About The Role
The Technical Support Engineer resolves complex customer issues across APIs, cloud infrastructure, integrations, and authentication workflows. The role combines hands-on troubleshooting with clear customer communication, using logs, requests, configuration data, and reproducible test cases to identify root causes.
You will support customers at scale through a ticketing platform, collaborate with software engineering and product teams on defects and improvements, and help strengthen the documentation and tooling that make technical issues easier to solve. The role is remote and based in Chicago, IL.
Key Responsibilities
- Troubleshoot customer issues involving REST APIs, webhooks, SDKs, OAuth, SSO, DNS, and cloud-based integrations
- Analyze application logs, HTTP requests, stack traces, and database or monitoring data to isolate root causes
- Reproduce technical issues in test environments and provide engineering teams with clear steps, impact assessments, and diagnostic evidence
- Manage escalated cases in Zendesk, Salesforce Service Cloud, or similar platforms while meeting response and resolution targets
- Write and maintain troubleshooting guides, API documentation, runbooks, and internal knowledge-base articles
- Monitor recurring incidents and customer feedback, then recommend product, documentation, and support-process improvements
- Partner with engineering, product, and solutions teams during incident response, releases, and complex customer implementations
What We Are Looking For
- 3-6 years of experience in technical support, site reliability, systems administration, implementation, or a related customer-facing engineering role
- Strong understanding of HTTP, REST APIs, JSON, webhooks, authentication, and common networking concepts such as DNS, TLS, and TCP/IP
- Hands-on experience using SQL, command-line tools, and scripting with Python, JavaScript, or Bash to investigate and automate technical support work
- Comfortable working with cloud platforms, observability tools, and logs, including environments such as AWS, Datadog, Splunk, or comparable systems
- Clear and precise written and verbal communication, with the ability to explain technical issues to both engineers and non-technical customers
- Bachelor’s degree in computer science, information systems, engineering, or a related field, or equivalent practical experience
- Bonus: Experience with Kubernetes, CI/CD, SAML, GraphQL, enterprise integrations, incident management, or developer-facing SaaS products
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