Senior POS Specialist, 99 Main Office
About The Position
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.
Requirements
- 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
- 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
Nice To Haves
- Prior experience in a grocery and retail environment, strongly desired
- Relevant POS or technical certifications 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
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What This Job Offers
Job Type
Full-time
Career Level
Senior
