Customer Support Specialist Job Washington District of Columbia USA,IT/Tech

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 elevate 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, Safe Send, 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

Preferred experience:

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.

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:

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…