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Senior Director of Technology

Greyson Clothiers, Detroit, MI, United States


Position Overview 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 a solution mindset from experience, comfortable training teams, and drive execution.

This is a hybrid position based out of our Detroit, MI office with three days per week required in-office.

Key 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

Required Skills and Qualifications

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

Experience supporting light manufacturing, decoration, or value-added workflows (preferred)

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

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

Candidates must reside in the Detroit Metro Area

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