CTO / Head of Engineering
SaaS, CRM, AI & Property Operations Platform
Location: Remote
Type: Full-Time / Long-Term Contract
Compensation: CAD $100,000 annually + Bonuses
About the Role
Royal York Property Management is hiring a CTO / Head of Engineering to take full technical ownership of a proprietary SaaS platform built for property operations.
The platform includes CRM functionality, leasing workflows, maintenance workflows, payments, owner/vendor payouts, compliance, communications, accounting/reporting, AI automation, tenant/owner/vendor portals, staff dashboards, integrations, and multiple user roles.
This is a senior leadership role 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. We are looking for a technical leader who can own the platform from architecture to execution.
Hiring Process
Qualified candidates will be asked to complete a video interview sent via email within minutes of applying.
Key Responsibilities
- Own the overall 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 and hold accountable remote engineering resources, including backend, frontend, AI/automation, integration, DevOps/cloud, QA, and security support where needed.
- 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 admins, staff, vendors, tenants, owners, Pro users, and external partners.
- 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, including developer costs, cloud infrastructure, AI/API usage, third-party tools, integrations, QA, security, DevOps, and ongoing maintenance.
- Make build-vs-buy recommendations that balance speed, cost, quality, security, and scalability.
- Communicate technical risks, trade-offs, timelines, budget concerns, and recommendations clearly to non-technical leadership.
Required Qualifications
- Bachelor's degree required in Computer Science, Software Engineering, AI/ML, Data Science, Computer Engineering, Information Systems, or a related technical field.
- Master's degree or PhD strongly preferred.
- 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.
- Proven 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.
Strongly Preferred Experience
- Master's degree or PhD in Computer Science, AI/ML, distributed systems, data engineering, cybersecurity, software architecture, or a related technical field.
- Property management technology, real estate technology, maintenance platforms, field service platforms, fintech, compliance systems, or marketplace-style applications.
- Platforms with admins, staff, vendors, tenants, owners, Pro users, and external partners.
- 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.
