In this episode of The Unlearn Podcast, Barry O’Reilly is joined by Steve Elliott, a serial entrepreneur, product leader, and investor with two decades of experience advising high-growth companies. Steve is the founder of Dotwork, an AI-driven platform that connects strategy to execution, and co-founder of The Uncertainty Project, a community for product leaders focused on better decision-making.

He previously served as Head of Product at Atlassian, where he helped scale Jira Align after selling his company AgileCraft for $166M—earning recognition as a Fortune Best Small Business in America and a finalist for the Ernst & Young Entrepreneur of the Year. With five successful exits under his belt, Steve brings rare depth to the art of building and unbuilding what no longer serves.

In this conversation, Barry and Steve explore how to design for the messy reality of modern work, the role of unlearning in leadership, and how AI is redefining what it means to be a decisive company.

Key Takeaways

• From CTO to CEO – Why Steve transitioned from tech leader to founder and the personal growth that came with it.
• Scaling after acquisition – The emotional and strategic shifts required when your startup becomes part of a larger machine.
• Why strategy execution breaks – Most alignment tools assume order—Steve builds for complexity.
• Agentic AI in the enterprise – How Dotwork uses knowledge graphs and AI to surface insight in context, not just dashboards.
• Decisive companies – What it really means to help leaders make faster, more confident decisions.

Additional Insights

• Unlearning the idea that startups are for the young—Steve didn’t found his first company until his 40s.
• How Dotwork is building a “context memory engine” for both executives and AI agents.
• The future of AI-native tools isn’t more interfaces—it’s less friction and smarter context delivery.
• Why the most valuable enterprise products aren’t flashy—they’re quiet, ambient, and deeply integrated.

Episode Highlights

00:00 – Episode Recap

Steve Elliott shares how each startup exit taught him something new—but also how returning to the founder’s seat means unlearning old assumptions. Now, with Dotwork, he’s not just building a tool—he’s rethinking how organizations make decisions in complexity.

01:45 – Guest Introduction: Steve Elliott

Barry introduces Steve Elliott, founder of AgileCraft (acquired by Atlassian) and CEO of Dotwork, with a track record of five successful exits and a deep focus on enterprise work management.

03:40 – Early career shifts

From a consulting career at PwC to software experiments that took off—how Steve found his way into entrepreneurship.

08:55 – From technologist to founder

The value of combining tech expertise with business empathy—and why startups offer unmatched learning opportunities.

11:05 – Unlearning post-acquisition mindsets

What Steve had to unlearn transitioning from CEO to leader within a larger company—and back again.

13:36 – Building tools for strategic decisions

Why enterprise tools fail to support real-time, strategic decisions—and how Steve is tackling the problem differently.

17:50 – The rise of agentic frameworks

How Dotwork is using knowledge graphs and agentic AI to reflect the dynamic, decentralized nature of modern organizations.

23:31 – Breaking through transformation fatigue

How Dotwork builds trust not through marketing, but by showing real, contextual results fast.

26:23 – Beyond dashboards: AI-native UX

Why true AI-native platforms don’t ask you to log in—they come to you with insight in the moment.

32:44 – Coaching execs on AI

Barry shares his experience coaching executives on AI—and why hands-on experimentation is the only path to mastery.

36:07 – Context engines for agents

Steve explains how Dotwork unintentionally became a context memory platform—crucial for the future of autonomous agents.

40:36 – Magic moments in enterprise UX

When engineering hasn’t seen the reports their software generates—because the platform is that intuitive.

43:17 – Closing Reflections

Steve reflects on the value of doing over theorizing—and the importance of staying close to the problem if you want to innovate meaningfully.