Customer Support Specialist

Relevance Ventures; Northern (KY); Hybrid; USD 55,000 - 75,000; Full time

Benefits offered by this job

Adventure travel stipend

Remote work culture

Flexible PTO

Health benefits

Stock options

401(k) matching

Job summary

Aiwyn is seeking a customer support specialist to help users resolve software issues and optimize their use of our accounting SaaS platform. You will work across tickets, live chat, and calls, guiding customers through troubleshooting and training while coordinating with engineering for complex problems.

Join a three-tier support structure, collaborate with implementations and success teams, and help improve documentation and best practices.

Qualifications

• 1-2 years in technical or customer support roles, or related training such as a bootcamp.
• Strong problem-solving skills and proactive troubleshooting.
• Clear written and verbal communication; able to explain technical concepts to non-technical users.
• Able to manage multiple tasks in a fast-paced environment.
• Experience with SQL and data in a support context.

Responsibilities

• Provide expert technical support via tickets, chat, and phone.
• Assist in setup, configuration, and optimization for customers.
• Collaborate with development and product teams to report and resolve bugs or feature requests.
• Train customers on best practices and product usage.
• Prioritize and manage support tickets for timely resolutions.
• Contribute to knowledge base and FAQs.

Skills

Technical support

SQL

Zendesk

JIRA

CRM familiarity

Tools

Zendesk

JIRA

Job description

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, 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

Preferred experience:

1. Familiarity with SaaS platforms and cloud‑based software solutions.
2. Experience with customer relationship management (CRM) systems including Zendesk and JIRA.
3. 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:

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
• YouTube page

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 CCAA privacy notice which can be found here: https://www.aiwyn.ai/ccpa