Senior Manager of Merchandising

Location: Remote in U.S (NY preferred) 

Reports to: Chief Product Officer 

Nice to meet you!

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

What we’re proud of:

• Remote-first, flexible, and human: We’re a fully remote-first team that values ownership, 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, profitability, 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.

This is where you come in: 

We are looking for a Senior Manager of Merchandising who is obsessed with data, motivated by insights, and energized by using those insights to influence customer behavior through product assortment and presentation. This candidate thrives on solving puzzles, is deeply passionate about understanding consumers and the competitive landscape, and excels at figuring out how to authentically drive profitable sales and repeat purchasing. They seamlessly combine data-driven insight with sales intuition—someone who naturally understands both our brand and the customers we serve. Candidates should be highly analytical and customer-centric, using insights to make meaningful, vertically designed assortment adjustments across our omnichannel marketplaces that maximize sales, profitability, retention, and lifetime value (LTV).

This role reports directly to the Chief Product Officer and is responsible for driving the day to day execution of merchandising strategy, ensuring alignment across teams, and delivering results within established strategic goals. The Senior Manager acts as a key connector across product development, production, planning, marketing, brand, and ecommerce teams, ensuring seamless execution of product positioning, assortment plans, and customer-facing initiatives.

Merchandising Execution & Assortment Planning: 

• Translate the Chief Product Officer’s strategic direction into actionable seasonal and annual merchandising plans by channel.
• Manage SKU and assortment architecture with a focus on profitability, inventory health, and aligning products to customer expectations.
• Partner with Planning to develop category forecasts, SKU productivity targets, and optimize in-season performance.
• Use data and customer insights to make in-season adjustments that drive revenue, margin, and overall results.
• Identify whitespace opportunities in products and presentations within brand and product guidelines.
• Track competitor activity and translate insights into actionable opportunities related to assortment, colors, fabrics, styles, curated edits, trends, and pricing.

Cross-Functional Collaboration: 

• Partner with Marketing, Growth, Operations, Ecommerce, and Product to ensure cohesive go-to-market execution aligned to sales and merchandising goals.
• Maintain alignment across teams on timelines, inventory, product priorities, and authentic brand storytelling.
• Build visual and analytical tools to support merchandising execution and cross-functional alignment.
• Manage, mentor, develop merchandising associates.

Omni Channel Site Merchandising (DTC and Marketplaces)

• Implement best-in-class site merchandising to maximize conversion, discoverability, and engagement.
• Drive seasonal and core sales to meet or exceed plan expectations.
• Leverage product reviews, graphics, video, and fit tips to highlight product benefits.
• Support PLP/PDP optimization, collections, and navigation to reinforce merchandising storytelling and sales plans.
• Identify asset needs (photography, styles, colors) and partner with ecommerce to fill gaps.
• Collaborate on A/B tests for content, pricing display, site pathing, and merchandising layouts.

Analytical Site Performance Leadership

• Partner to maximize site performance through analysis of sales, category & product trends, seasonality, launch timing, customer cohorts, and LTV behavior.
• Work with Marketing to align landing pages, sales plans, and campaign messaging.
• Analyze site metrics (conversion, click-through, search behavior, funnel drop-off), return/exchange data, and product journey insights to inform merchandising actions and improve LTV.
• Evaluate product combinations, bundles, and sets to optimize loyalty, retention, and customer lifetime value.
• Synthesize weekly reporting into quarterly summaries highlighting insights, recommended actions, challenges, and opportunities.
• Drive enhanced site presentation, copy, and assets to improve customer education and experience.
• Own customer calls, focus groups, and wear tests to unlock customer mindset and identify opportunities to improve products, increase purchase frequency, and grow LTV.

Requirements

What we're looking for.

• 6–8+ years of progressive experience in merchandising, assortment planning, buying, omnichannel sales, and cross-functional project management, ideally in DTC, consumer goods, or intimate apparel.
• Highly analytical, comfortable with complex datasets, forecasting, and translating insights into actionable, commercially impactful decisions.
• Deep customer empathy and experience in site merchandising and omnichannel or digital-native retail environments.
• Clear communicator, collaborative partner, and proactive problem-solver who inspires and elevates cross-functional work.
• Thrives in fast-paced, growth-oriented startup environments; self-motivated, curious, and eager to champion initiatives.
• Passionate about Pepper’s mission and products; bridges data, consumer insights, and merchandising expertise to drive inventory, planning, and growth outcomes.
• Connects customer-facing materials to backend actions, balancing analysis and execution, staying agile, confident, and thoughtful when prioritizing risk and cross-team impact.

Benefits

Perks.

• Robust health benefits including 100% company covered option for medical, vision, dental insurance, and supplemental insurance options
• Company matched 401K plan up to 3%
• Generous paid time off program including flexible PTO days, federal holidays, and sick days
• Flexible remote workplace
• Paid parental leave for qualifying employees
• Monthly wellness stipend
• Annual company-wide offsite
• Have a huge role in the growth of a company with a meaningful mission

Pepper values.

• 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.

Diversity

Pepper is an equal opportunity employer and makes employment decisions on the basis of merit. Pepper's policy prohibits unlawful discrimination based on race, color, religious creed, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy, or any other consideration made unlawful by federal, state, or local laws. It also prohibits discrimination based on a perception that anyone has any of those characteristics, or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful. Pepper will consider for employment qualified applicants with criminal history, including arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance.

What Personal Information We Collect

Professional, employment-related, or schooling information. Current or past job history, performance evaluations, and educational background, including grades and transcripts.

How We Use Your Information

For professional, internal analysis, or employment-related purposes, including job applications.

The expected salary for this role is $120,000-140,000, though the final offer will reflect several factors such as your experience, skills, and the role’s location and may be outside of this number. Candidates should expect offers that reflect their individual qualifications, experience, and location. The salary provided is directional and actual compensation may vary. At Pepper, we know that compensation is just one part of the package. That’s why we offer a robust total rewards package, including health and wellness benefits, remote work stipends, a generous flexible paid time off policy, product discounts, and more, that are designed to support your journey both inside and outside of work.