B2B Outbound Sales Manager

Wayfair; Chicago (IL); On-site; USD 82,000 - 86,000; Full time

Job summary

Wayfair is seeking an Outbound Sales Manager in the United States to lead and develop a team of outbound sales representatives. You will be accountable for performance, coaching, pipeline health, and day-to-day execution, translating priorities into actions and coaching customers conversations to improve outcomes.

Your role centers on driving sales execution, analyzing performance data, and guiding team actions.

Qualifications

• Experience leading, coaching, or developing a sales team.
• Proven track record in driving sales execution and achieving goals.
• Ability to analyze performance data and guide actions.
• Strong coaching and communication skills.

Responsibilities

• Lead, coach, and develop a defined team of outbound sales representatives.
• Set clear expectations and help the team meet sales, productivity, quality, and customer-outcome goals.
• Review performance trends and translate insights into coaching actions.
• Manage pipeline health and support reps with deal strategy and follow-through.
• Foster a team environment with clear priorities and timely feedback.
• Support new-hire onboarding and ramp, ongoing skill development, and performance conversations.
• Communicate results, risks, and recommendations to sales leadership; address issues with evidence.
• Partner with cross-functional teams to resolve customer or operational issues.

Skills

Sales leadership

Coaching

Data-driven decisions

CRM experience

Communication

Collaboration

Travel readiness

Tools

CRM software

Job description

Compensation

The estimated total compensation for this role ranges from $82,000 to $86,000, which includes a base salary range of $58,000 to $62,000, alongside a performance-based bonus of $24,000 per year. Please note: The base salary portion of this package is location-dependent and may be adjusted based on the cost of labor in your primary work region. We will provide a specific breakdown tailored to your location during the first interview.

Role summary

We are looking for an Outbound Sales Manager to lead and develop a team of Outbound sales representatives. In this role, you will be accountable for your team’s performance, coaching, pipeline health, and day-to-day execution. You will turn business priorities into clear actions, help representatives improve their sales skills and customer conversations, and use performance insights to address opportunities and risks early.

What you’ll do

• Lead, coach, and develop a defined team of outbound sales representatives through weekly 1:1s, call reviews, in-the-moment support, and ongoing feedback.
• Set clear expectations and help the team deliver against sales, productivity, quality, and customer-outcome goals.
• Review performance and activity trends, identify root causes, and turn insights into focused coaching and team actions.
• Manage pipeline health by reviewing opportunity quality, customer context, next steps, aging, and handoffs; support reps with deal strategy and follow-through.
• Build a team environment where people understand priorities, receive timely feedback, are recognized for strong contributions, and can raise issues early.
• Support new-hire onboarding and ramp, ongoing skill development, and appropriate performance or attendance conversations.
• Communicate team results, risks, and recommendations to sales leadership; escrow issues early with relevant evidence and a proposed path forward.
• Partner with cross-functional teams to resolve customer or operational issues and implement approved process and tooling changes.
• Identify recurring workflow challenges and contribute practical improvements that make team execution more effective and consistent.

What you’ll bring

• Experience leading, coaching, or developing a sales team, or equivalent experience demonstrating readiness for people leadership.
• A track record of driving sales execution and holding yourself and others accountable to clear goals.
• Ability to use performance data, CRM or pipeline information, and customer interactions to identify trends and guide action.
• Strong coaching and communication skills, including the ability to give direct, constructive feedback and adapt your approach to different people.
• Sound judgment in prioritizing competing needs, resolving day-to-day issues, and knowing when to involve leadership or partner teams.
• Strong organization and follow-through, with the ability to manage recurring coaching, pipeline, and operational responsibilities.
• A collaborative, customer-focused approach and interest in improving team processes over time.
• Willingness and ability to travel at least twice a year for team alignment, training, and leadership meetings.

How success will be measured

• Team performance and execution against applicable sales and quality goals.
• Rep skill growth, coaching consistency, and effective support for new‑hire ramp.
• Healthy pipeline practices, accurate opportunity context, and dependable next‑step follow‑through.
• Early identification and resolution or escalation of risks and operational blockers.
• Clear communication, effective partnership, and sustained improvements to team execution and customer experience.

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.

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.

State Specific Disclosures

Applications for this position are accepted on an ongoing basis, and the role will remain open until a suitable candidate is identified. We encourage interested applicants to apply as soon as possible, as we will review applications and conduct interviews on a rolling basis.