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.
Senior Software Engineer
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 and at least three days per week of onsite collaboration in Princeton, NJ is a must.
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