Customer Support Specialist

Aiwyn is a fast-growing SaaS platform for modern accounting firms, backed by investors including Bessemer, KKR, and Revolution. The Customer Support Specialist provides front-line technical product support, troubleshooting issues and guiding users to ensure successful outcomes. The role partners with support, implementations/success, and engineering teams to resolve bugs, improve the product experience, and maintain customer satisfaction.

• Provide expert technical support via support tickets, live chat, and phone by troubleshooting software issues and ensuring a seamless user experience.
• Investigate complex issues using database queries, user session replays, and network-level logs; trace data through integrations and transaction flows.
• Diagnose and resolve issues related to DNS, mail servers, and third-party integrations (e.g., practice management systems, SafeSend, Outlook).
• Assist with setup, configuration, and optimization of the software for new and existing customers.
• Collaborate with development and product teams to identify, report, and resolve bugs and communicate feature requests.
• Deliver customer training and guidance on best practices via email, chat, and virtual meetings.
• Manage and prioritize support tickets to deliver timely, accurate resolutions.
• Contribute to support documentation, FAQs, and knowledge base articles.

• 1–2 years of experience in technical support, customer support, or a technical-adjacent role, or completion of a technical bootcamp or equivalent training.
• Strong troubleshooting and problem-solving skills with a proactive approach.
• Excellent written and verbal communication; ability to explain technical concepts to non-technical users.
• Ability to adapt quickly and manage multiple tasks in a fast-paced environment.
• Experience with SQL.
• Process-oriented mindset focused on continuous improvement and operational efficiency.
• Commitment to data integrity and maintaining clean, accurate, well-documented records by following established processes.

Preferred:

• Familiarity with SaaS and cloud-based software solutions.
• Experience with CRM/ticketing tools such as Zendesk and JIRA.
• Understanding of accounting principles and experience with accounting or accounts receivable software.

• Remote, work-from-anywhere culture.
• Flexible PTO.
• Health benefits including health, vision, dental, HSA/FSA, and mental health support.
• Stock options for full-time employees.
• 401(k) matching.
• Annual adventure travel stipend: $1,000 travel reimbursement on each work anniversary.