Self guided onboarding for IT teams

When the world went remote, IT teams stepped up.

When the world went remote, IT teams became the backbone to every business moving online. They needed tools that moved fast and experiences that didn’t get in their way - scaling operations, responding to incidents and adapting in real-time. Jira Service Desk was rebranded into Jira Service Management to meet that need⁽¹⁾. But for new users, first impressions had to match the speed and ambition of modern IT team workflows.

This opened an opportunity for me to co-design the end-to-end onboarding experience. This case study focuses on Your Coach — a smart, accessible guide that helps teams get set up without second-guessing. A thoughtful approach to building trust early, setting the tone for long-term success.

OVERVIEW

With great customisability, comes great complexity.

What makes Jira so powerful is how customisable it is. What makes Jira so complex is knowing how to configure it In the right places. When our product strategy involved rearchitecting templates into modular practices, we were promising that day-to-day team workflows would be more automated and flexible. However, this risked shifting more complexity upstream, making setup a critical make-or-break moment for Admins and the teams that rely on them.

Before and after

Before: Service request focused Demo desk aimed at inspiring configuration options.

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After: Tailored to core IT Service Management practices⁽²⁾, Your coach provides users with clear steps on how to move forward on their first ITSM project. By offering multiple learning paths, to support all learning styles - including setup checklists, a walkthrough library and sample project.

DRIVING DECISIONS

Turning onboarding into a long-term learning layer

I reframed onboarding as a reusable learning entity. Not a one-time checklist. This shift informed how we:

• Revealed complexity gradually

• Created returnable walkthroughs for teams

• Honoured mental models from other tools

By using conceptual models and testing scrappy walkthroughs⁽³⁾, I got the team excited about onboarding as a trust-building system.

Designing for clarity when everything is connected

Due to technical constraints one of our biggest challenges became activating incident management (a core feature) across JSM and Opsgenie. I flagged a trust gap, as users were being asked to sign up for an additional tool mid-flow. This inspired cross-functional and leadership collaboration:

• Product Strategy: enable auto-provisioning, so we could streamline without extra steps.

• Technical Collaboration: Engineers built logic to detect config states, letting us dynamically update onboarding progress.

• Experience strategy: Cross-product alignment for modular learning systems, that provided contextual guidance to the users.

By documenting the existing experience and prototyping the contrast between a high-friction and smooth flow, I helped the organisation empathise with user pain and move decisions forward.

Discovering the power and laws of simplicity

To encourage user engagement, early iterations leaned playful and gamified. After several feedback rounds, I redirected us toward actionable clarity with human warmth⁽⁴⁾. The system had to:

• Support multiple roles (Admin vs Agent)

• Scale across Atlassian products

• Adapt to different ITSM template choices

By considering information architecture, voice and tone, and modular patterns that mirrored our product strategy, I designed a UI system that could stretch across multiple use cases without losing clarity.

I drew on my design system experience and working React knowledge to write a detailed spec for engineers in Figma, and co-wrote a simplified version for non-technical roles in Confluence. This helped bridge communication across disciplines, ensuring high-quality execution and shared understanding throughout the JSM team.

POST-LAUNCH

Impact

One month post-launch, we saw retention triple with no increase in support tickets — a strong signal that teams felt supported, not overwhelmed. A quarter of new projects chose the ITSM template, and requests for sandbox environments began to rise, showing growing confidence and a willingness to explore. Results affirmed our approach: onboarding isn’t just setup, it’s an early education layer that builds long-term trust and drives adoption.

What I learned

Challenging my own understanding, onboarding turned out to be much more than just feature education, it’s a business-critical trust layer that shapes perception and reduces churn risk. As the project grew and more voices joined the mix, I learned the importance of staying grounded and adaptable by leading early direction while supporting the team through key moments to keep the experience cohesive and user-centred. This taught me how quiet leadership and collaborative influence can move complex projects forward without losing sight of the original vision.