Escalation Engineer - Toronto

Island Island · Enterprise · Toronto, ON · Engineering

This role is for an Escalation Engineer on the Island Enterprise Platform team. The role involves owning complex investigations end-to-end, analyzing technical data, collaborating with R&D, and driving systemic improvements. It requires strong networking, web debugging, and log analysis skills, with an emphasis on customer advocacy and incident response within an enterprise environment.

What you'd actually do

  1. 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.
  2. 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.
  3. 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.
  4. Be the customer's advocate: Own the communication loop with enterprise customers from escalation through resolution, translating complex technical findings into clear updates.
  5. 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.

Skills

Required

  • 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

What the JD emphasized

  • 5+ years in a technical support escalation or similar customer-facing technical role
  • enterprise customers
  • complex investigations
  • root cause analysis
  • systemic improvements