Product Support Specialist

Datarails; Northern (KY); Hybrid; USD 85,000 - 110,000; Full time

Benefits offered by this job

Equity

401(k) match

HSAs & FSAs

Medical, dental, and vision coverage

Parental leave

PTO & holidays

Life insurance

Job summary

Datarails is hiring a Product Support Specialist to join our Tier 1 Support team. This fully remote role in the Pacific Time Zone involves owning complex customer issues, collaborating with CS, Product, and R&D to deliver exceptional support and a streamlined customer experience.

Requirements include 2–4 years in SaaS product support, strong troubleshooting, and the ability to explain technical concepts to non-technical users.

Qualifications

• 2-4 years in Product Support/Help Desk/Technical Customer Success in a SaaS environment.
• Troubleshooting and solving advanced technical problems in a fast-paced environment.
• Ability to explain complex concepts to non-technical audiences.
• Experience using AI assistants to improve troubleshooting and documentation.

Responsibilities

• Act as the initial contact for customer questions via Zendesk chat, email, and web form.
• Troubleshoot issues with a strong first-response and follow-ups.
• Monitor tickets and route unresolved issues to higher levels.
• Engage customers to deliver high satisfaction, advocacy, and loyalty.
• Expand and refine the knowledge base to enable self-resolution.

Skills

Customer focus

Troubleshooting

AI workflows

Excel basics

Tools

Zendesk

Jira

CLI tooling

Job description

Come build the future of finance with Datarails. We're a global, AI-powered FinanceOS company helping finance teams transform the way they work. By combining intelligent automation, AI, and seamless integrations with the tools finance teams already know and trust, we empower organizations to make faster, smarter decisions with confidence. With approximately 350 employees worldwide, we're building the next generation of finance technology - where innovation, collaboration, and customer success go hand in hand.

We’re looking for an experienced Product Support Specialist with a great eye for detail and a passion for technology to join our Tier 1 Product Support team.

As our inbound Product Support Specialist, you will take ownership of complex technical customer issues and collaborate cross-functionally with the CS, Product, and R&D teams to provide best-in-class support and execute a well-designed customer experience.

If you are looking for a fantastic opportunity to join a growing startup with lots of room for growth and impact, we would love to meet you!

This position is 100% remote, based in the Pacific Time Zone in the US. No sponsorship or relocation assistance is available.

What You’ll Do

• Act as the initial point of contact for all Datarails-related questions from both our customers as well as internal stakeholders via Zendesk (chat, email, and web form)
• Troubleshoot incoming issues, providing a first response and subsequent follow-ups to customers.
• Monitor incoming tickets, process, respond, and direct unresolved issues to the next level of support personnel.
• Support and engage customers to deliver high customer satisfaction, advocacy, and loyalty.
• Expand and refine the company's knowledge base to empower users to independently resolve issues.

Requirements

• 2-4 years of experience in roles such as Product Support/Help Desk/Technical Customer Success in a SaaS environment, with a proven track record of driving customer satisfaction and resolving complex issues.
• Extensive experience with troubleshooting and solving advanced technical problems in a fast-paced, dynamic environment.
• A customer-first attitude and the ability to effectively explain complex concepts to non-technical audiences.
• Proactive mindset, with the ability to anticipate customer needs, identify potential issues, and suggest improvements to processes or the product.
• Hands-on experience using AI assistants (e.g., Claude or comparable LLM-based tools) to improve troubleshooting, documentation, workflow automation, and response efficiency.
• Proven ability to build and maintain AI-assisted workflows and CLI-based tooling, including reusable prompts, templates, custom skills, scripts, or integrations that automate repetitive tasks, scale support operations, and improve team productivity and response quality.
• Intermediate experience in Excel functions (formulas, Vlookup, and Pivot Table).
• Experience with Zendesk and Jira or other support/project software - a plus.
• Finance background - a plus.

What We Offer

• A collaborative, team-oriented environment, the ability to own your schedule, and the opportunity to grow at Datarails over many years
• Target salary is $85-110k USD annually, depending on skillset, years, relevance of experience, and location.
• Meaningful equity
• 401(k) plan with up to 4% match and HSA & FSA Options
• 100% paid medical, dental, and vision coverage for employees and 100% paid medical and 80% paid dental and vision coverage for dependents
• $540/year toward glasses, sunglasses, or contact lenses from XP Health for employees enrolled in any Guardian Vision plan
• Parental leave
• Flexible, unlimited sick time and PTO (we recommend 18-25 vacation days annually)
• 12 paid company holidays
• Life insurance

We want to make sure everyone has an equal chance to participate and make a difference. Datarails is an equal opportunity employer and prioritizes building a diverse and inclusive workplace. We provide equal employment opportunities to all employees and applicants of any type and do not discriminate based on race, color, religion, national origin, gender, age, sexual orientation, physical or mental disability, genetic information or characteristic, gender identity and expression, veteran status, or other non-job related characteristics or other prohibited grounds specified in applicable federal, state, and local laws. Datarails’ policy is to comply with all applicable laws related to nondiscrimination and equal opportunity and will not tolerate discrimination or harassment based on any of these characteristics. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.