VP Brand
Pepper · United States
- Hybrid
- Full-time
- $250,000 / year
- United States
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Job highlights
- Lead brand strategy and storytelling for DTC apparel.
- Elevate positioning and deepen community connection.
- Drive business impact through compelling narratives.
- Manage creative, content, and integrated campaigns.
- Build and lead a high-performing marketing team.
About the role
About Pepper
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.
The Opportunity: VP Brand
This is where you come in. We’re looking for a highly strategic and creative 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 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 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 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
- Manage Creative and the development of 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 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 strategy or marketing, including at high-growth ad agencies
- Experience in women’s apparel strongly preferred
- Proven 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 and customer experience optimization
- Strong brand 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.
Key skills/competency
- Brand Strategy
- Content & Storytelling
- Integrated Go-to-Market & Campaigns
- Influencer, PR, Social, & Community Management
- Team Leadership
- E-commerce Marketing
- Brand Positioning
- Creative Direction
- Data Analysis
- Marketing Planning
Skills & topics
- VP Brand
- Brand Strategy
- DTC Marketing
- E-commerce
- Content Marketing
- Storytelling
- Campaign Management
- Influencer Marketing
- Public Relations
- Social Media Marketing
- Community Management
- Apparel Industry
- Remote Work
- Leadership
- Creative Direction
- Marketing Executive
How to get hired
- Tailor your resume: Highlight your 10+ years of brand strategy and marketing experience, focusing on high-growth DTC and women's apparel.
- Showcase leadership: Emphasize your proven ability to lead high-performing, collaborative, and creatively ambitious teams.
- Quantify impact: Provide examples of how you've driven business growth and optimized customer experiences through brand storytelling and data.
- Express mission alignment: Clearly articulate your passion for Pepper's mission, body positivity, and empowering women.
- Review the application process: Visit the provided Workable link to understand specific application steps and requirements.
Technical preparation
Behavioral questions
Frequently asked questions
- What is the work arrangement for the VP Brand role at Pepper?
- The VP Brand position at Pepper is a fully remote role, allowing you to work from anywhere within the U.S. This aligns with Pepper's remote-first, flexible, and human-centric work culture.
- What is the expected salary range for the VP Brand position at Pepper?
- The expected salary for the VP Brand role is between $230,000 and $275,000 annually. However, the final offer will be determined by factors such as your experience, skills, and location.
- What are the key responsibilities of the VP Brand at Pepper?
- The VP Brand will lead brand strategy, elevate positioning, deepen community connection, and drive business impact through storytelling. Key responsibilities include overseeing content, integrated campaigns, influencer/PR/social strategies, and team leadership.
- What kind of experience is Pepper looking for in a VP Brand candidate?
- Pepper seeks candidates with 10+ years of brand strategy or marketing experience, preferably in women's apparel and high-growth DTC environments. Strong leadership, analytical rigor, and a passion for Pepper's mission are essential.
- How does Pepper foster a positive work environment for its remote team?
- Pepper fosters a positive work environment through its remote-first approach, valuing autonomy, balance, and trust. They prioritize connection, collaboration, and career growth while maintaining a fun, energetic, and creatively ambitious culture.
- What are Pepper's core values that shape their culture?
- Pepper's core values are Curiosity, Resilience, and Community. These values drive their quest to understand their customers, persevere through challenges, and champion each other and their community.
- How does Pepper approach diversity and inclusion in its hiring process?
- Pepper is an equal opportunity employer committed to making employment decisions based on merit. They prohibit unlawful discrimination and consider qualified applicants with criminal histories in accordance with local ordinances.
- What are some of the benefits offered to employees at Pepper?
- Pepper offers robust health benefits (including 100% company-covered medical, vision, dental), a company-matched 401K, generous PTO, paid parental leave, a monthly wellness stipend, and an annual company-wide offsite.