Senior Manager, POS Support

You are not just supporting point-of-sale systems. You are helping keep 450+ sites running while building the platform that will support what comes next.

The Senior Manager, POS Support at Whistle Express is responsible for reliable day-to-day support across a mixed environment of DRB, Micrologic, ICS, and Sonny’s systems while helping the company transition every site to a unified Micrologic POS platform over the next 24 months.

This role brings together systems expertise, field partnership, problem-solving, and operational discipline. You will work closely with Operations, IT/Business Systems, Marketing, Finance, Customer Service, vendors, and regional and site teams to resolve issues quickly, strengthen support practices, prepare locations for conversion, and protect the guest and employee experience through go-live.

At this level, success is measured by system reliability, issue resolution, field trust, conversion readiness, clear communication, and the ability to improve support while the environment continues to change.

What You’ll Do

POS Support and System Reliability

• Own day-to-day support for POS systems across 450+ sites, including DRB, Micrologic, ICS, Sonny’s, and related technologies.

• Serve as the primary point of contact and escalation for POS issues, keeping business partners informed on impact, status, resolution, and follow-up.

• Triage and resolve hardware, software, payments, integrations, and system issues with urgency and sound judgment.

• Establish consistent support practices across platforms so site and regional teams know how to report issues, get help, and apply solutions.

• Prioritize the support backlog based on business impact, site disruption, customer experience, and operational risk.

• Monitor platform performance and recurring issues, identify root causes, and drive practical improvements that reduce repeat incidents.

• Maintain current system, process, troubleshooting, access, and support documentation across all POS platforms.

Unified POS Deployment and Conversion Support

• Support the 24-month phased conversion to a unified POS platform.

• Partner with the dedicated conversion team, which owns the overall project plan and timeline, to provide car wash operations and POS subject-matter expertise.

• Work directly with regional and site teams on readiness, training, cutover support, issue resolution, and post-go-live stabilization.

• Identify technical, operational, vendor, data, and site-readiness risks early and provide clear recommendations to the conversion team.

• Translate lessons from legacy platforms and field operations into requirements, standards, and best practices for the future POS environment.

• Help protect site performance, transaction continuity, employee usability, and the guest experience throughout each conversion.

• Participate in conversion planning, site visits, readiness reviews, go-live support, and post-conversion follow-up.

Field and Cross-Functional Partnership

• Build trusted relationships with Operations, Maintenance, IT/Business Systems, Finance, Marketing, Customer Service, Project Management, regional leaders, site teams, and external vendors.

• Serve as the connection between corporate teams and the field, making sure feedback, requirements, risks, and decisions move in both directions.

• Communicate clearly with audiences ranging from site team members to executive leadership, adjusting the level of detail and message for each group.

• Provide regular updates on support performance, conversion readiness, open risks, recurring issues, and results.

• Work effectively across teams and vendors that do not report directly to this role, creating alignment and follow-through without relying on formal authority.

• Maintain a clear roadmap for steady-state POS support that stays aligned with conversion priorities and timing.

Business Applications, Data, and Controls

• Partner with Operations and Customer Service to understand how sites use POS systems day to day and turn that insight into practical system requirements.

• Support accurate and consistent reporting across DRB, Micrologic, ICS, and Sonny’s while helping align future reporting with Whistle Express dashboards.

• Work with Customer Service and project partners to evaluate customer profiles, purchase history, memberships, loyalty programs, and related CRM capabilities.

• Partner with Human Resources, Operations, and project teams to review timekeeping, scheduling, and employee-management capabilities connected to current and future POS platforms.

• Oversee system access controls, audit trails, and data-protection practices in partnership with IT and other responsible teams.

• Support inventory and parts-management processes connected to POS platforms, including continuity through conversion.

• Partner with Finance, Operations, Procurement, and vendors on contract transitions, chargebacks, disputes, consumables, merchant-processing fees, and cost-saving opportunities.

Continuous Improvement and Accountability

• Use support data, field feedback, and recurring issue trends to identify opportunities to improve system performance, processes, documentation, training, and vendor service.

• Establish clear priorities, ownership, escalation paths, and success measures for POS support work.

• Hold vendors and internal partners accountable for issue resolution, service quality, communication, and follow-through.

• Bring forward problems with context, business impact, and recommended solutions—not just a description of what is wrong.

• Balance immediate operational needs with long-term platform standardization and scalability.

What We’re Looking For

• Experience supporting car wash, retail, hospitality, restaurant, or other multi-site POS environments.

• Hands-on experience with DRB, Micrologic, ICS, or Sonny’s is strongly preferred.

• Experience supporting large technology conversions, system migrations, or enterprise implementations across a distributed organization.

• Strong understanding of POS and payments technology, software support, integrations, user access, reporting, and operational workflows.

• Proven ability to diagnose complex issues, make sound decisions under pressure, and coordinate resolution across internal teams and vendors.

• Strong analytical skills with the ability to identify patterns, assess risk, prioritize work, and translate technical information into practical business action.

• Clear written and verbal communication skills, including the ability to communicate effectively with site teams, vendors, functional leaders, and executives.

• Strong organizational and project-management skills with the ability to manage steady-state support and conversion priorities at the same time.

• Comfortable operating in a fast-paced, highly matrixed, multi-vendor environment with changing priorities.

• Detail-oriented, self-directed, collaborative, and steady under pressure.

• Bachelor’s degree in business, technology, information systems, or a related field, or equivalent relevant experience.

• Ability to travel to sites and support conversion activity as needed (40-50% travel).

What’s In It for You

This is an opportunity to shape how Whistle Express supports one of the most important operating systems in the business while helping build a more consistent, scalable platform for the future.

Your work will be visible in every part of the operation: site uptime, employee experience, membership processing, reporting accuracy, guest service, conversion speed, and the field’s confidence in the tools it uses every day.

At Whistle Express, ownership is more than completing the task in front of you. It means seeing the full system, asking better questions, solving the underlying problem, and leaving the operation stronger than you found it.

If you are ready to keep today’s business running while helping build what comes next, we want to hear from you.

Base Pay Range