DESIGN LEADERSHIP
Caseware
September 2022 (refinements are ongoing)
Christopher Moorehead Head of User Experience
Marlene Aubin Product Design Manager
Ian Stewart Design Operations Manager
When I joined Caseware as its first Head of Design (a role shortly thereafter expanded to include all of User Experience), Product Design did not really exist as an independent entity. Previously, designers were hired on an ad hoc basis by the development teams, reporting into their respective product squads in a very siloed environment. The designers in one particular product squad had very little contact with their counterparts in other squads, and rarely worked together.
This siloed operating model presented some serious challenges to both efficiency and product quality. Uneven levels of work in product squads often resulted in one design team being overloaded, while others might have little to no work. Designers had very little knowledge of other platforms or products, and design knowledge was siloed and inaccessible to other design teams. As a result, there was no common look and feel to any of Caseware’s products.
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To address these issues, we made the decision to centralize Product Design as an entity separate from the individual product squads. In this structure, the senior designers remained attached to one of the three platform verticals — SE (the main audit engagement platform), Cloud & Hybrid Cloud, and Data Analytics — and assigned to their respective cost centres. The senior designers remained the primary points of contact with Product and Development, and oversaw all design work for their assigned platforms.
The more junior designers were assigned primary platform roles, but could move between platforms according to operational need. This model provided the opportunity to share design knowledge, develop a global information architecture and navigation system across platforms, and create a common look and feel across Caseware’s entire product line. Logistically, these designers were attached to the central cost centre UX Shared, along with managers and Design Operations staff.
This reorganization of the Product Design team provided a greater focus on “big picture” cross-product design initiatives, continuing our shift from a rigid, siloed product-based model to a more flexible and agile centralized model.
In parallel with the restructuring of the Product Design team, we established a dedicated Design Operations team. Its role was to execute on the essential (but perhaps less glamourous) initiatives that improved the team’s operational efficiency, reduced design and technical debt, and increased consistency throughout the product development life cycle. Key Design Ops initiatives included the operationalization of Caseware’s design system, ongoing improvements in Product Design’s tools and processes, and leading Caseware’s overall accessibility initiative with the goal of becoming fully WCAG 2.2 Level AA compliant across the entire product line.
Initially, the Design Operations team consisted of the Design Operations Manager, one relatively junior designer, and several front-end developers who did Design Ops work (primarily on the design system’s code base) but officially reported to the DevOps team.
After working with this Design Ops model for about a year, we made the decision to revise it. In the new structure, there were no dedicated designers except the Design Operations Manager. Instead, designers rotate between Design Ops and Product Design to provide more flexibility in resourcing as well as ensuring our design system reflected the realities of Product Design. The goal was to have each Product Designer spending at least 10% of their time in Design Ops.
This revised model allowed us to assign Design Ops work to less busy Product Design staff, while ensuring that Design Ops work never became divorced from core Product Design work. It increased the overall delivery of Design Ops initiatives, continuing the operationalization of Caseware’s design system, and ensuring that all components, use cases, and code were both system compliant and fully accessible.
While the team restructuring was being planned and implemented, we also made significant changes to the design career ladder. In most conventional business hierarchies, it is difficult if not impossible to rise above a certain mid-range level without moving into a management role. The field of design has many experienced and high-performing staff who would prefer to focus on their craft rather than become people managers. Retaining such people can therefore be a challenge.
To address this issue, we created an entirely new system for career development involving parallel management and individual contributor career tracks, with clear guidelines for progression and corresponding performance criteria.
The career progression path for both Product Design and Design Operations is identical. There is only one path for the first three levels: UX Designer I, UX Designer II, and Senior UX Designer. At the next level, the path splits into parallel Individual Contributor (IC) and Management (MGR) streams. The IC stream has three levels (Staff Designer, Senior Staff Designer, Principal Designer), which correspond to the three levels of the Management stream (Design Lead, Design Manager, Design Director). Movement between the IC and MGR streams is permitted, so progression decisions made above Senior Designer are not necessarily “cast in stone”.
A designer’s individual progression through the levels is based on a Competency Index, in which the designer is rated on a five-point scale (Novice to Master) using five criteria (Craft, Process, Collaboration, Organization, and Influence). At the lower levels, Craft and Process are the most important criteria, but as a designer increases in seniority, Collaboration and Organization become increasingly important. At the top levels (for both the Individual Contributor and Management tracks), Influence becomes the single most important criterion.
The Competency Index is a primary factor in each designer’s annual performance evaluation, as well as in general ongoing career discussions. Feedback is collected on a continuous basis using a customized spreadsheet (created by my brilliant colleague Marlene Aubin), and regular career conversations are held with each designer. This ensures that there are no surprises during performance conversations!
The restructuring of Design resulted in significant improvements in knowledge transfer between product teams. In particular, the ability to share components and use cases greatly reduced unnecessary design work, and made major inroads into ultimately creating a common look and feel across Caseware’s product line.
The restructuring initiative also resulted in a large jump in design capacity. In April 2022, the team was working on a total of 10 concurrent epics. By April 2023, this had increased to 83 concurrent epics.
The combination of team restructuring and development of the dual-track career ladder led directly to increased engagement among the entire Design team. According to the company’s semi-annual Employee Engagement Survey, overall engagement among designers increased from 58% (December 2021) to 77% (September 2023). The greater variety of design work increased job satisfaction. Most significant of all, since the new structure was implemented, there has not been a single resignation among the Design staff.