Senior Merchandise Planner

About Us

The Digital Stronghold is a modern commerce collective built around four distinctive, high-performance brands:
Taylor Stitch, The Tie Bar, Boston Scally, and Pedal Mafia. Each brand stands on its own with a loyal community and a clear sense of purpose, yet together, they define what contemporary menswear looks like across lifestyle, tailoring, and performance apparel.

Our Values

• Own the outcome
• Move with purpose
• Speak truth, listen fully
• Learn and share
• Drop the ego
• Build for the long haul

The Digital Stronghold is seeking a Merchandise Planner to support inventory strategy, forecasting, and merchandise planning initiatives for The Tie Bar, a premium menswear and accessories brand founded in Chicago over a decade ago.

This role will play a key part in balancing inventory across channels, supporting financial goals, and ensuring the right product is available at the right time. The ideal candidate is analytical, detail-oriented, and collaborative, with experience in merchandise planning within apparel, retail, or eCommerce environments.

You’ll work cross-functionally with buying, marketing, supply chain, eCommerce, and sales teams to help drive inventory optimization, assortment planning, and business performance across a fast-moving retail environment.

• Develop monthly, quarterly, and annual merchandise plans aligned with business objectives and sales targets
• Build and maintain demand forecasts based on historical sales data, seasonal trends, and market insights
• Support inventory planning and forecasting strategies to maximize product availability while minimizing excess inventory
• Manage open-to-buy budgets and provide reporting on performance, projections, and opportunities

• Monitor sales performance and inventory levels across channels, adjusting plans to meet changes in demand
• Analyze sell-through performance and inventory trends to identify opportunities for optimization
• Support allocation strategies to ensure timely and effective product distribution across markets
• Partner with supply chain teams to help manage product flow and delivery timelines

• Collaborate with buying teams to support assortment planning and sales forecasting initiatives
• Assist in monitoring sales, margin, and inventory performance against financial targets
• Provide analytical insights and recommendations related to assortment planning, inventory allocation, and sales performance
• Support planning adjustments tied to promotions, product launches, and evolving market conditions

• Partner closely with Marketing, Buying, Supply Chain, Sales, and eCommerce teams to execute merchandise plans effectively
• Help align planning strategies with promotional calendars and broader business priorities
• Prepare regular reporting and performance updates for stakeholders and leadership teams

• Bachelor’s degree in Business, Merchandising, or a related field
• 3–5 years of merchandise planning experience, preferably within apparel, retail, or eCommerce environments
• Strong experience with inventory management, forecasting, and sales analysis
• Must be eligible to work in the US
• Advanced proficiency in Excel and experience using merchandise planning systems such as Net Suite
• Strong analytical and problem-solving skills with a high attention to detail
• Experience collaborating cross-functionally with buying, marketing, supply chain, sales, and eCommerce teams
• Ability to manage multiple priorities in a fast-paced environment
• Experience supporting global markets and understanding regional consumer demand trends is a plus

At The Digital Stronghold, you’ll join a collaborative and entrepreneurial environment where thoughtful planning, creativity, and operational excellence come together to support a portfolio of distinctive brands. You’ll have the opportunity to make a meaningful impact while helping shape the future growth of modern menswear and lifestyle brands.

If you’re passionate about retail planning, inventory strategy, and data-driven decision making, we’d love to hear from you.