Senior POS Specialist, 99 Main Office

HI Steaks; Honolulu (HI); On-site; USD 70,000 - 90,000; Full time

Job summary

HI Steaks is seeking a Senior POS Specialist to administer and support our POS systems across multiple store locations. You will collaborate with Store Operations, vendors, and IT teams to ensure reliable day‑to‑day operations and successful upgrades.

The role requires hands‑on experience with traditional registers, mobile POS, and self‑checkout, plus strong troubleshooting and documentation skills. Expect after‑hours shifts and occasional travel to support deployments.

Qualifications

• Bachelor’s degree in Information Technology, Computer Science, or equivalent practical experience.
• 3+ years supporting POS systems or retail technology environments.
• Experience working with third‑party POS vendors and payment processors.
• Prior experience in a grocery and retail environment is strongly desired.
• Relevant POS or technical certifications are a plus.

Responsibilities

• Support and maintain enterprise POS systems across traditional, mobile, and self‑checkout environments.
• Serve as a senior escalation point for Tier 2 / Tier 3 POS hardware, software, and application issues.
• Plan and support POS software deployments, patches, configuration changes, and version upgrades.
• Perform and document regression testing to validate POS functionality before and after system changes.
• Validate end‑to‑end transaction workflows, peripherals, and integrations during upgrade testing.
• Monitor POS system health and respond to outages or performance degradation.
• Perform root cause analysis and implement corrective actions for recurring POS issues.
• Maintain clear documentation for POS configurations, procedures, and testing activities.
• Coordinate with POS vendors, payment processors, and third‑party support providers.
• Support store openings, remodels, lane expansions, and technology refreshes.
• Provide on‑call and after‑hours support for planned maintenance and critical incidents.

Skills

POS systems

Multi-store retail

POS peripherals

Software upgrades

Regression testing

Transaction flows

Networking

Payment processing

POS security

Documentation

Team collaboration

After-hours support

Education

Bachelor’s degree in IT/CS

3+ years POS/retail tech experience

POS/vendor certifications (plus)

Job description

The Senior POS Specialist is responsible for the administration, support, and ongoing reliability of the company’s Point‑of‑Sale (POS) systems and related retail technologies. This role supports traditional POS registers, mobile POS solutions, and self‑checkout systems across multiple store locations and serves as a senior technical subject matter expert for POS platforms and transaction workflows.

The Senior POS Specialist works closely with Store Operations, vendors, and internal IT teams to ensure stable day‑to‑day operations and successful execution of POS upgrades, enhancements, and new store initiatives. This position participates in change windows, on‑call rotations, and off‑hours support as required.

Key Responsibilities

• Support and maintain enterprise POS systems across traditional, mobile, and self‑checkout environments
• Serve as a senior escalation point for Tier 2 / Tier 3 POS hardware, software, and application issues
• Plan and support POS software deployments, patches, configuration changes, and version upgrades
• Perform and document regression testing to validate POS functionality before and after system changes
• Validate end‑to‑end transaction workflows, peripherals, and integrations during upgrade testing
• Monitor POS system health and respond to outages or performance degradation
• Perform root cause analysis and implement corrective actions for recurring POS issues
• Maintain clear documentation for POS configurations, procedures, and testing activities
• Coordinate with POS vendors, payment processors, and third‑party support providers
• Support store openings, remodels, lane expansions, and technology refreshes
• Provide on‑call and after‑hours support for planned maintenance and critical incidents

Required Skills & Knowledge

• Strong experience supporting POS systems in a multi‑store retail environment
• Working knowledge of traditional fixed registers, mobile POS devices, and self‑checkout systems
• Experience supporting POS peripherals (scanners, printers, pin pads, cash drawers, scanner‑scales, displays)
• Hands‑on experience with POS software upgrades and regression testing
• Solid understanding of POS transaction flows (sales, returns, tenders, exceptions)
• Familiarity with store networking concepts and POS connectivity
• Understanding of payment processing and POS security principles
• Strong troubleshooting, analytical, and documentation skills
• Ability to work independently and collaborate across technical and non‑technical teams
• Willingness to support nights, weekends, holidays, and change windows as required

Education & Experience

• Bachelor’s degree in Information Technology, Computer Science, or equivalent practical experience
• 3+ years supporting POS systems or retail technology environments
• Experience working with third‑party POS vendors and payment processors, required
• Prior experience in a grocery and retail environment, strongly desired
• Relevant POS or technical certifications a plus

Time / Travel Requirements

• Availability for after‑hours maintenance, testing, and critical incidents
• Occasional travel to store locations to support deployments, upgrades, and testing activities

Qualifications

Education

Required

Bachelors or better in Information Technology.

Experience

Required

3 years:

Experience working with third‑party POS vendors and payment processors

3 years:

Supporting POS systems or retail technology environments

Preferred

Experience supporting POS peripherals (scanners, printers, pin pads, cash drawers, scanner‑scales, displays)

Experience with supporting POS systems in a grocery and multi‑store retail environment

Equal Opportunity Employer
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