Regional Sales Development Representative

Wayfair is a leading global e-commerce company specializing in home goods and furnishings. Established as one of the world's largest online destinations for home products, Wayfair is renowned for its commitment to innovation, technology, and creative solutions in the retail space. Headquartered in Boston with operations spanning warehouses, offices, and fulfillment centers worldwide, the company continues to advance the way people shop for their homes. Its culture embraces diversity, values unique perspectives, and fosters a community where every voice and viewpoint is respected and celebrated. Wayfair is dedicated to providing equal employment opportunities and fostering an inclusive workforce where innovation and collaboration drive success.

Wayfair Professional, the B2B division of Wayfair, focuses on delivering tailored procurement solutions for businesses, ranging from boutique hotels and luxury homes to restaurants and multifamily properties. Since 2012, Wayfair Professional has simplified the process of sourcing furniture, fixtures, and décor by offering fast, reliable, and value-driven services that cater specifically to the needs of business clients.

The Regional Sales Development Representative (RSDR) role is a dynamic and pivotal sales position based in Chicago, IL, designed to foster top-of-funnel growth within the local market. This field sales role, combined with virtual engagement, is centered on cultivating relationships, driving enrollment, and supporting the onboarding of new business customers to the Wayfair Professional program. The RSDR operates through consistent, high-quality weekly outreach efforts both in person and virtually, using company-provided leads and self-sourced prospects to penetrate local business markets effectively.

In this role, the RSDR is tasked with engaging directly with key decision-makers in target verticals, educating prospects on the advantages of the Wayfair Professional program, and facilitating pipeline growth for the wider sales organization. Collaboration is a key aspect of the role, requiring the RSDR to coordinate closely with retail store employees, store leadership, in-store designers, and the Regional Business Account Manager to create a seamless customer experience from prospecting through onboarding.

Ideal candidates possess a strong sales mindset and are enthusiastic about community engagement, prospecting, and relationship building. They should be confident in navigating procurement discussions, resilient in the face of rejection, and capable of positioning Wayfair as a long-term supply chain partner rather than simply a product vendor. Success in this role depends on proactive outreach, strong organizational skills, clear communication of value propositions, and the ability to represent the Wayfair brand with professionalism and energy.

This position offers an annualized On Target Earnings (OTE) estimated at $75,000 to $95,000, which includes base pay and a monthly variable compensation plan with an on-target variable of approximately $4,000 per month. Actual compensation may vary by geographic location, experience, skills, and overall performance. The role requires local travel within a 50-mile radius of Chicago, providing diverse opportunities to connect with the business community and expand Wayfair's professional network. This position is ideal for sales professionals with 2 to 3 years of outbound sales experience, particularly those with a background in B2B, trade, or business development environments, looking to thrive in a community-facing sales role that combines in-person and virtual activities.