Vice President, Boutique Development & Operations

VP, Boutique Development & Operations 
Location: North Olmsted, Ohio or Remote
Reports To: VP, Sales and Marketing
Position Type: Full-Time, Salary Exempt

About Teddy
Teddy is a leading luxury watch retailer known for its trusted expertise, elevated brand presence, and deep commitment to educating and inspiring the global watch-enthusiast community. We partner with the world’s most respected watch brands and deliver exceptional experiences across e-commerce, boutiques, concierge services, and our luxury watch premium content and education services.

Position Overview
The Vice President, Boutique Development & Operations will lead the development, opening, and ongoing performance of Teddy Baldassarre’s growing network of retail boutiques.

This role owns the full lifecycle of each boutique, from identifying and evaluating markets and specific locations through lease negotiation, design, construction, staffing, opening, and ongoing operations. The VP will work closely with the Senior Leadership Team, landlords, brokers, architects, general contractors, brand partners, and internal functional leaders to ensure each new boutique is delivered on time, on budget, and at the standard expected of Teddy Baldassarre and our brand partners. Once boutiques are operational, this leader will be responsible for building a high-performing retail organization, including recruiting, developing, and retaining Boutique Directors, establishing operating standards, managing performance, and ensuring each location achieves its annual sales, profitability, customer experience, and brand objectives.

The ideal candidate is both a builder and an operator: someone who can assess a market and negotiate a lease one day, manage a complex construction project the next, and coach a Boutique Director on sales performance, staffing, and customer experience the following week. The role requires strong commercial judgment, disciplined project management, exceptional leadership, and a deep understanding of premium or luxury retail.

Key Responsibilities
Boutique Development & Market Expansion
• Own the company’s boutique expansion strategy and execute against the annual and long-term retail development plan.
• Identify and evaluate potential markets, trade areas, shopping centers, streets, and individual retail locations using customer data, market demographics, competitive analysis, brand presence, traffic patterns, economics, and other relevant factors.
• Develop business cases and financial models for new boutiques, including projected sales, occupancy costs, capital requirements, operating expenses, profitability, and return on investment.
• Partner with brokers, landlords, and internal leadership to evaluate potential sites and determine which opportunities best meet Teddy Baldassarre’s strategic and financial criteria.
• Lead negotiation of letters of intent, leases, renewals, expansions, and other real estate agreements in partnership with legal counsel and the Senior Leadership Team.
• Maintain a pipeline of future retail opportunities and provide clear recommendations regarding market prioritization, timing, investment, and risk.

Boutique Design, Construction & Opening
• Own each new boutique from approved location through opening, serving as the primary internal leader responsible for keeping the project on schedule, on budget, and aligned with the approved vision.
• Lead cross-functional coordination among the Senior Leadership Team, architects, designers, general contractors, landlords, brand partners, vendors, technology teams, operations, marketing, finance, and other stakeholders.
• Manage project budgets, timelines, permitting, construction milestones, landlord obligations, tenant improvement allowances, procurement, fixtures, technology, security, merchandising requirements, and opening readiness.
• Identify risks early, resolve issues quickly, and maintain clear accountability across internal and external project teams.
• Establish a repeatable boutique-development process that improves speed, quality, consistency, and economics as the retail footprint grows.
• Lead pre-opening planning, including staffing, training, inventory readiness, operating procedures, merchandising, events, marketing coordination, and launch execution.

Boutique Leadership & Talent
• Recruit, hire, develop, and retain exceptional Boutique Directors for each location.
• Lead and coach Boutique Directors, establishing clear expectations for sales leadership, team development, customer experience, operational excellence, and financial performance.
• Partner with Boutique Directors to build and develop teams of high-performing Client Advisors and other boutique personnel.
• Develop succession plans and a strong pipeline of retail leadership talent as the boutique network expands.
• Establish a performance-oriented culture centered on accountability, hospitality, product expertise, teamwork, and exceptional client service.
• Ensure compensation, staffing models, scheduling, training, and development programs support both employee retention and business performance.

Boutique Operations & Performance
• Own overall performance of the boutique network against annual sales, profitability, customer experience, and operational objectives.
• Develop annual boutique plans and translate company goals into clear location-level targets and initiatives.
• Monitor and improve key retail metrics including sales, conversion, average transaction value, productivity, clienteling, customer data capture, repeat business, staffing efficiency, inventory productivity, and profitability.
• Conduct regular business reviews with Boutique Directors and establish action plans to address performance opportunities.
• Develop and continuously improve operating standards, policies, procedures, and best practices across all locations.
• Ensure consistent execution of brand standards, visual merchandising, customer experience, security, inventory controls, compliance, and other operational requirements.
• Partner closely with Marketing, Merchandising, E-commerce, Finance, Operations, Customer Service, and Brand teams to create a seamless omnichannel customer experience.
• Build the infrastructure, processes, and leadership capabilities required to successfully operate an expanding multi-location boutique network.

Strategic & Financial Leadership
• Develop annual operating and capital plans for the boutique organization in partnership with Finance and the Senior Leadership Team.
• Manage boutique operating expenses and capital investments with a strong focus on return on investment and long-term profitability.
• Provide leadership with regular reporting and recommendations regarding boutique 
performance, development projects, market opportunities, risks, and investment priorities.
• Develop strategic perspectives on luxury retail, competitive activity, customer behavior, real estate trends, and emerging opportunities that may influence the company’s retail strategy.
• Take ownership of other retail-related initiatives that materially improve the customer experience, economics, or scalability of the boutique business.

Qualifications
Required
• 10+ years of progressive experience in retail development, retail operations, real estate, multi-unit retail leadership, or a combination thereof.
• Demonstrated experience opening and operating physical retail locations, ideally within luxury, premium, specialty, jewelry, watches, fashion, hospitality, or another high-touch customer environment.
• Experience evaluating markets and individual retail locations using financial, demographic, competitive, customer, and real estate data.
• Experience negotiating retail leases, letters of intent, landlord agreements, and related commercial terms.
• Demonstrated experience managing retail design, construction, and store-opening projects involving architects, general contractors, landlords, vendors, and cross-functional internal teams.
• Experience directly leading multi-location retail operations and managing senior store or boutique leaders.
• Proven ability to recruit, develop, coach, and retain high-performing retail leadership and sales teams.
• Strong financial acumen with experience developing store-level business cases, budgets, forecasts, capital plans, and performance analyses.
• Strong understanding of retail economics and key performance indicators, including sales productivity, conversion, average transaction value, labor productivity, occupancy costs, inventory productivity, and four-wall profitability.
• Exceptional project-management skills and demonstrated ability to simultaneously manage multiple locations, construction projects, and operating priorities.
• Strong negotiation, communication, and relationship-management skills.
• Ability to operate effectively in a fast-paced, entrepreneurial environment with a high degree of ownership and accountability.
• Willingness to travel frequently to existing boutiques, prospective markets, construction sites, and partner locations (25%+).
• Bachelor’s degree or equivalent professional experience.

Preferred
• Experience in luxury watches, jewelry, luxury goods, or another premium retail category.
• Experience scaling a retail organization from a small number of locations into a larger multi-unit network.
• Existing relationships with luxury retail landlords, brokers, architects, contractors, or other retail-development partners.
• Experience working directly with luxury brands and navigating brand approval, design, merchandising, and operating requirements.
• Experience with both mall-based and street retail environments.
• Experience working within a founder-led, entrepreneurial, or high-growth company.
• Strong understanding of omnichannel retail and how physical boutiques can complement e-commerce, content, events, clienteling, and other customer acquisition channels.