Jobs at TripStack

Own global IT operations across Toronto, Pune, and Krakow, including onboarding, offboarding, office infrastructure, SaaS administration, procurement, vendor management, budgeting, capital planning, endpoint security, identity administration, and IT service metrics. Lead an IT team, partner with Security, SRE, Finance, and People teams, improve processes through documentation and automation, and report operational performance and spending to executives.

Manage onboarding, offboarding, employee records, benefits administration, HR inquiries, and employment compliance for teams in Canada and Poland. Execute accurate payroll cycles, remittances, reconciliations, year-end filings, terminations, audits, and payroll improvements. Support office management, inventory, staff lunches, and social events while maintaining confidentiality and delivering a positive employee experience.

Plan and execute a zero-downtime migration of stateful data systems (Druid, Spark, Redpanda, Airflow, PostgreSQL, Elasticsearch) from bare-metal VMs to Kubernetes on OpenStack. Codify infrastructure as code, implement safe StatefulSet/PVC and upgrade patterns, and own day-to-day operational health. Build observability, SLOs, runbooks, KPIs, and optimizations. Partner with SRE on hardware, networking, and Kubernetes fundamentals while owning data applications end-to-end.