About The Digital Stronghold:

The Digital Stronghold (TDS) is a multi-brand e-commerce holding company aggregating digitally native companies in the men’s interest space. It is currently composed of Taylor Stitch, The Tie Bar, Boston Scally& Pedal Mafia. TDS exists to create an environment for men’s interest brands to thrive together. At the heart of our belief is that when you have shared learnings, shared services, and shared centers of excellence, you can create something that propels both growth and profitability.

The Digital Stronghold is targeting additional brands for acquisition, allowing us to reach new customers based on taste, style, and product assortment, to drive growth and share of the market. The Vice President of Product & Technology will sit within a shared services organization at The Digital Stronghold and be responsible for leading the product & technology strategy for Taylor Stitch, The Tie Bar, Boston Scally, & Pedal Mafia. They will also be responsible for supporting any additional brands we may acquire.

About the Role: Vice President of Product & Technology:

The Vice President of eCommerce Product and Technology is responsible for leading the strategic vision, development, and execution of the company’s eCommerce product and technology roadmap. This role will oversee digital platforms, user experience, and backend technologies that power multiple brands across global markets. The VP will collaborate closely with marketing, merchandising, operations, and IT teams to drive digital innovation, enhance customer experience, and optimize performance across all digital commerce channels.

Position Accountabilities:

• Strategic Leadership & Vision: Develop and execute a comprehensive digital commerce technology strategy aligned with business objectives, ensuring a scalable and future-ready digital ecosystem across all brands and regions.
• Consumer Experience & Conversion Optimization: Lead the development of best-in-class user experiences that drive engagement, conversion, and retention through data-driven UX/UI design, personalization, and omnichannel integration.
• Technology Innovation & Platform Management: Oversee the selection, implementation, and optimization of eCommerce platforms, integrations, and emerging technologies to enhance digital capabilities and operational efficiency.
• Cross-Functional Collaboration & Stakeholder Management: Partner with marketing, merchandising, supply chain, and IT teams to ensure alignment between digital initiatives and business goals while advocating for customer-centric, data-informed decision-making.
• Performance Metrics & ROI: Define, track, and optimize KPIs such as revenue growth, site performance, conversion rates, customer satisfaction, and operational efficiencies to ensure digital commerce success and profitability.

Essential Functions:

• Define and implement a multi-year digital commerce strategy that aligns with the company’s overall business objectives.
• Drive eCommerce product and technology innovation, staying ahead of industry trends and emerging digital solutions.
• Oversee the enhancement of eCommerce platforms, ensuring seamless shopping experiences across desktop, mobile, and omnichannel touchpoints.
• Lead UX/UI improvements, personalization strategies, and A/B testing to drive engagement and conversion.
• Manage eCommerce infrastructure, including CMS, PIM, OMS, and third-party technology integrations.
• Ensure optimal site performance, security, and compliance with best practices in data privacy and cybersecurity.
• Act as a key liaison across brand and performance marketing, merchandising, operations, and IT teams to ensure alignment of digital initiatives.
• Define and monitor key eCommerce performance metrics, leveraging analytics and testing frameworks.
• Develop and manage the digital commerce technology budget, ensuring investments drive tangible business outcomes.
• Coach and counsel a cross-functional team of developers, engineers, designers, analysts and product managers, both onshore and offshore.
• Partner with talent management to shape team structure and build plans for future needs related to capability expansion and business growth.

Preferred Education and Qualifications:

• 15+ years of experience in eCommerce, digital product management, or technology leadership roles within a retail or apparel organization.
• Proven track record of leading digital transformation initiatives, including eCommerce replatforming and omnichannel strategy execution.
• Deep expertise in eCommerce platforms such as Shopify Plus, Salesforce Commerce Cloud, or Magento.
• Strong understanding of customer experience design, analytics, personalization, and data-driven decision-making.
• Experience managing large cross-functional teams and external vendors/agencies.
• Excellent leadership, communication, and stakeholder management skills.
• Bachelor's degree in Computer Science, Business, or a related field (MBA preferred).