Technical Support Engineer (Weekend Lead)

Accountabilities:

• • Investigate and resolve complex financial, payment, product, integration, and operational issues, including settlement, reconciliation, payment status, reporting, business rules, APIs, callbacks, bulk files, and portal behavior.
  • Analyze system behavior using monitoring and reporting platforms, transaction data, logs, configuration, and other technical evidence to test hypotheses and distinguish defects from configuration, integration, or process issues.
  • Use approved AI tools, including conversational AI and AI-assisted development platforms, to support investigations and authorized code-level analysis; validate findings and prepare recommendations for Product and Engineering teams.
  • Own support cases through resolution or a well-documented handoff, prioritize issues according to customer and business impact, and escalate appropriately through established incident and ticketing processes.
  • Lead weekend Support operations by managing queue priorities, escalations, frontline handoffs, and real-time technical guidance for internal and outsourced teammates.
  • Serve as the lead customer liaison during daytime weekend incidents and escalations, coordinating impact assessment, mitigation, customer communications, incident calls, updates, and handoffs with on-call teams and management.
  • Coach teammates, strengthen documentation and runbooks, and help improve knowledge-sharing across technical and nontechnical support teams.
  • Collaborate with Account Management, Professional Services, Product, Engineering, SysOps, Finance, Security, Compliance, Legal, and external partners to resolve customer and operational issues.
  • Make authorized production configuration and operational changes through approved interfaces and established controls, while ensuring software code changes remain with Engineering.
  • Identify recurring issues and translate them into product, process, automation, and customer-experience improvements.
  • Help design and implement AI-assisted workflows and automation while assessing their effectiveness and impact on customers and support operations.
  • Participate in a paid on-call rotation to provide after-hours support for incidents and escalations.

  Requirements:

  • 7+ years of experience in technical product support, payments operations, implementation, or a related customer-facing technical environment, or an equivalent combination of education and experience.
  • Strong written and verbal communication skills, with the empathy, discretion, professionalism, and composure required to manage customers, colleagues, executives, and other stakeholders.
  • Demonstrated ability to investigate complex issues across software systems, APIs, data interfaces, financial questions, and business processes using logs, transaction data, reports, and configuration.
  • Strong analytical curiosity and independent judgment, including the ability to follow evidence, challenge assumptions, test hypotheses, work through ambiguity, and recognize when escalation is necessary.
  • Experience managing complex support cases, coordinating customer-facing incidents, and coaching teammates across technical and nontechnical environments.
  • Ability and willingness to learn and apply AI tools to technical investigations, workflow improvement, and business-process design.
  • Experience with payments or banking operations, such as settlement, reconciliation, payment files/NACHA, chargebacks, disputes, disbursements, or ACH, is preferred.
  • Familiarity with tools such as Datadog, Looker, Zendesk, Atlassian products, or comparable monitoring, reporting, incident-management, and support platforms is preferred.
  • Experience with SaaS products and partner integrations, APIs and webhooks, JSON/XML, SFTP, and batch processing is a plus.
  • Knowledge of workflow, knowledge-base, or business-process improvement using data, automation, or AI is advantageous.
  • Familiarity with digital wallets, card processing, cash-at-retail/POS, payment processors, gift card networks, or related payment technologies is beneficial.
  • Experience in online gaming environments, including sports betting, casino/poker, fantasy sports, or sweepstakes gaming, is a plus.
  • Familiarity with payments compliance concepts such as BSA, AML, OFAC, and UDAAP is advantageous.
  • Availability for a five-day schedule that includes Saturday and Sunday, with an example schedule of Friday through Monday plus one weekday, generally from 8:00 AM to 5:00 PM PT.
  • Ability to participate in ongoing weekend coverage and a paid after-hours on-call rotation.

  Benefits:

  • Annual base salary range of $80,000–$120,000 USD, with actual compensation dependent on factors such as experience, qualifications, skills, and work location.
  • Competitive benefits package and growth-company stock options.
  • Stock options with standard startup vesting: one-year cliff and four-year total vesting period.
  • $50 monthly communication stipend toward phone and internet expenses.
  • $250 work-from-home setup stipend.
  • Reimbursement for peripheral equipment, including monitors up to $400 and keyboards/mice up to $200.
  • Premium medical benefits, including vision and dental, with 100% employee coverage.
  • Company-sponsored life and disability insurance.
  • Paid parental bonding leave.
  • Paid sick leave, jury duty, and bereavement leave.
  • 401(k) plan.
  • Flexible Time Off, with team members typically taking approximately 3–4 weeks per year.
  • Volunteer Time Off.
  • 13 scheduled holidays.
  • Remote work environment with opportunities for cross-functional collaboration and internal growth.