Industry
HR, EdTech
Company
Eskalera
Digital Coach, Eskalera's Flagship Product
Micro-learning product focused on user engagement and employee retention
Eskalera was enhancing its workplace culture and DEI platform by launching Digital Coach, an AI-powered feature designed to guide employees through personalized learning, engagement, and self-assessment journeys. The goal was to deepen user engagement and drive meaningful workplace growth—but initial concepts risked being too abstract, leaving users unsure how to engage with or benefit from the tool.
Tasks
As lead product designer, I was responsible for shaping the end-to-end experience of Digital Coach, ensuring it felt approachable, actionable, and aligned with Eskalera’s mission to improve belonging, growth, and well-being in the workplace. The challenge was to translate complex behavioral science models and DEI frameworks into simple, motivating interactions that employees could connect with daily.
Design process
I collaborated closely with product managers, and engineers to fully understand the learning outcomes and psychological drivers we aimed to promote. My key initiatives included: — Designing a modular conversational framework that delivered personalized nudges, reflection prompts, and actionable exercises—tailored to each user’s progress and goals. — Simplifying dense psychological concepts into bite-sized, engaging content, reinforced through empathetic language and visual cues. — Integrating Digital Coach seamlessly into the broader platform experience, ensuring that guidance appeared at the right time and in the right context (e.g., after surveys, during learning modules). — Leading usability tests to gauge clarity, emotional resonance, and sustained engagement, iterating based on direct user feedback
87% of employees progress in power skills and 35% average reduction in employee attrition rates.
The Digital Coach launch was met with positive feedback from enterprise clients and users, who highlighted its clear, friendly, and motivating approach to personal growth. Internally, the project was credited with strengthening Eskalera’s position as a leader in culture and DEI innovation and provided a flexible framework to expand personalized learning experiences across the product.
STORIES
Dive into the stories of people that have noticed a difference when working with me.
Diego has demonstrated solid skills and dedication, significantly contributing to Procore design projects. Deliverables have consistently been of high quality considering design guidelines, time windows and team requirements"
Karen Fojas
Design Leader @Procore
Diego's speed and efficiency never ceased to impress me. Diego tackles complex challenges with incredible speed while maintaining top-quality results. He anticipates issues, adapts quickly, and executes flawlessly, keeping projects moving seamlessly. Beyond his efficiency, he’s a fantastic collaborator—proactive, insightful, and always striving for the best outcomes.
Marcelo Paiva
Head of Design @Clear Company
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. He quickly absorbs requirements and generates design concepts that reduce complexity. He's also a thoughtful and willing collaborator. I've truly enjoyed working with him and would do so again gladly!
Elizabeth Benker
Design Leader @Alteryx
Diego is a world class designer, a wonderful collaborator, and take a balanced approach to working across multiple functions and stakeholders while holding to top design standards and practices. His design sense is top grade, and was a great UI evangelist. I very much appreciated how he communicated (and educated) the teams on best practices.
Debra Kadner
CEO @Eskalera
Diego adapted quickly to our design team and standards, making him deliver great designs in a timely manner.
Liz Carter
Senior Design Manager @Venmo