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.