Director of Technology

Department: Technology
Reports to: Executive Leadership
Location: Remote (with some on-site presence at PA facilities)
Type: Full-time
Direct Reports: Information Technology Lead, External vendors and contractors

Gordon Sinclair is a promotional products supplier and manufacturer with over 35 years of experience bringing award-winning branded merchandise to market for some of the most recognized companies in the world. We design, source, and produce a curated line of premium lifestyle products: items built to carry a brand, not just a logo.

Gordon Sinclair is looking for its first dedicated technology leader to maximize the return on technology investment. This role will connect technology to business strategy, establish governance across systems and vendors, coordinate work across functions, build the technology team, and ensure it has the processes, priorities, and support to deliver.

This is not a maintenance role. This is a leadership role. You will own the technology strategy, the vendor relationships, the roadmap, and the cross-functional coordination. You will manage an existing IT Director and work alongside operational leaders across Sales, Operations, Product Development, and Supply Chain. You will sit on the leadership team with the authority to drive change across the organization.

The right candidate is someone who builds strong foundations. The first six months are about understanding what exists, documenting, introducing governance, and building trust across the business. You are here to make what exists work, evaluate what should change, and build a roadmap grounded in business outcomes.

• Own the technology strategy and create a prioritized 12-month roadmap aligned to revenue growth and margin improvement goals.
• Evaluate whether current platform decisions are right-sized for Gordon Sinclair, and recommend changes where justified by usage, cost, and strategic fit.
• Translate business priorities into technology investment decisions and ensure leadership understands the trade-offs.

• Introduce source control, code review, change control, and testing practices across all custom development.
• Implement monitoring and alerting across the integration layer so failures are detected in real time, not after the fact.
• Maintain a dependency map of production scripts, integrations, and data structures to prevent cascading failures during system changes.
• Maintain an infrastructure registry documenting every system, where it lives, who built it, and how to access it.
• Ensure that work done by contractors and IT personnel is documented, and that the company retains full knowledge of what was built.

• Own all technology vendor relationships with documented scope, deliverables, spend tracking, and accountability.
• Evaluate vendor performance and make build-vs-buy recommendations based on business need, not familiarity.
• Assess whether industry-focused middleware should be retained or brought in-house to enable greater cost effectiveness, control, and scalability.

• Implement workflow and project management tooling so that cross-functional processes live in systems that enforce accountability.
• Bridge the communication gap between technology and business functions by establishing a standing reporting cadence that translates technology work into business language.

• Provide leadership with visibility into backlogged work, work in progress, and delivered outcomes.
• Visualize the pipeline of technology work and its business value so investment decisions are grounded in outcomes, not assumptions.
• Identify key points of failure in existing technology and plan remediation proactively, before they become emergencies.
• Track and report on technology’s contribution to business outcomes, including integration success rates, time-to-market for new products, and data completeness.

• Manage the IT Lead, providing prioritization, direction, and a structured reporting cadence.
• Evaluate staffing needs and make the case for supplemental resources where the workload exceeds capacity.
• Establish cross-training and documentation practices to reduce key-person risk.

• Assess Promo Standards compliance gaps and create a prioritized implementation plan to support distributor growth and automated order flow.
• Ensure the distributor-facing technology quality…