Technical Support Analyst at Aiwyn

Who is Aiwyn and what do we do? Aiwyn is the first complete platform for modern accounting firms. Backed by top-tier investors like Bessemer, KKR, and Revolution, we’re one of the fastest-growing scale-up SaaS companies in the world. We build category-defining technology—and we’re doing it with world-class people, processes, and products. To learn more, visit our website [Upgrade to PRO to see link] Technical Support Analyst 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. How We Investigate Issues 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, validating customer-reported issues in the Aiwyn UI, reviewing session replay tools such as LogRocket, and 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, or a platform defect requiring engineering involvement. Just as importantly, they must 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. Key Responsibilities: - Triage and resolve escalated support tickets from Tier 1, owning issues that require elevated access, deeper investigation, or account-level corrections — including email delivery failures, resolving data discrepancies, translation errors, ETL flow corrections, various bugs across all Aiwyn products, and data export/import issues. - Apply a structured pre-escalation checklist mindset: validate that issues have persisted past expected sync windows, verify behavior directly in the Aiwyn UI and database, rule out common expected behaviors, and confirm all relevant data is captured before escalating to Tier 3. - Investigate and resolve data integrity issues across Aiwyn and integrated third-party systems, such as incorrect client records, mismatched financial balances, and failed PM system syncs. - Serve as the escalation point for Tier 1, providing guidance on triage, documentation, and when to escalate versus resolve. - 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. 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. Bonus Skills: - Familiarity with tools such as LogRocket, Logs Explorer, or similar session replay and monitoring platforms. - Experience with Zendesk, JIRA, or other support and issue-tracking platforms. - Understanding of accounting principles, accounts receivable workflows, or experience with accounting software. - Exposure to ETL pipelines, data sync processes, or integration monitoring. - Experience working within or supporting CPA firms or professional services organizations. We encourage you to apply even if you don't meet every qualification. We recognize that talent comes from many paths. If you're enthusiastic about this role and feel your skills and experience would enable you to succeed, we encourage you to submit an application. Benefits and Perks: - The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience. Other benefits include: 1. Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls. 2. Remote, work-from-anywhere culture 3. Flexible PTO 4. World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support. 5. Stock options - every Full Time Employee has ownership in Aiwyn's future and success. 6. 401(k) matching Our Values: - Relentless by Design - Owners not Renters - Trust at the Core Learn more about Aiwyn: - About us [Upgrade to PRO to see link] - YouTube page [Upgrade to PRO to see link] Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances. Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: [Upgrade to PRO to see link]