Technical Support Engineer

This is a fully remote position, open to applicants in United States.

📋 Description

• Conduct thorough investigations and resolve financial, payment, product, integration, and operational challenges, including settlement, reconciliation, payment status, reporting, business rules, APIs/callbacks, bulk files, and portal behavior.

• Utilize Datadog, Looker, transaction data, logs, and configuration to trace behaviors, test hypotheses, and differentiate defects from configuration, integration, or process-related issues.

• Employ authorized AI tools such as Claude, Cursor, ChatGPT / Codex for investigations, including approved code-level analysis; validate findings and suggest modifications for Product and Engineering consideration.

• Manage cases in Zendesk until resolution or a clear handoff, prioritizing customer and business impact, and escalate issues promptly via Jira or FireHydrant.

• Communicate professionally with IT and finance leaders, executives, payment agents, and individual consumers.

• Lead weekend support, overseeing queue priorities, escalations, and frontline handoffs; offer real-time technical guidance and coaching to both internal and outsourced team members; enhance documentation and runbooks.

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

• Implement authorized production configuration and operational changes through supported interfaces and established controls; note that Engineering is responsible for production code changes.

• Act as the lead customer liaison during daytime weekend incidents and escalations; coordinate impact assessments, mitigation, updates, and handoffs with on-call backup and management.

• Transform recurring issues into product and process enhancements; assist in the design and implementation of AI-assisted workflows and automation, while evaluating their impact on customer experience.

• Work a five-day schedule that includes Saturdays and Sundays, with a paid on-call rotation for after-hours incidents and escalations.

⛳️ Requirements

• Exceptional written and verbal communication skills, along with empathy, discretion, and composure when interacting with clients and colleagues at all levels, including setting expectations and handling difficult conversations.

• Over 7 years of experience in technical product support, payments operations, implementation, or related customer-facing roles, or equivalent education and experience.

• Demonstrated curiosity and independent judgment: follow evidence, test assumptions, navigate ambiguity, and recognize when escalation is necessary.

• Strong investigative abilities across software, APIs, data interfaces, financial inquiries, and business processes using logs, transaction data, reports, and configurations.

• Willingness to learn and apply AI in investigations and business-process design.

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

• Preferred: Experience in payments or banking operations, including settlement, reconciliation, payment files/NACHA, chargebacks, disputes, disbursements, or ACH.

• Preferred: Familiarity with Datadog, Looker, Zendesk, Atlassian, or similar logging, reporting, and support tools.

• Preferred: Knowledge of SaaS services and partner integrations, APIs/webhooks, JSON/XML, SFTP, and batch processing.

• Preferred: Experience in workflow, knowledge-base, or business-process improvement utilizing data, automation, or AI.

• Preferred: Background in digital wallets, card processing, cash-at-retail/POS, payment processors, or gift card networks.

• Preferred: Experience in online gaming, including sports betting, casino/poker, fantasy sports, and sweepstakes gaming.

• Preferred: Understanding of payments compliance concepts such as BSA, AML, OFAC, and UDAAP.

🏝️ Benefits

• Competitive salary and benefits complemented by growth-company options grant.

• Fast-paced and professional work environment.

• Stock options with standard startup vesting - 1 year cliff; 4 years total.

• $50 monthly communication expense stipend to assist with your phone/internet bill.

• $250 stipend to enhance your work-from-home setup.

• Reimbursement for peripheral equipment: monitor (up to $400), keyboard and mouse (up to $200).

• Premium medical benefits including vision and dental (100% coverage for employees).

• Company-sponsored life and disability insurance.

• Paid parental bonding leave.

• Paid sick leave, jury duty, and bereavement leave.

• 401k plan.

• Flexible Time Off (our team members typically take off approximately 3-4 weeks per year).

• Volunteer Time Off.

• 13 scheduled holidays.