About Taskstreamer - 25+ Years of Alignment Experience

25+ Years Experience

Maarten Rooseboom

Founder & Product Lead

I started my career in project management, becoming Prince2 certified and learning traditional planning approaches. Over the years, I transitioned to Agile and Scrum, embracing iterative development and continuous improvement.

But I kept hitting the same wall: the gap between development teams using agile practices and stakeholders requiring traditional planning and budgeting forecasts.

Teams were working in sprints, but management still needed roadmaps, timelines, and predictable delivery dates and most important: have teams work on the most valuable work at the right time. Alignment! Every organization I worked with had the same problem, and every "solution" was just another spreadsheet that would be outdated by next week.

That frustration became Taskstreamer.

The journey to understanding

Every lesson learned shaped what Taskstreamer became.

The Early Years

Traditional project management

Waterfall, Gantt charts, Prince2 certification. We learned to plan everything upfront, create detailed work breakdown structures, and track progress against fixed baselines. It worked—until requirements changed.

The Agile Transition

Embracing iterative delivery

Sprints, stand-ups, retrospectives. Teams became more responsive, delivered in shorter cycles, and adapted to change. But now leadership couldn't see the big picture. "When will it be done?" became an unanswerable question.

The Insight

Alignment is communication

We realized the problem wasn't Waterfall vs. Agile. It was the lack of a shared, living view of reality. Teams and stakeholders were looking at different pictures, updated at different times, telling different stories.

This experience shaped our philosophy

After years of watching strategies die in transit, roadmaps become fiction, and teams lose alignment, we crystallized what we believe alignment software must do differently.

These aren't abstract principles. They're hard-won lessons from decades of trying to make organizations work together toward common goals.

What we believe

Four principles that guide everything we build.

Belief 01

Roadmaps are communication tools, not bureaucratic artifacts.

Belief 02

Keeping roadmaps current should never be tedious manual work.

Belief 03

Organizations are systems where everything influences everything.

Belief 04

Strategy guides execution. Execution informs strategy. They must flow together.

We don't believe in one-size-fits-all

We learned from Dave Snowden's Cynefin Framework that different types of work require different approaches. The mistake isn't choosing Waterfall or Agile—it's applying the wrong approach to the wrong type of work.

Complicated Work → Waterfall

Difficult but knowable. The end state is clear. Plan thoroughly, execute systematically.

Complex Work → Agile

Unpredictable outcomes. Small bets with feedback loops. Learn and adapt continuously.

Taskstreamer supports both. Your roadmap should reflect the reality of your work—whether that's predictable delivery milestones or adaptive discovery cycles.

Learn more about Cynefin Framework

"Taskstreamer enabled us to align our teams and have them collaborate on our roadmap efficiently. We can plan our entire organization in Taskstreamer."

Arthur van Weeren Head of Technology & Innovation, Intergamma

Built by people who've lived the problem