From Fivetran's founding until now, our mission has remained the same: 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. We're proud that more organizations continue to leverage our technology every day to become truly data-driven.

About the Role

Fivetran is building data pipelines to power the modern data stack for thousands of companies.

We're looking for a Senior Systems Engineer within our Engineering Strategy and Operations group. Our Research and Development (R&D) department is dedicated to accelerating innovation. This role expedites internal R&D business systems development and bridges Fivetran feature development processes with business operations and data insights. You will be instrumental in building the infrastructure and tools that provide our R&D and business leaders with a unified, real-time view of R&D operations efficiency and market alignment.

We are seeking a highly motivated and skilled Systems Engineer to design, build, and maintain the critical systems and data pipelines that support our R&D organization. This role focuses on implementing technical solutions for key engineering and product processes, integrating core enterprise platforms, and transforming raw data into actionable business intelligence.

This is a full-time, hybrid position based out of our Toronto office. Our hybrid work model offers a blend of remote flexibility and in-person collaboration, including two days in the office each week to connect and build as a team.

Technologies You'll Use

TypeScript/JavaScript, Python, and React; extend Atlassian Cloud via Forge and ScriptRunner; manage data flows in BigQuery and SQL; and deploy solutions on GCP using modern CI/CD practices.

What You'll Do

• Lead the development of custom system solutions, tools, and dashboards that power the R&D operations and seamless data flow and process alignment across the Fivetran feature development lifecycle.
• Design, develop, and maintain bidirectional integrations between core platforms such as Jira, Zendesk, Salesforce, and other GTM and G&A Systems to streamline the feature development lifecycle and R&D operations.
• Create ground-up and maintain custom AI agents and internal tools to help engineering managers, product Managers and leadership quickly access relevant data, draft compelling technical requirements and design, synthesize customer feedback, and align with strategic goals and OKRs to improve operational efficiency and launch innovative products faster.
• 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 in real-time and Coding Agents, such as Claude Code, to automatically generate code for use cases such as 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, in partnership with our centralized analytics team.

Skills We're Looking For

• 5+ years of experience in the software industry with a passion for solving complex system engineering problems - experience designing and developing reusable libraries and experimentation platforms for backend and frontend from scratch, leveraging industry best practices
• Proven experience developing integrations using APIs (REST/GraphQL), webhooks, and modern programming/scripting languages (Python, Java), and building systems leveraging low-code and full code solutions, and deploying them using modern CI/CD practices and ensuring observability.
• Strong proficiency in SQL, experience working with cloud data warehouses (e.g., BigQuery, Snowflake, Redshift), and experience with BI and data visualization tools such as Sigma, Looker Studio, Tableau, or Power BI.
• Experience building ground-up and deploying AI/ML-powered utilities or agents using LLMs (e.g., OpenAI, Claude, etc.) to automate code writing, documentation, or deliver intuitive and effective user-facing prototypes and full-scale solutions.
• 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 the vision and overall OKRs.

Bonus Skills

• 3+ years of experience in automation/operations roles within high-growth SaaS or tech companies.
• Familiarity with the modern data stack (e.g., dbt, Airflow, Fivetran, Segment, or similar).
• Experience building custom internal tools, AI agents, or web applications to support business operations.

This role represents new headcount added to the team to support continued growth and expansion of capabilities.

#LI-HYBRID #LI-DC2

Perks and 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

• RSU stock grants*

• 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 in areas such as: therapy, coaching, and self-guided mindfulness exercises for all covered employees and their covered dependents.

• May vary by country and worker type - please reach out to your recruiter for more information

Click here to learn more about Fivetran's Benefits by Region.

We're honored to be valued at over $5.6 billion, but more importantly, we're proud of our core values of Get Stuck In, Do the Right Thing, and One Team, One Dream. Read about us in Forbes.

Fivetran brings together high-quality talent across the globe to make data access as easy and reliable as electricity for our customers. We value and recognize that our customers benefit from having innovative teams made of people from many backgrounds, experiences, and identities. Fivetran promotes diversity, equity, inclusion & belonging through attracting, recruiting, developing, and retaining a diverse workforce, not only because it is the right thing to do, but because it helps us build a world-class company to better serve our customers, our people and our communities.

To learn more about Fivetran's culture and what it's like to be part of the team, click here and enjoy our video.

To learn more about our candidate privacy policy, you can read our statement here.

We are committed to ensuring that all candidates have an equal opportunity 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. Your request and any information provided will be kept confidential and will not impact your candidacy. We look forward to hearing from you and accommodating your needs to the best of our ability.*