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.
Founding Software Engineer
Remote (Global)
June 16, 2026
Job description
At The Flex, we believe renting a home should be as effortless as booking a ride.
Our mission is ambitious: enable anyone to live anywhere, anytime, without friction.
Powered by Base360.ai, our proprietary technology platform, we are building the operating system for modern renting—automating operations, connecting fragmented systems, and creating seamless experiences for guests, landlords, and operators across the world.
We're looking for a Founding Software Engineer to help architect and build the technology that powers the future of The Flex.
This is not a typical engineering role.
You'll work directly with the founder, influence product strategy, make architectural decisions, and build systems that become the foundation of a global business.
You'll have extraordinary ownership, responsibility, and impact from day one.
What You'll Build
As a Founding Software Engineer, you'll help create and scale Base360.ai—the technology platform that powers every aspect of The Flex.
From AI-powered workflows and booking systems to operational automation and intelligent decision-making, you'll build products that directly impact revenue, efficiency, and customer experience.
You won't just ship features.
You'll create systems that replace manual work, unlock scale, and become a competitive advantage for the company.
Your Mission
Build Core Products
Design, build, and launch the software that powers bookings, pricing, payments, operations, communications, and guest experiences.
Architect the Platform
Make key technical decisions and help define the long-term architecture of Base360.ai.
Create Automation at Scale
Develop workflows and systems that automate operational processes across multiple countries and thousands of stays.
Leverage AI
Build AI-powered tools, agents, and workflows that improve productivity, decision-making, and customer experience.
Integrate the Ecosystem
Develop and maintain integrations with platforms including Airbnb, Hostaway, Stripe, Twilio, Google, OpenAI, and other strategic partners.
Move Fast
Operate with urgency and ownership, turning ideas into production-ready solutions quickly and effectively.
Solve Real Problems
Work on challenges such as:
- Reservation synchronization
- Dynamic pricing
- Smart access management
- Guest communication automation
- Operational forecasting
- Maintenance and cleaning automation
- AI-powered alerts and monitoring
- Revenue optimization
Help Build the Company
As one of the first engineers, your influence will extend beyond code. You'll help shape processes, culture, product direction, and the future engineering team.
Tech Stack
Our current stack includes:
- Python
- FastAPI
- React
- TypeScript
- Supabase
- PostgreSQL
- AWS
- OpenAI APIs
- Stripe
- Twilio
- Docker
- GitHub Actions
We care more about your ability to learn and build than your experience with any specific technology.
What We're Looking For
Must Have
- Strong software engineering fundamentals
- Experience building production-grade applications
- Strong understanding of APIs, databases, and system design
- Product mindset and customer obsession
- Ability to work independently with minimal supervision
- Strong problem-solving ability
- High level of ownership and accountability
Bonus Points
- Startup experience
- Experience with AI products or LLM integrations
- Experience building SaaS products
- Experience with FastAPI, React, AWS, or Supabase
- Marketplace, travel, or PropTech experience
What Success Looks Like
Within your first year:
- Critical company operations are automated through systems you've built
- Base360.ai becomes a core competitive advantage
- New products are shipped rapidly and reliably
- Engineering velocity increases significantly
- AI-powered workflows are embedded across the business
- The platform is ready to scale internationally
Why Join The Flex
Massive Impact
Your work will directly shape how thousands of people live, travel, and experience cities.
Founding-Level Ownership
You'll have significant influence over product, technology, and company direction.
Build Alongside the Founder
Work closely with leadership and help define the future of the business.
Learn Faster
Gain exposure to engineering, AI, product, operations, growth, and company-building.
Performance-Based Rewards
Competitive compensation with meaningful upside for exceptional contributors.
Remote-First
Work from anywhere. We care about results, not hours.
This Role Is Not For You If
- You're looking for a predictable corporate environment
- You prefer maintaining systems rather than building them
- You need constant direction and supervision
- You avoid ownership outside your immediate responsibilities
- You are uncomfortable with change, ambiguity, and rapid execution
If you're excited by building products, solving hard problems, leveraging AI, and helping create the operating system for modern renting, we'd love to hear from you.
#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.