About Us
The People Group is conducting a search on behalf of a Toronto-based Prop

Tech company building the leading cloud-based property management platform for multifamily housing in North America.

This company is trusted by 200+ clients managing over 500,000 units, we unify leasing, operations, accounting, and tenant experience into one powerful platform, now enhanced by our AI-first leasing and service automation.

We are remote-first, growing fast, and investing heavily in AI across every layer of the business.

About the Role
We are building an AI-first, high-accountability support ecosystem for our B2B SaaS platform.

We do not scale support by linearly hiring frontline agents.

We scale by leveraging advanced AI for Tier 1 frontline containment, backed by elite human technical operators at Tier 2 and Tier 3.

The Head of Technical Support is the operational owner of this 3-tier engine.

You will own end-to-end support operations, manage ticket backlog health with discipline, and lead our Tier 2 and Tier 3 technical support specialists.

Crucially,



you will act as the "training loop" between our human resolutions and our AI engine, ensuring that every edge-case solved by a human today is engineered into an automated Tier 1 resolution tomorrow.

Location: Remote (LATAM — Preferred: Buenos Aires, Argentina or Colombia)
Reporting To: Director of Customer Success
Compensation: $50,000 USD annually
Employment Type: Full-time contractor via Rippling Key Responsibilities

Tier 1 AI Optimization & Automated Containment
Own the AI Frontline: Act as the operational business owner of our Tier 1 AI support layer (custom LLM agents, Zendesk/Intercom AI bots, automated triage).

You configure, monitor, and continuously improve the AI's ability to resolve issues without human intervention.

The Continuous Learning Loop: Analyze weekly ticket escalations that bypass Tier 1.

Convert Tier 2 and Tier 3 human resolutions into structured knowledge articles, macro workflows, and automated p...

📌 Head of Technical Support & AI Service Operations (Remote LATAM) (Argentina)
🏢 The People Group
📍 Argentina