Senior Director of Technology

Greyson Clothiers • US,

2d • Remote

About The Position

We are seeking a hands-on and execution-focused Senior Director of Technology to lead the ongoing management, optimization, and scaling of Greyson’s technology ecosystem. This role is responsible for owning and operating core systems, with a primary focus on the NetSuite ERP, ensuring they function effectively to support a growing omnichannel retail apparel business. This position partners closely with cross-functional teams to drive system adoption, improve workflows, and deliver reliable, scalable solutions. The ideal candidate thrives in fast-paced, founder-led environments and is comfortable rolling up their sleeves to solve problems, dealing with ambiguity, bringing solution mindset from experience, comfortable training teams, and drive execution.
This is a remote role that may require some travel to our Detroit headquarters.

Requirements

• 10+ years of progressive experience in Technology or Business Systems leadership within apparel, retail, or consumer goods
• Expert-level NetSuite ERP expertise, including implementation, optimization, and administration in a multi-entity, omnichannel environment
• Proven success in high-growth, entrepreneurial environments, scaling systems alongside the business
• Deep understanding of omnichannel operations (eCommerce, wholesale, retail) and enabling technologies
• Strong command of end-to-end business processes, including order-to-cash, procure-to-pay, inventory, fulfillment, and financial integrations
• Expertise integrating third-party platforms (eCommerce, WMS, EDI, POS, 3PLs) using APIs and middleware
• Track record of leading ERP implementations and continuous improvement initiatives with a focus on scalability and data integrity
• Player-coach leadership style, with experience building and developing high-performing teams
• Strong program and project management skills, with the ability to prioritize in fast-paced environments
• Experience driving change management, training, and system adoption
• Excellent analytical, problem-solving, and communication skills, with the ability to translate technical concepts into business impact

Nice To Haves

• Experience supporting light manufacturing, decoration, or value-added workflows

Responsibilities

• Own and lead Greyson’s technology ecosystem, with primary accountability for NetSuite ERP, ensuring stability, scalability, and alignment with business growth
• Serve as the internal authority on systems architecture, driving optimization, troubleshooting, and continuous platform enhancement
• Lead delivery of system enhancements, integrations, and automation initiatives, including AI-driven solutions that improve cost, efficiency, and scalability
• Own the technology roadmap and portfolio, ensuring on-time, on-budget execution aligned to strategic priorities while architecting scalable solutions to support a high-growth, omnichannel business
• Partner with Finance to ensure data accuracy, reporting integrity, and compliance with financial controls and audit requirements
• Collaborate cross-functionally across Retail, eCommerce, Wholesale, and Operations to optimize order-to-cash, procure-to-pay, inventory, and fulfillment workflows
• Manage external vendors and technology partners, driving performance, accountability, and cost efficiency
• Build and lead a high-performing team with a hands-on, player-coach leadership approach
• Drive documentation, training, and adoption to ensure consistent and effective system use
• Own incident management, including prioritization, root cause analysis, and long-term resolution, inclusive of sharing KPI driven metrics with business in support of steady state operations
• Ensure data integrity, governance, and internal controls across all systems
• Translate business needs into scalable technical solutions and continuously improve system performance and reliability

Benefits

• Unlimited Paid Time Off
• Paid Sick Leave
• 13 annual paid company holidays
• Competitive employee discount
• Paid Family Leave Program (maternity and bonding)
• Company paid long-term and short-term disability
• Tax Advantage Accounts (FSA, HSA, FSA Dependent Care, 401(k), and 401(k) Roth
• Comprehensive Medical Coverage (medical, dental, vision) with company HSA contributions

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed