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Design that moves
the business forward.

I partner with Series B-C companies as a fractional Design Executive bringing 20+ years of design leadership to teams that are ready to take design seriously.

ABOUT

I started my career in e-commerce at the Gap and Williams-Sonoma where design was about customer conversion. Every pixel had a business case. That discipline has shaped everything I've done since.

At Rocket Lawyer I had the rare opportunity to build something from the ground up twice: first as VP of UX from 2011-2016, then returning as Chief Design Officer in 2019. Across both chapters, I grew the design team, established our research and systems culture, and helped steer the product through its most significant growth - including our push into AI-powered legal tools.

In between, I spent three years at Minted rebuilding the product development process and introducing the kind of design systems and user testing infrastructure that lets fast-moving teams stay consistent at scale.

I'm now taking that body of work fractional and partnering with a small number of companies as an embedded design leader, not an outside consultant.

A 20+ year career in design leadership.

2019-2024

 

2016-2019

2011-2016

2010-2011

2007-2010

2005-2007

2001-2005

Chief Design Officer

Rocket Lawyer

 

Senior Director, UX

Minted

 

VP, UX and Design

Rocket Lawyer

 

Founding Designer

Top Prospect

 

Creative Director

CBS Interactive

 

Creative Director

Williams-Sonoma

 

Designer

Gap Inc. / Banana Republic

HOW I WORK

What you can expect from me.

I'm not a consultant who arrives with frameworks and leaves you with a deck. I work as a member of your leadership team. I'm invested in the outcome, not just the engagement.

I lead from within, not above

I work alongside your team in Figma, in Slack, in standups. Design leadership at its best is invisible: it raises the floor for everyone, not just the output of one person.

I connect design to the business

I've co-owned roadmaps with Product and Engineering for over a decade. I know how to make the case for design in language that CEOs and CFOs understand.

I build things that outlast me

Every engagement leaves something durable behind: a design system, a hiring rubric, a research practice, a team that's better than when I arrived.

I bring curiosity to complexity

I've shipped across legal tech, e-commerce, consumer products, and enterprise SaaS . Complex problems with real stakes are where I do my best work.

Engagement types

01

Embedded fractional

1-2 days per week. Best for those that need consistent design leadership while they grow or search for a full-time hire.

02

Focused sprint

4-8 weeks on a specific challenge: design org audit, design system foundation, hiring, or a major product initiative.

03

Advisory

A few hours a month as a thinking partner for CEOs, CPOs, or design leaders who want an experienced outside perspective.

GET IN TOUCH

How can I help?

 

No pitch, no pressure. I'm happy to spend 45 minutes understanding your situation and being honest about whether I'm the right fit.

Let's chat.

EMAIL

PHONE

LINKED IN

m.courtney.oconnell@gmail.com

 

415.747.4112

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