Systems Administrator, Operations at Faire

About Faire Faire is an online wholesale marketplace built on the belief that the future is local — independent retailers around the globe are doing more revenue than Walmart and Amazon combined, but individually, they are small compared to these massive entities. At Faire, we're using the power of tech, data, and machine learning to connect this thriving community of entrepreneurs across the globe. Picture your favorite boutique in town — we help them discover the best products from around the world to sell in their stores. With the right tools and insights, we believe that we can level the playing field so that small businesses everywhere can compete with these big box and e-commerce giants. By supporting the growth of independent businesses, Faire is driving positive economic impact in local communities, globally. We’re looking for smart, resourceful and passionate people to join us as we power the shop local movement. If you believe in community, come join ours. About this role As the Systems Administrator, Operations, you’ll play a critical role in improving stability, cost efficiency, and customer experience across Risk, CX, and Marketplace Operations as our workflows and system complexity grow. You’ll lead high-impact systems work—from routing, to integrations, to automations, to ticket enrichment. This is a highly technical, hands-on-role that bridges AI, Operations, and platform development to create a seamless, intelligent experience for our teams. We’re looking for a hands-on systems builder, who is equal parts AI builder, Zendesk expert, and systems integrator, who can design with vision, execute with speed, and collaborate with empathy. What you’ll do • Design, build and manage case management routing in Zendesk (or similar), including complex workflow logic, SLAs, escalations, and operational controls. • Build and maintain reliable integrations between case management tooling, snowflake using iPaas tools , webhooks etc • Own platform health by monitoring data sync fidelity between Ops tools and backend systems; proactively troubleshoot issues and outages. • Implement case enrichment to give agents better context from back end tools and reduce manual investigation. • Own end to testing and deployment, and stand up robust monitoring systems to identify issues • Guide and uphold development best practices to ensure high-quality implementations, and stable integrations • Drive adoption of major platform changes through clear enablement and stakeholder partnership. • Serve as a bridge between technical and non-technical stakeholders—translating complex requirements into usable systems. • Support broader Ops strategy through thoughtful system design, Ops UX enhancements, and AI-first process optimization. Qualifications • 3–5 years business / ps systems experience in a SaaS, high-growth, and/or B2B environment. • Proven ownership of routing and automation in Zendesk (or another case management platform). • Proven ownership of integrations (APIs/webhooks and/or iPaaS like Workato/Hightouch), including operating in production and debugging failures. • Strong SQL skills used to validate data quality, investigate sync issues, and reason about end-to-end data flows (Snowflake a plus). • Track record of translating business needs into scalable system solutions and driving work from concept to adoption. • Able to manage multiple priorities, navigate ambiguity, and execute independently. • Experience leading a migration or large-scale workflow change with minimal disruption. Nice to have • Familiarity with LLM-powered tooling for classification, tagging, or workflow automation—and an intuition for where AI meaningfully improves ops vs. adds complexity. • Scripting ability in Python or JavaScript for lightweight automation or data manipulation tasks. • Prior experience working in or closely alongside a Support, CX, or Marketplace Operations team. • Familiarity with job orchestration concepts—dependencies, retries, alerting—for scheduled syncs and data pipelines. Salary Range Kitchener-Waterloo: the pay range for this role is $104,000 to $143,000 per year. This role will also be eligible for equity and benefits. Actual base pay will be determined based on permissible factors such as transferable skills, work experience, market demands, and primary work location. The base pay range provided is subject to change and may be modified in the future. Hybrid Faire employees currently go into the office 3 days per week on Tuesdays, Thursdays, and a third flex day of their choosing (Monday, Wednesday, or Friday). Additionally, hybrid in-office roles will have the flexibility to work remotely up to 4 weeks per year. Specific Workplace and Information Technology positions may require onsite attendance 5 days per week as will be indicated in the job posting. Why you’ll love working at Faire • We are entrepreneurs: Faire is being built for entrepreneurs, by entrepreneurs. We believe entrepreneurship is a calling and our mission is to empower entrepreneurs to chase their dreams. Every member of our team is taking part in the founding process. • We are using technology and data to level the playing field: We are leveraging the power of product innovation and machine learning to connect brands and boutiques from all over the world, building a growing community of more than 350,000 small business owners. • We build products our customers love: Everything we do is ultimately in the service of helping our customers grow their business because our goal is to grow the pie - not steal a piece from it. Running a small business is hard work, but using Faire makes it easy. • We are curious and resourceful: Inquisitive by default, we explore every possibility, test every assumption, and develop creative solutions to the challenges at hand. We lead with curiosity and data in our decision making, and reason from a first principles mentality. Faire was founded in 2017 by a team of early product and engineering leads from Square. We’re backed by some of the top investors in retail and tech including: Y Combinator, Lightspeed Venture Partners, Forerunner Ventures, Khosla Ventures, Sequoia Capital, Founders Fund, and DST Global. We have headquarters in San Francisco and Kitchener-Waterloo, and a global employee presence across offices in Toronto, London, and New York. To learn more about Faire and our customers, you can read more on our blog. Faire provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity or gender expression. Faire is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. Accommodations are available throughout the recruitment process and applicants with a disability may request to be accommodated throughout the recruitment process. We will work with all applicants to accommodate their individual accessibility needs. To request reasonable accommodation, please fill out our Accommodation Request Form ([Upgrade to PRO to see link] Privacy For information about the type of personal data Faire collects from applicants, as well as your choices regarding the data collected about you, please visit Faire’s Privacy Notice ([Upgrade to PRO to see link]