Senior IT Engineer

Chief Executive Officer @ AO Swag | Leadership, Strategy

AO Swag is building a small, high-ownership internal IT core to stabilize a complex legacy environment, reduce vendor dependence, and support our next phase of growth.

This is a hands‑on senior individual contributor role. Not a consultant. Not a manager. A true owner.

You will sit between strategy and execution, owning real systems that the business depends on every day. The expectation is simple: build, run, document, and continuously improve.

You’ll work closely with me, our IT leadership, application engineers, and a limited set of vendors with a clear mandate to internalize knowledge and reduce long‑term external dependency.

• Operational ownership and stability
  • Own reliability of core systems including order flows, integrations, infrastructure, and internal tools
  • Diagnose and resolve production issues without defaulting to vendors
  • Create runbooks, documentation, and incident response playbooks
  • Reduce recurring issues through automation and simplification
• Platform and integration leadership
  • Help own and evolve our integration layer connecting ecommerce, ERP, fulfillment, and third‑party systems
  • Design and build reliable APIs and workflows with traceability and failure handling in mind
  • Ensure systems are observable, understandable, and supportable internally
• Legacy transition and modernization
  • Work alongside vendors to absorb institutional knowledge from legacy systems
  • Help stabilize and isolate legacy platforms while supporting migration efforts
  • Ensure knowledge transfer results in internal capability, not vendor lock‑in
• Security, access, and controls
  • Partner on access control, credential management, and audit readiness
  • Support PCI posture improvements through system‑level controls and documentation
  • Move system and account ownership away from vendors and into AO
• Internal capability building
  • Mentor and support application engineers, including new hires
  • Set standards for code quality, documentation, and operational readiness
  • Help establish a culture of ownership, clarity, and accountability

• Not a pure architecture or strategy role
• Not a temporary bridge role

This is about owning outcomes.

• 8–12+ years of hands‑on engineering experience in production environments
• Strong backend and systems experience
• Experience building and operating integrations between complex systems
• Comfortable working in imperfect, partially documented environments
• Experience stabilizing legacy systems while building toward a future state
• Strong debugging instincts and clear written communication

• Ecommerce, ERP, logistics, or manufacturing experience
• Cloud infrastructure and CI/CD experience
• Experience in compliance‑driven environments (PCI, SOC)
• Experience replacing vendor‑led models with internal ownership

• Central to reducing vendor dependency
• Central to making systems operable and understandable internally
• Central to scaling the business without scaling chaos

We are intentionally building a small, high‑leverage IT team. This role is for someone who wants real ownership, real impact, and a seat at the table as we build the foundation for the next chapter.

If this resonates, DM me directly.