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Location: Remote in U.SReports to: CEORole type: Executive, Full-timeNice to meet you!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!What we’re proud of: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.This is where you come in. This is a rare opportunity to sit at the intersection of strategy and creativity and scale a brand with a clear, powerful mission and an unmistakable value proposition. We’re not just growing a business, we’re building a brand customers genuinely love, return to again and again, and proudly recommend and remember. There is real white space to push creativity, inject more brand magic, and turn emotional connection into measurable growth.We’re looking for a VP of Brand to lead Pepper into its next chapter by elevating our positioning, deepening emotional connection with our community, and driving business impact through brand storytelling and creative marketing that moves her to buy more and more often. The VP of Brand has the ability to translate merchandising vision and product strategy into clear, compelling creative narratives that drive demand and conversion. This leader will own the product storytelling framework across launches, collections, and seasonal moments, ensuring creative both elevates the brand and performs commercially.This is a high-impact, executive-level role partnering closely with the Co-founders/CEO, Merchandising and E-Commerce leaders, to serve as the strategic force behind brand, content, and community. Everything we put into the world – from our photoshoots to influencer content to go-to-market campaigns – will flow through this role, ensuring everything works in harmony to attract high-value purchasers, deepen retention, and fuel long-term growth. This is for someone who understands how to make a brand stand out in a crowded market, stand for a unique mission, and bring a bold and creative product vision to life, all while building a fun, energetic, and creatively ambitious culture that delivers against business goals. Brand StrategyIn collaboration with founders, evolve Pepper’s long-term brand vision, positioning, tone, and aesthetic as we scale into new categories, customer segments and expand channelsTranslate merchandising vision, product strategy, and line plans into clear, compelling creative narratives that drive demand and conversion.Own the product storytelling framework across launches, collections, and seasonal moments, ensuring creative both elevates the brand and is commercially effective.Ensure product benefits, fit innovation, and category leadership are communicated in ways that are emotionally resonant and easy for customers to understand and buy into.Serve as the ultimate brand steward, ensuring consistency across all customer touchpoints, channels, and teamsExecute brand strategy into creative briefs, campaigns, and visual identities that are memorable, consistent, and performance-drivenManage Creative and the development of all creative assets including design, copy, video, and photography in a way that reflects our brand values and inspires deeper engagement and higher order value.Define and track brand and creative performance metrics (awareness, engagement, perception); use insights and data to inform creative decisions and iterate on strategyContent & StorytellingOwn the brand content roadmap across channels, from website, organic social, paid media, email, influencer, ambassador, and affiliate programs.Drive the creation of brand guidelines, toolkits, and systems for internal and external use Build storytelling frameworks that move her from single-purchase to multi-category shopper, increasing frequency and basket size.Oversee the creation of high-performing, on-brand content across owned, paid, and earned channels.Drive the use of customer insights, data, and analytics to develop emotionally resonant stories and optimize performance of contentIntegrated Go-to-Market & CampaignsLead cross-functional, integrated go-to-market campaigns and commercialization strategy for product drops, seasonal moments, and key brand initiatives.Partner closely with Ecommerce to develop creative strategies that optimize the full customer journey, from first impression to product detail page to repeat purchase.Oversee creative for PDPs, landing pages, site storytelling, and merchandising moments to ensure clarity, consistency, and performance.Ensure a cohesive customer experience across creative, messaging, and media to maximize launch impact and long-term brand equity.Define and own the integrated marketing calendar that aligns relevant storytelling with strategic business objectives, product launches, and community initiatives Influencer, PR, Social, & CommunitySet the vision and strategy for influencer, PR, social, and community as integrated growth and brand engines, ensuring all storytelling positions Pepper as the category leader and a powerful advocate for women feeling perfectly enough.Drive our organic social strategy and execution, ensuring we’re building community while laddering up to growth goals.Identify, structure, and scale high-impact brand partnerships and community collaborations that expand awareness and trust through recommendation-led channels.Own the PR strategy and agency relationship, driving earned media strategy that builds cultural relevance and enduring brand credibility.Team Leadership & CultureBuild and lead a high-performing team; recruit, mentor, and develop top talent across copy, design, and contentSet high creative standards while balancing speed, quality, and scalability, owning the budgets and ensuring efficient use of resources aligned to business prioritiesChampion cross-functional collaboration, serving as a connector between brand, product, creative, and growthHelp define, evolve, and amplify the creative spark and cultural magic that makes Pepper, PepperRequirementsDeep passion for Pepper’s mission, brand, and impact, with a genuine commitment to advancing body positivity and helping women feel confident10+ years of experience in brand strategy or marketing, including at high-growth ad agencies Experience in women’s apparel or intimates is strongly preferredStrong portfolio demonstrating brand strategy, creative leadership, and executionProven experience leading high-performing teams and cultivating a work environment that is fun, energetic, collaborative, and creatively ambitious, while maintaining clear accountability to growth and performance goals.Deep understanding of ecommerce storytelling, PDP optimization, and customer journey design.Strong creative instincts paired with analytical rigor; comfortable using data, insights, and testing to inform creative strategy and optimize impact.Strong leadership presence and communication skills, with the ability to clearly articulate creative strategy, inspire teams, and align cross-functional partners.Organized and process-oriented with the ability to move fast in a thoughtful mannerExperience partnering closely with founders and executive teams, serving as a trusted thought partner who can both challenge and elevate the business through brand.Holds high standards for the brand and missionPepper 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.BenefitsRobust health benefits including 100% company covered option for medical, vision, dental insurance, and supplemental insurance optionsCompany matched 401K plan up to 3%Generous paid time off program including flexible PTO days, federal holidays, and sick daysFlexible remote workplacePaid parental leave for qualifying employeesMonthly wellness stipend Annual company-wide offsite Have a huge role in the growth of a company with a meaningful mission
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