Escalation Engineer - Toronto

Island is the ideal environment for enterprise work - security is everywhere without ever getting in the way. The Island Enterprise Platform unifies AI enablement, network access, data protection, identity, and endpoint control into one coherent workspace, giving organizations universal visibility and control while delivering a fast, fluid, beautifully simple experience to users. It's not just a better way to secure work. It's a better way to work.

Backed by Coatue Management, Insight Partners, Sequoia Capital, and others, and trusted by some of the largest enterprises on the planet, Island is redefining what the modern workplace can be.

Recent Awards:

2024 - Chosen as one of LinkedIn's Top Startups of 2024 in Dallas

2025 - Named #6 in the 2025 Dallas 100™ Entrepreneur Awards

2026 - CNBC Disruptor 50 List

Come join us in building something that's already changing how the world works.

What You'll Do

As an Escalation Engineer, you’ll join our growing global Escalation team that sits at the intersection of our customers and our engineering teams. You will deliver exceptional support experiences to some of the world’s largest enterprises by owning complex investigations end-to-end and driving systemic improvements back into the product. Your frontline insights will shape product priorities and directly impact how Fortune 500 enterprises experience Island.

• Own complex investigations end-to-end: Take escalated cases from initial triage through root cause analysis and resolution, spanning browser, network, cloud, and endpoint layers.
• Analyze real technical data: Work directly with support debug packages, Chromium traces, network captures, log platforms, and diagnostic tools to isolate browser behavior, analyze network infrastructure, and correlate logs across distributed systems.
• Collaborate with R&D: Write detailed, evidence-based escalation reports with reproduction steps, logs, and traces that enable engineering teams to act quickly to get issues resolved.
• Be the customer's advocate: Own the communication loop with enterprise customers from escalation through resolution, translating complex technical findings into clear updates.
• Drive systemic improvements & cross-team triage: Identify patterns across escalations, contribute to knowledge base articles and runbooks to reduce future volume, and participate in prioritization discussions where your insight directly influences what gets fixed and when.
• Incident Response & Coordination: You’ll occasionally join high-impact production incidents affecting enterprise customers, partnering with customer-facing teams and Engineering to help coordinate investigation and remediation efforts. You’ll also contribute to post-incident analysis, including root cause analysis (RCA) documentation and long-term corrective actions.

Requirements

Must Have

• 5+ years in a technical support escalation or similar customer-facing technical role
• Networking fundamentals: TCP/IP, DNS, TLS/SSL, proxy architectures, VPN concepts
• Web debugging proficiency: Browser developer tools, network traces (HAR, net-export), HTTP/HTTPS analysis
• Log analysis experience: Comfort working with observability platforms (Coralogix, Sentry, New Relic, or similar) to query logs, traces, and metrics
• OS knowledge: Windows and/or macOS internals, enterprise endpoint management concepts
• Cybersecurity awareness: Understanding of enterprise security concepts (zero trust, DLP, secure web gateways, endpoint protection)
• Excellent written communication: Ability to write clear, structured technical reports for both engineering teams and enterprise customers
• Self-directed investigation skills: Comfortable driving investigations autonomously, triangulating across multiple data sources without a predefined playbook
• Composure under pressure: Ability to manage frustrated enterprise stakeholders with empathy and ownership

Nice to Have

• Experience with enterprise browser, endpoint security, or SASE/SSE products
• Familiarity with Chromium architecture, extensions, or browser internals
• Identity and authentication expertise (SSO, SAML, OAuth/OIDC, Azure AD, Okta)
• Code reading ability: Can read and follow code in JavaScript, C#, Go, or similar languages to understand product behavior
• Scripting ability (Python, PowerShell, Bash) for log parsing or reproduction automation
• Background in incident response
• Experience supporting Fortune 500 or large enterprise customers