Senior Software Engineer

About Base360.ai and The Flex

Base360.ai serves as a comprehensive AI-driven platform tailored for short-term rental businesses, empowering property managers to automate and streamline their operations efficiently. Originating from The Flex—a successful short-term rental operator that scaled into a multimillion-dollar enterprise using proprietary software—Base360.ai now operates independently, catering globally to rental operators. The platform consolidates several critical areas such as reservations, guest communications, pricing strategies, payments, cleaning and maintenance management, and operational reporting to enhance automation, reduce expenses, boost revenue, and scale property portfolios.

Role Overview

We seek a highly motivated Senior Software Engineer eager to develop scalable systems tackling large-scale challenges. Your responsibilities will include building, deploying, automating, and delivering impactful products that benefit property managers, their teams, and their guests.

Key Responsibilities

• Architect and scale the Base360.ai platform to support all facets of short-term rental business operations.
• Develop customer-centric products, automation engines, AI-powered workflows, system integrations, and operational frameworks.
• Handle the entire short-term rental lifecycle: listing distribution, pricing, booking management, guest experiences, property maintenance, and financial reporting.
• Construct scalable applications, APIs, and services managing reservations, availability, dynamic pricing, guest interactions, payments, and property operations.
• Create event-driven workflows automating repetitive tasks such as scheduling cleanings, sending check-in details, and generating owner statements.
• Leverage large language models (LLMs) and AI agents to automate guest communication, maintenance request processing, pricing analytics, and portfolio management assistance.
• Design API-first architectures to seamlessly link internal services, booking platforms, external providers, and customer systems.
• Build and maintain integrations with key platforms like Airbnb, Hostaway, Stripe, Twilio, OpenAI, and Google.
• Deploy and manage cloud-native infrastructure emphasizing reliability, scalability, and performance across multiple property management clients.
• Address complex operational challenges including real-time reservation synchronization, smart lock management, operational forecasting, automated communications, cleaning and maintenance automation, owner reporting, and AI-based monitoring.
• Take ownership of projects throughout their lifecycle, encompassing problem analysis, design, implementation, deployment, and continuous improvements with senior-level engineering judgement.

Technical Stack

• Python and FastAPI
• React and TypeScript
• Supabase and PostgreSQL
• AWS with Serverless architectures
• OpenAI APIs, Twilio, and Stripe integrations
• Docker and GitHub Actions

Preferred Candidate Profile

• Proven experience developing and maintaining production-grade software systems.
• Strong expertise with FastAPI, Python, React, or comparable frameworks.
• Deep understanding of API design, distributed systems, and cloud-based infrastructure.
• Skilled in designing scalable backend systems and robust data models.
• Capable of working autonomously and making informed technical decisions.
• Excellent problem-solving ability combined with a product-oriented mindset.
• Keen interest in AI, automation, and enhancing operational efficiencies.
• Proactive attitude towards delivering outcomes, shipping features, and learning from user feedback.
• A balance of delivery speed alongside maintainability and system reliability.

Bonus Qualifications

• Experience in short-term rental, hospitality technology, or property management platforms.
• Knowledge of multi-tenant SaaS environments and marketplace business models.
• Familiarity with booking channel integrations and AI agent-driven workflow automation.
• Expertise in event-driven architecture, Supabase, and AWS serverless infrastructures.

Success Metrics Within 12 Months

• Automation of key short-term rental workflows through solutions you develop.
• Reduction in manual administrative work for property managers.
• Reliable data exchange for reservations, availability, payments, and operations.
• Deployment and upkeep of new integration solutions.
• Incorporation of AI-powered workflows in daily customer operations.
• Platform scaling to support more properties and operators while maintaining high reliability and performance.
• Enablement of customer growth, enhanced guest experiences, and increased profitability.

Why Join Base360.ai

• Work on impactful problems faced daily by short-term rental operators with direct access to operational feedback.
• Enjoy autonomy and responsibility in technical decision-making and system delivery.
• Collaborate in a small, focused team with founders influencing product and technology directions.
• Opportunity to learn rapidly across software development, AI, automation, hospitality operations, and scalability challenges.
• Competitive remuneration with performance-linked rewards.
• Fully remote work environment prioritizing results over hours.

Important Considerations

• This position is unsuitable for those who prefer slow corporate environments, narrowly defined roles, or lack desire for ownership and accountability.
• Candidates should be comfortable delivering quality work with responsibility for outcomes.