Director of Merchandising

Pepper is an innovative, fast-growing DTC intimate apparel brand created to celebrate small-chested women. Our iconic, solution-driven bras, swimwear, and apparel are thoughtfully designed to make every moment and outfit a confident and authentic expression of your best self. Pepper has been obsessed with uncompromising fit for small chests since 2017, with our 470% funded Kickstarter launch. Today, Pepper has grown into a global community of millions of women, united by the belief that women deserve to feel perfectly enough exactly as they are. We’re reshaping the conversation around fit, style, and confidence for small-chested bodies everywhere. Come join the movement!

• Remote-first, flexible, and human: We’re a fully remote-first team that values autonomy, balance, and trust. Pepper is built for people who want to do their best work from wherever they thrive. Without sacrificing connection, collaboration, or career growth.
• Women-founded & Self-funded: As a women-owned company that never took traditional VC funding, we’ve scaled to eight-figure revenue through focus, creativity, and scrappiness. People come here to help rewrite what success looks like in DTC, and to build alongside a team that loves breaking the “rules” of how startups should grow.
• Mission-driven with real impact: Everything we do is rooted in empowering small-chested people to feel confident and celebrated. Our mission shapes our products, our culture, and our decisions, from inclusive design to responsible manufacturing and community giving. Joining Pepper means using your work to make the world a little more comfortable, confident, and kind.

Pepper is seeking a strategic, customer-obsessed, DTC-first Director of Merchandising to drive the assortment and commercial strategy behind Pepper's next stage of growth across intimate apparel, swimwear, and activewear. As Director of Merchandising, you will lead assortment strategy and shape the pricing and inventory recommendations behind every season. You will translate customer insight, sales data, and market opportunity into a focused, profitable line, and lead the merchandising side of the go-to-market process in partnership with Design, Brand Marketing, Ecommerce, Sourcing, and Product Development, including how the assortment shows up on site.

This role is a key strategic and analytical partner to the Founders and Executive Team. You will contribute to long-range planning, present product strategy and business performance to leadership each quarter, and help build the merchandising function as Pepper scales. You will be accountable for assortment performance against the KPIs outlined below, and you'll be hands-on in the data, the line plan, and the day-to-day of a lean, fast-moving team.

• Lead development of the seasonal and annual line plan that delivers Pepper's revenue and growth goals, including category roles, core versus newness, and recommendations on where to grow, test, or exit.
• Own line planning execution: number of styles, colorways, and sizes by category and launch window.
• Build a strong core of best-sellers balanced with newness that drives customer acquisition and repeat purchase.
• Contribute to long-range planning with the Founders and Executive Team, translating company goals into multi-season category and assortment strategies.
• Monitor the competitive landscape and industry trends, and bring white-space and new category opportunities to leadership with a clear business case.

• Lead the merchandising side of the go-to-market process each season, including line reviews, product brief presentations, and seasonal launch planning.
• Partner with Design on seasonal creative direction, bringing customer and sales data into concept and line reviews.
• Represent the commercial and customer point of view in design decisions, including sales performance, fit feedback, and margin implications.
• Drive timely alignment between design and merchandising priorities, and bring a clear merchandising recommendation on the line to leadership.
• Manage the merchandising side of the product lifecycle, from concept through launch, reorder, and exit.

• Develop pricing strategy and architecture recommendations across the assortment, balancing profitability and customer demand, for final sign-off by the Executive Team.
• Partner with Product Development and Sourcing to set target costs and protect margin by style and category.
• Plan promotions and markdowns with Ecommerce and Marketing to protect full-price sell-through.

• Develop OTB recommendations, buy quantities, size curves, and reorder recommendations in partnership with Finance and Planning. The Director of S&OP has final ownership and decision-making authority for all buying decisions.
• Partner with Planning and S&OP in weekly business reviews to track sell-through, weeks of supply, and aged inventory.
• Drive action on slow sellers and chase opportunities on winners.

• Report on style, category, and colorway performance weekly and at the end of each season.
• Use sales data, returns and fit feedback, customer reviews, and surveys to shape future assortments.
• Share learnings with Design, Supply Chain, and Marketing so each season improves on the last.
• Present quarterly business and product strategy updates to leadership, and lead quarterly all-hands product presentations.

• Partner with Marketing and Ecommerce so product storytelling, presentation, and site merchandising reflect merchandising strategy across GTM and site, maximizing customer engagement and conversion.
• Define merchandising requirements for PDP content (imagery order, sizing and fit info, cross-sell and complete-the-look logic) with Ecommerce to support conversion.
• Partner with Product Development to hold merchandising deadlines on the product development calendar, and drive decisions and follow-through at milestone meetings.
• Serve as the product point of contact for cross-functional teams, providing product knowledge, assortment information, and product stories.

• Mentor and develop merchandising team members as the team grows.
• Help establish the processes, tools, and reporting the merchandising function needs to scale with the business.
• Stay hands-on in the data, the line plan, and day-to-day execution as a lean team.

• Lives in the NYC Tri-State area with the ability to collaborate in person with our Product Team at our NYC office as needed.
• 5–8 years in merchandising, preferably at a direct-to-consumer, apparel, or intimates brand, including experience leading assortment strategy for a category or brand.
• Must have DTC experience. Intimates or bra experience is a strong plus.
• Proven track record of owning commercial results: delivering revenue, margin, and inventory targets through assortment planning and pricing.
• Strong analytical skills, with hands-on experience in assortment planning, pricing, and margin management.
• Experience presenting strategy and business performance to senior leadership and influencing decisions across functions.
• Experience leading, mentoring, or developing team members.
• Experience partnering closely with design teams; a strong product eye is a plus, though this role does not own creative direction.
• Understanding of fit, construction, and product development processes.
• Comfortable setting strategy and rolling up your sleeves in a lean, fast-moving team.
• Passion for Pepper's mission and customer

• Curiosity 🤔: We’re relentless in our quest to understand the community we serve. We’re challengers who ask questions, pursue perspectives, and set the new standard.
• Resilience 🌊: We embrace the ups and the downs, learn from our mistakes, and courageously persevere to achieve our goals.
• Community 🤝: We champion each other the same way we champion our customer. We do big things together and are passionate about what we do, and how we do it.