Technical Operations Engineer

Guidepoint•Toronto, ON

1d•CA$105,000 - CA$145,000•Hybrid

About The Position

Qsight is a high-growth division of Guidepoint focused on building data intelligence solutions for the healthcare sector. Qsight leverages proprietary datasets and rigorous analysis of alternative data sources to generate actionable insights for top-tier institutional investors, medical device manufacturers, and pharmaceutical companies. The Qsight team develops market intelligence products designed to be highly relevant, accurate, and scalable – delivering superior insights to a diverse, global client base. We are seeking an experienced, motivated Technical Operations Engineer to join our growing team. This is a multiple-hats role focused on SaaS/platform operations and tier-2 support for client-facing systems. You will own the administration and reliability of key tools, troubleshoot and resolve escalations with clear documentation, and build lightweight automation and reporting to reduce manual work as we scale. You will partner closely with Customer Success, Product, and Engineering to proactively monitor, support, and improve critical systems. Through practical, creative problem-solving, you will strengthen reliability, accelerate time to resolution, and increase operational visibility. Day to day, you will triage and resolve client technical questions, manage vendor license administration and renewals, and produce reporting that informs operational decisions. This role is a launchpad toward an SRE/Platform Engineering track as you grow into deeper automation, reliability engineering, and systems design work. This is a hybrid position based out of our Toronto office.

Requirements

Bachelor’s degree in computer science or equivalent
4+ years of hands-on operational experience – configuring, supporting, and administering critical business SaaS tools
Strong expertise with scripting and automation
Proficiency with Python and SQL
Proficient with AI tools (e.g. Claude, ChatGPT, Copilot) for scripting, documentation, and troubleshooting workflows
Experience with creating and executing runbooks
Experience with dashboards, metrics, reports, alerts
Strong documentation habits (runbooks, checklists, user guides)
Excellent written and verbal communication skills
Demonstrated ability to work independently and in a team atmosphere with minimal supervision
Strong focus on quality, attention to detail, and addressing client needs

Nice To Haves

Interest in site reliability engineering, infrastructure-as-code, or systems programming
Experience with incident management
Technical project management skills

Responsibilities

Own routine ops and configuration changes for critical SaaS platforms – Including Tableau, Freshdesk, Datadog, and our own client facing and internal portals
Configure and maintain Freshdesk portals, routing, SLAs, permissions, integrations, etc. based on business requirements.
Automate manual operations with Python, PowerAutomate, and shell scripts – leveraging AI coding assistants where useful
Build custom client activity dashboards and reports with basic SQL
Manage vendor licensing (renewals, true-ups) and optimize seat utilization
Partner with Engineering to plan, implement, and maintain integrations
Assist users with desktop setup and using our technology stack
Actively monitor the health of our critical systems with tools like Datadog
Collaborate with engineering on configuring telemetry data sources
Coordinate with vendor support and internal IT to drive issues to resolution
Contribute to reliability metrics (SLIs/SLOs) as our practices mature – with regular 1:1s with Engineering leadership to build toward this path
Triage escalations from Customer Success
Reproduce and isolate issues
Collect logs, user context, and reproduction steps (e.g., Datadog, CloudWatch, Tableau) to accelerate Engineering/vendor resolution
Create and maintain runbooks, FAQs, and internal documentation
Help define alert thresholds and escalation paths for incidents
Proactively identify recurring issues and drive them to permanent fixes (not just workarounds)
Use AI tools to accelerate runbook creation, log triage, and issue reproduction