Design Leadership: People and Processes
COMPANY
Jetpack (WordPress)
ROLE
Design Director · Process Architect
YEAR
2018-2024
↑58%
TEAM PRODUCTIVITY
↑20%
FEATURE RELEASE
8
SENIOR DESIGNERS LED
THE 60-SECOND VERSION
CHALLENGE
A shared-service team of eight designers supporting six development teams faced ad-hoc requests that stretched capacity without a centralized intake system.
APPROACH
People-first, lead-from-behind leadership: standardized intake (GitHub, Zap, Slack), weekly cross-functional priority syncs, and quarterly designer rotation.
OUTCOME
Built and developed a team of eight senior designers supporting six development teams, 14 products, and 40+ features, with top-tier engagement scores.
PEOPLE FIRST - THEN THE PROCESS THAT PROTECTS THEIR CRAFT.
WHAT I SHIPPED
01
People leadership
Lead from behind: autonomy, mentoring, and a culture where the team shines.
02
Intake system
Standardized requests via GitHub, Zap, and Slack to prioritize impact.
03
Priority sync
Weekly 15-20 min alignment across product, design, and engineering.
04
Designer rotation
Quarterly rotation to streamline planning and reduce bottlenecks.
LEARNINGS
Lead from behind.
Clarity is kindness.
Protect focus with intake.
Culture is infrastructure.
Welcome to the bottom of the page. You 🤘
Want to get into more details? Continue on desktop for full case studies that cover the research, the tradeoffs, more artifacts in detail.
hello@ydoll.com
I have extensive experience in prioritization frameworks and cross-functional collaboration, driving faster iterations and impactful results.
As a hands-on, full-stack designer and emotionally intelligent leader, I support designers' growth, promote collaboration, and foster a positive team culture where everyone can thrive.
Impact Numbers
↑58%
Team productivity
↑20%
Feature Release
∞Joy
Team Engagement
I subscribe to a people-first lead from behind philosophy (HBG.org Leading from Behind ↗). I have extensive experience in prioritization frameworks and cross-functional collaboration, driving faster iterations and impactful results. As a hands-on, full-stack designer and emotionally intelligent leader, I support designers' growth, promote collaboration, and foster a positive team culture where everyone can thrive.
The vibe matters
In my six years as Senior Design Director, my team consistently ranked in the top three for team member engagement as measured by a quarterly company-wide engagement survey; members felt supported and contributed to a positive company culture. I’m very proud of this achievement.
Vibe Check
Key Strategies
Optimizing Tools and Processes
Created a standardized intake process to prioritize impact and manage ad-hoc requests via GitHub, Zap, and Slack.
Prioritization and Workflow Alignment
Initiated and led a weekly 15-20 min sync up where stakeholders from product, design, and engineering aligned on project priorities.
Enhancing Cross-Functional Communication
Introduced a quarterly designer rotation to streamline planning and reduce bottlenecks.
Tracking and Improving Velocity
Monitored team velocity in GitHub to ensure focus on impactful work.
Processes that work
I led a shared service team of 8 designers supporting 6 development teams, 14 applications, and over 40 features at Jetpack/WordPress.
The influx of ad-hoc tasks can stretch the team’s capacity without a centralized system for handling requests. I implemented structured processes & cross-functional collaborative prioritization, which resulted in a 58% increase in productivity.
Key Strategies
Optimizing Tools and Processes
Created a standardized intake process to prioritize impact and manage ad-hoc requests via GitHub, Zap, and Slack.
Prioritization and Workflow Alignment
Initiated and led a weekly 15-20 min sync up where stakeholders from product, design, and engineering aligned on project priorities.
Enhancing Cross-Functional Communication
Introduced a quarterly designer rotation to streamline planning and reduce bottlenecks.
Tracking and Improving Velocity
Monitored team velocity in GitHub to ensure focus on impactful work.
My leadership philosophy
FOCUS
I believe it's my job to inspire the team to pursue graceful, innovative solutions with a laser focus on the user problems we're trying to solve.
LEAD FROM BEHIND
Mentor and guide, but let the team shine. Foster a culture of autonomy and self-leadership. Build trust and collaboration so team members feel confident to experiment and grow.
ADAPT
One size doesn't fit all. People are unique, and I mentor and lead them accordingly. I'm wildly interested in team dynamics and enjoy facilitating an organic flow.
REMAIN CURIOUS
Outstanding leadership isn’t about having all the answers but asking the right questions. It’s about staying curious and continually learning from your team.
BE KIND, BE CLEAR
Inspired by books like Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity, I follow a "clarity is kindness" approach.
I lead with curiosity, empathy, and authenticity, fostering a team culture built on the same values.
" A Rising tide lifts all boats"
This is one of my favorite expressions, often attributed to JFK, who used it to promote inclusive economic growth. I love it in the context of innovation and a team spirit of lifting each other up.
Kind words from excellent humans
I thrive on building supportive, innovative, and action-oriented teams that uplift one another and collaborate to create exceptional work.
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!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!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!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!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!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!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!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!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!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!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!