
The New Generation of Engineers Start With Prompts
This line stuck with me: “New devs start with a comment—not code.”
Jordan is seeing early-career engineers use tools like Cursor as their baseline tool, while more senior engineers (like him) still start with actual code and work backward.
This is more than a style preference—it’s a sign that the entire software development workflow is shifting at the foundational level. And leaders need to adapt.
Delegation Is Harder Than Engineering
Like many technical founders, Jordan started as the sole developer and eventually had to let go of his codebase. It took him three years to move from acting CEO to CTO—but when he did, it unlocked a new level of servant leadership.
Today, his focus is making the team better, not holding onto control.
Culture Doesn’t Scale Without Intentionality
When COVID hit, Woflow went fully remote. But it took two full years to build an effective remote-first culture. Jordan’s fix? Quarterly in-person Shipathons. These events realign the team, rebuild trust, and set the tone for the next quarter. Now, Woflow also does annual offsites—with legendary swag and team-building exercises designed for both fun and alignment.
The 90/90 Rule
If you only remember one thing from this episode, let it be this:
“If you think you're 90% done… you probably have 90% left to go.”
Shipping software is hard. The final polish, testing, and coordination always takes longer than expected. Jordan uses this principle to set better expectations and coach persistence on his team.
Listen to the Full Episode
If you’re a senior engineering leader navigating GenAI, distributed teams, or scaling systems—this episode is a must-listen.
Final Thoughts
Jordan’s approach to engineering leadership is grounded, self-aware, and deeply future-focused. He’s not chasing hype—he’s building systems that work today while staying ready for what’s next.
If you’re hiring engineers, scaling AI teams, or wrestling with delegation and culture—I promise this episode will give you at least one idea you’ll want to steal.
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