CTO / Head of Engineering

The platform includes CRM functionality, leasing workflows, maintenance workflows, payments, owner and vendor payouts, compliance, communications, accounting/reporting, AI automation, tenant, owner and vendor portals, staff dashboards, integrations, and multiple user roles.

This role is for someone who can evaluate an existing platform, challenge weak technical decisions, lead remote engineering resources, improve architecture, control technology costs, and move the product toward a stable, scalable launch.

The right person must be able to own the platform from architecture to execution, communicate technical risks clearly, and make practical decisions that balance speed, cost, quality, security, and scalability.

How to Apply

• Apply with your resume
  
• If your background aligns, you’ll receive a link to a short pre-recorded video interview shortly after applying
  

What You’ll Do

• Own the technical direction, architecture, engineering execution, and launch readiness of the platform
  
• Evaluate the existing tech stack, codebase, backend, frontend, database schema, APIs, integrations, AI workflows, infrastructure, security, CI/CD, and deployment process
  
• Identify technical debt, weak architecture, scalability risks, security gaps, incomplete workflows, poor development practices, and launch blockers
  
• Create and manage the technical roadmap across backend, frontend, AI, integrations, DevOps, QA, security, and infrastructure
  
• Lead remote engineering resources across backend, frontend, AI/automation, integrations, DevOps/cloud, QA, and security
  
• Review and improve CRM architecture, workflow logic, pipelines, statuses, tasks, notifications, reporting, audit history, and automation rules
  
• Ensure financial workflows are reliable and secure, including payments, rent collection, owner payouts, vendor payments, ledger activity, reconciliation, audit trails, and permission controls
  
• Oversee role-based access control, protected APIs, document access, least-privilege permissions, audit logs, and permission testing across user types
  
• Ensure AI automation is properly engineered, tested, monitored, cost-controlled, privacy-conscious, and tied to measurable business value
  
• Improve third-party integration reliability using proper error handling, retries, webhooks, monitoring, logging, and failed-sync recovery
  
• Establish engineering standards, code review processes, sprint planning, QA automation, CI/CD practices, incident response, documentation, and release controls
  
• Manage technology budget planning across developer costs, cloud infrastructure, AI/API usage, third-party tools, integrations, QA, security, DevOps, and ongoing maintenance
  
• Make build-versus-buy recommendations that support speed, cost control, product quality, security, and scalability
  
• Communicate technical risks, trade-offs, timelines, budget concerns, and recommendations clearly to non-technical leadership
  

Requirements

• Bachelor’s degree in Computer Science, Software Engineering, AI/ML, Data Science, Computer Engineering, Information Systems, or a related technical field
  
• 10+ years of software engineering experience
  
• 5+ years in a CTO, Head of Engineering, VP Engineering, Software Architect, Technical Lead, or senior engineering leadership role
  
• Experience leading, scaling, auditing, or rescuing SaaS platforms, CRM-style systems, marketplace platforms, fintech/payment systems, property/field-service platforms, or multi-role operational software
  
• Strong backend architecture experience, including database design, API architecture, authentication, authorization, RBAC, scalability, security, performance, and data integrity
  
• Strong understanding of CRM architecture, workflow engines, custom fields, audit logs, event history, reporting structures, automation rules, and business logic flexibility
  
• Experience with financial workflows, including payments, payouts, transaction handling, idempotency, reconciliation, ledger logic, accounting/reporting workflows, and financial data security
  
• Experience with AI/LLM integrations, AI automation, structured outputs, prompt/version control, RAG where applicable, human review, AI evaluation testing, hallucination risk, data privacy, and AI cost control
  
• Experience designing reliable third-party integrations using APIs, webhooks, retries, queues, rate-limit handling, logging, monitoring, and failure recovery
  
• Experience managing remote engineering teams across backend, frontend, AI/automation, integration, DevOps/cloud, QA, and security
  
• Experience with CI/CD, cloud infrastructure, observability, monitoring, incident response, automated testing, deployment controls, and launch readiness
  
• Ability to manage technology budgets, engineering resources, cloud costs, AI/API costs, third-party tools, vendor costs, and ongoing maintenance priorities
  
• Ability to explain technical issues in plain business terms to non-technical leadership
  

Nice-to-Have

• Master’s degree or PhD in Computer Science, AI/ML, distributed systems, data engineering, cybersecurity, software architecture, or a related technical field
  
• Experience with property management technology, real estate technology, maintenance platforms, field service platforms, fintech, compliance systems, or marketplace-style applications
  
• Experience building platforms with admins, staff, vendors, tenants, owners, Pro users, and external partners
  
• Experience with AI automation for task routing, document handling, vendor matching, communications, compliance, reporting, or operational decision support
  
• Experience inheriting messy platforms, identifying technical debt, restructuring teams, and moving products toward launch
  
• Experience hiring and evaluating developers, architects, AI engineers, integration specialists, QA, DevOps, and security resources
  

Ideal Candidate

The ideal candidate is a technical leader who can assess what exists, identify what is broken, and create a realistic plan to move the platform forward.

They are strong enough technically to challenge poor architecture, weak engineering practices, bad vendor decisions, security gaps, and incomplete workflows.

They can lead remote developers, manage engineering execution, control costs, and communicate clearly with non-technical leadership.

They understand that this role is not only about writing code. It is about architecture, launch readiness, reliability, security, AI, integrations, financial workflows, user permissions, reporting, and long-term scalability.

They are practical, direct, organized, and comfortable taking ownership of a complex operational platform.

Remote Tech Requirements

• Dual monitor setup
  
• Computer with 16GB RAM minimum
  
• 100+ Mbps reliable internet speed
  
• Webcam
  
• Noise-cancelling headset
  
• Quiet and professional remote work environment
  

Important Location Requirement

This is a remote position; however, candidates must be located in the same country, city, or region where the job is posted. The successful candidate must be available to attend a local office, meeting, training session, or company event if requested.

Please only apply if you are based in the location listed on this job posting. Remote does not mean the position is open worldwide. #LI-DNP