Director of Finance - Remote

About Proper Cloth

Proper Cloth is a fast-growing menswear brand specializing in made-to-order shirts, suits, jackets, and pants. A modern luxury brand, Proper Cloth combines exceptional craftsmanship, custom fit, and concierge-level service for a fundamentally better way to buy men’s clothing.

Our unique approach, anchored by a best-in-class ecommerce platform and supply chain for custom clothing, gives Proper Cloth a clear advantage in the men’s luxury space. Today, Proper Cloth employs more than 100 people and operates physical showrooms in New York, Washington, D.C., and Chicago.

Growing over 30% in 2025, Proper Cloth continues to outperform the industry. In 2026, we are focused on elevating product quality further, strengthening and unifying the brand identity, further improving our high-touch sales experiences, continuing to improve our standard sizing, and opening two additional U.S. locations.

Proper Cloth is a highly collaborative, detail-driven team that values craftsmanship, ownership, and continuous improvement. We have a solid foundation today and this role is an exciting opportunity is to help shape the next phase of a category-defining brand.

The Role

Proper Cloth is seeking a Director of Finance to own and elevate the company’s operational finance and accounting function. This role will be responsible for ensuring financial accuracy, discipline, and clarity across the organization-while serving as a thought partner to department leaders as they evaluate plans, investments, and operational changes.

This is a senior, hands-on role for someone who can manage accounting outcomes, ensure the financial plumbing works reliably, and translate financial data into clear, actionable insights for teams across the company.

What You’ll Do

• Own and Improve Accounting Operations
• Manage the accounting function (internal team and/or external partners)
• Ensure accounting processes remain up to date, documented, and continuously improving
• Maintain clean, consistent expense categorization and a well-structured chart of accounts
• Ensure financial data pipelines and integrations remain accurate and reliable
• Own the accuracy of financial reporting across P&L, balance sheet, and cash flow
• Ensure Bills Are Paid
• Own the accounts payable process and controls
• Manage the people/vendors responsible for paying bills, wires, and ACH payments
• Ensure all payments are made accurately and on time
• Establish clear approval workflows and payment policies
• Deliver Department-Level Financial Clarity
• Build and maintain department-level P&Ls and cost reporting
• Help departments understand their costs and unit economics, for example:
• CX team costs and unit economics
• Photography team unit economics
• Showroom profitability by location
• Present financial information in clear, digestible formats that department leaders can use
• Track trends over time and help teams understand what’s driving changes
• Act as a Thought Partner to CEO and Department Heads
• Partner with department leaders to evaluate plans, experiments, and operational changes
• Help think through tradeoffs, ROI, and cost implications of decisions
• Provide financial perspective on headcount changes, tooling investments, and process improvements
• Support leadership in making data-informed, economically sound decisions
• Support team leaders in vendor contract negotiations
• Support leadership in budgeting and projections

Why Proper Cloth

• A senior role with real ownership and impact
• Direct exposure to company leadership and decision-making
• A thoughtful, detail-oriented culture that values rigor and clarity
• The opportunity to help build scalable financial infrastructure during a key growth phase
• Competitive compensation and benefits

Location: New York, NY (Hybrid)

Reports to: CEO

Salary: $200k

Requirements

• 8-12+ years of experience in finance, accounting, or operational finance roles
• Experience owning or managing accounting functions (including AP, close, and reporting)
• Strong understanding of cost accounting and operational finance
• Proven ability to translate financial data into clear insights for non-finance stakeholders
• Comfortable managing processes, systems, and people (not just financial models)
• Strong judgment, attention to detail, and follow-through
• Collaborative mindset and low ego; comfortable partnering closely with operators
• Experience in ecommerce, retail, consumer brands, or inventory-heavy businesses is a plus.

Benefits

• Competitive 401(k)
• Comprehensive benefits (medical, dental, vision)
• Access to OneMedical Membership
• Generous clothing allowance and discount
• Salary: $200k