AI-native product design leader
For 20+ years I've led product design, UX strategy, and distributed teams through major technology shifts. Mywork focuses on AI and agentic product experiences where trust, quality, and human judgment matter.
Vision.
Systems.
Scale.
Hello, I'm Yvonne Doll.
For 20+ years, I've led product design, UX strategy, and globally distributed teams through major technology shifts: CSS, Mobile, and A.I
My work focuses on AI and agentic product experiences where trust, quality, and human judgment matter.
I help design teams become AI-native: prototypes, prompts, product patterns, skills, and evaluation loops.
I have deep experience in SaaS, CRM, healthcare, publishing, e-commerce, PLG, and AI-powered platforms at scale.
Chicago, IL · open to travel or relocate.
eeeeevon@gmail.com
AI-first design org Kustomer.com. ★ Context1.md
Rebuilt AI-first design workflows from static handoffs into live loops across design, engineering, and models. Codified prompts, evaluation criteria, and guardrails, reducing idea-to-working-output from days or weeks to hours.
~hrs
Idea to Prototype
1B+
Conversations
served at scale
0
hand-off time
Empowers engineers, amplifies designer productivity. Hunts undefined states, every flow, every failure, every dead end.
# AUDIT UX: {FEATURE}
## What we scan for
Undefined states→ behavior nobody accounted for.
DEAD ENDS→ loops, hidden exits, no way back
ABANDON RISKS→ moments of doubt, no next step
## OUTPUT
Flow inventory + priority matrix. Critical → Low.
Scores AI output across correctness, usefulness, voice, and safety so quality is judged by behavior, not vibes.
## Rubric 1-4
1. Correct→ answers the actual ask
2. Useful→ moves the user forward
3. Voice→ sounds like us
4. Safe→ refuses what it should
## Ship gate
Median ≥ 3.5 across all four axes.
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)
Move design critique from static feedback to operating rules. Turn observed AI behavior into changes the system can learn from.
## What we critique
- Behavior→ not the screen
- Prompt→ not the wording
- Refusal→ not the success case
## Output
Spec updates, not Figma annotations
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
CONTEXT2.MD
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
USER INTERVIEWS
~175
INSIGHtS SHIPPED
375
USABILITY TESTS
Case 03·RAPID INSIGHTS
CONTEXT3.md
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 show.
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 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.
Jeffery Zeldman Executive Creative Director | 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!
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 Lead Product Manager | Sprout Social
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.
James Grierson CEO | Jetpack
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.
EDER RENGIFO Senior ai designer | 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
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 Design director | Jetpack
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
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!
Andrei Slobstov Brand Design | 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.
Ballio Chan Creative Director | 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 Principle Designer/ Product Mgr. | Automattic
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 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.
Jeffery Zeldman Executive Creative Director | 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!
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 Lead Product Manager | Sprout Social
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.
James Grierson CEO | Jetpack
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.
EDER RENGIFO Senior ai designer | 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
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 Design director | Jetpack
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
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!
Andrei Slobstov Brand Design | 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.
Ballio Chan Creative Director | 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 Principle Designer/ Product Mgr. | Automattic
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.
“Ship and learn” sounds great until you realize most teams only measure the shipping...
Chicago, IL · open to travel or relocate
01
I turn ambiguity into buildable systems:prototypes, prompts, product patterns, and evaluation loops.
02
I lead AI & agentic product work where trust, quality, and human judgment matter most.
03
I build teams, research practices, and operating models that move fast without losing quality.
Conversations served
Users supported
Productivity
// selected 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
Rebuilt the design model for AI-first product work, moving teams 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.
Read the case →
// 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
+
Behavior specs, skills, eval rubrics
+
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.
behavior-spec.md
Skill 01
behavior-spec.md
Skill 01
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
Move design critique from static feedback to operating rules.Turn observed AI behavior into changes the system can learn from.
## What we crique
Behavior
→ not the screen
Prompt
→ not the wording
Refusal
→ not the success case
## Output
Spec updates, not Figma annotations
critique.md
Skill 04
Move design critique from static feedback to operating rules.Turn observed AI behavior into changes the system can learn from.
## What we crique
Behavior
→ not the screen
Prompt
→ not the wording
Refusal
→ not the success case
## Output
Spec updates, not Figma annotations
// let's talk
Email me
© 2026 · Yvonne Doll
