Systems Operations Specialist

The Company At Nylas, we specialize in making it easier for developers to add email, calendar, and contact management features into their applications. We provide APIs, which streamline the integration of these functionalities, ensuring they are secure and effective. This enables better, safer, and more reliable communication within apps. Supporting over 100,000 developers and collaborating with more than 900 companies globally, Nylas plays a pivotal role in how digital communication tools are built and utilized. Our technology spans various sectors, from healthcare to education, simplifying the complex process of app development related to communications. By reducing the barriers in communication technology, we empower developers to innovate and enhance user interaction across platforms. ABOUT THE TEAM At Nylas, Central Operations is the operational backbone of our go-to-market organization. We build and support the systems, workflows, and processes that enable our Sales, Customer Success, Marketing, Finance, and Product teams to work efficiently and scale effectively. As Nylas grows, so does the complexity of the systems that power our business. Our team partners across the company to improve operational workflows, maintain trusted data, automate repetitive work, and ensure our teams have the tools they need to focus on delivering great customer experiences. ABOUT THE ROLE We're looking for a Business Systems Operations Specialist to help support and improve the operational systems behind our go-to-market organization. Reporting to the Program Manager, Business Operations, you'll work across Sales, Customer Success, Marketing, Finance, and Product to maintain business systems, troubleshoot operational issues, improve workflows, and support day-to-day operations. This role is ideal for someone who enjoys solving problems, learning new systems, improving processes, and working across multiple teams. You'll have the opportunity to leverage automation and emerging AI tools to help reduce manual work, improve operational efficiency, and scale internal processes as the company grows. WHAT YOU'LL DO - Support and maintain our go-to-market systems, including HubSpot, Vitally, and other operational platforms.

• Build, maintain, and troubleshoot workflows, automations, lifecycle stages, routing rules, and operational processes.
• Investigate and resolve system issues, workflow failures, data inconsistencies, and operational requests from internal teams.
• Partner with Sales, Customer Success, Marketing, Finance, and Product to improve business processes and operational efficiency.
• Create and maintain dashboards and reporting that provide visibility into pipeline, customer health, renewals, forecasting, and other key business metrics.
• Support integrations and data flow between CRM, billing, product, analytics, and customer support systems.
• Perform data cleanup, improve CRM hygiene, and help maintain data accuracy across business systems.
• Document processes, troubleshooting guides, and operational playbooks to improve scalability and enable self-service.
• Identify opportunities to automate repetitive work using workflows, AI tools, and other operational technologies.
• Assist with cross-functional operational projects that improve how teams work together and scale.

• Internal teams receive timely, effective support for operational questions and system issues.
• Data across our go-to-market systems is accurate, consistent, and trusted.
• Manual processes are reduced through thoughtful automation and workflow improvements.
• Reporting provides leaders with reliable visibility into business performance.
• Documentation enables teams to solve common operational issues independently.
• Operational processes continue to scale as Nylas grows.

• Experience working with CRM platforms such as HubSpot, Salesforce, or similar systems.
• Experience creating or supporting workflows, automations, reporting, and operational processes.
• Strong analytical and problem-solving skills with the ability to troubleshoot issues across multiple systems.
• An understanding of data quality and how information flows between business applications.
• Strong organizational skills with the ability to manage multiple priorities in a fast-moving environment.
• Excellent communication skills and the ability to work effectively with both technical and non-technical stakeholders.
• A continuous improvement mindset with curiosity for learning new tools and technologies.

• Experience with workflow automation tools such as Zapier, Make, n8n, Workato, or similar platforms.
• Familiarity with APIs, integrations, or low-code automation.
• Experience using AI tools such as ChatGPT, Claude, GitHub Copilot, or MCP-enabled tools to improve workflows or productivity.
• Experience with reporting tools such as Looker, Sigma, Tableau, or Power BI.
• Basic SQL knowledge.
• Experience supporting SaaS go-to-market organizations.

• Show concrete HubSpot & Salesforce automations: Build a short case study (1–2 pages) of a workflow you created that synced leads between HubSpot and Salesforce using Zapier, Workato, or custom API calls. Include screenshots of the flow, key metrics (e.g., time saved, error‑rate reduction), and a brief code snippet or request log to demonstrate technical depth.
• Demonstrate data‑driven ops with Excel: Prepare a mini‑dashboard (Excel or Google Sheets) that tracks a typical systems‑operations KPI—such as API latency, error rates, or ticket resolution time. Use pivot tables, conditional formatting, and a chart. Attach the file to your application or embed a screenshot in your résumé’s “Key Projects” section to prove you can turn raw logs into actionable insights.
• Highlight API‑centric troubleshooting: In your cover letter, reference Nylas’s email/calendar APIs and describe a real‑world incident where you diagnosed and fixed an integration issue (e.g., OAuth token refresh failure, webhook misfire). Emphasize the steps you took, tools used (Postman, cURL, logging platforms), and the outcome (downtime ↓ X %, SLA met).
• Prepare for remote‑team fit questions: Nylas values asynchronous collaboration. Have specific examples ready of how you used Slack, Notion, or Jira to coordinate ops tasks across time zones—e.g., writing clear runbooks, tagging stakeholders, or running “on‑call” handoffs. Mention any experience with “follow‑the‑sun” support models.
• Negotiate with data on Toronto remote rates: Research current market salaries for Systems Operations Specialists in the Toronto remote market (e.g., $90‑$115 k CAD base). Bring a one‑page salary justification that cites your automation ROI numbers, certifications, and years of SaaS ops experience. Be ready to discuss a flexible package—stock options, remote‑work stipend, or professional‑development budget—to align with Nylas’s growth‑stage incentives.