Find out how a century-old insurance leader initiated a culture of constant improvement and agile strategy, dismantling silos to align the whole organization.
The learnings in this blog post are based on the session, “From Vision to Action with Atlassian Strategy Collection”, presented at Atlassian’s Team Europe ’25 conference. You can check out this session and others on demand.
If you’ve ever tried to run enterprise strategy through disconnected tools, manual reporting, and rear‑view dashboards, you’ll recognize CNA Insurance’s “before” picture. A top‑quartile underwriting leader, CNA had the ambition and the portfolio scale—but lacked a clear, consistent way to connect investment, execution, and outcomes.
The result: stalled decisions, lagging data, and clouded visibility at the executive level.
CNA’s turning point came when they brought strategic planning and execution into one integrated environment with Atlassian’s Strategy Collection, anchored by Jira Align. The shift replaced static slides and spreadsheet choreography with live insights, shared language, and measurable value—at portfolio scale.
CNA outcomes at a glance
- 1.2M–1.5M automations executed annually
- $3.5M–$4M time savings from workflow enhancements
- 50% of agile coaches reallocated to higher‑value work
The “before”: Fragmented planning, stale data, limited visibility
“The data was always stale, and we were just doing a lot of ineffective and inefficient processes, so something had to change.”
– Colton Kosicek, Assistant Vice President of Global Agile Operations, CNA Insurance
- Decentralized planning across teams and Agile Release Trains (ARTs) using disparate add-ons with insufficient reporting
- Execution status tracked in shared spreadsheets; leadership reviews via exported slide decks
- Information was already outdated by the time decisions were needed
- No consistent way to connect investment to outcomes or see cross‑portfolio dependencies
With major initiatives on the horizon and dependencies spanning the organization, CNA recognized the need for a platform that could provide transparency and keep everyone moving in the same direction.
Bringing strategy and execution together
CNA chose Atlassian’s Strategy Collection, specifically for its interoperability with Jira, Microsoft Azure DevOps, and their proprietary HR systems, allowing them to roll out Jira Align across 15 portfolios in just seven months. This move replaced manual processes with a unified system, giving teams and leaders instant access to live data and actionable insights.
Kosicek noted the value of an integrated solution:
“We took an honest look at everything, and we recognized that keeping everything in the family was gonna be a very important thing for us. We didn’t want to have to context-switch between Jira tools and different competitor tools.”
– Colton Kosicek, Assistant Vice President of Global Agile Operations, CNA Insurance
The results: alignment, efficiency, and visibility
Since adopting Strategy Collection, CNA has seen measurable improvements across the board. Teams are now aligned on strategy and execution, and leaders have the visibility they need to intervene early and manage dependencies proactively.
Since beginning their transformation, CNA has realized:
- Strategic alignment between leadership and teams: all working from a single source of truth.
- Enhanced visibility into where strategies are succeeding or drifting: enabling faster course correction.
- Streamlined communication and a unified language: bridging business and technology.
- Significant operational efficiency: with only two admins supporting 3,000 users, and half of the coaching staff reallocated to higher-value work.
- Automation at scale: running over a million automations per year and saving millions in time.
Looking ahead: AI and a culture of continuous improvement
CNA is now exploring how AI, including Atlassian’s Rovo, can further connect strategy to execution and empower every employee—from interns to executives—to see the impact of their work.
Kosicek is optimistic about the future:
“We’re now able to connect strategy from the executive level directly to our team members. That way, they know how they contribute to the overall success of CNA… It’s all live data, and so they can self-serve as well, which is amazing.”
– Colton Kosicek, Assistant Vice President of Global Agile Operations, CNA Insurance
cna insurance’s tips for transformation
- Create a culture of change and success.
- Focus on solving real problems, not just adopting new tools.
- Move forward at a pace that matches your challenges—even a slow journey is still progress.
Transform your leadership just like the world’s largest enterprises
CNA’s story isn’t about buying a new toolset—it’s about changing the operating system of the enterprise. When strategy, funding, and delivery live together, you get more than dashboards. You get decisions that compound.
Bring your leadership conversations into the product where the work lives. Explore Atlassian’s Strategy Collection and join CNA Insurance, as well as other industry leaders like Datasite, NVIDIA, and more.
