Vice President of Sales

Vice President, Sales
Location: North Olmsted, Ohio or Remote
Reports To: VP of Sales and Marketing
Position Type: Full-Time
Compensation: Base salary plus performance-based incentive

About Teddy

Teddy is a leading luxury watch retailer and content platform serving a global community of watch enthusiasts. We partner with many of the world’s most respected brands and serve clients across e-commerce, concierge, boutiques, and events.

The Opportunity

The Vice President of Sales will own performance across Teddy Baldassarre’s digital inbound and concierge teams, retail boutiques, and events. The mandate: maximize revenue by turning strong customer demand into exceptional client relationships, higher conversion, repeat business, and long-term customer value.

This is a hands-on leadership role for someone who can build and scale a disciplined, data-driven sales organization without losing what makes luxury watch selling special. The VP will own sales strategy, team development, funnel management, CRM and clienteling, training, forecasting, execution, and continuous optimization across channels. A strong command of CRM systems, including hands-on experience driving adoption, improving sales processes, and leveraging data to increase productivity and conversion, is essential.

We are looking for a proven sales leader with a track record of building high-performing teams, implementing scalable sales processes, and driving measurable revenue growth. Experience in B2B, SaaS, or other sophisticated, CRM-driven sales organizations is a strong plus, particularly for candidates who can bring best practices in pipeline management, sales coaching, accountability, and performance optimization into a luxury retail environment.

While prior watch industry experience is welcome, it is not required. More important is a genuine curiosity, enthusiasm, and willingness to develop a deep understanding of horology, luxury watch brands, and the collector community. The ideal candidate will combine commercial rigor with a passion for learning the product, building authentic client relationships, and embracing what makes Teddy Baldassarre unique.Key Responsibilities

Sales Leadership & Revenue Growth

• Own sales performance across digital inbound, concierge, boutiques, and events, establishing clear revenue targets and performance expectations at the channel, team, and individual level.

• Build and scale a high-performing sales organization that maximizes inbound demand while developing proactive outbound, reactivation, referral, and relationship-based selling capabilities.

• Recruit, develop, and coach sales leaders and frontline teams, establishing a performance-driven culture built on accountability, consultative selling, exceptional client experience, and continuous improvement.

Sales Process, CRM & Clienteling

• Take full ownership of CRM strategy, adoption, data integrity, and optimization, ensuring the platform serves as the central operating system for sales management, pipeline visibility, and client relationships.

• Own the end-to-end sales funnel, including lead qualification, routing, response times, follow-up, opportunity management, conversion, lost-opportunity recovery, and repeat-client development.

• Leverage CRM data, automation, segmentation, and reporting to improve sales productivity, strengthen clienteling, identify revenue opportunities, and increase customer lifetime value.

Retail, Events & Omnichannel Execution

• Partner with Boutique Directors and Store Managers to improve store performance, advisor productivity, conversion, average transaction value, appointments, and repeat business.

• Develop scalable sales playbooks for digital and physical retail, including event execution, product launches, proactive outreach, appointment setting, and post-event follow-up.

• Collaborate with Marketing, E-commerce, Merchandising, Customer Service, Operations, and Brand teams to create a seamless client journey and maximize commercial opportunities across channels.

Training, Product Expertise & Enablement

• Establish a consistent Teddy Baldassarre sales methodology and training program covering discovery, consultative selling, storytelling, product recommendations, objection handling, closing, and relationship development.

• Build structured onboarding, coaching, and performance-development programs that accelerate productivity, reinforce best practices, and establish consistent selling behaviors across teams.

• Partner with internal product experts and brand teams to develop watch knowledge and product confidence, ensuring advisors can effectively serve both first-time buyers and experienced collectors.

Forecasting, Analytics & Optimization

• Own sales forecasting and performance reporting, leveraging CRM data, pipeline health, and leading indicators to identify opportunities and risks early.

• Establish clear KPIs, dashboards, and a consistent operating cadence of pipeline reviews, performance meetings, and individual accountability to drive predictable revenue growth.

• Continuously test and optimize lead routing, staffing, sales processes, outreach, follow-up, incentives, and other commercial levers, scaling successful practices across the organization.

Required

• 10+ years of progressive sales experience, including significant responsibility leading, developing, and scaling high-performing sales teams.

• Demonstrated success managing teams of 10+ sales professionals, with direct accountability for meaningful revenue targets, conversion, productivity, and business growth.

• Proven ownership of CRM systems and sales processes, including pipeline architecture, adoption, data integrity, reporting, automation, forecasting, and ongoing optimization.

• Strong understanding of structured sales methodologies, pipeline management, lead qualification, follow-up discipline, and performance management.

• Track record of building scalable sales processes, coaching programs, accountability systems, and operating cadences that deliver measurable improvements in performance.

• Strong command of consultative and relationship-based selling, with the ability to apply proven sales practices to high-value, considered purchases and long-term client relationships.

• Strong analytical capabilities, including forecasting, funnel analysis, KPI development, and translating sales data into actionable priorities.

• Experience coaching both frontline sales professionals and sales managers, with demonstrated success improving team productivity, conversion, and individual performance.

• Excellent communication, judgment, and cross-functional leadership skills, with the ability to thrive in a fast-paced, founder-led, entrepreneurial environment.

• Genuine interest in horology and a willingness to invest in developing product knowledge, industry understanding, and appreciation for the luxury watch customer.

• Willingness to travel regularly to boutiques, customer events, brand meetings, and other company activities.

Preferred

• Sales leadership experience in B2B, SaaS, or other sophisticated, CRM-intensive sales organizations with established methodologies, pipeline discipline, and performance-management practices.

• Experience leading both digital/inside sales and physical retail teams, or demonstrated ability to transfer structured sales practices across different channels.

• Experience scaling a high-volume inbound sales organization, including lead distribution, speed-to-lead optimization, conversion improvement, and sales automation.

• Experience developing outbound, reactivation, referral, and proactive relationship-development programs.

• Hands-on experience with HubSpot, Salesforce, or comparable CRM platforms, including significant responsibility for implementation, optimization, automation, and sales reporting.

• Experience in luxury retail, watches, jewelry, specialty retail, or other high-touch, high-consideration consumer categories.

• Personal interest in watches, collecting, and horology, with enthusiasm for developing expertise in major brands, collections, movements, and the broader watch community.

Why This Role Matters

Teddy already has an engaged audience, trusted brand relationships, growing boutiques, and meaningful inbound customer demand. This role can build the sales system that connects those advantages – combining watch expertise, personal client relationships, disciplined execution, and modern sales management into a scalable growth engine. As the company expands, the VP of Sales can help shape a much larger digital inbound/outbound organization and the future of Teddy’s customer-facing sales model.

As a rapidly growing brand, we are always looking for smart and driven individuals to join our expanding team! Teddy Baldassarre is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We’re searching for individuals with a passion for solving challenges, a creative mindset, and ambitious goals with experience in Ecommerce, Operations, Creative, Photography and Videography, Marketing, Content, Social Media and Retail to help us drive initiatives and continue to grow our brand.