What you’ll find here
Loads of DocuSign
Half of the pieces here talk about work I did at DocuSign because I worked there for four years as a leader most recently. Those pieces tell stories about my work and its impact on areas like career ladders and hiring for the design organization, a documented effort to advance design maturity on a larger team I led for a short while, and one of the most successful workshops I’ve ever done to date.
A sprinkle of Avanade — because I helped rapidly scale a team to over 100 people and did most of the design operations work myself, that one is in here even though it dates back to 2010.
A spoonful of MorningStar — work that will give you an idea of how I approach designing both services (Accessible Investing) and products (Modern Portfolio Theory), including a few assets created for the work I did.
I only put work in my portfolio that is less than 5 years old if it contains actual design artifacts. That work must also meet my bar for quality and success, which is objectively described as “a lot” and does not always mean it has commercial success or can be measured that way.
Design maturity FTW
It’s a pretty simple maxim — wherever I go, I try to leave things better than I found them.
I use time-tested methods of strategy and design. I typically apply it to how I set up and run teams, develop partnerships, and see impact.
Whoa! obvious Problems
When I was asked to take on a team of nearly 20 designers and managers at DocuSign after a tsunami of executive and leadership departures, I started out like I usually do: listening, watching, and talking to people.
I saw
a set of overwhelmed managers, lead designers who felt pretty stifled, and mid-level designers craving mentorship
three separate teams of designers who almost never spoke working on “editions” of the same SaaS enterprise product
a sub-par user experience that designers felt they were having no impact on
a leadership team that believed design was there to execute on a vision, but the vision couldn’t be developed because of…
dangling product strategy questions about whether or not we’d integrate with the company’s flagship product, which stalled vision and design work
I started by mapping out the process and all of the red flags I saw in it.(See below)
The Diagnosis
We had
a product that wasn’t so much a product, more a disparate, disjointed, kinda-sorta “workflow” thing
a process that was simply not friendly to design or designers
product managers incentivized to ship but not focus on quality
engineers working on an aging tech stack — minimal changes only, please and thank you
a high percentage of churning customers who would declare on departure that “this isn’t a DocuSign product”
I drew out a huge whiteboard on Miro with the process, my goals for improvement, and a big space in between for ideas on how to get there. I filled it, then deleted half the post-its right before I talked to my team to see how they responded and what they thought. (See Below)
In the changes I decided to make first, I prioritized the team’s health and the improvements I thought would have a high impact on people feeling more motivated or better about their work, because, well, that’s where you always have to start.
Changes I made
I only had six months here — we re-organized again — but because I thought this was going to be my team for while, I got moving.
Here’s what I was able to do in the time I had:
I moved designers from a product-centric model to a core jobs to be done model so that everyone would learn about similar functionality across editions without breaking the flow of work.
I asked lead designers to be responsible for a job to be done category, supporting product quality overall by leading critique and mentoring designers, with a focus on de-duplicating and bringing better continuity to the work being done between editions, which gave them a differentiated role from senior designers.
I also asked leads to use what they learned about inconsistency in conversations with engineering leaders to start bringing the idea of streamlining the user experience and product, which helped them start seeing better impact.
Managers were moved away from managing design work to managing relationships with product so that we could mature the conversations, which helped us get more involved in up-front planning — when we could propose research and testing.
I started escalating the product strategy issues to senior leadership in product experience and in forums where I had a chance to ask questions about it, which helped surface the need for clear decision making at the executive level.
The changes started to take hold and we started moving forward in more productive ways. Had I stayed in that role, I would have kept going with my plan, evolving it as I saw impact and need.