Introduction
Hi, I'm Skipper. Yes, that's my real name.
I've been designing for humans and our screens for over a decade. I revel most in the collaborative and iterative process of crafting digital/physical experiences that are enduring and delightful — this includes strategy, research, testing, and discovery facilitation — while unblocking and growing others’ careers.
I currently consult a handful of hours a month for Shep, a travel startup — as I have for the last three years. Previously, I led design full-time at thoughtbot, Sesame, mediabistro, and Brabble among others.
Hi, I'm Skipper. Yes, that's my real name.
I'm on the hunt for my next full-time director-level role. I'm looking for it to be more parts coach than player, but I'm always game to roll up my sleeves and practice my craft as a designer and working alongside my team when necessary.
I currently consult and design direct a few hours a month for Shep, a travel startup partnering with Travel Centre among others. Previously, I led design at thoughtbot, Sesame, mediabistro, and Brabble among others.
My work
My work
Leadership
Shep
Design direction, consulting, and general advising for an early stage travel startup in Austin, TX currently partnering with Flight Centre among others »
Consulting product and brand design director for a travel startup in Austin, TX — more here »
thoughtbot
Led design and strategy while advising client engagements to success while mentoring the team as well as sales/ prospecting efforts in San Francisco, CA »
Responsible for leading design, strategy while advising client engagements to success as well as sales and prospecting — more here »
Sesame
Built and managed the design team in Brooklyn, NY while launching a two-sided marketplace collaboratively with a blended effort, local and remote »
Product design team built from scratch in Brooklyn, NY while launching a two-sided marketplace with a blended team, local and remote — more here »
Design
I came up as a designer and I've done lots of kinds of work over the years — some have required leadership by doing while some have been fully in the camp of individual contributorship. Shep and Sesame had (more or less) their fair share of design work in parallel with leadership while other IC projects to peruse here include Prudential, two Bank of America undertakings (one for bankers, one for investors), Council of Fashion Designers of America at Cadillac House, mass transit in the greater Toronto area (Metrolinx), and Starwood — all done during my time at Fjord. Also available, packaging design for DayNa Decker.
I came up as a hands-on designer and I've done lots of kinds of work over the years — some of it has had leadership baked in, some have required leadership by doing, and some have been fully in the camp of individual contributorship. Shep and Sesame both had their fair share of IC work along with leadership; other projects include Prudential, two Bank of America undertakings (one for bankers, one for investors), Council of Fashion Designers of America at Cadillac House, mass transit in the greater Toronto area (Metrolinx), and Starwood — all done during my time at Fjord. Packaging design for DayNa Decker is also available.
Audio
I'm currently hosting/producing How This Works and am psyched about it. Over the years, I've done a number of interviews, talks, and podcasts. With the latter, sometimes it's been in front of the microphone, sometimes backstage. Examples include tentative, Fjord Fika, and Design Voices.
My values
Perfect is the enemy of done
Move quickly, build, and test solutions for specific problems iteratively, collaboratively, and in the shortest amount of time. Generally, ship it faster than you think you should — but not so fast that you're compromising on quality. (Voltaire would agree with most of this.)
Get out of your own way
One of my biggest pet peeves is when someone says, I can't do a particular thing — whether that's about drawing or giving speeches or getting in shape. Because, unless there's some kind of physical limitation, the reality is that anyone can do these things. "I can't draw", for instance, is an excuse because someone thinks they should be better at drawing than they are at that moment. Let it go, do what you can, and don't listen to those inner Statlers and Waldorfs.
Make time to be curious, create the space to fail
Listen more than you speak and always step into someone else's shoes while embracing the tension of silence — for user research, for our team members, for home, for peers, for strangers. We live in an age of distraction, that's true, but this will create fundamentally better design outcomes, stronger teams, and better individuals which makes for stronger products.
Invite everyone in
The idea of inclusion means bringing everyone in — and this means all voices and all beliefs, no matter if it aligns with my specific version or with yours. When we set up safe spaces to have conversations (to listen and to share), for our teams and for ourselves to give and receive feedback, when we engage our collective experiences, strengths, and different points of view to inform, challenge, and stretch our thinking, we can make better decisions and have better outcomes for everyone.
You can read more about the first two principles in a longer write-up on Medium. And then you can read about the second two principles in a follow-up to that.
Make the time to be curious, make space to fail
Listen more than you speak and always step into someone else's shoes while embracing the tension of silence
Perfect is the enemy of done
Move quickly, build, and test solutions for specific problems iteratively, collaboratively, and in the shortest amount of time
Get out of your own way
One of my biggest pet peeves is when someone says, I can't do a particular thing — whether that's about drawing or giving speeches or getting in shape
Invite everyone in
Inclusion means bringing everyone in — and this means all voices and all beliefs, no matter if it aligns with my specific version or with yours
My tools
My tools
I believe in using the right tool for the job — not just the thing with which you’re most comfortable. Stretch, reach, and try something different. These days, I tend to use:
- A moleskine notebook for notes, capturing them in Evernote, and setting up tasks in Todist
- Figma for creating pixel-perfect mockups and simple prototyping (though not quite Principle, Flinto, or InVision) with its solid versioning, and multi-player collaboration — although Sketch has a headstart with its huge community of designers, the wealth of third-party plugins, and the fact that it plays well-ish with Adobe; I also think Adobe XD is breaking new ground and is potentially a year or two away from owning the space outright IMO
- Keynote for deck work
- Notion for creating team notes and wikis
- Magnet for organizing workspaces
- Contrast to check WCAG 2.0 accessibility standards
And in 2020, I'm looking to have more experience with:
- Storybook or some other UI environment that partners design with code — we had several dozen components built out at Sesame and used it in very small ways at thoughtbot
- Making, maintaining, and growing a new podcast
- As much analog as digital forms of creation — drawing, painting, playing guitar, etc.
One last note, I’m a proponent of using the right tool for the job — not just what you’re comfortable with as a designer. Stretch, reach, and try something different. These days, I tend to use:
- A moleskine notebook for notes, transcribing later in Evernote, and setting up tasks in Todist
- Figma for creating pixel-perfect mockups and simple prototyping (though not quite Principle, Flinto, or InVision) with its solid versioning, and multi-player collaboration — although Sketch has a headstart with its huge community of designers, the wealth of third-party plugins, and the fact that it plays well-ish with Adobe; I also think Adobe XD is breaking new ground and is potentially a year or two away from owning the space outright IMO
- Notion for creating team notes and wikis
- Keynote for making decks
- Magnet for organizing workspaces
- Contrast to check WCAG 2.0 accessibility standards
In 2020, I'm looking to have more experience with:
- Storybook or some other UI environment that partners design with code — we had several dozen components built out at Sesame and used it in very small ways at thoughtbot
- Making, maintaining, and growing a new podcast
- As much analog as digital forms of creation — drawing, painting, playing guitar, etc.
I believe in using the right tool for the job — not just the thing with which you’re most comfortable. Stretch, reach, and try something different. These days, I tend to use:
- A moleskine notebook for taking notes, transcribing later in Evernote, and setting up tasks in Todist
- Notion for creating team notes and wikis
- Figma — although Sketch has quite a headstart with its huge community of designers and I think Adobe XD is breaking new ground and is two years from owning the space outright IMO
- Keynote for making decks
- Magnet for organizing my laptop workspace
- Contrast to check WCAG 2.0 accessibility standards