Restaurant Client Success & Support Specialist (Winfield)

ALPHA RESTAURANT TECHNOLOGIES

Restaurant Client Success & Support Specialist

Winfield, IL / Chicago area | Full-time | Office-based support and local restaurant visits

Position Summary

Use your restaurant experience to help other restaurants run better.

Alpha is looking for a restaurant professional who enjoys building relationships, teaching others and figuring out how to make things work. Perhaps you’re the manager, shift lead, bartender or trainer coworkers turn to when the POS acts up, someone needs help, or the usual process isn’t working.

You’ll become a dependable resource for restaurant owners and their teams—solving technology problems, training staff and helping clients improve how they operate. We provide training on our systems; you bring restaurant knowledge, curiosity and ownership.

The role is planned around approximately 60% technical support and 40% proactive client success, with dedicated time scheduled for each responsibility. You will manage a portfolio expected to grow to approximately 90 restaurant accounts, adjusted for complexity, geography and service needs. Both support and client success are core responsibilities, with dedicated time and performance expectations for each.

Training & Development

Prior professional IT employment is not required. Training on Alpha’s supported technology and procedures will be provided, including deeper POS configuration, integrations and technical support processes. Bring hands-on restaurant experience, familiarity with using a POS, and demonstrated curiosity and persistence when solving unfamiliar problems.

You will develop skills across restaurant systems such as POS, payment processing, kitchen displays, online ordering, inventory management, labor scheduling, loyalty and reporting tools. You must be willing to learn, practice and develop the technical skills needed to support assigned systems independently.

About Alpha

Alpha Restaurant Technologies helps restaurants get more value from their technology through implementation, support and ongoing guidance. We are a small, growing company where initiative, practical problem-solving and dependable follow-through improve daily operations and make a visible difference for clients.

Key Responsibilities

• Own client relationships. Get to know each restaurant's operation, goals and concerns. Build trust through clear communication, a planned contact schedule and dependable follow-through. Recognize signs of dissatisfaction and coordinate timely recovery plans.
• Train and support adoption. Help owners, managers and staff understand the tools they already have. Explain technology in plain language, provide patient training and confirm that new features or solutions are being used effectively.
• Deliver useful guidance. Conduct account reviews and restaurant visits, evaluate workflows and available reporting, and recommend practical improvements in areas such as ordering, kitchen operations, loyalty, labor efficiency and guest experience.
• Solve problems and find workarounds. Troubleshoot POS software, payments, hardware, printers, connectivity and integrations. Research unclear issues, test practical alternatives and draw on documentation, teammates and vendors. Explain limitations, document the solution and confirm it works.
• Address recurring problems. Connect patterns in support requests with training, configuration or operational needs. Work with teammates and vendors to address underlying causes and reduce repeat issues.
• Follow through on improvements. Recommend additional solutions when they address a real business need. Coordinate with Sales, Admin, Projects and Support for quoting, implementation and fulfillment, then confirm the client's needs were addressed.

Required Qualifications

• Hands-on experience working in restaurant operations, with a practical understanding of service, kitchen workflows and the pressures restaurant teams face.
• Clear verbal and written communication, patience when teaching others, and the ability to earn trust through listening and dependable follow-through.
• A resourceful problem-solving mindset: willingness to investigate, learn, test alternatives and find workable solutions when instructions, standard features or immediate answers are unavailable.
• Familiarity with using a POS in a restaurant and demonstrated technical aptitude. You should be comfortable learning unfamiliar systems and working methodically through a problem.
• Strong organization and the ability to manage support requests alongside scheduled account responsibilities.
• Ability to work from Alpha’s Winfield office, visit local restaurant clients and work scheduled night and weekend technical support shifts.

Preferred Experience

Responsibility for running shifts, training staff, resolving guest concerns or improving restaurant operations is especially relevant. Restaurant managers, assistant managers, shift leads, bar managers, bartenders, servers and trainers who have taken ownership beyond their immediate tasks are encouraged to apply.

Customer success, account management, restaurant technology training, POS administration or professional technical support experience is a plus.

Schedule & Travel

This role is based in Alpha’s Winfield, Illinois office and includes local restaurant visits throughout the Chicago area. Dedicated client success time generally falls during normal business hours.

Night and weekend technical support shifts may be required as part of Alpha's 24/7 coverage. Candidates must be willing and available to work these shifts when scheduled. Employees will not ordinarily be scheduled for both Saturday and Sunday in the same workweek. Occasional travel between Alpha offices or client markets may be required.

What Success Looks Like

Success means restaurant clients trust you to listen, take ownership and follow through. You help their teams use technology confidently, find effective solutions, verify that workarounds meet their needs and prevent repeat problems. We evaluate resourcefulness, sound judgment and communication alongside completed client engagements, technology adoption, retention and meaningful improvements for the restaurant.

Compensation & Benefits

Base salary: $55,000–$70,000 annually, depending on experience and qualifications. Eligible for annual performance bonuses based on established individual, team and company performance targets.

Full-time benefits include health, dental, vision and life insurance; a SIMPLE IRA retirement plan; paid time off; applicable holidays and sick leave; gym reimbursement; a Book of the Month or Audible benefit; and training and professional development. Approved mileage and business travel expenses are reimbursed.

How to Apply

Submit your resume and a brief note stating how many years you have worked directly in restaurant operations, the roles you held and your responsibilities. Describe a time you earned someone’s trust by taking ownership of a recurring problem, including how you communicated and followed through. Include an example of a problem with no obvious solution, how you investigated it, and the workaround or resolution you found.