Senior Systems Engineer, R&D Business Systems (Winnipeg)

Overview Fivetran’s mission remains to make access to data as simple and reliable as electricity. With Fivetran, customer data arrives in their warehouses, canonical and ready to query, with no engineering or maintenance required. Fivetran is building data pipelines to power the modern data stack for thousands of companies. We are looking for a Senior Systems Engineer within the Engineering Strategy and Operations group. This role expedites internal R&D; business systems development and bridges feature development processes with business operations and data insights. Responsibilities Lead the development of custom system solutions, tools, and dashboards that power R&D; operations and seamless data flow across the feature development lifecycle. Design, develop, and maintain bidirectional integrations between core platforms such as Jira, Zendesk, Salesforce, and other GTM and G&A; systems. Create ground‑up custom AI agents and internal tools to help engineering managers, product managers, and leadership quickly access relevant data, draft technical requirements, synthesize customer feedback, and align with strategic goals and OKRs. Design and build production‑grade backend services and integration workflows in Python and TypeScript. Define API contracts, data models, and integration patterns with strong attention to reliability, idempotency, and security. Write high‑quality, tested code with clear standards for unit, integration, and end‑to‑end testing. Own observability, operational readiness, and production support for internal tools and data pipelines. Build maintainable React‑based internal applications with strong UX, accessibility, and performance practices. Leverage AI assistants to streamline IDE‑based development and coding agents such as Claude Code to automatically generate code for incident resolution, feature development, testing, investigations, and documentation. Create comprehensive technical documentation for all integrations, data models, and deployed systems. Build, maintain, and govern self‑service analytics dashboards using tools such as Sigma and Looker Studio to measure and drive operational excellence in feature delivery and business velocity. Qualifications 5+ years of experience in the software industry with a passion for solving complex system engineering problems. Proven experience developing integrations using APIs (REST/GraphQL), webhooks, and modern programming/scripting languages (Python, Java). Strong proficiency in SQL, experience with cloud data warehouses (e.g., BigQuery, Snowflake, Redshift). Experience building ground‑up and deploying AI/ML‑powered utilities or agents using LLMs (e.g., OpenAI, Claude, etc.). Hands‑on experience using, administering, and customizing core enterprise systems: Jira, Slack, Zendesk, Salesforce, Aha!, etc. Excellent communication skills in English with the ability to bridge the gap between technical details and business outcomes. Experience working cross‑functionally with global, engineering, product, design, and data analytics teams. Ability to independently drive complex projects, breaking down large‑scale initiatives into phased deliverables that provide eminent value to users without compromising on vision and overall OKRs. Bonus: 3+ years of experience in automation/operations roles within high‑growth SaaS or tech companies. Bonus: Familiarity with the up‑to‑date data stack (e.g., dbt, Airflow, Fivetran, Segment, or similar). Bonus: Experience building custom internal tools, AI agents, or web applications to support business operations. Benefits 100% employer‑paid medical insurance. Generous paid time‑off policy (PTO), plus paid sick time, inclusive parental leave policy, holidays, and volunteer days off. Professional development and training opportunities. Company virtual happy hours, free food, and fun team‑building activities. Monthly cell phone stipend. Access to an innovative mental health support platform that offers personalized care and resources for all covered employees and their covered dependents. Compensation $125,882 — $151,064.50 CAD. We are committed to ensuring that all candidates have an equal chance to participate in our interview process. If you require accommodations at any stage of the process due to a disability, medical condition, or any other circumstance, please don't hesitate to submit your request by filling out this form. We will work with you to provide reasonable accommodations to facilitate your participation and ensure a fair and accessible interview experience. Apply on Kit Job: kitjob.ca/job/2prfw3