I redefined Design as a strategic partner for the business and led the team in launching dozens of projects at the feature, system, and company levels.
Redefining Design at StreetEasy
Getting Up to Speed Quickly
I arrived at StreetEasy (Zillow’s NYC brand) after a period of extended transition for Design. Turnover was high and Design was seen as a visual renderer of prescribed requirements.
I immediately got to work hiring for several open roles including StreetEasy’s first UX Researcher. I began building relationships and getting to know the product and complex multi-side marketplace business. The team size was initially 5, eventually expanding to 10.
Building Relationships, Socializing a Vision
I learned what was important to senior leaders and my peers as a foundation for creating shared wins in the future. This was also an opportunity to begin sharing an ambitious vision for the impact that the new design team would create. I knew that to succeed, the team would have to emphasize strong critical thinking and EQ in addition to design craft.
Hiring and Operationalizing a New Team
After hiring several talented team members, I led them in creating a new set of processes, artifacts, and rituals. The new design process was expressed in 3 docs that describe:
the high-level process
how design operates within the product development cycle
how the process is applied to a specific project
To achieve this, I had to document a more accurate representation of the existing product development process. This document was used to create space for high-value contributions by Design and align with leaders on other pain points to improve the process. The resulting new process was fully adopted by the company.
An excerpt from the high-level design process
How design is integrated throughout the product development process
A planning and working doc used by designers to apply the process to a project
Establishing the Design System
Establishing the StreetEasy Design System was an early major shared win. I learned that previous attempts to do this had been unsuccessful and there was reasonable skepticism.
I worked closely with the head of engineering to clear technical hurdles and set up a cross-functional design system team that established the structure and first components. I identified a designer passionate about this area to lead this initial phase for the sake of speed and focus.
Once the foundations were established, I distributed Design System responsibilities to a larger set of designers and supported the team directly to bring more knowledge and perspective to its ongoing development.
Today the design system, living in React libraries, Figma, and Storybook, has over 35 thoroughly documented components and has been adopted by 100% of development pods. It has sped design and development delivery, integrated accessibility into the experience at scale, and reduced system complexity and maintenance costs.
The Design System documentation in Storybook
Establishing Design as Facilitator
Another important initiative was the StreetEasy Workshop Playbook. I worked closely with a senior designer to create this facilitation guide. It established Design’s role as the leading facilitator of structured conversations. Other teams began seeking our guidance and using the playbook to run their own workshops after participating in Design-led workshops.
A Global Remote Team
Later I added 2 additional designers to the team as part of a major initiative and related acquisition. And promoted a Senior Designer to Product Design Manager. At this point, we had become a global remote team with members stretching from California to Ukraine, with about half living in NYC.
Cross-functional Approach: Multiplicative Power
During this time I hired StreetEasy’s first (and an exceptionally talented) UX Content Strategist. This addition to the team set up our transformation from a Product Design team – that also had a researcher – to an Experience Design Team. This new structure allowed Product Designers to dive deep with a vertical focus while benefitting from UXR and UXC’s horizontal view.
This structure enabled us to create stronger systems as we delivered isolated projects. It bridged silos and surfaced critical context in projects – and resulted in more connected experiences and more successful customer and business outcomes.
Content Strategy (with an Emphasis on Strategy)
With funding for a single UX Content Strategist, I had a choice between a writing-focused or systems-focused practitioner. I chose the systems focus as a way to ensure UXC’s impact at scale.
A great example of this in action: UX Content created a StreetEasy content model by collaborating with several active project teams. This content model was a major time saver and quality driver for engineering’s product-wide service-based architecture initiative.
UXC was also a critical contributor to the Design System, leading the creation of component guidelines that sped design system adoption and accelerated development work. All this while bringing a systems-wide and product-wide perspective to several embedded engagements with project teams.
UXC was new to StreetEasy, so I invested in significant evangelism in the first year to enable the utilization of its full capabilities long-term
UX Research… Beyond UX
By this time I was hiring a new researcher. I gave this person a challenging and exciting goal to pursue with my support: centralize and drive quality in research throughout StreetEasy while supporting design partners and business stakeholders. In other words, establish UXR as the org-wide leader in customer-related knowledge creation.
In about a year, this challenge had been met. Marketing, business analysts and others increasingly came to rely on UXR for guidance on research far beyond the scope of UX Research.
I also turned to UXR for several foundational studies that drove the product roadmap and led to major improvements to the end-to-end StreetEasy search experience.
Driving Experience Quality
With the team established and rapidly expanding its impact and influence, I shifted focus to the quality of the StreetEasy experience through several initiatives.
Product-wide Visual Brand Update
The marketing team had worked with an agency to develop an exciting and long-overdue update of StreetEasy’s visual brand elements. However, the overall org structure made it very difficult to execute projects that cover the entire product surface area. Ownership was hard to determine and no one wanted to give up any of their pre-allocated resources to make this happen.
I assembled a cross-functional team (including brand, product design, engineering, and PMO), drafted a plan, and worked with leaders in product and engineering on resourcing.
We completed the product-wide upfit while minimizing expense and disruption to the experience – much of it integrated into pre-planned product initiatives. This approach became the template for addressing future product-wide changes.
The Design System documentation in Storybook
Driving Accessibility Adoption
Another product-wide initiative (and in this case, company-wide) was accessibility adoption.
This major change management project required building support from leaders at all levels. In addition to remediating current experiences to WCAG 2.1 AA standards, I made sure we had clear accessibility standards in place going forward for both design and engineering (working with a great front-end manager as well as the head of Engineering).
I established a designer as our a11y SME with a charge of up-skilling the rest of the team on a11y best practices, both for the web and mobile. I then kickstarted the remediation process by mapping the web site and prioritizing a “golden path.” This provided the clarity the team needed to start working quickly. And it gave senior leaders confidence that were addressing requirements thoroughly and efficiently.
I also made sure each team at StreetEasy (including senior leaders) had an understanding of what web accessibility is, why it’s important, and how it’s directly relevant to their work.
I did this through an All Hands presentation, a lot of 1:1 campaigning and follow-up, and by integrating this work with the development of the still-young Design System.
From an all-hands presentation I gave introducing a wide audience to web accessibility
Creating an Experience Vision
As a complex product with multiple coexisting business models, it was always challenging to communicate the year’s business and product strategy in a way that everyone could understand and get excited about.
I developed a StreetEasy Experience Vision that showed what it could be like to use StreetEasy in the future once we had built all the things we had planned. This was informed by the current roadmap and backlog, conversations with senior and peer leaders as well as a series of workshops I facilitated in partnership with mobile developers to understand emerging mobile technology and its potential application to our known customer problems and business priorities. I then worked with a brand designer to create the final visual presentation.
This vision energized teams across StreetEasy and provided clarifying points of reference in countless strategic conversations.
Excerpts from my Experience Vision presented at an all-hands meeting and referred to frequently thereafter
Addressing Gaps in Experience Quality
To drive quality in our day-to-day design work, I established a robust system of standards, reviews, and other quality checks.
I also established a program to document and address the many existing experience quality issues and opportunities. I created the Design Debt Backlog to capture, stack rank, and address small issues.
Then I worked with UX Research to conduct a study comparing StreetEasy’s home search experience (on desktop and mobile) to a competitive set. In the following product planning period, I used insights from the study to argue for and win a significant investment in core search.
Insights from that work were the foundation of the Experience Opportunity Backlog – an ongoing ranked list of larger experience challenges and opportunities. This document was used in product planning to see where business-driven initiatives could be opportunities to address the items on this list.
The Experience Opportunity Backlog and the flow from identifying quality gaps to implementing solutions
Modernizing Search for Customers and the Business
As demonstrated by the competitive search study and Experience Opportunity Backlog, it was clear that much of StreetEasy’s core search experience was out of date, risking its dominant position as the preferred real estate search app in NYC. Additionally, there was significant friction and inconsistency in the search funnel working against the new and growing success-fee model.
After I won the investment in the core search experience, I helped hire a product manager and assigned a product designer.
I supported this work closely in a number of ways:
I led the initial definition of the work-stream for the project team, ensuring that all involved were aligned on the scope and ambitions of the work.
I worked with the team to navigate challenges in getting this new and unique work-stream to fit within the existing product development process.
Then, I closely supported project teams as they made large and small improvements to the search experience.
These changes helped bring the experience up to current standards while boosting several key business metrics. Along the way, I worked with business partners to make sure they knew about and valued the team’s wins. And to ensure that the metrics we were watching were in line with current business priorities.
In the end, we were able to make significant improvements to each part of the search funnel, driving several wins in key metrics and reducing our vulnerability to new competitors offering experiences that don’t carry the design and tech debt associated with being the industry leader for over a decade.
After: High-performing map/list hybrid search results
Before: Old list view search results page with small, less helpful map
Augmented Reality Feature
A very different example is StreetScape AR. This was an augmented reality feature that we designed and launched quickly, proving the power and flexibility of our design process and collaborative approach. Check out the case study for details on how I defined and delivered project success.
Refining Product Ops and Supporting the Evolution of the Product Org
Just as I initiated and co-led the effort to redefine the official product development process, I had several other opportunities to influence the composition and operation of the product team: I was deeply involved in the hiring process for half of the current PMs in addition to the new head of Product.
And, since Design now reports to Product, I led several activities to integrate the Product and Design teams under the new leader, paving the way for a new level of close collaboration. I also led the creation of key milestones in the product development process such as the shared product and design Discovery Review.
These improvements reduced churn on project teams and increased the impact of projects across the board. Senior stakeholder were given the appropriate level of visibility and participation and project teams were finally receiving the right level of feedback at the right times.
