Demo

Chief Sales Officer

Wayfair
Boston, MA Full Time
POSTED ON 5/28/2026
AVAILABLE BEFORE 6/26/2026
Wayfair Professional is growing rapidly (>20% YoY) and our sales program is crucial for accelerating this growth. We are looking for an ambitious sales leader to transform the organization and grow their revenue from $XXXM to $XB. This growth requires re-envisioning our end-to-end GTM approach, with an emphasis on leveraging Wayfair’s growing physical retail footprint and elevated customer experience with AI. You will build the engine that powers this growth.

What You’ll Do

Lead Wayfair Professional’s 200 person sales team, and associated enablement functions, through a transformation.

  • Align your strategic vision up to the CEO and board.
  • Work with the leadership team to set strategy for customer acquisition, activation, and retention across digital and physical channels.
  • Set the technical roadmap for Sales enablement - providing a personalized, omnichannel experience for our customers and a targeted, highly automated toolset for our sellers.
  • Champion a strong sales culture across the 200 person sales team and hire talent to align with your vision.

What You’ll Need

  • Demonstrated experience shifting a sales organization from inbound/reactive to a proactive, outbound "hunter" model at scale.
  • A track record of owning $1B revenue targets.
  • Excitement about driving adoption of new technologies (like GenAI) across a large, diverse sales force.

Assistance For Individuals With Disabilities

Wayfair is fully committed to providing equal opportunities for all individuals, including individuals with disabilities. As part of this commitment, Wayfair will make reasonable accommodations to the known physical or mental limitations of qualified individuals with disabilities, unless doing so would impose an undue hardship on business operations. If you require a reasonable accommodation to participate in the job application or interview process, please let us know by completing our Accomodations for Applicants form.

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About Wayfair Inc.

Wayfair is one of the world’s largest online destinations for the home. Whether you work in our global headquarters in Boston, or in our warehouses or offices throughout the world, we’re reinventing the way people shop for their homes. Through our commitment to industry-leading technology and creative problem-solving, we are confident that Wayfair will be home to the most rewarding work of your career. If you’re looking for rapid growth, constant learning, and dynamic challenges, then you’ll find that amazing career opportunities are knocking.

No matter who you are, Wayfair is a place you can call home. We’re a community of innovators, risk-takers, and trailblazers who celebrate our differences, and know that our unique perspectives make us stronger, smarter, and well-positioned for success. We value and rely on the collective voices of our employees, customers, community, and suppliers to help guide us as we build a better Wayfair – and world – for all. Every voice, every perspective matters. That’s why we’re proud to be an equal opportunity employer. We do not discriminate on the basis of race, color, ethnicity, ancestry, religion, sex, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, veteran status, genetic information, or any other legally protected characteristic.

Your personal data is processed in accordance with our Candidate Privacy Notice (https://www.wayfair.com/careers/privacy). If you have any questions or wish to exercise your rights under applicable privacy and data protection laws, please contact us at dataprotectionofficer@wayfair.com.

Salary.com Estimation for Chief Sales Officer in Boston, MA
$445,532 to $640,735
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