Head of Engineering

Role

You are the founding Head of Engineering reporting to the CFO, responsible for architecting, building, and operating a custom AI-first operating system that replaces third-party SaaS across property management, investor management, and employee management. This is a hands-on role: you will write production code, make long-lived architecture decisions, and lead a small engineering team.

Mission

Design, build, and deploy a unified AI-first platform that replaces all third-party SaaS tools at the company and becomes the organization’s permanent competitive advantage in multifamily real estate.

Key Objectives

• Establish the technical foundation from zero: choose stack, deploy cloud environments, CI/CD, monitoring, security, and development workflows with daily production shipping by month 3.
• Ship the first wave of AI-enhanced production applications (months 3–9) and continue expanding the platform and AI capabilities (months 6–18).
• Architect and deploy AI agents to automate workflows and multiply team output.
• Migrate data from legacy SaaS tools (notably Entrata) with data integrity and minimal downtime.

Key Performance Indicators (KPIs)

• Number of SaaS tools cancelled and custom apps in active daily use
• Reduce SaaS spend by 50% vs baseline by month 18
• Production uptime across deployed applications ≥ 99.5%
• Deploy at least 3 AI agents in first 6 months; 12 in first 12 months
• Internal user satisfaction ≥ 8/10
• Average time-to-ship new features < 2 weeks

Key Responsibilities

• System architecture and technical vision: design unified data model and microservices architecture across business domains and own major technical decisions.
• AI/LLM strategy & execution: architect the AI layer, design agent workflows, prompt engineering pipelines, model orchestration, and evaluation frameworks.
• Hands-on development: write production code daily and personally build critical systems, especially during the early months.
• Team leadership & mentorship: lead ~2 engineers, guide “vibe coders”, establish code review standards and development workflows.
• Production infrastructure & DevOps: own cloud, CI/CD, monitoring, security, disaster recovery for systems handling financial data and PII.
• SaaS replacement execution: prioritize roadmap with CFO and deliver on aggressive timelines.
• Data migration & integration: build ETL pipelines to migrate data from legacy SaaS tools (Entrata) ensuring integrity and backward compatibility.

Required Qualifications

• 8+ years software engineering experience with at least 3 years in a technical leadership or architect role.
• Deep full‑stack web development expertise: React/Next.js frontend and Python (FastAPI) or Node.js backend; PostgreSQL.
• Hands-on production experience building with LLMs (Claude, GPT-4, open-source models) and shipping AI-powered features to real users.
• Strong infrastructure and DevOps skills: AWS or GCP, Docker/Kubernetes, CI/CD pipelines, infrastructure-as-code (Terraform).
• Experience building internal tools, enterprise applications, or platform products where the user is the business.
• Proven ability to translate business requirements into scalable architecture and ship quickly in ambiguous, resource-constrained environments.

Preferred Qualifications

• Experience or passion in real estate, property management, proptech, or financial services technology.
• Background in accounting systems, payment processing, or financial reporting.
• Familiarity with property management workflows (leasing, maintenance, rent collection, compliance reporting).
• Experience designing multi-agent AI systems or complex orchestration workflows.
• Experience building systems that handle financial data with SOC 2 or equivalent compliance.

What We Offer / Perks

• Greenfield build with modern tools and AI-first architecture
• Work directly on a platform that operates a $2B+ real estate portfolio with real operational impact
• Executive access and direct reporting to the CFO
• Growth trajectory toward VP/CTO as the platform and team scale
• Scottsdale lifestyle and lower cost-of-living vs coastal tech hubs

Logistics

• Job Type: Full-time
• Work Location: In person
• Salary: $180,000 - $200,000 per year