‍Nice 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.

We’re looking for a highly strategic and creative VP of Brand Creative to lead Pepper into its next chapter by elevating our positioning, deepening emotional connection with our community, and driving business impact through brand storytelling that moves her to buy more and more often. You will own content and storytelling across launches, collections, and seasonal moments, ensuring creative both elevates the brand and performs commercially. This role will inspire creativity, inject more brand magic, and turn emotional connection into measurable growth.

This is a high-impact, executive-level role partnering closely with the Co-founders/CEO and the Leadership team to serve as the creative and strategic force behind brand, content, and community. You understand 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 & Creative Strategy

• In collaboration with founders, evolve Pepper’s long-term brand vision, positioning, tone, and aesthetic as we scale into new categories, customer segments and expand channels
• Translate merchandising vision, product strategy, product benefits, fit innovation, and line plans into clear, compelling creative narratives that drive demand and conversion
• Own the marketing plan across launches, collections, and seasonal moments, ensuring creative both elevates the brand and is commercially effective.
• Serve as the ultimate brand steward, ensuring consistency and quality
• Oversee creative briefs, campaigns, and visual identities that are memorable, consistent, and performance-driven
• Lead development of all creative assets including copy and art in a way that reflects our brand values and inspires deeper engagement and meets goals
• Define and track brand creative performance metrics (awareness, engagement, perception); use insights and data to inform decisions and iterate on strategy
• Develop and maintain brand guidelines, toolkits, and systems for internal and external use

Content & Storytelling

• Build storytelling frameworks that move her from single-purchase to multi-category shopper, increasing frequency and basket size.
• Own the brand content roadmap across channels and oversee the creation of high-performing, on-brand content across site, owned, paid, and earned channels.
• Drive the use of customer insights, data, and analytics to develop emotionally resonant stories and optimize performance of content

Integrated Go-to-Market & Campaigns

• Lead cross-functional, organized, cohesive go-to-market campaigns and commercialization strategy for product drops, seasonal moments, and key 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.
• Define and own the integrated marketing calendar that aligns relevant storytelling with strategic business objectives, product launches, and community initiatives

Influencer, PR, Social, & Community

• Set the vision and strategy for Pepper's earned media strategy that builds cultural relevance and resonance including influencer, PR, social, and community as integrated growth and brand engines, driving earned ensuring all storytelling positions Pepper as the category leader and a powerful advocate for women feeling perfectly enough.
• Identify, structure, and scale high-impact brand partnerships and community collaborations that expand awareness and trust through recommendation-led channels.

Team Leadership & Culture

• Build, mentor and develop a high-performing team
• Set high creative standards while balancing speed, quality, and scalability, owning the budgets and ensuring efficient use of resources aligned to business priorities
• Champion cross-functional collaboration and serve as a connector across the org
• Help define, evolve, and amplify the creative spark and cultural magic that makes Pepper, Pepper

What we’re looking for.

• Deep passion for Pepper’s mission, brand, and impact, with a genuine commitment to advancing body positivity and helping women feel confident
• 10+ years of experience in brand, creative, or design leadership roles, including at high-growth creative agencies
• Experience in women’s apparel or intimates strongly preferred
• Proven experience leading high-performing creative 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 and customer experience optimization
• 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 manner
• Experience reporting into 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 mission

The 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 $230,000-275,000, 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.

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