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Customer Support Specialist

Direct Supply · Milwaukee, WI · Full time

Posted Aug 26, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you solved a technical problem for someone who was not comfortable with technology.

What they are checking: Patience and the ability to explain systems in plain language, since many customers are not technical.

You support customers by phone, email and other channels. How do you change your approach between a phone call and an email?

What they are checking: Awareness that tone and clarity work differently in writing and on the phone.

Tell me about a time you went beyond the request to help a customer use a system better.

What they are checking: Whether they look for ways to optimize a customer's use of the platform, not just close tickets.

What would you do

A customer calls frustrated because they cannot find an order in our system. Walk me through how you handle the call.

What they are checking: Whether they can calm a frustrated caller and work the problem step by step at the same time.

How do you decide when to keep troubleshooting yourself and when to escalate an issue?

What they are checking: Judgment about escalation, which the posting says keeps operations running smoothly.

A customer asks you to update data in their account, but something about the request does not look right. What do you do?

What they are checking: Care with data accuracy and willingness to verify before making changes that affect orders.

You get a question you have never seen and nobody is available to ask. How do you respond to the customer?

What they are checking: Comfort with ambiguity and honesty about what they know while still moving the issue forward.

Our customers serve seniors in senior living communities. Why might a delayed order matter more to them than to a typical business?

What they are checking: Empathy for the end impact on residents and caregivers, which raises the stakes of each call.

About the work

How do you keep track of open issues so nothing falls through the cracks when you are handling many at once?

What they are checking: Organization and follow-through, which drive customer satisfaction and loyalty.

What systems or support tools have you used, and how quickly do you usually learn new software?

What they are checking: Technical comfort and learning speed, since the job centers on helping people navigate platforms.

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The full job description

As published by Direct Supply.

Position Summary: Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. In the Customer Support Specialist role, you’ll be the frontline connection to our customers, ensuring seamless interactions through phone, email, and other support channels. You’ll help customers navigate our systems, update data, and optimize their use of our platforms. Your expertise in troubleshooting and resolving issues will drive customer satisfaction and loyalty, while your ability to escalate complex problems ensures smooth operations. Skills Needed: • Provides Customer Value - Delivers cutting-edge, tech-driven solutions paired with outrageous customer service with an eye to profitability. Seizes opportunities that reward both the customer and DS, fostering robust customer relationships. • Communicates Effectively - Develops and delivers impactful communications for diverse audiences across channels. Excels in both small and large group interactions. Captures attention, actively listens, and guides discussions towards targeted goals. • Deals with Ambiguity - Adapts smoothly to change and thrives in ambiguity, maintaining composure and productivity. Maintains progress despite incomplete information and tackles complex issues constructively. • Solves Problems - Uses technology and sharp logic to craft inventive solutions to complex issues, digging deep to tackle root causes. Conducts impartial analysis, leaving no stone unturned for comprehensive insights. • Applies AI and Technology - Identifies opportunities to boost efficiency and add value using AI and tech. Embraces and applies digital innovations and tech solutions to build business. Eagerly learns and integrates new technologies where they matter most. • Demonstrated ability to mediate and resolve conflicts effectively, fostering positive relationships with both customers and team members. • Proficient in Microsoft Word and Excel and eager to learn and leverage new AI-enhanced processes and technology • Provide occasional off hours support when needed and when approved by manager What You’ll Do and Impact: • Provide high-quality customer support to internal and external users, ensuring timely resolution aligned with SLA standards. • Address incoming supplier and customer requests through the ticketing system, phone, and email, adhering to SLA requirements. • Utilize AI-assisted automation for efficient execution and review of configuration updates. • Perform customer data updates using operational tools • Support various functions within the DSSI Operations team as needed. • Gather and document insights from customer interactions to improve processes. Educate providers and suppliers on the DSSI interface, guiding them on request submission and system navigation. • Maintain thorough documentation of issue resolution activities, integrating AI-driven insights where applicable. • Identify and implement AI-powered process improvements to enhance efficiency and customer satisfaction. • Support project initiatives as assigned by the Operations Manager. Experience: • Proven track record of delivering exceptional customer service. • Experience with AI-powered customer support tools, chatbots, or automation is a plus. • High energy, positive attitude, and a strong commitment to exceeding customer expectations. Additional Items of Interest: • Associate’s or Bachelor’s degree in technology or a related field. • Experience with ticketing software (such as Zendesk). • Background in database management and maintaining large datasets. • Experience in business process improvement, particularly AI-driven solutions. Job to be performed in the location listed. Generous benefit package available. © 2013 to 2026 Direct Supply, Inc. All rights reserved.

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