AI Engineer

At Cubby, we're building the future of self-storage.

More than 70,000 self-storage properties across North America serve the 10%+ of Americans who need storage during major life transitions—new jobs, moves, divorces, family changes. These 35,000+ independent operators are under tremendous pressure: self-storage has become the fastest-growing commercial real estate asset class, surpassing $50 billion annually in the U.S., and institutional capital is flooding in.

If you want to equip this industry with best-in-class technology and help operators compete at the highest level, Cubby offers a rare opportunity. Today we serve over 400 operators with 500k units under management.

We're a venture-backed company with a focused product team and phenomenal investors who've given us years of runway. We ship new features weekly and serve clients from $10k to $5mm+ ACV. We're now seeking an AI Engineer to build intelligent features that transform how self-storage operators run their businesses.

What you'll do

Design and implement AI-powered features that directly impact customer operations—from intelligent lead routing to predictive occupancy forecasting
Build and optimize LLM integrations for customer communication, document processing, and operational insights
Develop ML models for pricing optimization, demand forecasting, and customer behavior prediction
Work closely with Product and Engineering to identify high-impact AI opportunities and ship them quickly
Establish best practices for AI development, testing, and monitoring in a production environment
Partner with CSMs and customers to understand operational challenges and translate them into AI solutions
Stay current with the latest AI/ML research and tools, bringing innovative approaches to practical problems

Requirements

Based in NYC with enthusiasm for our in-person culture (4 days/week in office)
6+ years of industry experience as a product oriented software engineer
3+ years of experience building production ML/AI systems, ideally in a product-focused environment
Strong foundation in machine learning fundamentals, particularly NLP and time-series forecasting
Hands-on experience with LLMs and modern AI frameworks (OpenAI API, Anthropic Claude, LangChain, etc.)
Proficiency in Python and ML libraries (PyTorch, TensorFlow, scikit-learn)
Experience with data pipelines, model deployment, and monitoring in production environments
Product mindset—you care about building features customers love, not just impressive models
Comfortable with ambiguity and excited to define AI strategy in an early-stage startup
Bonus: Experience with PostgreSQL, cloud platforms (AWS/GCP), or real estate/operations tech

Benefits

Competitive salary and meaningful equity
Unlimited PTO
401k and top-tier health, vision, and dental insurance
In-person work culture (4x per week) with lunches provided
Luxury gym membership
A hard-working and innovative team

Cubby is committed to promoting equality, inclusion, and diversity and that's already represented on our team. We're an equal-opportunity employer of the brightest minds we can find — regardless of race, gender, age, religion, sexual orientation, or identity.