[Hiring] Technical Support Analyst @Aiwyn

Role Description

At Aiwyn, our Support team plays a key role in our success. As a Technical Support Analyst (Tier 2), you'll serve as the critical bridge between our front-line customer support team and senior engineering resources, handling escalated issues that require deeper investigation into financial data, account-level corrections, and third-party integration troubleshooting. You will work directly with CPA firms and internal teams to resolve complex product issues efficiently and prevent escalation to engineering wherever possible.

Investigations at the Tier 2 level require elevated access, structured troubleshooting, and strong judgment across multiple systems. This work often includes:

• Querying production data to investigate A/R discrepancies
• Invoice and payment behavior validation
• Validating customer-reported issues in the Aiwyn UI
• Reviewing session replay tools such as LogRocket
• Tracing sync behavior between Aiwyn and integrated practice management systems such as CCH

Analysts must determine whether an issue is caused by:

• Expected product behavior
• Customer configuration
• Stale or incorrect source data
• Integration timing
• A platform defect requiring engineering involvement

They must also translate technical findings into clear, actionable communication for both internal teams and customers—documenting investigations thoroughly, setting accurate expectations, and explaining complex issues in a way that is understandable to non-technical users.

Qualifications

• 2–4 years of experience in technical support, customer support operations, or a related technical role, ideally within a SaaS environment.
• Solid working knowledge of SQL for querying and investigating data issues.
• Experience investigating issues across integrated systems, including APIs, data syncs, and third-party platform connections.
• Strong analytical and problem-solving skills with the ability to distinguish user error, configuration issues, and platform-level bugs.
• Excellent written and verbal communication skills, with the ability to document findings clearly for both technical and non-technical audiences.
• Highly organized with the ability to manage and prioritize multiple open investigations simultaneously.
• Strong data integrity mindset with a commitment to accurate, well-documented ticket records.

Requirements

• Identify patterns in escalated tickets that may signal systemic bugs or process gaps and communicate findings clearly to the Tier 3 team and engineering.
• Collaborate with Customers and cross-functional teams including Customer Success, Implementation, and Engineering to coordinate timely resolution of complex customer issues.
• Contribute to the development and maintenance of internal support documentation, escalation guidelines, and knowledge base articles.
• Provide clear, empathetic communication to customers throughout the resolution process, setting accurate expectations and following up proactively.

Benefits

• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year.
• Remote, work-from-anywhere culture.
• Flexible PTO.
• World Class health benefits - including health, vision, dental, HSA/FSA, and mental health support.
• Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
• 401(k) matching.