Director of Finance

About Proper Cloth

Proper Cloth is a fast-growing menswear brand specializing in made-to-order shirts, suits, jackets, and pants.

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.

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.

• 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

• 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

New York, NY (Hybrid)

CEO

$200k

• 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.

• Competitive 401(k)
• Comprehensive benefits (medical, dental, vision)
• Access to One Medical Membership
• Generous clothing allowance and discount