Agile Journeys is an initiative of the Catapult Labs' Blog. An ongoing series of candid conversations with Agile professionals from across the spectrum – from technical leads and enterprise architects to Scrum Masters, Agile coaches, and transformation leaders.
Each conversation dives into the realities of Agile transformations, adoption, and scaling: the frameworks that work (and the ones that don’t), the processes and tools that enable change, the techniques and tips that make a difference, and the challenges teams face along the way.
Our goal is simple: share unfiltered, practical insights from the people living Agile every day – so you can learn, adapt, and make your own teams thrive.
In the first installment of Agile Journeys, we sit down with Charlotte D’Alfonso, Enterprise Transformation Leader and Principal Enterprise Architect at Praecipio, a leading Atlassian Solution Partner; to explore how a diverse career can shape impactful enterprise level Agile transformations.
Charlotte’s journey into Agile is not the typical tech origin story. With a background that bridges business leadership, entrepreneurship, and transformation work, she has lived agility in many forms. In this conversation with Catapult Labs, Charlotte shares her perspective on aligning people, systems, tools, and culture; why real time visibility matters more than ever; and how retrospectives, governance, and AI fit into the future of collaboration.
“Agile success isn’t just about better metrics – it’s about trust, alignment, and consistent progress.” — Charlotte D’Alfonso
A Career Built on Adaptability
Charlotte’s career has been anything but linear, building expertise across operations, finance, HR, leadership, and strategy before moving into enterprise technology.
“I had a broad career – operations, HR, finance, marketing, coaching & bio-informatics– but I was missing the IT piece. That’s where Praecipio gave me a chance to dive into technology, Agile, and Atlassian tools. I also got started managing Enterprise-level projects”
This diverse foundation shapes her transformation philosophy: integrating people, systems, tools, strategy, and culture to break down silos and deliver measurable outcomes.
Agile Transformation: Beyond Vanity Metrics
"Metrics are only meaningful when they're paired with context." -Charlotte D'Alfonso
Charlotte is quick to challenge the idea that success can be measured by prettier dashboards or sanitized reports.
“True success happens when Agile becomes part of the company culture. It’s when teams consistently work in aligned, empowered, and collaborative ways. It’s when the team trusts the system and leadership can make informed, real time decisions.”
In enterprise environments, Charlotte sees real time visibility as essential for informed decision making. Weekly or monthly reports play an important role, but they can’t be the only source of insight. Dashboards in Jira, connected to company goals through OKRs, help provide a clear and continuous line of sight from strategy to execution.
“Orphan stories are a symptom. You need clear continuity from company goals down to the smallest story. That’s where Atlassian shines. Weekly or monthly reports have their place, but real time visibility gives leaders and teams the ability to act in the moment.”
Retrospectives That Create Change
One recurring failure Charlotte sees in Agile is the retrospective that produces no action.
“If no actions come out of the retrospective, it’s wasted time. The goal is improvement, not just discussion.”
She recommends asynchronous input to better serve distributed teams and maintain energy. The measure of a good retrospective, in her view, is whether it drives real change in team practices.
📌 Read more: How Anonymous Feedback Builds Psychological Safety in Agile Teams
Balancing Governance and Developer Autonomy
Jira often gets labeled as restrictive for developers — and Charlotte believes that perception usually comes from how workflows are designed.
“You need standardization to be a company that pulls in the same direction. And standardization is critical for alignment and reporting, but it has to work for the people using it. When developers are part of the design, they’re more likely to see the workflow as valuable rather than busy work.”
She advocates for involving developers early in workflow decisions, using tools like automation, Scrum Poker, and centralized definitions of “done” to create alignment without bureaucracy. The goal: less reporting, more building.
AI and the Collaborative Stack
Charlotte sees AI not as a threat, but as an opportunity to elevate human work.
“It doesn’t replace people. It frees us to do more creative and problem solving work. Meeting notes, summaries, formatting — AI can handle all that — as long as it’s applied responsibly, with safeguards to protect accuracy, privacy, and fairness.”
Tools like Loom, Slack, and tighter integrations between Jira and Confluence are part of her vision for seamless collaboration in distributed environments.
“If Jira automatically generates Confluence docs, that’s real value. Developers don’t want more admin work — they want to build.”
📌 Related: Agile Best Practices for Remote Teams: A Comprehensive Guide
The Hardest Challenge in Agile transformations: Alignment
When asked about the most difficult obstacle in Agile transformation, Charlotte doesn’t hesitate.
“Goals not being tied to work. Leaders think they’ve set direction, but it doesn’t reach the teams. You end up with effort that adds no value.”
For her, alignment is the cornerstone — linking top down strategy with bottom up execution, reinforced through tools and practices like OKRs.
“Atlassian helps connect strategy to execution. From themes to initiatives to stories. You shouldn’t have orphaned tasks.”
Advice for Agile Newcomers
Charlotte offers three key pieces of advice for leaders working with Atlassian and distributed teams:
- Join the Atlassian Community – “Someone’s already solved your problem.”
- Embrace AI – “Automate the repetitive, focus on what matters.”
- Prioritize alignment and collaboration – “Culture beats tools if people pull in the same direction.”
“You don’t need to reinvent the wheel. Learn from the best practices in your industry and listen to your team. Alignment – top down and bottom up – is critical. Atlassian tools, combined with OKRs, make that possible.”
Agile in 2025 and Beyond
Charlotte believes the Agile Manifesto’s core principles remain highly relevant, even as organizations adapt their practices to fit their own culture and context.
“Most organizations can benefit from greater agility. The key is taking what works for your culture and adapting the rest so it drives the right outcomes.”
About the Interviewee
About Charlotte: Enterprise Transformation Leader and Principal Enterprise Architect at Praecipio, specializing in large scale Agile transformations, governance, and strategic alignment using the Atlassian ecosystem. Connect with her on LinkedIn.
About Praecipio: Praecipio is an Atlassian Platinum Solution Partner, they align Atlassian tools with your vision—delivering strategic solutions, seamless implementations, and efficient migrations that empower clarity, modernization, and real-time insights for unparalleled success.
About Catapult Labs: Atlassian Marketplace Partner building tools for Agile retrospectives, planning, and collaboration. Learn more at catapultlabs.com.