About Us
The People Group is conducting a search on behalf of a Toronto-based PropTech 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 ResponsibilitiesTier 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 prompt logic so the AI continuously learns and expands its containment boundary.
- Deflection Quality Control: Monitor AI response accuracy, hallucination rates, and customer sentiment. Ensure high containment (>80%) does not come at the expense of enterprise customer trust or CSAT.
- Own the Metrics: Establish and maintain dashboards, reporting views, and KPIs across support channels. Share visibility with cross-functional stakeholders as needed.
Tier 2 & Tier 3 Operational Rigor
- Lead the Human Engine: Directly manage, coach, and scale our Tier 2 (Advanced Technical Support) and Tier 3 (Escalations / Engineering Liaison) teams.
- Escalation Governance: Build strict, standardized triage and debugging playbooks. Ensure Tier 2 completes exhaustive technical reproduction (log analysis, environment simulation, API payload verification) before any ticket is permitted to cross into Tier 3 or Engineering.
- Enterprise Escalation Management: Act as the executive escalation point for severe technical incidents affecting major institutional accounts, providing professional, transparent communication until resolution.
- Own KPIs / SLAs / Metrics: Ensure transparency, benchmarks, and reporting are in place to identify where processes need refining or are working as expected.
Backlog Governance, SLA Accountability & Reporting
- Queue Management: Manage ticket backlog health across all channels. Build automated routing, prioritization rules, and alerting to prevent aging tickets and SLA breaches.
- SLA Enforcement: Hold the team accountable to hard operational metrics: First Response Time (FRT), Time to Resolution (TTR), and strict adherence to our 48-Hour Update SLA for complex Tier 3 engineering investigations.
- Resource Planning: Identify seasonal or cyclical ticket spikes (e.g., month-end accounting cycles, leasing turnover) and dynamically reallocate technical specialists or adjust AI deflection rules to protect the backlog.
- Dashboards & Reporting: Own the support tooling and reporting layer. Ensure all teams that receive escalated tickets are adhering to their SLAs. Identify trends and patterns to inform operational improvements.
The Engineering Feedback Loop & Root-Cause Elimination
- Defect Prevention: Treat support as a quality control instrument, not a cost center. Use structured frameworks (5 Whys, Pareto analysis) to conduct root-cause analyses on recurring ticket clusters.
- Product & Tech Alignment: Partner directly with the Director of Customer Success and VP of Product. Translate qualitative support friction into quantifiable data (e.g., "Bug X cost us 140 support hours and $12K in churn risk this month") to drive engineering fixes onto the core product roadmap.
What You Bring
- Experience: 5+ years leading technical support or tech-ops teams in a high-growth B2B SaaS environment ($10M+ ARR scale).
- AI & Automation Fluency: Proven track record of configuring, optimizing, and training AI support tools (Zendesk AI/Copilot, Intercom Fin AI, Salesforce Service Cloud, or custom LLM workflows). You know how to build decision-tree logic and clean knowledge bases that AI agents can consume.
- Technical Depth: Solid understanding of modern web architecture, REST APIs, JSON payloads, SQL database queries, and log analysis. You can comfortably read a Postman error or browser console log to challenge an engineer's assessment.
- Operational Rigor: Deep expertise in ticket routing design, SLA governance, and workforce capacity planning. You manage by numbers, dashboards, and scorecards.
- Language: C1/C2 English proficiency (written and spoken). You will handle North American enterprise escalations daily — clarity and professionalism in English are non-negotiable.
- High-Accountability Mindset: You thrive in a lean, accountable culture where mediocre execution is challenged, processes are built for speed, and leadership dives into the data to unblock their teams.