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.
hello@ydoll.me
See my work
★ AI-first design org Kustomer.com: Case study 1 ★
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
AI reviews working prototypes against shared UX standards before release.
# AUDIT UX: {FEATURE}
## What we encode
Undefined states
Dead ends
Abandonment risks
Recovery failures
Broken user journeys
## OUTPUT
Prioritized findings tied to specific routes, screens, and states.
Version-controlled rules give humans and AI the same system to build from.
## What we encode
Accessibility requirements
Content standards
Component usage
Brand voice
Error handling
Interaction patterns
## Output
Reusable AI instructions and testable implementation constraints.
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
Expose rationale, sources, confidence, and an undo path.
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
Evaluation criteria, prompt and UI changes, guardrail revisions, and new design rules.
WordPress/Jetpack | Kustomer
At Kustomer, I rebuilt design around AI-native workflows, cutting concept-to-validation from days to hours with prompts, evals, and design–engineering loops. At WordPress (Automattic), I led five AI launches for 27M+ users across 14 products (+58% productivity), built a lean research program adopted org-wide, and demo’d my design intake and triage model as a reference for teams across the company..
VARIOUS
Designed the complicated workflows behind AI agent setup, guardrails, procedures, monitoring, and human review, turning an open-ended configuration problem into a guided, trustworthy experience for both end users and administrators tasked with setting up the AI agents.
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.
A thought excercise UX teams
Breaking the grid with Kim.
Detangling complex AI built prototypes.
AI is very good at making vague product ideas look finished. That is the problem.
It Still Needs Someone Who Can Play.
Detangling complex AI built prototypes.
Vision.
Systems.
Scale.
Hello, I’m Yvonne Doll.
I’m a hands-on product design leader who sets strategy and designs AI-powered products, turning complex systems and 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
★ AI-first design org Kustomer.com: Case study 1 ★
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
AI reviews working prototypes against shared UX standards before release.
# AUDIT UX: {FEATURE}
## What we encode
Undefined states
Dead ends
Abandonment risks
Recovery failures
Broken user journeys
## OUTPUT
Prioritized findings tied to specific routes, screens, and states.
Version-controlled rules give humans and AI the same system to build from.
## What we encode
Accessibility requirements
Content standards
Component usage
Brand voice
Error handling
Interaction patterns
## Output
Reusable AI instructions and testable implementation constraints.
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
Expose rationale, sources, confidence, and an undo path.
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
Evaluation criteria, prompt and UI changes, guardrail revisions, and new design rules.
WordPress/Jetpack | Kustomer
Leading product design across WordPress, Jetpack, and Kustomer, building and mentoring teams, aligning work across functions, and shaping products used at scale. I create the systems, strategies that help orgs make better decisions and deliver stronger work.
VARIOUS
Designed the complicated workflows behind AI agent setup, guardrails, procedures, monitoring, and human review, turning an open-ended configuration problem into a guided, trustworthy experience for both end users and administrators tasked with setting up the AI agents.
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 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.
Jeffrey Zeldman Executive Creative Director | Automattic
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.
Heidi Beacham Senior Director Product | CoPilotIQ
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.
Jeff Golenski Principal Designer/ Product Mgr. | Automattic
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.
FILIPE Varela Senior Design Director | Jetpack
Yvonne is a triple threat leader in that she understands 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.
James Grierson | Head of Global Expansion and Education for 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.
Jeff Golenski Principal Designer/ Product Mgr. | Automattic
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.
Ilona Jaudžemytė Senior UX Designer | Jetpack
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.
Ballio Chan Creative Director | Automattic
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.
Nick Kovacevich Head of UX Design & Research | AWS Marketplace
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!
Andrei Slobstov Brand Design | automattic
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.
Caiti Vincel Senior Director Product Manager | Sprout Social
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,
Rachel Hughes VP Product | Kustomer
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→
Applying the Myers-Briggs approach to team dynamics and planning my career
Your help agent is hiding the cost of your bad UX.
Detangling complex AI built prototypes.
Vision.
Systems.
Scale.
Hello, I’m Yvonne Doll.
I am a hands-on design leader who builds and scales high-velocity design organizations. I specialize in AI-native transformation, turning complex systems into clear, trustworthy experiences by operationalizing design at scale.
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.
hello@ydoll.me
Choose your own adventure
★ AI-first design org Kustomer.com: Case study 1 ★
Moving from Figma-first handoffs to a code-first design system.
Tokens, coded components, UX rules, and AI instructions live in version control. Storybook makes the system visible, while Figma remains an optional surface for exploration and communication.
~hrs
Idea to Prototype
1B+
Conversations
served at scale
0
hand-off time
AI reviews working prototypes against shared UX standards before release.
# AUDIT UX: {FEATURE}
## What we encode
Undefined states
Dead ends
Abandonment risks
Recovery failures
Broken user journeys
## OUTPUT
Prioritized findings tied to specific routes, screens, and states.
Version-controlled rules give humans and AI the same system to build from.
## What we encode
Accessibility requirements
Content standards
Component usage
Brand voice
Error handling
Interaction patterns
## Output
Reusable AI instructions and testable implementation constraints.
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
Expose rationale, sources, confidence, and an undo path.
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
Evaluation criteria, prompt and UI changes, guardrail revisions, and new design rules.
WordPress/Jetpack | Kustomer
At Kustomer, I rebuilt design around AI-native workflows, cutting concept-to-validation from days to hours with prompts, evals, and design–engineering loops. At WordPress (Automattic), I led five AI launches for 27M+ users across 14 products (+58% productivity), built a lean research program adopted org-wide, and demo’d my design intake and triage model as a reference for teams across the company.
VARIOUS
Designed the complicated workflows behind AI agent setup, guardrails, procedures, monitoring, and human review, turning an open-ended configuration problem into a guided, trustworthy experience for both end users and administrators tasked with setting up the AI agents.
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. A rising tide lifts all boats.
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
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.
Jeffrey Zeldman Executive Creative Director | Automattic
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.
Heidi Beacham Senior Director Product | CoPilotIQ
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.
Jeff Golenski Principal Designer/ Product Mgr. | Automattic
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.
FILIPE Varela Senior Design Director | Jetpack
Yvonne is a triple threat leader in that she understands 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.
James Grierson | Head of Global Expansion and Education for 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.
Jeff Golenski Principal Designer/ Product Mgr. | Automattic
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.
Ilona Jaudžemytė Senior UX Designer | Jetpack
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.
Ballio Chan Creative Director | Automattic
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.
Nick Kovacevich Head of UX Design & Research | AWS Marketplace
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!
Andrei Slobstov Brand Design | automattic
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.
Caiti Vincel Senior Director Product Manager | Sprout Social
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,
Rachel Hughes VP Product | Kustomer
I had the pleasure of working with Yvonne during our time at Automattic, where I led the software engineering team for Jetpack AI, and she was the design director of Jetpack, leading the team collaborating with us. Yvonne’s team consistently delivered high-quality design work on time, and their responsiveness and openness to feedback made our collaboration seamless. Yvonne fosters a culture of creativity within her team, and works great in cross-team collaboration.
Senior Software Engineer | Front
I had the privilege to work with Yvonne during my time at Kustomer, where I found her to be a user empath with a strong sense of direction and usability. An advocate and a builder, Yvonne makes your product relatable and useful. Not only usable. Yvonne is someone who is not only adaptable, she leads on the front lines. And personally, she is a joy to work with and speak to.
Richard Bashara | Senior Technical Writer, Kustomer
Yvonne is a rock star, both literally and figuratively. Having had the chance to work closely with her, I can state with emphasis that she is the very best of leaders, designers, and humans, that you will find. I consider it a privilege to have learned from her, and to be able to call her a friend.
Creative Team Lead | WordPress
Welcome to the Museum of Abandoned AI Features, where every exhibit began with the sentence, ‘Could we put a copilot in it?’
Your help agent is hiding the cost of your bad UX.
Detangling complex AI built prototypes.
I made a small Design Spec Gatekeeper file for UX teams working with AI-assisted tools.