Software Technical Support Specialist 1

Drips•Cleveland, OH

10h•Remote

About The Position

Software Technical Support Specialist 1 Role Overview The Software Technical Support Specialist 1 is responsible for monitoring, triaging, and resolving production issues across Drips’ core systems, with a focus on Azure Logic Apps, FTP-based integrations, and billing/data workflows. This role serves as the first line of defense for production-impacting incidents, ensuring data accuracy, prompt incident response, and clear communication with internal stakeholders. You will partner closely with Engineering, QA, and Production teams to investigate system alerts, diagnose integration or configuration problems, and document both the issue and the resolution path for future reuse. This role closely works with the Drips implementation team, helping implement client programs accurately, swiftly and at volume. This role sits at the intersection point for all Drips operations. This is an ideal role for someone who enjoys technical troubleshooting, structured processes, and continuous improvement. This is a remote role within Drips’ Production department. While the schedule is generally flexible, candidates who are able to work a second-shift (afternoon/evening) schedule are strongly preferred to provide coverage for later-day production monitoring and incident response. Key Responsibilities Monitor and Support Systems Proactively monitor system health, alerts, and integrations in Azure (Logic Apps, related services) and other monitoring tools. Identify anomalies or failures in near real time and ensure appropriate escalation to internal teams when needed. Help refine monitoring thresholds, alerting rules, and dashboards as the environment evolves. Troubleshoot Technical Issues Diagnose and resolve software, configuration, and integration issues across Azure Logic Apps, FTP/SFTP connections, APIs, and related workflows. Perform structured root-cause analysis on incidents, including reviewing logs, API responses, and configuration history. Recommend and implement repeatable fixes and guardrails to prevent recurrence. Integration & Workflow Management Oversee Logic App and FTP integrations, ensuring reliable and accurate data flow between Drips and third-party systems. Validate data mapping, file formats, and connection settings align with expected configurations. Support billing and data integration workflows, helping to identify where data is missing, malformed, or misrouted. Act as a key stakeholder in the client implementation process, working collaborative with integration specialists, helping solution and implement new client integrations Incident Response Serve as the first point of contact for billing processor failures and other production-impacting incidents. Quickly assess severity and customer impact; initiate appropriate escalation paths and communication. Track incidents from detection through resolution, ensuring proper closure and documentation. Cross-Functional Collaboration Work closely with Engineering, QA, Production, and Client-facing teams to identify, document, and resolve system defects or recurring failure patterns. Translate complex technical issues into clear, concise language for both technical and non-technical stakeholders. Participate in process-improvement and automation initiatives related to monitoring, alerting, and support workflows. Documentation & Knowledge Management Create and update tickets in Azure DevOps (or equivalent tools), ensuring each issue is fully documented from initial report through resolution. Maintain internal knowledge base articles for recurring issues, standard operating procedures, and runbooks. Contribute to training and troubleshooting materials for internal stakeholders. Data Accuracy & Reporting Update system data from third-party sources where needed, ensuring integrity, compliance, and consistency across systems. Identify trends in recurring technical issues and provide structured reporting and insight to leadership. Support the development of monitoring and incident dashboards for visibility into failures, response times, and remediation outcomes.

Requirements

Professional experience: Typically 2–5 years in a technical support, production support, systems operations, or similar role in a software/SaaS environment.
Cloud & Integration Technologies Proficiency with Microsoft Azure, especially Logic Apps and related DevOps/monitoring tooling is required.
Working understanding of FTP/SFTP integrations, APIs, and network connectivity troubleshooting (timeouts, DNS, authentication, credential issues, etc.).
Data & Analysis Familiarity with SQL and Excel for investigating data issues, validating assumptions, and supporting ad-hoc analysis.
Comfort reading and interpreting error logs, API responses, and system health metrics.
Problem-Solving & Execution Strong analytical and problem-solving skills with high attention to detail and data accuracy.
Ability to manage multiple incidents and workstreams simultaneously in a high-volume, time-sensitive environment.
Communication & Collaboration Effective written and verbal communication skills, including the ability to distill complex technical issues into clear documentation for broader audiences.
Demonstrated success working cross-functionally with Engineering, QA, and Operations/Production teams.
Mindset & Work Style Process-driven, with a focus on root cause analysis, repeatable procedures, and identifying opportunities for automation and improvement.
Organized, reliable, and comfortable working with structured ticket queues, SLAs, and documented workflows.

Nice To Haves

Education: Bachelor’s degree in Computer Science, Information Systems, Engineering, or a related technical field preferred but not required.
Experience working with: Production support for billing, payment processors, or other financial/transactional systems.
High-volume, integration-heavy environments where data moves between multiple internal and external systems.
Incident management, ITSM, or DevOps tools (e.g., Azure DevOps, Jira, ClickUp) for structured tracking and collaboration.
Exposure to or interest in: Building or refining monitoring and alerting strategies for cloud-based applications.
Automation of routine operational tasks and incident workflows.

Responsibilities

Monitor and Support Systems Proactively monitor system health, alerts, and integrations in Azure (Logic Apps, related services) and other monitoring tools.
Identify anomalies or failures in near real time and ensure appropriate escalation to internal teams when needed.
Help refine monitoring thresholds, alerting rules, and dashboards as the environment evolves.
Troubleshoot Technical Issues Diagnose and resolve software, configuration, and integration issues across Azure Logic Apps, FTP/SFTP connections, APIs, and related workflows.
Perform structured root-cause analysis on incidents, including reviewing logs, API responses, and configuration history.
Recommend and implement repeatable fixes and guardrails to prevent recurrence.
Integration & Workflow Management Oversee Logic App and FTP integrations, ensuring reliable and accurate data flow between Drips and third-party systems.
Validate data mapping, file formats, and connection settings align with expected configurations.
Support billing and data integration workflows, helping to identify where data is missing, malformed, or misrouted.
Act as a key stakeholder in the client implementation process, working collaborative with integration specialists, helping solution and implement new client integrations Incident Response Serve as the first point of contact for billing processor failures and other production-impacting incidents.
Quickly assess severity and customer impact; initiate appropriate escalation paths and communication.
Track incidents from detection through resolution, ensuring proper closure and documentation.
Cross-Functional Collaboration Work closely with Engineering, QA, Production, and Client-facing teams to identify, document, and resolve system defects or recurring failure patterns.
Translate complex technical issues into clear, concise language for both technical and non-technical stakeholders.
Participate in process-improvement and automation initiatives related to monitoring, alerting, and support workflows.
Documentation & Knowledge Management Create and update tickets in Azure DevOps (or equivalent tools), ensuring each issue is fully documented from initial report through resolution.
Maintain internal knowledge base articles for recurring issues, standard operating procedures, and runbooks.
Contribute to training and troubleshooting materials for internal stakeholders.
Data Accuracy & Reporting Update system data from third-party sources where needed, ensuring integrity, compliance, and consistency across systems.
Identify trends in recurring technical issues and provide structured reporting and insight to leadership.
Support the development of monitoring and incident dashboards for visibility into failures, response times, and remediation outcomes.