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 role for someone who can build a disciplined commercial engine without losing what makes luxury watch selling special. The VP will own sales strategy, funnel management, CRM and clienteling, training, scripting, forecasting, execution, and optimization across channels. Just as important, this person must be a true watch person: passionate about horology with deep, practical knowledge of the industry, major brands, collections, specific references, positioning, and collector interests. Credibility with clients and the team will come from understanding the product as deeply as the sales process.

Key Responsibilities

Sales Leadership & Revenue Growth

• Own sales performance across digital inbound, concierge, boutiques, and event‑driven selling, with clear goals at the channel, location, team, and individual level.
• Build a scalable sales organization that converts inbound demand effectively today while developing stronger outbound, reactivation, referral, and relationship‑based selling capabilities over time.
• Coach sales leaders and frontline teams, establish performance standards, and create a culture of accountability, hospitality, product expertise, and continuous improvement.

Sales Process, CRM & Clienteling

• Own the end‑to‑end sales funnel, including lead routing, response time, follow‑up cadence, opportunity management, conversion, lost‑opportunity recovery, and repeat‑client development.
• Make CRM an active sales‑management and clienteling platform, with disciplined data capture, pipeline visibility, books of business, segmentation, reactivation, and measurable follow‑up.
• Develop and continuously improve scripts, talk tracks, outreach templates, and selling frameworks across phone, email, SMS, chat, appointments, events, and in‑store interactions.

Retail, Events & Omnichannel Execution

• Partner with Boutique Directors and Store Managers to maximize store sales, advisor productivity, conversion, average transaction value, repeat business, appointments, and clienteling.
• Build the commercial playbook for events and launches, including customer targeting, pre‑event outreach, appointment setting, on‑site selling, and disciplined post‑event follow‑up.
• Work closely with Marketing, E‑commerce, Merchandising, Customer Service, Operations, and Brand teams to remove friction and create a seamless client journey across digital and physical channels.

Training, Product Expertise & Enablement

• Build a consistent Teddy Baldassarre sales methodology and training program covering discovery, storytelling, product recommendation, objection handling, closing, follow‑up, and relationship development.
• Set a high bar for watch knowledge across the organization, ensuring sales teams can confidently discuss brands, collections, references, movements, complications, positioning, and competitive alternatives.
• Identify the behaviors of top performers, translate them into practical coaching and playbooks, and ensure managers consistently reinforce them.

Forecasting, Analytics & Optimization

• Own weekly, monthly, quarterly, and annual sales forecasting, using pipeline health and leading indicators to identify opportunities and risks early.
• Track and improve the metrics that drive revenue, including conversion, response time, pipeline value, sales productivity, average transaction value, repeat purchase behavior, and clienteling effectiveness.
• Continuously test and optimize staffing, lead routing, outreach, scripting, appointments, follow‑up, incentives, and other commercial levers; scale what works across the organization.

Candidate Profile

We are looking for a commercial leader who combines sophisticated sales management with authentic enthusiasm for watches. The right person can move comfortably from a pipeline review or forecast to coaching an advisor on how to position two references for a knowledgeable collector.

Required

• 10+ years of progressive sales leadership experience, ideally in luxury, watches, jewelry, specialty retail, e‑commerce, or another high‑touch, considered‑purchase environment.
• Deep passion for horology and strong working knowledge of the watch industry, including major brands, collections, specific references, product positioning, collector behavior, and competitive dynamics.
• Demonstrated success leading and developing high‑performing sales teams across multiple channels, locations, or customer touchpoints.
• Strong command of consultative and relationship‑based selling, particularly for high‑value purchases requiring trust, education, and long‑term client development.
• Proven ability to build and improve sales processes, CRM discipline, clienteling programs, sales training, scripting, and performance‑management systems.
• Strong analytical and forecasting capability, with the ability to translate funnel data and sales metrics into clear priorities and actions.
• Experience coaching both frontline sales professionals and sales managers, with a track record of improving conversion and productivity.
• Excellent communication, judgment, and cross‑functional leadership skills; able to operate effectively in a fast‑paced, founder‑led, entrepreneurial environment.
• Willingness to travel regularly to boutiques, customer events, brand meetings, and other company activities.

Preferred

• Experience leading both digital/inside sales and physical retail teams, including scaling a high‑volume inbound sales operation.
• Experience developing outbound, reactivation, referral, or proactive client‑development capabilities.
• Experience implementing or materially improving CRM, clienteling, sales‑enablement, or incentive programs in an omnichannel environment.

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.

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.