How do you ensure your company’s strategy is connected to its ability to execute? This is exactly the question that preoccupied Jim Alison, VP of Engineering at Kespry. Kespry is a fast-growing company that provides a drone-based aerial intelligence platform that’s transforming how organizations capture, analyze, and share insights about their business, providing the information they need to accelerate their operations.

As Kespry’s VP of Engineering, Jim oversees development of hardware, software, and QA. Before purchasing Portfolio for Jira, he had just completed a quarter where the company had approached the planning process in spreadsheets and docs. While a lot of very positive collaboration had occurred between the product and engineering teams, one problem with this approach was that deliverables on the roadmap were not immediately tied to the execution plans of the engineering team. While this process worked during the early days of the company, Jim felt there should be a better way to empower the product and engineering teams to communicate about, develop, and finalize a roadmap. Jim began to look for tools that would help the team capture the big picture of the organization’s scope and improve alignment across teams about that scope.

Kespry used Portfolio for Jira to paint a comprehensive picture of what the engineering team could accomplish in a quarter

Fast forward to the subsequent quarter and Jim decided to use Portfolio for Jira to help facilitate an improved collaborative planning process that was tightly connected to execution. He chose Portfolio for Jira because it would help the team create a comprehensive picture of how much work could be accomplished in the quarter by bringing the team’s velocity into the planning process, better enabling release timeframes to be estimated and strategic trade-offs to be made.

In order to get a clear view into regular deliverables, Jim set up a quarterly release cadence in Portfolio. Additionally, having levels of hierarchy enabled the leadership team at Kespry to quickly zero in and see work both at a high and granular level. In this view, Jim could also rearrange priorities and modify the estimates on specific work items in a sandbox environment, getting visibility into how each modification changes the likelihood of hitting the company’s quarterly release targets.

Portfolio for Jira brings alignment across different teams

At Kespry they approach the planning process with a self-directed model. Empowering teams to be self-directed means it’s especially important for the company to ensure all work maps back to the bigger picture. Portfolio helps with this by providing additional levels of hierarchy that tie the smaller chunks of work to a higher level of hierarchy. Having consistent definitions and a consistent method of estimating is important for extracting a meaningful plan from Portfolio for Jira. Accordingly, at Kespry Portfolio has served as a good mechanism for aligning teams around common processes and terminology. For example, the product and engineering teams created clear definitions of a story, as well as a shared understanding of how each level of hierarchy should be estimated.

How Kespry built their Portfolio for Jira plan

To understand Kespry’s approach to building a plan in Portfolio for Jira, it’s important to understand the way the company is structured and how their Jira Software instance is organized. Kespry has five different scrum teams aligned to various areas of the business: hardware, systems software, data platform, cloud-based applications, and machine learning. To get started with Portfolio for Jira, Jim chose to bring each of his team’s Jira Software “projects” into a single plan, which displays every issue in those projects.

Kespry’s approach to issue hierarchy

Many of the benefits that Portfolio brings to Kespry start with Kespry’s thoughtful approach to defining their levels of hierarchy. At the very top, Kespry has defined a “themes” level that represents a long term demarcation of work that could last forever. One example of a theme at Kespry is hardware cost reduction. Below these themes there are initiatives, which are long-range time-bound work items that can be finished and estimated. Below initiatives are epics, which are all the individual projects that make up an initiative. Finally, below epics are stories, which are the smaller chunks of work that make up a project.


With Portfolio for Jira, Kespry has been able to help bridge the gap between product and engineering and bring alignment across different teams. This has been instrumental in helping the company scale the planning process for five (and growing) autonomous agile teams. Additionally, the management team is able to get a clearer view of how their plans are coming together. The end result is more standardization in their processes, clearer definitions of their work, and a more successful quarterly planning cycle that helps products ship on time.

Get Started with Portfolio for Jira

How Kespry used Portfolio for Jira to bring its product and engineering teams closer together