Roadmap

I worked in a large organization with an expansive portfolio roadmap that crossed multiple teams. The leadership regularly struggled to follow which teams were working on which initiatives and keep track of changing priorities and timelines, and they were regularly frustrated when the expected completion date moved or was missed. To improve alignment and visibility, I maintained a working space that was used internally with our team where we could plot out a tentative roadmap based on sprint capacity, priorities, upcoming holidays, etc. When the dates became more stable and ready to be communicated, I updated the outward facing Jira roadmap and communicated on a routine cadence with stakeholders and leadership what work was recently completed, in flight, and upcoming. This enabled me to assess risks and prioritize changes, working collaboratively with the team to navigate the logistical challenges and identify mitigating strategies to minimize impacts on timelines. Throughout this process, I also built trust with stakeholders and leadership by maintaining transparency.

Project Brief

One of the biggest challenges in large projects is maintaining focus on the “why” and consistently connecting individual deliverables back to the broader purpose. To address this, I designed and implemented a Project Brief template that centralized all project documentation in one place. It ensured that key elements – such as the problem statement (why), target audience (who), business value, and success metrics – were clearly defined and accessible to the entire team, stakeholders, and users. I tailored the content and supporting pages to fit each initiative’s specific needs, using the template as a flexible foundation. For every new project, I created and maintained a dedicated Project Brief to keep goals aligned and decision-making grounded.

Level of Effort Estimates

Understanding and prioritizing a backlog of features requires a clear grasp of relative cost. To support level-of-effort (LOE) evaluations, I explored different strategies: adjusting scope to fit a fixed budget or timeline, extending timelines to accommodate full scope, or increasing resources to deliver more within a shorter period – the classic iron triangle. These trade-offs can be hard to visualize and communicate, so I created a cost-impact view for leadership that illustrated the rough effort associated with each feature and how changes to scope, time, or resources would affect delivery. I used this tool during roadmap discussions with leadership, helping us evaluate scenarios more effectively. As a result, we re-scoped and re-staffed a project originally estimated at two years, ultimately delivering a strong feature set in just six months.