Hey, I’m Kiley!

Kiley at a design leadership event, speaking with attendees

I love a good messy problem. The kind where the customer journey is complicated, the system underneath it is even more complicated, and there are a lot of smart people with different ideas about what to do next. I’m usually the one connecting the dots, and the people, to find a path through.

Across Intuit, Nextdoor, and Chegg, that’s meant platforms, growth and monetization, design systems, and AI-assisted experiences. Most recently, I built and led the design team shaping QuickBooks’ expansion into industry-specific solutions, and wrote the AI design principles behind its agentic workflows. I see AI as a way to help teams align on a direction faster, but holding the bar for judgment and craft is still the designer’s job.

I moved into leadership because my biggest impact came from making both products and people stronger. I’ve built a design org from zero to 15+, hired 20+ designers, and watched many of them grow into bigger roles. I hire for curiosity, because skill can be taught and curiosity can’t.

I care about building inclusive products and leaving teams stronger than I found them. Outside my day job, I mentor designers and emerging leaders through ADPList and Hop Design Buddies.

When I’m not working, you’ll usually find me biking around San Francisco in my gold helmet, digging through record crates, or catching a local show.

 

How I lead

Good design makes complex things feel simple. That only happens when a team understands the real problem, shares a high bar, and has someone close enough to the work to say “not yet.”

🎯 Connect customer value to business impact
I use customer insight and data to shape what we build and why, so design influences the roadmap, not just the screens.

🔍 Stay close without becoming the bottleneck
I step in when my perspective unlocks the work, and step back when the team is ready to own it.

🤝 Build trust through candor and care
I leave room to challenge a direction, share unfinished thinking, and hear honestly what needs to improve.

🧭 Create clarity before asking for execution
I help teams understand the customer, the business stakes, and which decisions matter most.

🌱 Give people ownership, not just tasks
I set clear expectations, tailor coaching to the person, and give designers room to lead.

⚙️ Raise quality through systems
I build shared principles and critique practices, so quality never depends on last-minute heroics.

 

What it’s like to work with me

“[Kiley] has a unique talent to both translate business and customer needs into well-designed product, and to also get buy-in and support from partners and executives on those well-founded design decisions.”
— Susan Dunavan, Director of Product, Strategy & Growth · Chegg · Cross-functional partner

“She can quickly and accurately identify user needs and translate them into effective design solutions. She is also skilled at communicating the team’s ideas and vision to both technical and non-technical stakeholders. A natural leader, Kiley is supportive, empowering, and results-oriented.”

Gary Yip
Product Manager · Chegg
Product partner

“Kiley has a real talent for creating an environment where people feel comfortable asking questions and being honest when they don’t have all the answers… She built a culture that was genuinely collaborative instead of competitive—all while moving the needle on the business side of things.”

Jenna Davis
Senior Content Designer · Intuit
Former direct report