Technical Support Specialist II (Accounting)

Clubessential

3d•Remote

About The Position

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 Level 3 Support, Development, IT, Payments, leadership, Customer Success, or another resource should become involved. The position combines accounting and payments knowledge with technical troubleshooting, case management, de-escalation, and sound escalation judgment to protect the client experience and strengthen Support effectiveness. This is a fully remote position for candidates residing in the United States who have full working rights and do not require sponsorship. The role may require working the defined support schedule, including evening, weekend, or emergency coverage when assigned.

Requirements

Strong working knowledge of accounting and financial workflows, including payment processing, reconciliation, transaction reporting, billing, or financial reporting.
Experience independently troubleshooting complex software, SaaS, payments, accounting, or financial-system issues where the cause or resolution is not immediately known.
Demonstrated ability to manage complex or financially impactful cases while maintaining accurate documentation, timely communication, and strong case ownership.
Strong analytical and critical-thinking skills, including the ability to trace activity across interconnected workflows and identify patterns or discrepancies.
Demonstrated ability to communicate technical and financial-system concepts clearly and de-escalate frustrated client situations.
Ability to recognize client, financial, and operational risk and determine when additional technical or leadership involvement is required.
Ability to work the defined support schedule, including evening, weekend, or emergency coverage when assigned.
Must reside in the United States, have full working rights, and not require sponsorship.

Nice To Haves

Experience supporting payment processing, accounting software, financial technology, POS systems, or club management software.
Experience with merchant processing, payment devices, settlements, chargebacks, ACH, or third-party financial integrations.
Experience with Salesforce Service Cloud, Zendesk, or a similar case management platform.
Bachelor’s degree in Accounting, Finance, Business Administration, or a related field, or an equivalent combination of education and relevant professional experience.

Responsibilities

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, PayCloud, 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 Support, 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.