Head of Engineering
Mentions and will guide "vibe coders" — hands-on, fast iteration building AI agents and prototypes.
About the Role
Founding Head of Engineering responsible for designing, building, and operating a custom AI-first operating system that unifies property, investor, and employee management. This is a hands-on leadership role: you will write production code, architect systems, build AI agents, and lead a small engineering team while reporting to the CFO.
Job Description
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