AI-native product design leader
HI, I'm Yvonne Doll, a product design leader, musician, and fine artist. My experience as both a creator and a technology leader shapes how I think about UX, products, people, and the future of AI. For 20+ years, I've helped teams navigate major technology shifts and build products at scale.
Vision.
Systems.
Scale.
Hello, I'm Yvonne Doll.
I lead and design AI-powered products and complex systems, turning messy workflows into clear, trustworthy experiences.
I’m also a musician and oil painter.
Music and painting shape how I think about rhythm, balance, restraint, and creative judgment.
Chicago, IL · open to travel or relocate.
eeeeevon@gmail.com
Choose your own adventure
Get the one pager →
Get the one pager →
Get the one pager →
AI-first design org Kustomer.com. ★ Context1.md
At Kustomer, I brought the design team into a new AI-first way of working, replacing static handoffs with live collaboration, shared prompts, evals, and guardrails that cut idea-to-output from days to hours.
~hrs
Idea to Prototype
1B+
Conversations
served at scale
0
hand-off time
Reusable AI skills transformed expert UX review into a repeatable system.
# AUDIT UX: {FEATURE}
## What we encode
Undefined states
Dead ends
Abandonment risks
Recovery failures
Broken user journeys
## OUTPUT
Flow inventory + priority matrix. Critical → Low.
Turn design standards into reusable AI instructions.
## What we encode
Accessibility requirements
Content standards
Component usage
Brand voice
Error handling
Interaction patterns
## Output
Reviewable design specification + implementation guidance
A decision rule for where automation ends and human judgment begins.
## Decision tree
- Reversible / Low-Stakes → model decides, log it
- Reversible / High-Stakes → model proposed, human confirms
- Irreversible → human decides, model assists
## Default
Show your work (trust)
Review the AI behavior, not just flows and screens
## What we critique
- Outputs → are responses useful and correct?
- Recovery → what happens when the model fails?
- Confidence → can users trust the result?
- Boundaries → where does automation stop?
## Output
Design rules, prompt updates, evaluation criteria, and system improvements.
Sr. Design Director · Jetpack/WordPress
Fifteen designers, seven engineering squads, fourteen apps, forty plus features. I rebuilt intake, prioritization, and rhythm. A weekly 15 minute sync killed the politics.
↑58%
PRODUCTIVITY Y.O.Y
↑20%
FEATURE RELEASES
27M
USERS SUPPORTED
Case 02 · DESign org PRODUCTIVITY
Sr. Design Director · Jetpack/WordPress
Built a research system that ran in parallel with engineering. An adapted Eisenhower matrix for “just enough research” so the loop never slowed shipping.
~250
~623
USER INTERVIEWS
STUDIES
~175
INSIGHtS SHIPPED
375
USABILITY TESTS
Case 03·RAPID INSIGHTS
I’m a hands-on product design leader who brings executive judgment, creativity, and systems thinking to complex work. Music and abstract painting shape how I think about timing, ambiguity, restraint, and clarity, whether I’m leading a team or running the whole design show myself.
Company culture is everything. I'm proud of the strong relationships I've built with my colleagues. I help build supportive, innovative, and action-oriented teams that uplift one another and collaborate to create exceptional work.
Jeffery Zeldman Executive Creative Director | Automattic
Yvonne Doll is a one-in-a-million, multi-talented designer, artist, musician, and, above all, design leader. It was my pleasure and privilege to watch Yvonne mentor, encourage, inspire, and support the Jetpack design team. Beyond being a model colleague, she’s also tremendous fun, supremely cool, and somehow, despite being fun and cool, a grownup and mensch. I would hire her myself if I were in a position to do so, and consider myself fortunate indeed if she accepted the offer. Meet her. Hang out with her. Interview her. You’ll be glad you did.
Andrei Slobstov Brand Design | automattic
I had the pleasure of working alongside Yvonne during her time as a Design Director at Automattic, where she made a big impact on the Jetpack design team and our company culture overall. Yvonne created a supportive and inspiring environment, making everyone feel valued and motivated to do their best work, and it showed!She was a fantastic mentor to me, always leading by example and pushing for creativity. Yvonne is an empathetic leader and genuine creative spirit!
Caiti Vincel Lead Product Manager | Sprout Social
Yvonne encompasses the most attractive qualities you'd want in a leader. She hires quality people and trusts them to do good work. Her style of management fosters engaged developers and designers that feel free to be creative while offering valuable input. She is a fantastic listener and outwardly demonstrates respect for all points of view and is always looking out for the best interest of the user. Yvonne brings energy to any team and has demonstrated that her work has the power to re-inspire a company during a pivot. She is an invaluable asset.
James Grierson CEO | Jetpack
Yvonne is a triple threat designer in that she understand design architecture, visual design and product design. It was a pleasure working with and learning from her during our time together in Jetpack. Yvonne not only led our design team, but was also an integral member of our executive leadership group at Jetpack. Her experience and insights into understanding customers helped us to revolutionize the Jetpack experience. She was also a driving force in aligning our design, development and customer service teams and building a collaborative environment that fostered better customer focused experiences.
EDER RENGIFO Senior ai designer | automattic
Yvonne is one of the best leaders I have worked with. She recognized my skills and interests and helped me define my career goals. Under her leadership, I always felt included and supported. She created an amazing environment where everyone stayed motivated and committed to doing their best work while having a great time. Any company looking for someone to manage, lead, and inspire talented people would be lucky to have her. I also learned a lot about user research from her, knowledge that has helped me grow as a designer focused on validating hypotheses and delivering value to the business.
Ilona Jaudžemytė Senior UX Designer | Jetpack
I’ve had the pleasure of working with Yvonne for the past 2.5 years, and it’s clear that her leadership goes far beyond technical expertise. What sets Yvonne apart is her ability to cultivate an environment where creativity thrives while maintaining a sharp focus on results. She has a rare combination of vision, empathy, and the drive to push teams toward success, always balancing strategic thinking with a deep understanding of individual team members’ strengths.
FILIPE Varela Design director | Jetpack
Yvonne has a gift for unifying teams and keeping everyone focused on delivering the best possible experience for the user. She brought her deep expertise in user research and implemented practical, effective research processes that have seeped through the entire company. Yvonne is highly impact-driven and doesn’t waste time on unnecessary fluff. She’s as pragmatic as they come, always focused on what will move the needle and deliver results, fast. But what really sets her apart is her integrity and the genuine care she has for her team.
Nick Kovacevich Head of UX Design & Research | AWS Marketplace
I was very lucky to be able to work for Yvonne. She's a fantastic UX design leader and product thinker. She has a data-driven approach to UX that fuels excellent product design. 10/10 would work with her again.
Andrei Slobstov Brand Design | automattic
I had the pleasure of working alongside Yvonne during her time as a Design Director at Automattic, where she made a big impact on the Jetpack design team and our company culture overall. Yvonne created a supportive and inspiring environment, making everyone feel valued and motivated to do their best work, and it showed!She was a fantastic mentor to me, always leading by example and pushing for creativity. Yvonne is an empathetic leader and genuine creative spirit!
Ballio Chan Creative Director | Automattic
I had the pleasure of working under Yvonne for a few years. The way she leads the design team with extreme efficiency, knowledge, and empathy is truly remarkable. She is what you'd call a player/coach, helping the team through complex design problems and jumping in to assist whenever needed. She will tirelessly fight for your team and deliver results. I am grateful to have worked with Yvonne and wish to be like her for a day. :) Take advantage of the opportunity to work with Yvonne; you won't regret it.
Jeff Golenski Principle Designer/ Product Mgr. | Automattic
Yvonne was my Design Director at Automattic for nearly 4 years. Exceptionally creative and organized, she built incredibly efficient UX Research workflows, led the division's roadmap and strategy, and mentored a team of 8 senior designers. Yvonne excelled at both detailed design feedback and strategic, big-picture thinking across products. Yvonne is a true multiplier—uplifting everyone around her and giving them the tools to become the best person they can.
I’m a product design leader, musician, and abstract oil painter, and that creative range shapes how I work. Music taught me timing and listening. Painting taught me composition, restraint, and how to work through ambiguity. In product design, I bring that same judgment to strategy, UX, research, systems, and execution. I can lead the team, partner with executives, or operate as a one-woman design show when the work needs clarity fast.
View all work→
Company culture is everything. I'm proud of the strong relationships I've built with my colleagues. I help build supportive, innovative, and action-oriented teams that uplift one another and collaborate to create exceptional work.
Yvonne is a cheetah-mounted hot pink laserbeam.
At Kustomer she killed the handoff. Not metaphorically. She moved the entire design org out of static specs and into AI-native co-creation with engineering: prototyping directly in IDEs, testing outputs against real data, shipping in hours instead of days.
She codified the whole thing into reusable markdown-based skills (prompt structures, fidelity rules, eval criteria, human-in-the-loop guardrails) so AI stopped being individual experimentation and became a shared operating system. Then she moved critique from vibes to observable output quality. Then she cut time to decision by 80% because why not.
There's a specific kind of person who can hold systems thinking and creative instinct in the same hand without dropping either. Yvonne is that person. She has the taste to know when the model is wrong and the engineering fluency to fix it herself. Also, great hair.
Design is entering its builder era and she's already there, tuning the instrument while everyone else is still reading the manual. The new shape of design leadership is one she's been painting for years. I'm out of art metaphors, you get it.
Hire her before someone with better pattern recognition than you does, my dude!
Arkady Sokolov
Product, AI | ClickUp
Jeffery Zeldman Executive Creative Director | Automattic
Yvonne Doll is a one-in-a-million, multi-talented designer, artist, musician, and, above all, design leader. It was my pleasure and privilege to watch Yvonne mentor, encourage, inspire, and support the Jetpack design team. Beyond being a model colleague, she’s also tremendous fun, supremely cool, and somehow, despite being fun and cool, a grownup and mensch. I would hire her myself if I were in a position to do so, and consider myself fortunate indeed if she accepted the offer. Meet her. Hang out with her. Interview her. You’ll be glad you did.
Andrei Slobstov Brand Design | automattic
I had the pleasure of working alongside Yvonne during her time as a Design Director at Automattic, where she made a big impact on the Jetpack design team and our company culture overall. Yvonne created a supportive and inspiring environment, making everyone feel valued and motivated to do their best work, and it showed!She was a fantastic mentor to me, always leading by example and pushing for creativity. Yvonne is an empathetic leader and genuine creative spirit!
Caiti Vincel Lead Product Manager | Sprout Social
Yvonne encompasses the most attractive qualities you'd want in a leader. She hires quality people and trusts them to do good work. Her style of management fosters engaged developers and designers that feel free to be creative while offering valuable input. She is a fantastic listener and outwardly demonstrates respect for all points of view and is always looking out for the best interest of the user. Yvonne brings energy to any team and has demonstrated that her work has the power to re-inspire a company during a pivot. She is an invaluable asset.
Rachel Hughes VP Product | Kustomer
Highly recommend Yvonne. She leads by example, rolling up her sleeves on the highest-leverage work alongside her team, which earns trust and raises everyone's bar. She operates AI-native as a core part of how she thinks, works, ships and leads, and her and her team's output shows it. What sets her apart, though, is how genuinely she invests in the people around her. She knows how to push her team in the right way - challenging them to do their best work while fostering accountability and proactivity. An organization that needs a design leader who can operate at the pace of AI-era product development while building a strong,
James Grierson CEO | Jetpack
Yvonne is a triple threat designer in that she understand design architecture, visual design and product design. It was a pleasure working with and learning from her during our time together in Jetpack. Yvonne not only led our design team, but was also an integral member of our executive leadership group at Jetpack. Her experience and insights into understanding customers helped us to revolutionize the Jetpack experience. She was also a driving force in aligning our design, development and customer service teams and building a collaborative environment that fostered better customer focused experiences.
EDER RENGIFO Senior ai designer | automattic
Yvonne is one of the best leaders I have worked with. She recognized my skills and interests and helped me define my career goals. Under her leadership, I always felt included and supported. She created an amazing environment where everyone stayed motivated and committed to doing their best work while having a great time. Any company looking for someone to manage, lead, and inspire talented people would be lucky to have her. I also learned a lot about user research from her, knowledge that has helped me grow as a designer focused on validating hypotheses and delivering value to the business.
Ilona Jaudžemytė Senior UX Designer | Jetpack
I’ve had the pleasure of working with Yvonne for the past 2.5 years, and it’s clear that her leadership goes far beyond technical expertise. What sets Yvonne apart is her ability to cultivate an environment where creativity thrives while maintaining a sharp focus on results. She has a rare combination of vision, empathy, and the drive to push teams toward success, always balancing strategic thinking with a deep understanding of individual team members’ strengths.
FILIPE Varela Design director | Jetpack
Yvonne has a gift for unifying teams and keeping everyone focused on delivering the best possible experience for the user. She brought her deep expertise in user research and implemented practical, effective research processes that have seeped through the entire company. Yvonne is highly impact-driven and doesn’t waste time on unnecessary fluff. She’s as pragmatic as they come, always focused on what will move the needle and deliver results, fast. But what really sets her apart is her integrity and the genuine care she has for her team.
Nick Kovacevich Head of UX Design & Research | AWS Marketplace
I was very lucky to be able to work for Yvonne. She's a fantastic UX design leader and product thinker. She has a data-driven approach to UX that fuels excellent product design. 10/10 would work with her again.
Andrei Slobstov Brand Design | automattic
I had the pleasure of working alongside Yvonne during her time as a Design Director at Automattic, where she made a big impact on the Jetpack design team and our company culture overall. Yvonne created a supportive and inspiring environment, making everyone feel valued and motivated to do their best work, and it showed!She was a fantastic mentor to me, always leading by example and pushing for creativity. Yvonne is an empathetic leader and genuine creative spirit!
Ballio Chan Creative Director | Automattic
I had the pleasure of working under Yvonne for a few years. The way she leads the design team with extreme efficiency, knowledge, and empathy is truly remarkable. She is what you'd call a player/coach, helping the team through complex design problems and jumping in to assist whenever needed. She will tirelessly fight for your team and deliver results. I am grateful to have worked with Yvonne and wish to be like her for a day. :) Take advantage of the opportunity to work with Yvonne; you won't regret it.
Jeff Golenski Principle Designer/ Product Mgr. | Automattic
Yvonne was my Design Director at Automattic for nearly 4 years. Exceptionally creative and organized, she built incredibly efficient UX Research workflows, led the division's roadmap and strategy, and mentored a team of 8 senior designers. Yvonne excelled at both detailed design feedback and strategic, big-picture thinking across products. Yvonne is a true multiplier—uplifting everyone around her and giving them the tools to become the best person they can.
Heidi Beacham Senior Director Product | CoPilotIQ
Yvonne is an exceptional design leader who combines deep customer obsession with a strong ability to build meaningful relationships across teams. She excels at conducting research, engaging directly with customers and clients, and getting to the heart of the problems that matter most. Her experience spans both B2B and B2C products, giving her a valuable perspective on designing solutions that meet customer needs while driving business value. She is also a phenomenal partner to Product and Engineering. Yvonne brings a strong, credible design point of view to the table and is always willing to advocate for the customer and for great design. Her collaborative approach, interpersonal skills, and presence make her a highly respected and effective leader.
I made a small Design Spec Gatekeeper file for ux teams working with AI-assisted tools.
AI is a multiplier. If the judgment is shallow, AI makes shallow work faster.
And what comes next. Design/Engineering Co-authorship
Demos Are Theater. They are seductive because they make everything look easy.
Chicago, IL · open to travel or relocate
01
I turn complex product problems into clear, intuitive experiences people can actually use.
02
I lead AI product work where trust, quality, and human judgment are not optional..
03
I build the teams and systems that help good work survive speed, politics, and scale.
Conversations served
Users supported
Productivity
I'm a hands-on product design leader who brings executive judgment, creativity, and systems thinking to complex work. My background in music and abstract painting shapes how I handle timing, ambiguity, restraint, and clarity, whether I'm leading a team or moving fast as a one-woman
design team.
View all work→
Each one is an operating system built behind the screens,not a redesigned interface.
★AI-first design org · kustomer.com
Head of Product Design · 2024 → now
At Kustomer, I rebuilt the design model for AI-first product work, moving the team from static handoffs to live collaboration across design, engineering, and AI systems. Codified prompts, evals, and human guardrails, cutting idea-to- working-output from days to hours.
// ai practice
A set of operating contracts that codify how decisions get made, what "good" looks like, and where humans go.
// the shift · artifact → ai-native
~/design-stack
diff
–
Figma file is the source of truth
–
Specs, tickets, handoff docs
–
Critique is taste. Slow.
–
AI bolted on as a productivity hack
+
The running prototype is the source of truth
+
The UX audit, codified
+
Critique is observable output quality
+
Loops measured in hours
// operating artifacts · tap to open
Reusable artifacts I created to help teams define, evaluate, and safely ship AI product behavior.
ux-audit-codified.md
Skill 01
Empowers engineers, amplifies designer productivity. Hunts undefined states, every flow, every failure, every dead end.
# UX Audit: {feature/flow}
## What we scan for
Flows, friction, errors
1. Correct
2. Useful
STATES
DEAD ENDS:
RISKS:
## Output
Flow inventory + priority matrix. Critical → Low.
ux-audit-codified.md
Skill 01
Empowers engineers, amplifies designer productivity. Hunts undefined states, every flow, every failure, every dead end.
# UX Audit: {feature/flow}
## What we scan for
Flows, friction, errors
1. Correct
2. Useful
STATES
DEAD ENDS:
RISKS:
## Output
Flow inventory + priority matrix. Critical → Low.
output-eval.md
Skill 02
output-eval.md
Skill 02
human-in-the-loop.md
Skill 03
human-in-the-loop.md
Skill 03
critique.md
Skill 04
critique.md
Skill 04
// let's talk
Email me
© 2026 · Yvonne Doll