Senior Software AI Engineer

The Role

We're looking for a senior software engineer with deep AI engineering experience to help design and scale the core intelligence systems of the Tailorbird platform. This is a high-ownership role focused on building production-grade AI workflows for automation, orchestration systems, and data models and APIs ecosystems that directly power real-world capital planning and operational decisions. You'll build customer-facing features and the underlying systems that make AI useful in production. Your work will power AI-driven workflows used daily by institutional real estate operators managing billions of assets.

What You’ll Do

• Help define system architecture and technical patterns for reliable, scalable AI-native workflows.
• Build end-to-end product features, from design through deployment.
• Develop Assistants, Co-pilots, and agents to improve user experience and automate workflow tasks.
• Integrate AI into real processes (not just prototypes), with guardrails, monitoring, HIL, and fallback paths.
• Design APIs, services, and data models that stay maintainable as usage grows.
• Improve system performance, reliability, and developer experience (testing, observability, review practices).
• Work closely with product, design, and customers to refine requirements and iterate quickly.

What We’re Looking For

• Founding team experience
• 5+ years of building and shipping production software
• Experience with an early team at a VC-backed startup (or similar environment) where you owned meaningful outcomes
• Clear examples of shipping a new product from scratch and/or scaling an existing product quickly
• AI workflow automation experience
• Built automation that coordinates multiple steps (complex data retrieval from other operations support systems, in-logic transformations, context engineering, memory management, LLM calls, and output validations)
• Designed for real-world failure modes: monitoring, retries, fallbacks, and human-in-the-loop when needed
• Practical approach to quality and correctness, especially where model output can be wrong
• A deep understanding of limitations of thin semantics of RAG based AI systems
• Familiarity with techniques that use domain specific entity models to create trustworthy AI systems
• Experience evaluating and improving AI system performance using logging, feedback loops, and structured iteration
• Full-stack skillset
• Strong backend skills (Python and/or Node/TypeScript)
• Good frontend experience building modern web apps
• Good with databases and data modeling (SQL/relational), including basic performance and reliability practices
• Customer collaboration
• Very comfortable working directly with customers to understand problems, confirm assumptions, and iterate toward the right solution
• Can translate unclear requests into a plan, ship, and refine based on feedback
• Ownership and execution
• Works well with light process, high responsibility, and moving targets
• Proactive in identifying risks, proposing solutions, and driving projects to completion
• Good judgment on tradeoffs: when to move fast, when to invest in cleanup, and when to simplify

Success Looks Like (First 3-6 Months)

• Ship meaningful features that customers use daily
• Improve core workflow or system so it’s more reliable and easier to extend
• Increase team speed and quality through better patterns, reviews, and practical standards

Why This Role is Unique

• You’ll work directly on production of AI systems solving complex, real-world operational problems
• You’ll have meaningful ownership over system design, architecture, and implementation
• Your work will directly shape how AI integrates into real estate decision-making workflows at scale

Benefits & Perks

• Equity opportunity
• Open PTO
• Company-paid medical/dental/vision for employees and dependents

Qualifications

• Valid US citizenship, lawful permanent residency (Green Card), or an existing valid work visa that does not require sponsorship/transfer is required.