Founding AI Product Design Lead

As our founding designer, you’ll own design end to end across product, brand, and everything in between. You’ll define how Maestro looks, feels, and behaves across every touchpoint.

You’ll design the full member experience: our mobile app, travel advisor touchpoints, internal ops interfaces, and the AI agents woven throughout. You must care deeply about quality, whether a human or an AI is on the other end.

Our product and engineering teams live in Claude Code daily. You’ll be embedded in that process, shaping how AI shows up across the product rather than just designing around it. Using AI tools to move fast is core to how we work, and it’s non-negotiable for this role.

What You’ll Do

• Design product flows, interfaces, and interaction details for our consumer app, advisor tools, and ops workflows
• Shape how AI shows up in the product by designing agentic and human-in-the-loop experiences that feel effortless and trustworthy
• Own the brand: identity, site, decks, and all company touchpoints
• Prototype and test with real members and advisors, iterating quickly
• Run design review and hold the quality bar as we ship, keeping standards high without slowing the team down
• Set the design culture, systems, and quality standards future hires will inherit

Product Design, Artificial Intelligence (AI), Product Design, Artificial Intelligence (AI), Customer Experience, Startup, Artificial Intelligence (AI) Agents, Mobile Applications, Embedded Systems, Product Engineering, * Senior or leadership-level experience at a startup, with the drive to run design without a playbook

• A portfolio of shipped product work (not just concepts), especially consumer app design and operational backends (advisor tools, internal ops, dashboards)
• Comfort with complex internal workflows and polished consumer surfaces alike
• Fluency with modern design and AI tools (Figma, Claude, and the latest developments), plus a genuine excitement for AI-native experiences
• Product-focused but able to flex into brand when needed
• Speed and pragmatism: you ship and refine, rather than polish forever
• Strong opinions about quality, loosely held about everything else

Maestro is building the future of luxury travel: a member experience where world-class human advisors and AI agents work side by side to plan and execute extraordinary trips. We’re an early-stage, Austin-based startup with top-tier VC backing and a team that lives inside modern AI tools every day. We’re small, moving fast, and building something people will love.