Designing Sidekick for Avenue 8
Avenue 8 is a modern brokerage with AI-enabled agent tools. Agents juggle endless workflows across CMAs, client emails, scheduling, and marketing, often without guidance on how to integrate AI into their practice. My role: design an interface that was both intuitive and educational, helping agents adopt Avenue 8's Sidekick as a daily AI co-pilot.
Role
Sole UX Designer
User interviews, co-design workshops, prototyping
Mid-fi and high-fi wireframes and prototypes
San Francisco, CA
2019
Proptech / AI
Series B
~80
Challenge
Real estate agents faced two barriers:
Workflow chaos: Research, emails, comps, and scheduling lived in separate tools.
AI unfamiliarity: Agents didn’t know what to ask, how to trust outputs, or how to use Sidekick without training.
Chat v. GUI: Agents needed both the flexibility of chat and the clarity of GUIs. Pure chat UIs required too much typing and context, while pure GUIs risked feeling rigid. The design had to balance simplicity with discoverability.
Avenue 8 needed Sidekick’s UI to accelerate adoption—teaching agents new AI behaviors while fitting seamlessly into their existing workflows.
Solution
I designed Sidekick’s interface as both workspace and teacher:
Hybrid workspace: A central chat for flexibility, paired with contextual prompts and quick-action buttons to reduce typing and guide agents through common tasks.
Split-screen UI: Chat on the right, live drafts and history on the left, helping agents refine content while previewing reports, emails, or marketing assets in real time.
Contextual views: Map and People tabs added geographic and client context, supporting showing routes, neighborhood filters, and relationship tracking.
Co-designed system: Through workshops, I shaped flows for CMAs, newsletters, and scheduling, then built a neutral design system to scale with Avenue 8’s evolving brand.
Results
The redesigned Sidekick UI gave Avenue 8 a competitive edge in a crowded proptech market:
Faster adoption: Agents learned AI workflows directly inside the product, accelerating onboarding.
Trust & usability: Clearer commands, inline editing, and branded output options built agent confidence.
Business alignment: Aligned the MVP with Avenue 8’s pivot, contributing to its nomination for Company of the Year and Best Use of AI by a leading real estate awards organization.
8
agent interviews conducted
6
core workflows mapped
30+
hi-fi screens designed
Process
Research & Analysis: I conducted 1:1 interviews with 8 agents. Findings: agents wanted neighborhood-level comps, editable outputs, graphs by default, and branded deliverables.
Information Architecture: I mapped workflows across 5 daily tasks—market reports, comparative market analysis (CM)A), scheduling, follow-ups, and marketing.
Wireframing & Prototyping: Explored multiple layouts (calendar/map in chat, tab-less navigation) and pure chat and GUI-first directions, but mid-fi testing showed that a hybrid approach worked best.
Inspired by Nielsen Norman Group’s critique of chat-only UIs, I introduced contextual prompts and eventually a split-view layout. Agents immediately found this more efficient.
Visual Design & Style Guide: Created a grayscale, type-agnostic design system for MVP. Delivered high-fidelity screens in Figma.
Testing & Iteration: Through structured usability sessions with 8 agents, I refined Sidekick with:
More default graphs in reports
Clearer status and pricing fields in comps
Editable newsletters with branded placeholders
Smarter suggestions (e.g., “Compare Glen Park vs SF”)
MVP Prototype: The Sidekick UI blended education and execution—guiding agents into AI-powered workflows while keeping outputs trustworthy, editable, and aligned with their brand. Below is a video of the top 2 top realtor task flows: creating a market report and a CMA.
Responsive High Fidelity Wireframes
“ I like this much better because otherwise it feels like just a chatbot. This feels more like a workspace. ”
Hanne Vastveit
Top Real Estate Agent San Francisco | Pacific Advisory
Conclusion
This project showed me how design can de-risk AI adoption—teaching users new mental models while meeting them where they are. By co-designing with agents, I helped Sidekick evolve from confusing prototype to intuitive co-pilot, supporting Avenue 8’s bold pivot and helping them stand out in real estate’s AI transformation.
Get Athos Pro