About Outcome
We\'re building an AI orchestration platform that automates entire workflows for the commercial real estate industry. Our mission is to move business teams from spending time on manual outputs to focusing on strategic outcomes. We eliminate "swivel chair" work by connecting siloed SaaS applications and unlocking billions of dollars in value trapped in disparate systems. Founded by the team behind Rise Buildings (acquired by VTS), we have deep real estate industry expertise and are scaling our AI-powered automation platform to transform how the $7T+ global real estate industry operates.
Note: Required: Must live in or near Toronto and be a permanent resident of Canada (no sponsorship support available)
The Role
We\'re seeking a Senior Python Developer with deep expertise in Generative AI to join our core engineering team. You\'ll be responsible for building and scaling our AI orchestration platform that ingests data from multiple sources, normalizes it through industry-specific fine-tuned models, and automates complex workflows that currently take analysts 4+ hours per week.
Key Responsibilities
- AI Pipeline Development: Design and implement robust data ingestion pipelines that process emails, PDFs, Excel files, and API data from property management systems
- LLM Integration: Build and optimize integrations with multiple LLM providers (OpenAI, Anthropic, etc.) for document processing, data extraction, and workflow automation
- Data Processing & Normalization: Develop sophisticated data transformation systems using Pydantic for schema validation and normalization across diverse real estate datasources
- Workflow Orchestration: Create intelligent automation workflows that can process property management reports, generate box score summaries, and trigger downstream actions
- Vector Database Management: Implement and optimize vector storage solutions for our private data warehouse and retrieval-augmented generation (RAG) systems
- API Development: Build robust APIs for our automation engine and third-party integrations with real estate software platforms
- Performance Optimization: Ensure sub-10 minute processing times for complex multi-document workflows while maintaining 99.9% accuracy
- Monitoring & Reliability: Implement comprehensive logging, error handling, and monitoring for production AI workflows
Required Technical Skills
- Core Python: 5+ years of professional Python development with expertise in async programming, multiprocessing, and production-grade code
- Generative AI Libraries: Hands-on experience with:
- LlamaIndex for building RAG applications and document processing
- OpenAI API (GPT-4, embeddings, function calling)
- Anthropic Claude API integration
- Hugging Face transformers and model deployment
- Data Processing: Expert-level experience with:
- Pydantic for data validation and serialization
- Pandas/Polars for data manipulation
- Document processing (PDFs, Excel, emails) using libraries like PyPDF2, openpyxl, and email parsing
- Vector Databases: Experience with Qdrant, Weaviate, Chroma, or similar vector storage solutions
- Databases: PostgreSQL, Redis, and experience with time-series data
- Cloud Platforms: AWS (Lambda, S3, RDS, SQS) or Azure with infrastructure-as-code experience
- API Development: FastAPI, RESTful services, and webhook handling
- DevOps: Docker, CI/CD pipelines, monitoring tools (DataDog, New Relic)
Preferred Qualifications
- Background in document AI, OCR, or intelligent document processing
- Experience with browser automation (Selenium, Playwright) for SaaS integrations
- Understanding of enterprise security and data privacy requirements
- Experience with fine-tuning language models or building domain-specific AI applications
What We Offer
- Equity Ownership: Equity stake in a fast-growing AI automation company
- Technical Impact: Build cutting-edge AI systems that automate entire industries
- Industry Expertise: Work alongside founders with proven real estate and AI experience
- Growth Opportunity: Ground-floor opportunity to shape our technical architecture and team
- Competitive Package: Market-rate salary plus equity and comprehensive benefits
- Flexible Work: Remote-friendly culture with optional Chicago office access
Ideal Candidate Profile
You\'re a senior Python developer who gets excited about applying cutting-edge AI to solve real business problems. You have experience building production AI systems that handle complex, unstructured data and can architect solutions that scale. You thrive in fast-paced environments and want to be part of a team that\'s automating workflows worth billions of dollars in economic value.
You understand that building reliable AI automation requires deep technical expertise, attention to detail, and the ability to work closely with domain experts to understand complex business workflows.