Strategic Finance Associate

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

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 moment and outfit 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 in 2017, and has since grown into a global community of millions of women united by a mission of inspiring 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.

This is where you come in.

We are seeking a highly analytical and operationally minded Strategic Finance Associate to support financial planning and business performance analysis. Reporting to the CFO, this role will serve as a key cross-functional partner to Marketing, Merchandising, Operations and Executive Leadership, helping drive visibility into business performance, identify risks and opportunities, and support execution against company priorities.

The ideal candidate brings strong financial and analytical capabilities, intellectual curiosity, and a proactive approach to problem-solving. They are comfortable navigating ambiguity, synthesizing complex data into clear recommendations, and operating in a fast-paced environment where balancing strategic thinking with operational execution is critical. This individual should be equally comfortable diving into details while maintaining a broader understanding of how decisions impact the business holistically.

Financial Planning and Analysis

• Build and maintain consolidated financial model and own the monthly rolling forecasts, ensuring we stay ahead of risks to growth and profitability targets
• Partner with CFO to shape annual operating and long-range plans by serving as the lead on assumptions builds and scenario outputs, including recommending targets and trade-offs 
• Drive the month-end close processes with Accounting team; build and distribute timely monthly financial packages to leadership
• Run quarterly OpEx reviews with department leads to track spend against annual targets, surfacing risks and opportunities against budgets
• Own forecast accuracy and present informed narrative around pacing against goals

Revenue Strategy and Analysis

• Manage weekly performance reporting to business teams and drive underlying analyses to identify key performance drivers with cross-functional partners
• Lead revenue forecasting and driver analysis across DTC, wholesale, and marketplace channels
• Analyze customer cohorts, retention, AOV, CAC, and LTV and inform spend guardrails
• Build ad-hoc analyses to evaluate promotional strategy and opportunities and make informed recommendations to influence decisions in partnership with Growth & Retention teams

Cross-Functional Collaboration

• Translate complex financial data into clear recommendations for non-finance stakeholders
• Collaborate closely with Marketing, Product, Operations, Supply Chain, and Merchandising teams to improve financial visibility, reporting accuracy, and decision-making processes
• Drive the development of scalable processes and solutions for ease of information sharing and accurate reporting 
• Support reporting structures and tools that improve data adoption and transparency
• Own seamless integration between external finance support partners and the FP&A tech stack
• Support executive presentations, investor reporting, and strategic planning deliverables with clear analysis and concise storytelling

Location: Remote in U.SReports to: Chief Financial OfficerNice 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...

• 2–5 years of experience in strategic finance, investment banking, consulting, corporate finance, or related analytical roles
• Experience in retail, consumer products, e-commerce, or high-growth environments
• Experience presenting directly to executives and/or stakeholders
• Advanced proficiency in Microsoft Excel is required
• Familiarity with SQL, Tableau, PowerBI, or other BI/data visualization tools; working proficiency preferred
• Highly analytical and quantitative-minded; intellectually curious; a self-starter with the ability to manage projects independently
• Ability to manage multiple priorities and work independently in a fast-paced environment
• High attention to detail with strong problem-solving capabilities