Proper Cloth

Compensation

Full Description

Proper Cloth is a fast-growing menswear brand specializing in made-to-order shirts, suits, jackets, and pants. A true 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 VP of Operations to own and lead the day-to-day operational execution of the business. This role will oversee Logistics & Fulfillment, Virtual Support, and Showrooms, and be responsible for ensuring that Proper Cloth consistently delivers a high-quality, reliable, concierge-level experience to customers. Reporting directly to the Founder & CEO, the VP of Operations will act as a senior operating leader and trusted thought partner, translating company priorities into disciplined execution, coaching team leaders, and ensuring teams are staffed, supported, and performing at a high level. This is a broad, people-centered leadership role for someone who combines strong operational judgment, analytical thinking, and exceptional people skills. What You’ll Do Improve Systems and Processes Think holistically about operational systems and workflows and how to consistently deliver the best possible customer experience Improve reporting and visibility into operational performance Communicate clearly and proactively to the CEO on what’s working, what’s changing, and what needs attention Lead and Develop Operational Leadership Directly manage and coach senior leaders across operational functions including: Showrooms, Fulfillment, Buying, In-House Tailoring, Virtual Support, and Virtual Sales Set clear expectations, priorities, and accountability across teams Support leadership development and handle escalated people issues with sound judgment and empathy Own Operational Execution and Service Levels Ensure core service metrics are consistently met or improved, including: Identify operational gaps and drive durable fixes—not just short-term workarounds Translate Strategy into Execution Partner closely with the CEO to shape operational strategy and priorities Turn high-level direction into clear plans, follow-through, and measurable progress Ensure teams stay focused on the most important initiatives and drive lasting improvements Manage Staffing and Capacity Planning Review operations regularly to ensure teams are staffed appropriately Partner with leaders on hiring plans, org structure, and role design Balance speed and service quality with costs Location: New York, NY (Hybrid) Reports to: CEO Salary: $250k 10+ years of experience in operations, service, retail, or multi-site leadership roles Proven experience managing senior leaders across multiple functions Excellent people leadership skills—supportive, direct, and inspiring Excellent analytical skills with the ability to make sense of complex data Ability to think in systems and scale processes thoughtfully Strong judgment, ownership mindset, and follow-through Experience in ecommerce, retail, consumer services, or hospitality-driven businesses is a plus but not required. Competitive 401(k) Generous clothing allowance and discount Comprehensive benefits (medical, dental, vision) Access to OneMedical Membership