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.

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.

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