Demo

Product Designer

The Flex
Chicago, IL Full Time
POSTED ON 9/28/2026
AVAILABLE BEFORE 10/26/2026
At Base360.ai, we believe running a short-term rental company should feel effortless.

Our mission is ambitious: enable anyone to launch, operate and scale a short-term rental business on AI autopilot.

Born from the technology powering The Flex, Base360 brings property management, guest communications, bookings, cleaning, maintenance and finance into one platform.

We’re looking for a highly ambitious UX/UI Product Designer who wants to turn complex operations into simple, beautiful experiences. You’ll work directly with the founders and engineers to design products that solve real problems for property managers, operational teams and guests.

If you’re excited by thoughtful UX, exceptional interfaces, AI agents and building products from the ground up, we want to meet you.

What You’ll Design

As a UX/UI Product Designer, you’ll help shape every touchpoint of Base360—from the first website visit to the workflows operators rely on every day.

  • Core product experiences: Design dashboards and workflows for reservations, properties, guest communications, cleaning, maintenance and finance.
  • AI interactions: Make it easy to configure AI agents, understand their actions, review decisions and step in when needed.
  • Onboarding and setup: Help operators connect their channels, add properties and get value from the platform quickly.
  • Booking and guest journeys: Create smooth experiences for direct bookings, check-in, extensions and upsells.
  • Our design system: Build reusable components and consistent interaction patterns that keep the platform coherent as it grows.
  • Website and marketing assets: Design landing pages, feature visuals and launch assets that make the product’s value clear.

What You’ll Do

  • Own design from problem definition and user research through to prototypes, final interfaces and implementation reviews.
  • Speak with operators and internal teams to understand how they work and where they struggle.
  • Turn complex requirements into clear user journeys, wireframes and polished interfaces.
  • Work closely with engineers to deliver designs that account for real data, edge cases and technical constraints.
  • Test ideas early, incorporate feedback and improve experiences after launch.
  • Use AI tools to accelerate exploration and production while maintaining a high standard of design.
  • Take initiative: identify problems, propose solutions and drive them through to completion.

What We’re Looking For

  • A strong portfolio demonstrating both UX thinking and excellent visual design.
  • Experience designing SaaS products, dashboards or applications with complex workflows.
  • Strong Figma skills, including auto layout, components, design systems and interactive prototyping.
  • Excellent judgement in typography, spacing, hierarchy, colour and responsive design.
  • The ability to simplify complex information without hiding what users need.
  • Experience working directly with engineers and seeing designs through to production.
  • Clear communication and the ability to explain your decisions and respond constructively to feedback.
  • High ownership, attention to detail and the ability to move forward when requirements are still evolving.

Experience with short-term rentals, hospitality, AI products, conversion optimisation or front-end development is a plus.

Why Join Us

  • Make a visible impact. Design experiences that directly influence how short-term rental businesses operate.
  • Build with real users. Get access to the operational teams behind The Flex and learn from their daily challenges.
  • Work directly with the founders. Help shape product decisions and design direction from an early stage.
  • Own what you build. Take meaningful responsibility across discovery, design and delivery.
  • Push beyond conventional software. Help define how people work alongside AI agents.
  • Grow with the company. Take on broader responsibility as the product and design function expand.

You Should NOT Apply If

  • You're looking for a predictable corporate role with a fixed playbook.
  • You engage in office politics or gossip instead of communicating directly.
  • You're looking for a slow-paced role with limited ownership.
  • You don't aim to become one of the best at what you do.

Salary.com Estimation for Product Designer in Chicago, IL
$113,588 to $136,233
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