Senior Enterprise Support Engineer — AI-Driven, On-Call

JobCubby; New York, Northern (NY, KY); Hybrid; USD 130,000 - 190,000; Full time

Job summary

SCAYLE is a fast-growing enterprise commerce platform enabling brands and retailers to realize their D2C ambitions. We seek a hands-on enterprise support engineer to investigate complex issues, analyze symptoms, and verify root causes across distributed services.

You will use observability tools (Datadog, logs, traces, dashboards), read code, query databases, and manage tickets end-to-end while collaborating with engineering. On-call rotations and domain ownership are part of the role.

Qualifications

• 5+ years in hands-on technical support or systems engineering in a B2B SaaS/enterprise environment.
• Experience supporting enterprise customers in a SaaS or cloud-based product environment.
• Ability to read server-side code in at least one language.
• Experience with observability and central logging tooling (Datadog preferred).
• Strong SQL skills to verify state and data models.

Responsibilities

• Investigate technical issues reported by enterprise customers and root-cause.
• Use Datadog to diagnose issues across distributed services.
• Read code across repositories to verify hypotheses.
• Query databases to confirm state and reproduce issues.
• Manage tickets end-to-end from intake to escalation.
• Communicate updates professionally with customers.
• Collaborate with engineering for escalations and evidence.
• Document findings and contribute to knowledge bases.
• Participate in on-call rotations for high-severity incidents.
• Own a technical domain and develop playbooks and runbooks.

Skills

5+ years hands-on technical support or

Enterprise SaaS support

Documentation / playbooks

Mentoring colleagues

Reading server-side code

Observability tooling (Datadog)

Logging platforms (Kibana/OpenSearch/

SQL

Distributed systems concepts

HTTP/API debugging

Cloud-based multi-tenant SaaS

AI tooling usage

Tools

Datadog

Kibana

OpenSearch

Elasticsearch

cURL

Job description

SCAYLE is a fast-growing enterprise commerce platform enabling brands and retailers to realize their D2C ambitions. We seek a hands-on enterprise support engineer to investigate complex issues, analyze symptoms, and verify root causes across distributed services.

You will use observability tools (Datadog, logs, traces, dashboards), read code, query databases, and manage tickets end-to-end while collaborating with engineering. On-call rotations and domain ownership are part of the role.