Senior Software Engineer

About The Flex

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.

We bring reservations, guest communication, pricing, payments, cleaning, maintenance, and reporting into one platform—helping operators automate manual work, reduce costs, increase revenue, and scale their portfolios.

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.

If you're excited by APIs, automation, AI agents, cloud infrastructure, and building products from the ground up, we want to meet you.

Responsibilities

• As a Senior Software Engineer, you'll help architect and scale

Base360.ai

• —the platform powering every aspect of a short-term rental business.
• You'll build customer-facing products, automation engines, AI-powered workflows, integrations, and operational systems that help property managers grow without increasing their workload at the same rate.
• Your work will span the entire short-term rental lifecycle: from listing distribution, pricing, and bookings to guest stays, property operations, and financial reporting.

Build the Core Platform

• Design and develop scalable applications, services, and APIs that power reservations, availability, pricing, payments, guest experiences, and property operations.
• Build event-driven workflows that eliminate repetitive work—from scheduling cleaning after a booking to sending check-in instructions and generating owner statements.
• 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
• Real-time reservation and availability synchronization
• Dynamic pricing intelligence
• Smart lock access and key management
• Automated guest communication across channels
• Operational forecasting
• 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.
• Bring senior engineering judgment to technical decisions, code reviews, and the reliability of the systems you build.
• Event-driven architectures

Requirements

• Serverless architecture
• OpenAI APIs

Twilio

• You Might Be a Great Fit If You Have
• 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
• Supabase
• AWS serverless infrastructure
• You need detailed instructions for every task

You avoid ownership and accountability

• You're comfortable shipping work without taking responsibility for its quality
• We're looking for someone who wants to help build the AI operating system for the short-term rental industry.

Preferred

• Short-term rentals, hospitality technology, or property management systems
• Multi-tenant SaaS platforms
• Marketplace businesses and booking channel integrations

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.
• 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.
• Competitive compensation with substantial upside for exceptional performers.

Tech Stack

• We care more about capability than specific technologies, but our current stack includes:
• Python
• FastAPI
• React
• TypeScript
• Supabase
• PostgreSQL

What Success Looks Like

Within your first 12 months

Core short-term rental workflows are automated through systems you've built

Property managers spend less time on manual administration

• Reservations, availability, payments, and operational data move reliably between systems
• New integrations are deployed and maintained reliably

AI-powered workflows become part of customers’ everyday operations

The platform supports more operators and properties while maintaining reliability and performance Base360.ai helps customers grow their portfolios, improve guest experiences, and operate more profitably

Remote-First

• Work from anywhere. We care about outcomes, not hours.
• This Role Is Not For You If

You're looking for a slow-paced corporate environment

You prefer a narrowly defined role with limited product involvement