Director of Planning

Reports to: Chief Financial Officer Location: Remote in U.S 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.

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’re looking for a strategic, data-driven Director of Planning to own our end-to-end inventory planning strategy, purchasing, and sales planning. Reporting into the executive team, you will lead the company’s Sales & Operations Planning (S&OP) process, balancing demand forecasts, inventory investment, production capacity, and supply constraints to support profitable growth.

This role will build bottom-up forecasts rooted in SKU and size-level insights and translate those into sales plans by channel, inventory buys, and operational strategies that enable us to capture demand, scale new categories, and efficiently replenish our core business.

You’ll operate seamlessly between detail and strategy: diving into SKU and size-level performance, customer behavior, trend patterns, production lead times, and supply risks, while connecting those insights to broader business planning and growth objectives.

As a key cross-functional leader, you’ll partner closely with Marketing, Design, Merchandising, Finance, Production, Sourcing, and Supply Chain to align commercial demand with operational execution and ensure the business is positioned to scale effectively.

Own the company inventory sales plan forecast across seasonal launches, replenishment businesses, and new category expansion

Build and manage bottom-up forecasts at the SKU, color, and size level using historical performance, customer behavior, trend analysis, and business inputs

Develop forecasting methodologies that account for lifecycle dynamics including launch ramps, replenishment curves, cannibalization, and demand decay

Partner with Marketing and Merchandising to incorporate promotional activity, product launches, and customer acquisition trends into forecasts

Lead forecast reviews and continuously improve forecast accuracy across channels and categories

Supply Planning & Inventory Management

Translate strategic sales forecasts into inventory buy plans and vendor production plans that optimize in-stock rates, inventory productivity, freight optimization, warehouse storage, and cash flow

Own inventory targets including weeks of supply, safety stock, reorder points, and inventory health metrics

Balance forecasted inventory needs by category against operational constraints including production capacity, lead times, MOQ requirements, vendor capabilities, and raw material availability

Partner with sourcing and production teams to ensure timely replenishment and successful execution of product launches

Manage inventory risk mitigation, scenario planning, and contingency planning to reduce stockouts and excess inventory

S&OP & Cross-Functional Leadership

Lead the company’s Sales & Operations Planning (S&OP) process, aligning inventory efficiency, product sales forecasting by style, and inventory health and turn

Facilitate recurring cross-functional planning meetings and drive alignment on forecasts, risks, opportunities, and operational tradeoffs

Serve as the central point of coordination between marketing, operational, and financial teams

Own departmental planning objectives and communicate clear recommendations and perspectives during executive and cross-functional meetings

Act as a strategic thought partner to executive leadership on inventory investment, capacity planning, growth opportunities, and operational risk

DTC & Channel Optimization

Own in-stock rates and size-level availability to ensure a strong customer experience across e-commerce and marketplace channels

Optimize inventory allocation across DTC, marketplaces, Amazon, and wholesale partners based on demand signals and channel performance

Partner with Merchandising to align inventory with product lifecycle strategies including launch, growth, replenishment, and markdown optimization

Analytics, Systems & Process Improvement

Track and report on key metrics including forecast accuracy, fill rate, inventory turns, stockouts, excess inventory, and service levels

Build dashboards, reporting tools, and scalable planning processes that improve visibility and decision-making

Identify operational risks and opportunities early and recommend data-driven actions

Partner with leadership to implement and improve planning systems, forecasting tools, and operational workflows to increase efficiency and scalability

8-12+ years of inventory planning experience displaying career progression, leadership and profit optimization.

Foundation in bottoms up inventory management with both core and fashion styles managing lifecycle efficiencies across categories.

Experience with DTC or vertically designed products with end-to-end inventory planning ownership for apparel, intimates, or other size intensive consumer products preferred.

Strong understanding of apparel planning fundamentals including size curves, replenishment models, lifecycle planning, and inventory optimization

Proven experience leading end-to-end S&OP or Integrated Business Planning (IBP) processes

Experience balancing commercial demand with operational and supply chain constraints

Advanced analytical and financial modeling skills; advanced proficiency in Excel and planning systems

Strong leadership, communication, and cross-functional collaboration capabilities

Experience building scalable planning processes in high-growth environments preferred

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.

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

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 $150,000-180,000, 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.

Originally posted on Himalayas