Kevin Steigerwald
Design Leadership
Building cross-functional teams to deliver meaningful solutions
- Senior Director, Product Design @ Jama Software
- kevin@sproutworx.com
- About me →
Design Leadership
Building cross-functional teams to deliver meaningful solutions
Serving as sole designer and product manager, I led a small development team to build the Live Trace Explorer—a proof-of-concept designed to make traceability intuitive, explorable, and actionable for a new audience: executives needing data-driven insights into project health and risk.
The challenge was proving both visual feasibility and technical capability while expanding Jama’s appeal beyond traditional users. Rather than requiring users to navigate complex data structures, we created an interface that surfaced critical information at a glance.
Working with limited resources, I facilitated rapid design exploration with key stakeholders, iterating through use cases to land on an approach that balanced ease of setup with demonstrable meaningful impact. This collaborative process secured executive alignment early, allowing us to move quickly with confidence.
I designed directly in code using HAML and SCSS, enabling developers to focus on APIs and backend infrastructure while ensuring seamless integration when our parallel workstreams converged. This approach eliminated traditional design handoff friction and accelerated development velocity.
By the time we delivered the tech preview, we were running in production with real customer data—positioning us to expedite general availability and gather authentic user feedback immediately.
Kevin’s work on Live Trace Explorer for Jama Connect was of huge benefit to the company. Using a small team, Kevin was able to work with users and executives to deliver a breakthrough UX/UI for visualizing complex, multi-dimensional data in an easily approachable way. The project was a success and is in constant use across the world. Josh T, Chief Strategy Officer
As a founder of Notion Data and with just 18 months of runway, I led product development to deliver an MVP that solved a critical pain point: enabling product teams to consolidate tool data into unified dashboards without relying on BI teams or expensive platforms.
With my co-founder focused on sales and marketing, I owned the end-to-end product experience—defining requirements for core workflows (onboarding, authentication, custom metrics, dashboards, integrations, and notifications) and creating all design assets, including writing the frontend HAML and SCSS for the product that our two developers would then wire up to the backend.
To enable early adopters, we prioritized an onboarding flow that let users build custom metrics or select from a “metric cookbook,” supporting both manual data entry and integrations with tools like Pivotal Tracker. This hybrid approach unlocked immediate value by displaying cross-tool data before we could scale integrations.
If you took Notion away, it would be like going back to bearskins and spears. Andrew M, VP of Engineering (Customer)
Beyond product delivery, my most significant contributions have been in developing and scaling design teams. I believe investing in people and culture creates compounding returns that extend far beyond any single feature or release.
When I took over design at Jama in 2019, I inherited an undersized team stretched across a growing organization, lacking clear roles and responsibilities. To deliver on roadmap objectives and establish a foundation for growth, I led the creation of a team vision, mission statement, and guiding principles.
I established structured team rituals to strengthen coaching and collaboration. This included bi-weekly Design Studios where team members reviewed work in progress and exchanged feedback. On planning days, we held cross-check meetings with our design engineer and documentation team to ensure visibility across concurrent initiatives and identify areas requiring additional support.
This framework enabled autonomous collaboration, cross-product alignment, and set clear expectations for development partners to ensure consistency while allowing me to dedicate more time to supporting individual team members' growth and development.
Kevin built a design organization I could depend on. The design team under him operated with clarity, accountability, and momentum, which made product decisions faster and far less chaotic. That stability was the direct result of how he led. Katie H, Product Line Manager, Advisor/AI
Kevin's approach to people development expertly balances empathy and inclusivity with a high standard of excellence. At Jama, he developed a team of junior designers into highly collaborative contributors who significantly elevated the quality of our product.
Kevin was never "just" our Director of Design. His big-picture perspective, deep understanding of the business, and exceptional product expertise led him to naturally step into additional roles as a strategic product advisor, company culture contributor, and mentor. As a product line manager and new people manager myself, I regularly turned to Kevin for advice—whether I was making a strategic decision about my product, hiring new team members or developing my management skills. Debbie M, Product Line Manager, Interchange/Integration
Accessibility compliance had languished at Jama over the past decade despite good intentions, creating risk as we pursued government contracts with strict ADA requirements. Remediating our 15-year-old monolithic application required a strategic approach that would demonstrate commitment to prospects and customers while making measurable progress.
I partnered with a designer to conduct an initial VPAT assessment, establishing our compliance baseline and creating a remediation roadmap. Using these artifacts, we secured executive buy-in and resources for a dedicated development team by demonstrating clear ROI and opportunity costs of inaction.
I facilitated the strategic design direction of AI features in Jama Connect, partnering with designers to establish a cohesive framework for capabilities being implemented across the application. Without a unified approach, users would struggle to discover AI functionality and understand how it enhanced their workflows.
This design strategy created visual and interaction patterns that surfaced AI capabilities in context, integrating them seamlessly into existing workflows while maintaining clear differentiation. AI features became discoverable and built the user’s trust, reducing cognitive load and encouraging exploration—transforming scattered capabilities into a strategic advantage that drove engagement and positioned Jama as an AI-forward platform.
Kevin's direction on our AI initiatives pushed the work beyond novelty and forced the team to solve the hard problems that actually move our customer outcomes. Katie H, Product Line Manager, Advisor/AI
Design inconsistency plagued Jama’s application after years of rotating development teams, resulting in a myriad of misaligned components that hindered both user experience and developer productivity.
While the design team supported existing roadmap work, I led the effort to define and design a modern React component library that would ensure consistency, address UX gaps, and streamline development. I secured executive buy-in by presenting the ROI of this foundational investment and the risks of continued technical debt if we did nothing about it.
I led a comprehensive cleanup of our Pendo installation to establish a reliable source of truth for product usage data, enabling data-driven decisions across Product, Marketing, and Sales teams while supporting customer health scoring.
This included auditing our Salesforce integration to ensure proper metadata flow, allowing granular segmentation to understand behavior and adoption across targeted user cohorts. I also uncovered a critical data collection gap that falsely indicated customer churn, partnering with SaasOps and Pendo support to resolve it and restore data integrity.
I worked with a cross-functional team of leaders to develop an internal scoring mechanism to evaluate customer health and predict potential churn. This initiative addressed critical business needs around unexpected customer attrition and declining renewal rates that were impacting recurring revenue forecasting.
Working with business intelligence and customer support teams, we designed a predictive analytics framework synthesizing multiple data streams. We systematically tested product usage patterns, support ticket data, feature adoption rates, and engagement metrics against historical churn data, using iterative model refinement and continuous validation to ensure accuracy and reliability.
The solution transformed our customer success operations by providing actionable, real-time insights that enabled proactive account management and strategic intervention strategies.
Kevin was an invaluable team member during this project - He helped us navigate the technical complexities of our product data, he provided guidance on designing a complex data solution that was both consumable and actionable for non-technical users, and he brought a rigor to our project management that enabled us to achieve an aggressive target given to us by executive leadership. All the while, Kevin served as a mentor and a source of positivity for our project team - I really valued Kevin’s knowledge, demeanor and effectiveness, and I thoroughly enjoyed getting to work with him. Kevin P, Vice President, Analytics & GTM Operations
I led the redesign of content headers across Jama Connect to eliminate inconsistency and reduce friction in user adoption. Years of fragmented development had resulted in dozens of views presenting similar content with different layouts, forcing users to relearn patterns throughout the system.
My team established a simple, repeatable header structure with clear guidelines that could scale to all existing and future layouts. We rolled out improvements systematically in a planned release, monitoring impact and iterating based on user behavior.
I led product management and design for a complete overhaul of CrowdCompass’s conference app suite across iPhone, iPad, Android, and mobile web.
We introduced an innovative event hub app paired with a new admin CMS that let customers customize and publish event apps to all platforms with a single click. This architecture eliminated our customers’ biggest risk: Apple app store rejections on tight conference timelines. More than a decade later, this solution is still driving conference apps for CrowdCompass and has been mimicked by competitors.
I led the initial concept and design of Document View in Jama Connect, fundamentally transforming how users edit and consume information within the platform.
This feature introduced inline editing within a document-like reading experience, aligning with user expectations set by familiar tools like Confluence and Google Docs. The design bridged the gap between Jama’s item-based structure and the fluid authoring experience users expect from modern collaboration tools.
To accelerate implementation and ensure design fidelity, I delivered a mockup written in HAML and SCSS (draft viewable here) with interactive elements that demonstrated key workflows and interactions. This hands-on approach reduced ambiguity for developers and minimized design-development iteration cycles.
Once the foundation was established, I transitioned day-to-day execution to a designer on my team while maintaining strategic oversight, enabling the feature to progress efficiently while freeing capacity for other initiatives.
