POS Systems Engineer

JOB TITLE: Sr. POS Systems Engineer

LOCATION: Andover, MA (Onsite 5 days every other week; 1 week onsite, 1 week remote)

DURATION: 6 Months Contract to Hire

INTERVIEW: 1 Video & 1 In-Person

Position Overview

Senior POS Systems Engineer to join our retail technology team and help support the continued evolution of our point-of-sale environment.

We are looking for an experienced retail technology professional with a strong background in POS systems, preferably in grocery. This is a senior, hands-on role for someone who can bring practical experience to the team, learn our environment, and take ownership of both day-to-day challenges and longer-term initiatives.

As the team continues to grow, there will be opportunities to take deeper ownership of specific areas based on experience and interest. Payments is one area where we would like to strengthen our capabilities, making experience with payment technologies valuable, but not required. Our priority is finding a strong POS professional who can contribute broadly, grow into new areas, and help strengthen the team around them.

Primary Responsibilities

• Support and engineer the POS platform and related store technologies.
• Troubleshoot complex issues across POS software, hardware, peripherals, networks, integrations, databases/services, and external vendor systems.
• Develop a strong understanding of end-to-end system and transaction flows rather than focusing on individual components.
• Participate in POS upgrades, configuration changes, testing, deployments, new store openings, and technology rollouts.
• Work directly with POS and technology vendors to diagnose issues, test solutions, and drive problems through resolution.
• Help improve monitoring, documentation, supportability, automation, and engineering practices across the POS environment.
• Serve as a senior escalation point for difficult or recurring production issues and help identify root cause and long-term corrective actions.
• Share knowledge and help develop technical depth across the broader POS team.

Payments Focus:

• Developing deeper technical ownership of payments within the POS environment.
• Supporting payment terminals and their integration with the POS.
• Understanding and troubleshooting payment transaction flows from the point of interaction through the POS and downstream processor/acquirer.
• Supporting payment implementations, certifications, testing, configuration changes, and production issues.
• Working with payment vendors, processors/acquirers, Finance, and other internal teams.
• Building team knowledge around concepts such as EMV, contactless, debit, EBT/SNAP/WIC, authorization, reversals, settlement, encryption/tokenization, and P2PE.

Ideally, the candidate would bring:

• 3+ years of hands-on experience supporting or engineering retail POS systems.
• Grocery/supermarket POS experience strongly preferred.
• Practical hands-on experience troubleshooting Windows-based computers, hardware, peripherals, operating systems, and basic connectivity issues.
• Experience with enterprise POS platforms such as NCR, Toshiba, GK/Fujitsu, ECRS, or comparable platforms.
• Strong troubleshooting and root-cause-analysis skills.
• Experience working across integrated systems and multiple technology vendors.
• Comfort working with logs, interfaces, transaction flows, application configuration, networking concepts, and distributed store systems.
• Experience operating technology in a high-volume production retail environment.
• Payments or payment-terminal experience is a plus.
• Ability and willingness to learn unfamiliar systems rather than relying solely on expertise with a particular product.
• Strong sense of ownership and willingness to take a problem from initial investigation through resolution.
• Ability to document what they learn and help build the capabilities of the team around them.

Additional Requirements

• Direct retail POS experience is important.
• Senior, hands-on experience with a modern enterprise POS platform.
• Strong understanding of POS applications and integrations with internal systems.
• Experience working with vendors and managing vendor processes.
• Ability to troubleshoot beyond the surface level and understand end-to-end application and integration flows.