Lead Enterprise Tooling Engineer — Tenant Inc.
Overview
Tenant Inc. is modernizing its enterprise tooling, automation, and visibility ecosystem to better support our engineering, operations, finance, sales, and customer support teams. The Lead Enterprise Tooling Engineer plays a critical role in this transformation by owning the strategy, architecture, and execution of integrations across Jira, Microsoft 365, HubSpot, Zendesk, Intuit Enterprise, ERP systems, and internal platforms. This role ensures that our business systems work together seamlessly, data flows reliably across the organization, and leaders have a unified view of operational performance.
By connecting enterprise tools with application telemetry and APM insights, this position enables a single source of truth for workflow health, customer impact, and cross-system reliability. The ideal candidate blends technical expertise with business acumen, ensuring that tooling investments directly support Tenant’s operational goals and modernization roadmap.
Key Responsibilities
Enterprise Tooling Architecture & Integration
• Design and maintain the integrations that connect our core business systems, ensuring information flows consistently across Jira, Microsoft 365, HubSpot, Zendesk, Intuit Enterprise, ERP platforms, and internal applications.
• Build automated workflows and API-driven processes that reduce manual effort, eliminate redundant work, and improve data accuracy.
• Lead the unification of identity, permissions, and user lifecycle management across enterprise tools to support operational efficiency and compliance.
• Oversee cross-platform data synchronization for contacts, leases, tickets, financial data, and operational workflows to ensure a consistent and reliable customer and business experience.
APM, Observability & Unified Visibility
• Integrate observability and APM platforms (OpenSearch, Prometheus, Grafana, New Relic, Catchpoint, CloudWatch, clickstream analytics) with enterprise systems to provide end-to-end visibility across the business.
• Connect system telemetry with business workflows—linking application performance to Jira issues, Zendesk tickets, HubSpot activities, and ERP events.
• Develop executive-ready dashboards that consolidate operational KPIs, workflow performance, integration health, and customer impact into a single pane of glass.
• Implement alerting and automated correlation to help teams identify issues faster and understand their business implications.
• Partner with DevOps and SRE to ensure observability data is actionable and accessible across the organization.
Workflow Automation & Process Optimization
• Design automated workflows that streamline processes across engineering, support, sales, finance, and operations.
• Build Jira workflows, dashboards, and governance structures that support predictable releases and cross-team alignment.
• Automate HubSpot → Jira → Zendesk → ERP workflows to reduce handoffs, shorten cycle times, and improve customer responsiveness.
• Partner with Finance to automate Intuit Enterprise and ERP processes such as invoicing, reconciliation, and reporting.
API Engineering & Custom Development
• Develop and maintain custom integrations, middleware, and internal tools that improve operational efficiency and reduce manual work.
• Implement reliable error handling, monitoring, and logging to ensure integrations remain stable and transparent.
• Ensure all integrations meet security, scalability, and compliance requirements.
Data Quality, Governance & Observability
• Establish data governance standards that ensure accuracy, consistency, and auditability across enterprise tools.
• Implement monitoring and alerting for integration health and workflow performance.
• Partner with Security and Compliance to maintain SOC2, PCI, and internal governance standards.
Cross-Functional Leadership & Collaboration
• Serve as the strategic and technical leader for enterprise tooling, automation, and observability initiatives.
• Partner with Engineering, Product, Support, Sales, Finance, and Operations to understand business needs and translate them into scalable solutions.
• Mentor engineers and administrators across Jira, HubSpot, Zendesk, and Microsoft 365.
• Promote best practices for automation, documentation, and cross-system reliability.
Operational Excellence
• Lead root cause analysis for integration and workflow issues, ensuring long-term solutions rather than short-term fixes.
• Reduce manual effort across departments through automation and improved tooling.
• Maintain clear documentation for integrations, workflows, and system dependencies.
• Evaluate new tools, vendors, and opportunities to improve operational efficiency and business outcomes.
Required Qualifications
• 7+ years in enterprise tooling, business systems engineering, DevOps, or integration engineering.
• Deep experience with APIs for Jira, Microsoft 365, PowerBI, HubSpot, Zendesk, and similar SaaS platforms.
• Hands-on experience with observability and APM platforms (OpenSearch, Prometheus, Grafana, New Relic, Catchpoint, CloudWatch, clickstream analytics).
• Strong scripting and automation skills (Python, Node.js, PowerShell).
• Experience designing workflow automation across multiple business systems.
• Strong understanding of identity management, SSO, and permission models.
• Experience with data governance, monitoring, and integration reliability.
• Proven ability to lead cross-functional initiatives and collaborate with business stakeholders.
Preferred Qualifications
• Experience with Intuit Enterprise, ERP systems, or financial system integrations.
• Background in multi-tenant SaaS environments.
• Experience improving customer experience through event-driven architectures (webhooks, queues, EventBridge, SNS/SQS).
• Familiarity with ETL pipelines, data warehousing, and analytics platforms.
• Experience supporting engineering release workflows and IT DevOps processes.
Success Indicators at Tenant Inc.
• A unified, executive-ready view of operational performance that connects APM telemetry, enterprise workflows, and business outcomes.
• Automated, reliable workflows across Jira, HubSpot, Zendesk, Microsoft 365, and ERP systems.
• Significant reduction in manual work across engineering, support, sales, and finance.
• Clean, consistent, and governed data across enterprise tools.
• Reliable integrations with clear dashboards, alerting, and business impact visibility.
• Strong cross-team alignment and measurable improvements in operational efficiency.
• A scalable, well-documented tooling architecture that supports Tenant’s modernization strategy.
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