[Hiring] Senior Software Engineer @The Flex

Role Description

We're looking for a highly ambitious Senior Software Engineer who wants to build systems that solve real problems at scale. You'll build, ship, automate, and deliver products that directly impact property managers, their teams, and their guests.

As a Senior Software Engineer, you'll help architect and scale Base360.ai—the platform powering every aspect of a short-term rental business. Your work will span the entire short-term rental lifecycle:

• From listing distribution, pricing, and bookings to guest stays, property operations, and financial reporting.

Your mission includes:

• Build the Core Platform: Design and develop scalable applications, services, and APIs that power reservations, availability, pricing, payments, guest experiences, and property operations.
• Create Powerful Automations: Build event-driven workflows that eliminate repetitive work—from scheduling cleaning after a booking to sending check-in instructions and generating owner statements.
• Develop AI-Powered Systems: Use LLMs and AI agents to automate guest communication, triage maintenance requests, support pricing decisions, and help operators manage their portfolios more efficiently.
• Design API-First Architecture: Create robust APIs that connect internal services, booking channels, third-party providers, and customer systems.
• Integrate the Ecosystem: Build and maintain integrations with platforms including Airbnb, Hostaway, Stripe, Twilio, OpenAI, Google, and other strategic partners across the short-term rental ecosystem.
• Scale Infrastructure: Deploy and manage cloud-native infrastructure designed for reliability, performance, and global growth across multiple property management businesses.
• Solve Complex Operational Problems: Build solutions for:
  • Real-time reservation and availability synchronization
  • Dynamic pricing intelligence
  • Smart lock access and key management
  • Automated guest communication across channels
  • Operational forecasting
  • Cleaning and maintenance automation
  • Owner reporting and financial workflows
  • AI-powered monitoring and alerts
• Move Fast and Own Delivery: Own projects end-to-end—from understanding an operator’s problem to architecture, implementation, deployment, and ongoing improvement.

Qualifications

• Strong experience building and owning production-grade software systems
• Experience with FastAPI, Python, React, or similar frameworks
• Strong understanding of APIs, distributed systems, and cloud architecture
• Experience designing scalable backend systems and reliable data models
• The ability to work independently and make sound technical decisions
• Strong problem-solving skills and a product mindset
• Curiosity about AI, automation, and operational efficiency
• A bias toward action, shipping, and learning from real users
• The ability to balance delivery speed with maintainability and reliability

Requirements

• Bonus points for experience with:
  • Short-term rentals, hospitality technology, or property management systems
  • Multi-tenant SaaS platforms
  • Marketplace businesses and booking channel integrations
  • AI agents and workflow automation
  • Event-driven architectures
  • Supabase
  • AWS serverless infrastructure

Benefits

• Build Something Meaningful: Solve problems experienced daily by short-term rental operators, with direct access to The Flex’s operations to test ideas and see their impact.
• Extreme Ownership: Have the freedom and responsibility to make technical decisions and deliver systems that matter.
• Small Team, Massive Opportunity: Work closely with the founders and directly influence the product and technical direction of Base360.ai.
• Learn Faster: Solve real-world challenges across software, AI, automation, hospitality operations, and scale.
• Performance-Based Rewards: Competitive compensation with substantial upside for exceptional performers.
• Remote-First: Work from anywhere. We care about outcomes, not hours.

Company Description

Base360.ai is the AI operating system for short-term rental businesses, helping property managers run their operations on autopilot. Born out of The Flex, a short-term rental operator that scaled to an eight-figure business using its own software, Base360.ai is now launching as a standalone platform for short-term rental operators worldwide.