Escalation Engineer - Toronto

Island

$90K — $120K *
Information Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 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 with observability platforms (Coralogix, Sentry, New Relic)
  • OS knowledge: Windows and/or macOS internals, enterprise endpoint management concepts
  • Understanding of enterprise security concepts: zero trust, DLP, secure web gateways
  • Excellent written communication: Ability to write clear, structured technical reports
  • Self-directed investigation skills: Comfortable autonomy across multiple data sources

Responsibilities

  • Own complex investigations end-to-end: Manage escalated cases from initial triage through resolution
  • Analyze real technical data: Utilize support debug packages and diagnostic tools to analyze system behavior
  • Collaborate with R&D: Provide detailed escalation reports to support engineering teams in issue resolution
  • Be the customer's advocate: Communicate effectively with enterprise customers throughout the escalation process
  • Drive systemic improvements: Identify patterns in escalations to reduce future issues and influence product fixes
  • Incident Response & Coordination: Participate in high-impact incidents and contribute to post-incident analysis

Benefits

  • Supportive and growth-oriented work environment
  • Opportunities for professional development and skill enhancement
  • Culture that values problem-solving and technical challenges
  • Chance to work with Fortune 500 enterprises
Full Job Description
Description

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


At Island, we value our team members and strive to create a supportive and growth-oriented environment. If you are a problem-solver who enjoys technical challenges, has a passion for customer service, and possesses a strong background in Cyber Security and coding, we would love to hear from you.

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