Head of Technical Support & AI Service Operations

About Property Vista Property Vista is a B2B SaaS platform purpose-built for enterprise real estate and property management. We serve institutional landlords, REITs, and property management companies across North America with a platform that automates tenant communications, payments, leasing, and operations at scale. About the Role We do not scale support by linearly hiring armies of 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 master of this 3-tier engine. You will own end-to-end support operations, ruthlessly govern our ticket backlog, 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. Key Responsibilities1. Tier 1 AI Optimization & Automated Containment Own the AI Frontline: Act as the operational business owner of Property Vista's Tier 1 AI support layer (custom LLM agents, Zendesk/Intercom AI bots, automated triage). 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. Metrics Ownership: Establish and maintain dashboards, reporting views, and KPIs. Share across teams as necessary to drive visibility and accountability. 2. Tier 2 & Tier 3 Operational Rigor Lead the Human Engine: Directly manage, coach, and scale the 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 crosses into Tier 3 or Engineering. Enterprise Account Management: Act as the executive escalation point for severe technical incidents affecting major institutional accounts, providing professional, transparent communication until resolution. KPIs / SLAs / Metrics: Ensure transparency, benchmarks, and reporting are in place to identify where processes need refining or are working as expected. 3. 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 Deflection: 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: Ensure transparency and clarity around the technical support team's throughput. Own the support tooling and ensure all teams that tickets are escalated to are adhering to their SLAs. Identify trends and patterns to improve operating practices. 4. Engineering Feedback Loop & Root-Cause Elimination Defect Prevention: Treat support as a quality control instrument, not a cost center. Use structured frameworks (e.g., 5 Whys) 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 configuring, optimizing, and training AI support tools (Zendesk AI/Copilot, Intercom FinAI, Salesforce Service Cloud, or custom LLM workflows). You know how to build decision-tree logic and clean knowledge bases that AI 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: Exceptional, native-level English (both written and spoken) is an absolute requirement for handling North American enterprise escalations. Culture Fit: 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. Compensation & Benefits Total Rewards: Competitive base starting at $100,000 Comprehensive Benefits: Full health and dental benefits package to support your well-being. Work Flexibility: A remote-first operating model designed for high-performance autonomy. Time Off: Generous paid vacation time to ensure elite operational output. Equity & Growth: Employee stock options and professional development pathways to scale your career with the company. Timeline: Immediate start date available for the right candidate.

Lead a three-tier technical support engine by optimizing AI-driven Tier 1 containment and managing elite Tier 2 and 3 human specialists. Act as the operational bridge between human resolutions and AI training to automate edge-case resolutions and maintain strict SLA accountability.

Requires 5+ years of experience leading technical support in a high-growth B2B SaaS environment with fluency in AI support tools and modern web architecture. Must possess strong operational rigor in managing dashboards, KPIs, and native-level English proficiency for North American enterprise clients.

• Health benefits • Dental benefits • Remote-first operating model • Paid vacation time • Employee stock options • Professional development pathways

• SQLSouhaitée
• API RESTSouhaitée

Relevées dans la description du poste. Confirmez les exigences importantes ci-dessus.

• AI Support Optimization
• Technical Support Management
• SLA Governance
• REST APIs
• SQL
• JSON
• Log Analysis
• Zendesk AI
• Intercom FinAI
• Root-Cause Analysis
• Workforce Capacity Planning
• B2B SaaS Operations
• Ticket Routing Design
• Enterprise Account Management
• LLM Prompt Logic
• Knowledge Base Management

• Customer Service & Support
• Management & Leadership
• Technology
• Software
• Engineering

Expérience minimale

5+ ans

Postuler avant le

17 févr. 2027

Langue de l’offre

anglais

Heures de travail

40 heures par semaine

Exigences de lieu

Country, Toronto, Ontario, Canada

Niveau d’expérience

Director

Mode de candidature

La candidature directe est offerte