Technical Support Specialist II; Accounting

Join Clubessential under Golf & club as a Technical Support Specialist II, Accounting to make a real impact every day. We say that because we know that every conversation we have, every interface we design, and every new feature we ship is another opportunity for us to elevate everyday life experiences for our customers and the people and communities they serve.

The Technical Support Specialist II provides specialized technical support for Clubessential accounting, CE Payments, membership billing, reporting, reconciliation, and related financial workflows. The role independently owns cases ranging from standard support requests to complex, financially impactful investigations that may span multiple systems or workflows. The specialist traces system activity, investigates discrepancies, manages client expectations, and determines when Technical Support Specialist Level 3, Development, IT, Payments, leadership, Customer Success, or another resource should become involved.

This role protects the client experience and strengthens Support effectiveness by combining accounting and payments knowledge with technical troubleshooting, case management, de-escalation, and sound escalation judgment.

• Own Accounting and CE Payments cases from initial investigation through resolution or appropriate escalation while maintaining timely and consistent client communication.
• Investigate issues across Accounts Payable, General Ledger, bank reconciliation, membership billing, Member AR, payment and charge batches, month-end workflows, online payments, Pay Cloud, card-present payments, settlements, refunds, disputes, reporting, inventory, and supported integrations.
• Trace transactions and system behavior across applicable workflows by reviewing configuration, mappings, transaction activity, batches, reporting, synchronization, and supporting examples.
• Investigate financial discrepancies by comparing expected versus actual system behavior and identifying whether configuration, workflow, data, integration, synchronization, or another technical factor contributed to the result.
• Identify patterns across transactions, members, batches, dates, accounts, or other records and assess potential financial, operational, or downstream impact.
• Manage complex or frustrated client situations by establishing a clear investigation plan, setting realistic expectations, maintaining ownership, and applying effective de-escalation techniques.
• Prioritize cases based on financial impact, client impact, urgency, case age, service expectations, and escalation risk.
• Determine when Level 3, Development, IT, Payments, leadership, Customer Success, or another internal resource should become involved and provide complete troubleshooting, examples, impact, and reproduction details.
• Guide clients through Clubessential’s accounting functionality and system behavior while leaving financial decisions and changes to the client’s books to their accounting team.
• Identify recurring issues, product concerns, and knowledge gaps and contribute findings, troubleshooting practices, and documentation that strengthen Accounting and Payments support.

• Fully Remote in the United States: You can work remotely in this position, provided you reside in the United States, have full working rights and do not require sponsorship.

We are looking for curious and empathetic people. We also love to hear from people who are motivated by meaningful work, resonate with our core values, have a positive outlook, are comfortable with ambiguity and thrive working in an ever-evolving and complex environment. We are inspired by meeting big-picture thinkers and doers, people who can be…