Digital Coach for Growth
A human-feeling self-coaching experience that increased weekly engagement by 63% and reduced attrition by 35%.
Company
Eskalera Inc. (HR & Education)
Scope
Make DEI coaching feel personal and frictionless so people actually use it
Role
Led UX redesign of core coaching flow, gamification UI, and progress tracking.
Engagement
Retainer
More than just creative output, he's able to manage a creative process from idea through to completion. Collaborative, curious, and creative are three of the many positive words I'd use to describe him. Diego took a validated and functional product with an MVP design, and turned it into a beautiful and modern interface ready for the enterprise
More than just creative output, he's able to manage a creative process from idea through to completion. Collaborative, curious, and creative are three of the many positive words I'd use to describe him. Diego took a validated and functional product with an MVP design, and turned it into a beautiful and modern interface ready for the enterprise
More than just creative output, he's able to manage a creative process from idea through to completion. Collaborative, curious, and creative are three of the many positive words I'd use to describe him. Diego took a validated and functional product with an MVP design, and turned it into a beautiful and modern interface ready for the enterprise
Rich Kneece
Rich Kneece
Rich Kneece
CTO @Eskalera
CTO @Eskalera
CTO @Eskalera
Designing a DEI tool that feels human, not another HR task.
Most DEI and wellbeing tools get ignored because they feel generic, impersonal, and like another HR task. Eskalera wanted a coaching product that feels human, not like a form.
What I owned:
The end-to-end coaching session UX (short, focused, repeatable).
The tone + interaction system to keep it conversational, friendly, and lightweight.
A scalable design system so the product could grow without losing consistency.
How we worked:
Async walkthroughs for concepts and flows (clear decisions documented).
One weekly decision review with the Co-founder and PM to unblock trade-offs fast.
Workstream focus: one primary experience slice at a time (session → guidance → completion).
Weekly shipped progress (design + specs) so engineering never waited.
Designing a DEI tool that feels human, not another HR task.
Most DEI and wellbeing tools get ignored because they feel generic, impersonal, and like another HR task. Eskalera wanted a coaching product that feels human, not like a form.
What I owned:
The end-to-end coaching session UX (short, focused, repeatable).
The tone + interaction system to keep it conversational, friendly, and lightweight.
A scalable design system so the product could grow without losing consistency.
How we worked:
Async walkthroughs for concepts and flows (clear decisions documented).
One weekly decision review with the Co-founder and PM to unblock trade-offs fast.
Workstream focus: one primary experience slice at a time (session → guidance → completion).
Weekly shipped progress (design + specs) so engineering never waited.
Designing a DEI tool that feels human, not another HR task.
Most DEI and wellbeing tools get ignored because they feel generic, impersonal, and like another HR task. Eskalera wanted a coaching product that feels human, not like a form.
What I owned:
The end-to-end coaching session UX (short, focused, repeatable).
The tone + interaction system to keep it conversational, friendly, and lightweight.
A scalable design system so the product could grow without losing consistency.
How we worked:
Async walkthroughs for concepts and flows (clear decisions documented).
One weekly decision review with the Co-founder and PM to unblock trade-offs fast.
Workstream focus: one primary experience slice at a time (session → guidance → completion).
Weekly shipped progress (design + specs) so engineering never waited.
Key decisions
Make sessions 5 minutes or less
We designed sessions to be short (5 minutes or less) and focused on a single action so usage fits into a real workday instead of becoming a “someday” task.
Conversation, not forms
The interaction model prioritized a conversational feel over HR-style checklists, so users feel guided rather than evaluated.
Adaptation without complexity
We built the experience to adapt to the user while keeping flows simple: only what you need, when you need it, so personalization didn’t add friction.
Key decisions
Make sessions 5 minutes or less
We designed sessions to be short (5 minutes or less) and focused on a single action so usage fits into a real workday instead of becoming a “someday” task.
Conversation, not forms
The interaction model prioritized a conversational feel over HR-style checklists, so users feel guided rather than evaluated.
Adaptation without complexity
We built the experience to adapt to the user while keeping flows simple: only what you need, when you need it, so personalization didn’t add friction.
Key decisions
Make sessions 5 minutes or less
We designed sessions to be short (5 minutes or less) and focused on a single action so usage fits into a real workday instead of becoming a “someday” task.
Conversation, not forms
The interaction model prioritized a conversational feel over HR-style checklists, so users feel guided rather than evaluated.
Adaptation without complexity
We built the experience to adapt to the user while keeping flows simple: only what you need, when you need it, so personalization didn’t add friction.
Impact
The redesigned experience helped people reflect, grow, and take practical steps forward without feeling like a chore.
63% increase in weekly engagement
35% reduction in attrition (as stated in the project headline)
87% progress in power skills
4.7/5 average satisfaction score
Why it worked
Lower time cost (micro-sessions) + clearer next actions
Higher emotional safety (conversational tone)
Consistency at scale (design system foundation)
Impact
The redesigned experience helped people reflect, grow, and take practical steps forward without feeling like a chore.
63% increase in weekly engagement
35% reduction in attrition (as stated in the project headline)
87% progress in power skills
4.7/5 average satisfaction score
Why it worked
Lower time cost (micro-sessions) + clearer next actions
Higher emotional safety (conversational tone)
Consistency at scale (design system foundation)
Impact
The redesigned experience helped people reflect, grow, and take practical steps forward without feeling like a chore.
63% increase in weekly engagement
35% reduction in attrition (as stated in the project headline)
87% progress in power skills
4.7/5 average satisfaction score
Why it worked
Lower time cost (micro-sessions) + clearer next actions
Higher emotional safety (conversational tone)
Consistency at scale (design system foundation)
Wondering how's like to work with me?
Don't take my word for it, take theirs.
Diego works smart and fast, communicates clearly, and is a great team player. He’s thoughtful, professional, and brings clarity to complex design problems.
Mindy @Clear Company
Diego is a world-class designer and strong UI advocate. He collaborates seamlessly, sticks to standards, and clearly communicates across stakeholders. His work is top-tier.
Debra @Eskalera
Diego consistently delivered high-quality design work that aligned with Procore’s guidelines and timelines. He brought dedication, skill, and reliable execution to every project.
Karen @Procore
Diego is a talented UX designer and a pleasure to work with. He approaches his work with a solid understanding of users and tasks and seeks to make experiences clean and simple.
Elizabeth @Alteryx
Diego solves complex challenges fast without compromising quality. He’s proactive, insightful, and always focused on outcomes. A fantastic collaborator I’d team up with again.
Marcelo @Clear Company
Diego listens well and delivers design on time with great attention to detail. He is not shy about discussing trade-offs in design choices and is always ready to collaborate on creating user experiences that users find valuable.
Natalie @GroundTruth
Diego adapted fast to our design system and delivered great work on tight timelines. He’s efficient, detail-oriented, and easy to work with.
Liz @Venmo
Diego ramped up fast, shipping MVPs within weeks. He’s efficient, creative, and user-centered. Always open to feedback, he brings high value to any design team.
Brian @Alteryx
Diego works smart and fast, communicates clearly, and is a great team player. He’s thoughtful, professional, and brings clarity to complex design problems.
Mindy @Clear Company
Diego is a world-class designer and strong UI advocate. He collaborates seamlessly, sticks to standards, and clearly communicates across stakeholders. His work is top-tier.
Debra @Eskalera
Diego consistently delivered high-quality design work that aligned with Procore’s guidelines and timelines. He brought dedication, skill, and reliable execution to every project.
Karen @Procore
Diego is a talented UX designer and a pleasure to work with. He approaches his work with a solid understanding of users and tasks and seeks to make experiences clean and simple.
Elizabeth @Alteryx