Senior Technical Support Engineer - Customer Support (all genders)

SCAYLE•New York, NY

About The Position

SCAYLE is a rapidly growing enterprise commerce platform that empowers brands and retailers to achieve their D2C goals. We foster innovation, international collaboration, and a data-driven approach. We encourage stepping out of comfort zones and making bold decisions for professional and personal growth. We view challenges as opportunities for better solutions, working in an environment that values flexibility, creativity, and continuous development. Our shared motivation is to make a significant impact and shape the future of eCommerce.

Requirements

5+ Years of hands-on technical support or systems engineering in a complex B2B SaaS or enterprise environment.
Proven experience supporting enterprise (B2B) customers, ideally in a SaaS or cloud-based product environment.
Experience improving support team operations, including documentation, playbooks, processes, and quality standards.
Experience supporting or mentoring less experienced colleagues.
Comfortable reading server-side code in at least one language to trace logic and verify code paths.
Hands-on experience with observability and central logging tooling (Datadog preferred; familiarity with central logging platforms like Kibana, OpenSearch, or Elasticsearch is a strong plus).
Comfortable searching logs, reading distributed traces, and querying metrics.
Solid SQL skills for querying relational databases, verifying system state, reproducing issues, and understanding data models.
Working knowledge of distributed systems concepts (async vs. synchronous communication, queues, retries, idempotency, eventual consistency).
Comfort with HTTP and API debugging (curl, response headers, status codes, basic DNS, REST and webhook flows).
Familiarity with cloud-based, multi-tenant SaaS architectures, including understanding tenant isolation and configuration delivery (a strong advantage).
Hands-on experience with AI tooling, beyond basic chat interactions, such as building agents, automating workflows, writing against APIs, or serious experimentation.

Nice To Haves

Experience reading PHP.
Experience in e-commerce or digital commerce platforms (storefront, checkout, payments, catalog, 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, analyzing symptoms, forming hypotheses, and identifying root causes.
Utilize observability tooling (Datadog logs, traces, metrics, 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.
Manage tickets throughout their lifecycle, from intake to resolution, across the support to engineering escalation chain.
Communicate proactively and professionally with enterprise customers, providing structured updates, clear next steps, and managing expectations.
Partner with engineering teams during escalations by clearly framing issues, providing reproducible evidence, and advocating for customer impact.
Document findings, contribute to internal knowledge bases, and identify recurring patterns to drive systemic improvements.
Participate in rotational on-call coverage for high-severity incidents, including evenings and weekends.
Take ownership of a technical domain within the platform and serve as a team reference point.
Develop and maintain investigation playbooks, runbooks, escalation paths, and knowledge base content.
Analyze recurring failure patterns to drive platform improvements and advocate for customer-impacting fixes by communicating systemic risk and business impact.
Apply AI tooling to daily work, evaluating tools and agents, identifying leverage points, and sharing effective methods.
Support the onboarding of new team members and help elevate the standards for technical investigation and customer communication.