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AI
Customer Support Specialist
AiwynRemote (US based)Remotefull_timeVerifiedPosted 5 Feb 2026
About the role
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
This role:
As part of our Customer Support team, you’ll provide front-line product support to users, troubleshoot software issues, and ensure customer satisfaction by resolving technical problems efficiently. You’ll develop a deep understanding of the company's software products to guide users, offer product training, and escalate complex issues to the engineering team when necessary. Working within our three-tiered support structure, you’ll work closely with other support teammates, customer implementations and success, and software developers in order to drive positive outcomes for our customers.
How We Investigate Issues:
Investigations often require deep technical analysis across multiple systems, including database queries, user session replays, and network-level logs. The role involves tracing data from source systems through integrations into Aiwyn’s platform, analyzing transaction flows, and diagnosing issues related to DNS, mail servers, and third-party integrations such as practice management systems, SafeSend, and Outlook.
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
This role:
As part of our Customer Support team, you’ll provide front-line product support to users, troubleshoot software issues, and ensure customer satisfaction by resolving technical problems efficiently. You’ll develop a deep understanding of the company's software products to guide users, offer product training, and escalate complex issues to the engineering team when necessary. Working within our three-tiered support structure, you’ll work closely with other support teammates, customer implementations and success, and software developers in order to drive positive outcomes for our customers.
How We Investigate Issues:
Investigations often require deep technical analysis across multiple systems, including database queries, user session replays, and network-level logs. The role involves tracing data from source systems through integrations into Aiwyn’s platform, analyzing transaction flows, and diagnosing issues related to DNS, mail servers, and third-party integrations such as practice management systems, SafeSend, and Outlook.
Key Responsibilities:
- Provide expert technical support to customers via support ticket, live chat, and phone, troubleshooting software issues and ensuring a seamless user experience.
- Assist in the setup, configuration, and optimization of our software for new and existing customers.
- Collaborate closely with our development and product teams to identify, report, and resolve software bugs or feature requests.
- Offer training and guidance to customers on best practices for using our software, via email, chat and virtual meetings.
- Manage and prioritize support tickets, ensuring timely and accurate resolutions.
- Contribute to the development of support documentation, FAQs, and knowledge base articles.
Qualifications:
- 1-2 years of experience in a technical support, customer support, or technical-adjacent role or completion of a technical bootcamp or equivalent training
- Excellent problem-solving skills with a proactive approach to troubleshooting.
- Strong communication skills, both written and verbal, with the ability to explain complex technical concepts to non-technical users.
- Ability to adapt quickly and manage multiple tasks in a fast-paced, evolving environment.
- Experience with structured query language (SQL)
- Strong process-oriented mindset with a focus on continuous improvement and operational efficiency
- Appreciation for data integrity, with a commitment to maintaining clean, accurate, and well-documented records by following established processes
- Familiarity with SaaS platforms and cloud-based software solutions.
- Experience with customer relationship management (CRM) systems including Zendesk and JIRA.
- Strong understanding of accounting principles and experience with accounting or accounts receivable software.
Preferred experience:
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.
- 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.
- Remote, work-from-anywhere culture
- Flexible PTO
- 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.
- Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
- 401(k) matching
Other benefits include:
Our Values:
- Relentless by Design
- Owners not Renters
- Trust at the Core
Learn more about Aiwyn:
Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry,Apply for this role
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