Director of DTC, Lifestyle and Apparel
Overtime
New York, NY, USA
USD 120k-145k / year + Equity
Posted on Aug 22, 2025
About the Role
We’re hiring a Director of DTC, Lifestyle & Apparel to lead the vision, drive the strategy, and lead the growth of our eCommerce and retail business. This leader will be responsible for our full DTC across Shopify, retail stores, League events, and digital marketplaces, overseeing the growth and empowerment of a high-performing team to deliver against ambitious goals.
We’re hiring a Director of DTC, Lifestyle & Apparel to lead the vision, drive the strategy, and lead the growth of our eCommerce and retail business. This leader will be responsible for our full DTC across Shopify, retail stores, League events, and digital marketplaces, overseeing the growth and empowerment of a high-performing team to deliver against ambitious goals.
You’ll build a best-in-class experience through site strategy, merchandising, fulfillment, and customer experience while also managing operational complexity and cross-functional priorities. Accountable for delivering financial targets, you will champion data-driven decision making, elevate assortment curation, and orchestrate innovative strategies that keep us ahead of market trends. This is a high-impact, hands-on leadership role focused on both optimizing daily performance and building the long-term infrastructure for sustained growth.
Strategy & Leadership
- Define the vision and growth strategy for our eCommerce business across desktop, mobile, retail, and events, ensuring alignment with consumer trends and internal KPIs.
- Translate brand and business goals into clear DTC execution plans—balancing customer experience, storytelling, and revenue goals.
- Build, mentor, and lead a high-performing team across site operations, merchandising, planning, retail, and customer experience.
- Develop talent and serve as a leadership role model within the broader organization, driving cross-functional communication and collaboration.
Merchandising & Planning
- Define and oversee the strategy for seasonal line planning and in-season management across the total eCommerce portfolio.
- Guide the Product Creation team on strategic needs of the DTC consumer, ensuring your team’s line planning includes Style, SKU, Color, Expression, Price, Channel, and ISD coverage for both new opportunities and carry-over business.
- Align DTC vision with Merchandising, Marketing, and Finance teams on inventory management, storytelling moments, and seasonal buy planning across all categories and distribution channels.
- Direct team in assortment management, size runs, sell-through tracking, and lifecycle reporting to ensure optimal inventory health and profitability.
E-commerce Analytics & Consumer Insights
- Lead and direct the team in building and maintaining the DTC analytics framework, setting KPIs and developing dashboards to monitor sales, traffic, conversion, AOV, retention, and customer lifetime value.
- Guide the team in deep-diving into consumer behavior data—including purchase patterns, site navigation, drop performance, and cohort analysis—to uncover growth opportunities and identify friction points.
- Oversee the use of analytics tools (e.g., Shopify Analytics, Google Analytics, Dynamic Yield, CRM reports) to segment customers, optimize merchandising, and refine promotional strategy.
- Direct cross-functional insight-sharing, ensuring marketing, merchandising, and product teams receive clear, actionable recommendations to drive acquisition, retention, and upsell.
- Lead post-mortem analysis of major launches, campaigns, and drops, using findings to adjust future assortments, release calendars, and CX strategies.
- Ensure ongoing monitoring of competitor benchmarks and industry trends to keep our DTC experience ahead of the market and aligned with consumer expectations.
eCommerce Site Management (Shopify)
- Oversee Shopify suite management, guiding the team on site roadmap, content, and functionality.
- Lead strategy for site rebuild, optimizing for mobile-first UX and conversion.
- Foster a culture of continual innovation, leveraging A/B testing, UX enhancements, and back-end upgrades.
Operations & Fulfillment
- Lead the team in delivering operational excellence from product upload through order delivery to improve consumer satisfaction.
- Drive 3PL performance improvements, identifying logistics tools and best practices to modernize current process for scale.
Marketing Collaboration
- Direct alignment of site content, email, SMS, and paid strategies with merchandising calendars and product launches. Ensure marketing activations are fully supported by site merchandising and operational readiness.
- Align DTC vision and revenue goals with growth marketing team to set the campaign roadmap and promotional calendar.
Finance & Reporting
- Lead monthly reporting for eCommerce, CX, and Retail, presenting insights and recommendations to cross-functional partners with a focus on driving future product development and business decisions.
- Oversee coordination with Finance on PO tracking, royalty payments, gifting, and invoice approvals.
Wholesale, Licensing & External Sales
- Provide strategic oversight to wholesale, licensing, and team sales partnerships, ensuring alignment with DTC strategies, marketplace brand management and inventory flow.
- Lead execution of external partner launches across DTC channels where relevant.
Who You Are:
- 10+ years of DTC/eCommerce experience, ideally in youth culture, sportswear, or streetwear.
- Deep knowledge of Shopify, CX platforms, digital merchandising, and retail .
- Proven leader with a track record of scaling eCommerce businesses, building high-performing teams, and delivering results.
- Have an innovative, forward-thinking mindset to anticipate and identify white space within the athletic and streetwear space to best serve our consumer
- Analytical and operationally minded—able to manage complexity, drive clairty and move quickly.
- Collaborative communicator who can ensure alignments with Product Creation, Marketing, Planning, and Finance teams.
- Passionate about building experiences for young athletes and culture-driven consumers.
Overtime expects the base salary of this role to be approximately $120-145K annually based on the experience of the individual hired into the role. Additionally we offer benefits, paid time off, and stock options.