We exist to cause problems
For inefficiency. For busywork. For the endless manual tasks that slow businesses down. Troublesome builds AI that does the work that doesn't need a person — so your team can focus on the work that does.
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.
What we build
Taskwell is an agentic AI platform that executes work rather than merely tracking it. Businesses connect Taskwell to the tools they already use and hand off the repetitive work — reconciling the books, calculating commissions, turning emails into quotes, assembling financial reports — and it runs accurately, on its own, on schedule.
We're our own first customer
Before we sell it to you, we run it ourselves. The founders use Taskwell inside Troublesome every day, testing its capabilities against real business stakes — so what reaches you has already been proven where it counts.
Leadership
Decades of building, running, and automating real operations.
Matt Bergen
Chief Executive Officer
A technology executive with 25+ years leading IT transformation, data, AI, cloud, and automation initiatives.
Let's cause some good trouble
See what Taskwell can take off your team's plate.