Who we are At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to hundreds of thousands of businesses and empower millions of developers worldwide to craft personalized customer experiences.
Software Engineer
Remote (Global)
June 15, 2026
Job description
At The Flex, we believe renting a home should feel as effortless as booking a ride.
Our mission is ambitious: enable anyone to live anywhere, anytime, without friction.
Powered by Base360.ai, our proprietary automation platform, we are building the operating system for modern renting—connecting property data, orchestrating operations, automating workflows, and enabling seamless stays across continents.
We're looking for a highly ambitious engineer who wants to build systems that create leverage at scale. This isn't a role where you'll spend months debating specifications. You'll build, ship, automate, and solve real-world problems that directly impact thousands of guests and properties.
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 Founding Software Engineer, you'll help architect and scale Base360.ai—the technology platform powering every aspect of The Flex.
You'll build internal products, automation engines, AI-powered workflows, integrations, and operational systems that eliminate manual work and allow the business to scale globally.
Your work will touch everything from guest journeys and property operations to pricing intelligence and AI-driven decision-making.
Your Mission
Build the Core Platform
Design and develop scalable applications, services, and APIs that power bookings, pricing, payments, guest experiences, and operations.
Create Powerful Automations
Build event-driven workflows that automate tasks previously performed by humans.
Develop AI-Powered Systems
Leverage LLMs, AI agents, and machine intelligence to streamline operations, improve decision-making, and enhance customer experiences.
Design API-First Architecture
Create robust APIs that enable seamless communication between internal systems, third-party providers, and future products.
Integrate the Ecosystem
Build and maintain integrations with platforms including Airbnb, Hostaway, Stripe, Twilio, OpenAI, Google, and other strategic partners.
Scale Infrastructure
Deploy and manage cloud-native infrastructure designed for reliability, performance, and global growth.
Solve Complex Operational Problems
Build solutions for:
- Real-time reservation synchronization
- Dynamic pricing intelligence
- Smart key management
- Automated guest communication
- Operational forecasting
- Cleaning and maintenance automation
- AI-powered monitoring and alerts
Move Fast
Own projects end-to-end—from idea to deployment—and continuously improve 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 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
- Ability to work independently with minimal supervision
- Strong problem-solving ability and product mindset
- Curiosity about AI, automation, and operational efficiency
- A bias toward action and shipping
Bonus points for experience with:
- Property technology (PropTech)
- Marketplace businesses
- AI agents and workflow automation
- Event-driven architectures
- Supabase
- AWS serverless infrastructure
What Success Looks Like
Within your first 12 months:
- Core operational processes are automated through systems you've built
- Manual work across the business is significantly reduced
- New integrations are deployed and maintained reliably
- AI-powered workflows become part of everyday operations
- Base360.ai becomes a competitive advantage that enables rapid global scaling
Why Join The Flex
Build Something Meaningful
Your work will directly impact how people live, travel, and experience cities around the world.
Extreme Ownership
You'll have the freedom to make decisions and build systems that matter.
Small Team, Massive Opportunity
Work closely with founders and have a direct influence on product and technical direction.
Learn Faster
You'll solve real-world challenges across software, AI, automation, 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 maintaining systems rather than building them
- You need detailed instructions for every task
- You avoid ownership and accountability
- "Good enough" is your standard
We're not looking for someone to fill a position.
We're looking for someone to help build the future operating system of modern renting.
#LI-Remote
Available regions
Each region below is open to applicants in that country only. Apply through the link for your region.
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Who we are At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to hundreds of thousands of businesses and empower millions of developers worldwide to craft personalized customer experiences.