Q3 Tweener Founder Spotlight: Taskora
Where SOPs Meet the Future of Automation: Turning Everyday Operational Pain Into an AI Superpower
Tweener Founder Spotlights
Tweener Founder Spotlights are about the story behind the startup, the moments, the motivations, and the people who decide a problem is worth solving.
Before Taskora became a company, it started as something far more familiar to most founders: two people noticing the same problem over and over again in every customer meeting, every integration project, every late-night troubleshooting session.
Eventually, the pattern became too loud to ignore.
This spotlight features Shawn Mims (CEO) and James Jordan (CTO), co-founders of Taskora. Their backgrounds overlap just enough to work seamlessly, and diverge just enough to build something new. The result? A platform tackling one of the quietest but most painful operational problems inside high-volume businesses: SOP compliance and the impossible last mile of automation.
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Building the bridge between today’s workflows and tomorrow’s agentic automation.
Lessons You’ll Hear Between the Lines
Shawn and James don’t sugarcoat the realities of building a company. Their experience leaves a few clear takeaways:
Don’t fall in love with your first idea. Your initial concept is rarely the winning one. The market will tell you what matters if you’re willing to listen and let go.
Look for urgency, not politeness. A polite “cool idea” means nothing. The real signal is when a customer stops the pitch and says, “Where do I sign?”
Red-team everything, especially yourself. Actively seek critiques, pressure-test assumptions, and let bad ideas die fast. Their best insights came from breaking their own thinking.
Solve the problem you’ve actually lived. Taskora works because they’ve been inside this pain for over a decade. Lived experience creates the kind of insight competitors can’t copy.
The right co-founder makes the valleys survivable. Startups swing between the highest highs and lowest lows. Reliability, shared motivation, and mutual trust make the hard parts possible.
The Work Nobody Talks About But Every Company Feels
Ask Shawn to describe Taskora in one sentence and he’ll tell you:
“We help companies with SOP compliance and automation, the human-in-the-loop work that’s too complex, too nuanced, or too painful for deterministic software to handle.”
The customers they serve have systems of record that run their entire business.
But the real work? It happens between the screens:
Opening records
Checking fields
Interpreting messy data
Verifying billing readiness
Moving processes forward
Catching exceptions
It’s too complex for rule-based automation, too repetitive for skilled humans, and too business-specific for generic SaaS to solve.
AI, it turns out, is really good at this in-between zone, if it has the right guardrails.
Taskora’s approach overlays directly on a company’s existing software via a browser extension. It speeds up work, reduces errors, and frees people from the rote work so they can focus solely on exceptions.
The Moment Everything Clicked
Taskora wasn’t their original idea. Their original dream was fully agentic automation, think hands-off AI that could run operational workflows end-to-end. But as they explored the space, they realized something crucial:
“Agentic AI isn’t ready for full automation,” James explained. “Not yet. It needs a knowledge base, the same way a new employee does. And that means SOPs.”
When they shifted from “let’s automate everything” to “let’s encode the operational knowledge companies already run on,” something dramatic happened. Customers didn’t just nod politely during calls. They interrupted mid-pitch.
One prospect literally stopped James halfway through the deck:
“I got about halfway through, and he told me, ‘stop and don’t talk to any other customer until you get me a contract to sign, because I want to be in front of them.’”
That’s when they knew: They had product-market fit before they had a product.
The Hard Part Founders Don’t Talk About
When early ideas don’t resonate, most founders panic, but Shawn and James didn’t. Years of startup battle scars taught them how to “red team” their own ideas:
Don’t fall in love with your first idea
Ask AI to critique your assumptions
Seek bad feedback
Kill anything that doesn’t have obvious customer pull
Follow excitement, not politeness
“Don’t chase tepid ‘yeah, that’s kind of cool,’” Shawn said. “Look for: ‘Holy sh**, give it to me now’.”
Taskora only emerged because earlier ideas died, quickly, and on purpose. But ideas aren’t the only things that get tested. Founders do too, and that’s the other hard part no one prepares you for.
The Other Hard Part Founders Don’t Talk About
Killing bad ideas is one thing. Surviving the emotional whiplash of building a company is another.
Building a company means riding an emotional rollercoaster: the late nights, the gut-punch setbacks, the “are we completely out of our minds?” moments. Strategy can be learned. Grit can be developed. But choosing a co-founder who will weather every valley with you? That determines whether you survive long enough to execute anything at all.
After more than a decade of working shoulder-to-shoulder, they know exactly what that looks like. Yes, they have deep domain expertise, elite applied-AI specialization, and seasoned go-to-market experience. But their biggest advantage isn’t technical.
It’s human.
As Shawn put it:
“We’ve both gone through enough valleys of despair to know you need a cofounder who is reliable, motivated, smart, and willing to do literally anything the business needs. We’ve seen each other do that for over a decade.”
A good idea is valuable. A good co-founder is invaluable.
Why the Triangle?
The people you build with matter, but so does where you build. And for Taskora, the Triangle has become the perfect home base.
Both founders came for school, NC State for Shawn, UNC Chapel Hill for James, and stayed for everything else. If you’re from the triangle, you get it:
Proximity to mountains and beaches
A thriving tech and startup ecosystem
A concentration of universities
Cost of living that still makes sense
RDU’s convenience
Smart, motivated people everywhere
As we talked about locations, the Taskora team summarized it nicely:
“If you wrote down the checklist of what you want, opportunity, talent, quality of life, geography, there aren’t many places that beat Raleigh.”
Image from The Local Reporter
What’s Next for Taskora?
For now, the focus is simple: make their pilot customers unbelievably happy.
If they get that right, everything else opens up: new verticals, richer agentic workflows, and ultimately the long-term dream of autonomous operational agents.
And as they reflected on what keeps them moving, one line stood out:
“What really matters is finding the people who can push you forward. We’d love more of that.”
Noted. 😉
If you’d like to connect with Taskora for pilots, partnerships, or to learn more about their approach to SOP automation, you can reach Shawn and James on LinkedIn and explore their work at: https://www.gettaskora.com
Explore more Tweener portfolio companies at tweenerfund.com.
Next on Tweener Founder Spotlights
Stay tuned! We have more founder stories, more lessons, and more momentum from across the Triangle startup ecosystem coming your way.