Technical Support Engineer (Weekend Lead)

At PayNearMe, we manage the product and customer experience through the lens of Support. We want a curious investigator who connects the dots across payments, systems, and business processes and owns the customer outcome. Support is primarily email, with limited phone handoffs and internal or client conference calls.

This support role combines financial, payment, product, and integration investigations with AI-assisted problem solving. It is not a software development role. Professionalism, empathy, and clear communication with clients and colleagues are essential. Cross-functional work offers opportunities to broaden your skills and grow internally.

Schedule and Coverage

A five-day schedule including Saturday and Sunday is required. Example: Friday through Monday plus one weekday, 8:00 AM to 5:00 PM PT.

Holiday schedules, alternate days off, and weekends off are coordinated with management.

Weekend coverage is an ongoing requirement; future schedule changes depend on business needs and available opportunities.

Participate in the paid on-call rotation, providing after-hours support for incidents and escalations.

Responsibilities

Investigate and resolve financial, payment, product, integration, and operational issues, including settlement, reconciliation, payment status, reporting, business rules, APIs/callbacks, bulk files, and portal behavior.

Use Datadog, Looker, transaction data, logs, and configuration to trace behavior, test hypotheses, and distinguish defects from configuration, integration, or process issues.

Apply approved AI tools such as Claude, Cursor, ChatGPT / Codex to investigate, including authorized code-level analysis. Validate findings and propose changes for Product and Engineering to evaluate.

Own cases in Zendesk through resolution or a clear handoff, prioritize customer and business impact, and escalate promptly through Jira or FireHydrant. Communicate professionally with IT and finance leaders, executives, payment agents, and individual consumers.

Lead weekend Support, owning queue priorities, escalations, and frontline handoffs. Provide real-time technical guidance and coaching to internal and outsourced teammates; improve documentation and runbooks.

Partner with Account Management, Professional Services, Product, Engineering, SysOps, Finance, Security, Compliance, Legal, and external partners to resolve issues.

Make authorized production configuration and operational changes through supported interfaces and established controls. Engineering owns production code changes.

Serve as lead customer liaison during daytime weekend incidents and escalations. Coordinate impact assessment, mitigation, calls, updates, and handoffs with on-call backup and management as severity warrants.

Turn recurring issues into product and process improvements. Help design and implement AI-assisted workflows and automation, and assess their impact on the customer experience.

Qualifications

Excellent written and verbal communication, empathy, discretion, and composure with clients and colleagues at all levels, including expectation setting and difficult conversations.

7+ years in technical product support, payments operations, implementation, or related customer-facing work, or equivalent education and experience.

Curiosity and independent judgment: follow evidence, test assumptions, persist through ambiguity, and know when to escalate.

Strong investigative skills across software, APIs, data interfaces, financial questions, and business processes using logs, transaction data, reports, and configuration.

Aptitude and willingness to learn and apply AI to investigations and business-process design.

Experience managing complex cases, coordinating client-facing incidents, and coaching teammates across technical and nontechnical teams, with sound judgment, clear documentation, and follow-through.

Preferred Qualifications

Payments or banking operations: settlement, reconciliation, payment files/NACHA, chargebacks, disputes, disbursements, or ACH.

Datadog, Looker, Zendesk, Atlassian, or comparable logging, reporting, and support tools.

SaaS services and partner integrations, APIs/webhooks, JSON/XML, SFTP, and batch processing.

Workflow, knowledge-base, or business-process improvement using data, automation, or AI.

Digital wallets, card processing, cash-at-retail/POS, payment processors, or gift card networks.

Online gaming, including sports betting, casino/poker, fantasy sports, and sweepstakes gaming.

Payments compliance concepts such as BSA, AML, OFAC, and UDAAP.

The annual base salary range for this role represents PayNearMe's good-faith estimate of the base salary it reasonably expects to offer for this position at the time of hire. Actual compensation may vary based on factors including the candidate's experience, qualifications, skills, and work location. PayNearMe may offer compensation outside of this range in certain circumstances. This position will remain posted until filled.

Annual Salary Range

$80,000—$120,000 USD