Senior Technical Support Engineer - Customer Support (all genders)

SCAYLE•New York, NY

About The Position

SCAYLE is hiring a Senior Technical Support Engineer for Customer Support. The role investigates technical issues reported by enterprise customers, using evidence from observability tools, code, and databases to identify root causes. The engineer manages support tickets through resolution, communicates proactively with customers, and partners with engineering teams on escalations. The position also includes rotational on-call coverage for high-severity incidents during evenings and weekends. The successful candidate will own a technical domain, develop investigation resources, identify recurring patterns that could lead to platform improvements, and help onboard and mentor team members. They will also evaluate and apply AI tools to support daily work and share effective approaches with the team.

Requirements

At least 5 years of hands-on technical support or systems engineering experience in a complex B2B SaaS or enterprise environment.
Proven experience supporting enterprise B2B customers, ideally with a SaaS or cloud-based product.
Experience improving support-team practices, including documentation, playbooks, processes, or quality standards.
Comfort reading server-side code in at least one language to trace logic and verify code paths.
Hands-on experience with observability and centralized logging tools; Datadog is preferred.
Ability to search logs, read distributed traces, and query metrics.
Solid SQL skills, including querying relational databases to verify system state, reproduce issues, and understand data models.
Working knowledge of distributed systems concepts, including synchronous and asynchronous communication, queues, retries, idempotency, and eventual consistency.
Comfort debugging HTTP and APIs using tools such as curl, and understanding response headers, status codes, basic DNS, REST, and webhook flows.
Familiarity with cloud-based, multi-tenant SaaS architectures; understanding tenant isolation and configuration delivery is an advantage.
Hands-on use of AI tooling beyond chat, such as building an agent, automating a workflow, using an API, or substantial personal experimentation.

Nice To Haves

Familiarity with central logging platforms such as Kibana, OpenSearch, Elasticsearch, or similar.
Experience reading PHP; the platform is largely PHP.
Experience with e-commerce or digital commerce platforms, such as storefront, checkout, payments, catalog, or order management.
Prior incident management or major-incident response experience.
Familiarity with PSP integrations, OMS, PIM, or search platforms.

Responsibilities

Investigate technical issues reported by enterprise customers, analyze symptoms, develop hypotheses, and determine root causes.
Use Datadog logs, traces, metrics, and dashboards to diagnose issues across distributed services.
Read code across multiple repositories to verify hypotheses and trace request flows.
Query databases to confirm system state and reproduce issues when needed.
Manage tickets from intake through resolution across the support-to-engineering escalation chain.
Provide enterprise customers with structured updates, clear next steps, and realistic expectations.
Partner with engineering teams on escalations by clearly framing issues, providing reproducible evidence, and advocating for customer impact.
Document findings, contribute to internal knowledge bases, and identify recurring patterns that can drive systemic improvements.
Participate in rotational on-call coverage for high-severity incidents, including evenings and weekends.
Own a technical domain within the platform and serve as the team's reference point for that area.
Develop and maintain investigation playbooks, runbooks, escalation paths, and knowledge base content.
Analyze recurring failure patterns and advocate for customer-impacting fixes by communicating systemic risk and business impact to product and platform teams.
Evaluate and apply AI tools and agents in daily work, and share effective approaches with the team.
Support onboarding of new team members and help improve the team's technical investigation and customer communication standards.