TROUBLESOME
INCORPORATED
Our Mission
Free businesses from the work that slows them down — partnering with our customers to turn AI's potential into competitive advantage, one outcome at a time.
Our Vision
A world where the work that doesn't need a person no longer falls on one — where any business can run lean, move fast, and grow without being buried by its own operations.
Our Company Name
Troublesome exists to cause problems — for inefficiency, for busywork, for the endless manual tasks that slow businesses down. We automate what holds you back so you can focus on what moves you forward.
what is Taskwell™
Troublesome's Taskwell is agentic AI that doesn't just track your work — it does the work. You connect Taskwell to the tools your business already runs on, hand it the tasks that eat your team's time, and it carries them out: reconciling the books and flagging anomalies before they compound, calculating and paying commissions, turning an inbound email into a finished quote, generating the financial briefing your board keeps asking for. Work that used to need a person at every step now runs accurately, on its own, on schedule. That's the belief Taskwell is built on — your team's time is too valuable to spend on work that shouldn't need them. Less busywork. More momentum.
Customer Zero
We're our own first customer. Troublesome runs on Taskwell™. Our own books, reconciliations, and back-office work are handled by the same agentic AI we sell — so every capability we ship has already been pressure-tested against a real business with real stakes: ours. We don't ask customers to trust automation we wouldn't run our own company on.
Our Founders
Decades of building and running companies — with no patience for the work that gets in the way.
CEO
Matt Bergen
Matt is one of our founding partners. He is an innovative technology executive with over 25 years of experience leading large-scale IT transformation and delivering business value through data, AI, cloud, and automation. Matt is using that experience to help launch & grow Troublesome, Inc. as our Chief Executive Officer.
CFO
John Harrington
A technologist for 30 years, John has led large IT organizations, developed strategy, and optimized internal operations through automation — long before it became the headline. As a founding partner, board member, and chief financial officer of Troublesome, Inc., he brings that operator's instinct to how the company runs and grows, helping redefine how work gets executed inside modern businesses. And he pays the bills.
COO
Cody Scott
With 20 years of IT experience, Cody has lived every layer of the technology stack — from project delivery to the boardroom. As Chief Operating Officer of Troublesome, Inc., he turns that full-stack perspective outward: owning how the company runs day to day, how customers succeed with what we build, and how the business grows. Equal parts technical depth and people-first leadership, Cody is the bridge between the product and the people it's built for.