Senior Software Engineer

About Us
[protected info] 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, [protected info] 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.
What You'll Build
As a Senior Software Engineer, you'll help architect and scale [protected info]-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.
Your Mission
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.
Bring senior engineering judgment to technical decisions, code reviews, and the reliability of the systems you build.
Tech Stack
We care more about capability than specific technologies, but our current stack includes:
Python
FastAPI
React
TypeScript
Supabase
PostgreSQL
AWS
Serverless architecture
OpenAI APIs
Twilio
Stripe
Docker
GitHub Actions
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
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
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
[protected info] helps customers grow their portfolios, improve guest experiences, and operate more profitably
Why Join Us
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 [protected info].
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.
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
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.