Senior Software AI Engineer

Senior Software Engineer

About Tailorbird

Tailorbird is building an agentic AI platform for institutional multifamily real estate owners that turns structured and unstructured data from planning and operations into a consistent, trusted system of intelligence to make smarter acquisition and capital planning decisions and to enable agent-automated workflows.

We’re a distributed team across the U.S., Latin America, and India. U.S. East Coast (EST) is strongly preferred for this role. This is a hybrid position in the greater NYC area.

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, who has founding-team experience (early-stage, high-ownership environment) and has helped ship and scale products from 0-1MM and/or 1-10MM.

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. You will have an opportunity to build specifications-based validation agents to create trusted AI solutions.
• 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).
• Designs 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. You must have a deep understanding of limitations of thin semantics of RAG based AI systems. You should be familiar 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.

What 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

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