Senior Software Engineer

About Base360.ai and The Flex

Base360.ai is an AI-driven operating system designed specifically for short-term rental businesses. It empowers property managers by automating operations such as reservations, guest communication, pricing, payments, cleaning, maintenance, and reporting through a single platform. Initially developed by The Flex, a short-term rental operator that grew to an eight-figure business with its own proprietary software, Base360.ai has now launched as a standalone global platform for short-term rental operators.

Role Overview

We are seeking a highly motivated Senior Software Engineer to design, build, and scale core systems that solve real-world problems for property managers and their guests. The role involves building products that cover the entire short-term rental lifecycle, including listing distribution, pricing, bookings, guest stays, property operations, and financial reporting. This position emphasizes developing automation, AI-powered workflows, integrations, and scalable infrastructure.

Main Responsibilities

• Architect and build scalable applications, APIs, and services powering reservations, pricing, payments, and property operations.
• Create event-driven automation workflows to reduce repetitive tasks such as cleaning schedules, check-in instructions, and owner statements.
• Design and implement AI-driven systems using large language models and AI agents to automate guest communication and operational decisions.
• Develop API-first architecture facilitating integrations with internal services, booking platforms, and third-party providers.
• Build and maintain integrations with platforms like Airbnb, Hostaway, Stripe, Twilio, OpenAI, and Google.
• Deploy and manage cloud-native infrastructure focused on reliability, performance, and supporting global growth.
• Deliver solutions for complex operational challenges including real-time reservation sync, dynamic pricing, smart lock access, automated guest communication, operational forecasting, cleaning and maintenance automation, owner reporting, and AI monitoring.
• Take full ownership of projects from problem analysis to design, implementation, deployment, and ongoing optimization.
• Participate in technical decision-making, code reviews, and ensuring system reliability and maintainability.

Technical Environment

The current technology stack includes Python, FastAPI, React, TypeScript, Supabase, PostgreSQL, AWS cloud infrastructure, serverless architectures, OpenAI APIs, Twilio, Stripe, Docker, and GitHub Actions. While demonstrated capability is valued above specific tech knowledge, familiarity with these technologies is beneficial.

Candidate Profile

• Extensive experience designing and supporting production-quality software solutions.
• Proficient with frameworks like FastAPI, Python, React, or analogues.
• Strong grasp of APIs, distributed systems, and cloud-based architectures.
• Experience in architecting scalable backends and robust data models.
• Ability to work autonomously and make well-founded technical decisions.
• Excellent problem-solving aptitude combined with a product-oriented mindset.
• Interest in AI technologies, automation, and operational efficiencies.
• Bias towards swift delivery, iterative learning, and real user feedback.
• Balanced approach to speed, maintainability, and reliability in software delivery.

Preferred Additional Skills

• Experience with short-term rentals, hospitality tech, or property management systems.
• Understanding of multi-tenant SaaS platforms.
• Knowledge of marketplace business models and booking channel integrations.
• Exposure to AI agent-driven workflows and event-driven architectures.
• Familiarity with Supabase and AWS serverless infrastructure.

Success Metrics for the First Year

• Automated core short-term rental workflows through systems you develop.
• Significant reduction in manual administrative tasks for property managers.
• Reliable synchronization of reservation, availability, payment, and operational data across systems.
• Deployment and maintenance of new platform integrations with high reliability.
• Routine incorporation of AI-powered workflows into customer operations.
• Platform scalability supporting more operators and properties without compromising performance or reliability.
• Helping customers grow their portfolios, enhance guest experiences, and improve profitability.

Company Culture and Benefits

• Opportunity to build impactful software that addresses everyday challenges of rental operators with direct operational insights.
• Freedom to own and make technical decisions that shape the product and organization.
• Small, agile team working closely with founders, offering significant influence on product direction.
• Fast-paced learning environment covering software development, AI, automation, hospitality operations, and scaling challenges.
• Competitive compensation with performance-based incentives.
• Remote-first work culture prioritizing outcomes over hours, allowing work from any location.

Important Considerations

• This role may be unsuitable if you prefer a slow, corporate environment or narrowly scoped roles without product engagement.
• Applicants who require detailed task instructions or avoid accountability may not thrive here.
• We seek proactive engineers committed to quality and ownership of their work.