Director of Planning

Reports to: Chief Financial Officer 

Location: Remote in U.S 

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.

We're looking for a strategic and data-driven Director of Planning to own inventory planning, purchasing, and sales planning end to end. This is a chance to build the planning function that gets us to our next stage of growth: the forecasting methodology, the buy process, the S&OP cadence, and the reporting that lets leadership see risk early.

In this role, you'll move fluently between detail and strategy, digging into SKU and size-level performance, customer behavior, trend patterns, lead times, and supply risk. You'll work across Product, Marketing, Finance and Operations to answer the questions that shape our business: which categories deserve the biggest bets, where we're exposed, and how much risk we can afford to take.

• Build bottom-up forecasts at the SKU, color, and size level across seasonal launches, core replenishment, and new category expansion, with methodology that handles how products actually behave: launch ramps, replenishment curves, cannibalization, and demand decay
• Partner with Marketing and Merchandising to build comprehensive goals and buys to support promotional activity, launches, and acquisition trends 
• Translate forecasts into buy plans and vendor production plans that balance in-stock rates, inventory productivity, cost, and cash, and set the targets that govern them: weeks of supply, safety stock, reorder points, and inventory health by category
• Own the risk work — scenario and contingency planning inside real constraints like capacity, lead times, and MOQs — and establish forecast accuracy as a key metric that improves over time

• Partner with Merchandising on assortment architecture: how wide we go, how deep we buy, which styles carry the business and which are there to round out the line
• Own size curve strategy across categories, which is uniquely consequential in a business built on fit
• Align inventory to product lifecycle from launch through growth, replenishment, and markdown
• Allocate inventory across DTC, marketplaces, Amazon, and wholesale based on channel demand and unit economics, including return rates

• Design and run our S&OP process, aligning inventory efficiency, product sales forecasting by style, and inventory health and turn 
• Act as the connective tissue between Marketing, Design, Merchandising, Finance, Production, and Sourcing, and bring clear recommendations to executive discussions on inventory investment, capacity, and risk
• Build the dashboards and reporting that make the business legible: forecast accuracy, fill rate, inventory turns, stockouts, excess inventory, and service levels
• Act as a strategic thought partner to executive leadership on inventory investment, capacity planning, growth opportunities, and operational risk

• Sales and unit forecast accuracy
• In-stock rate and fill rate
• Inventory turnover
• Weeks of supply
• Gross margin impact
• Stockout and excess inventory reduction

• 8-12+ years of inventory planning experience displaying career progression, leadership and profit optimization
• Must have experience in DTC or vertically designed products with end-to-end inventory planning ownership for apparel, intimates, or other size intensive consumer products
• Strong understanding of apparel planning fundamentals including size curves, replenishment models, lifecycle planning, and inventory optimization
• Advanced analytical and financial modeling skills; experience with planning systems is preferred
• Strong leadership, communication, and cross-functional collaboration capabilities
• Proven track record of building scalable planning processes in high-growth environments preferred

• 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.