Wayfair
Senior Associate, Training & Onboarding
🇺🇸 Remote - US
🕑 Full-Time
💰 TBD
💻 Learning & Development
🗓️ July 4th, 2025
Edtech.com's Summary
Wayfair is hiring a Senior Associate, Training & Onboarding to enhance new hire success and foster continuous skill development within the Global Sales team. This role involves delivering dynamic training sessions, coaching new hires during ramp-up periods, collaborating with stakeholders to keep training content relevant, and tracking learning outcomes to improve effectiveness.
Highlights
- Facilitate onboarding, upskilling, and process change training for B2B and B2C sales teams through virtual and occasional in-person sessions.
- Coach new hires during nesting and ramp periods to identify and address skill gaps.
- Monitor training effectiveness using metrics like time to productivity, engagement, and knowledge retention.
- Collaborate with Learning Experience Designers and sales leaders to ensure accurate and timely content.
- Manage training logistics including scheduling, communication, and attendance tracking.
- Utilize virtual facilitation platforms such as Google Meet and Slack, and LMS tools.
- Require 2–4 years experience in training, onboarding, or sales enablement, preferably in sales or contact center environments.
- Strong facilitation, presentation, communication, and organizational skills required.
- Experience with performance coaching, onboarding program design, or content authoring tools (Articulate, Rise) is a plus.
- Engage in fostering an inclusive learning culture and may travel occasionally for in-person sessions.
Senior Associate, Training & Onboarding Full Description
Senior Associate, Training & Onboarding
Remote, US
Job Description
Training & Onboarding Senior Associate, Global Sales
As a Training & Onboarding Senior Associate for Wayfair’s Global Sales team, you’ll play a critical role in accelerating new hire success and enabling continuous skill development across our sales organization. You will facilitate engaging, high-impact learning experiences and serve as a trusted partner to sales leadership, ensuring our teams are equipped with the knowledge, skills, and tools to thrive.
What You’ll Do
- Facilitate dynamic training programs for adult learners—including new hire onboarding, upskilling/cross-skilling sessions, continuing education, and process change rollouts—across B2B and B2C sales teams.
- Deliver training through multiple modalities (virtual (primarily), in-person (occasionally), synchronous/asynchronous), utilizing materials and tools developed by the Learning Experience Design team.
- Coach during nesting and ramp periods, supporting new hires as they apply learning on the job, identifying skill gaps, and offering targeted follow-up.
- Monitor and measure learner success, using predefined metrics and checklists to track performance for a minimum of the nesting period and up to 60 days post-training.
- Track and report on metrics such as time to productivity, training satisfaction, learner engagement, and knowledge retention.
- Provide detailed learner insights to sales leaders, including strengths, development opportunities, and tailored coaching recommendations.
- Partner cross-functionally with Learning Experience Designers, SMEs, and sales stakeholders to ensure training content is accurate, relevant, and timely.
- Continuously improve training programs by logging trends, learner feedback, and common challenges; recommend updates to improve impact and learner retention.
- Manage training logistics and operations, including scheduling, communication, attendance tracking, and material preparation.
- Reinforce key concepts through small group coaching, shadow sessions, and performance observations.
- Stay current on learning trends in sales enablement, adult learning, and virtual facilitation to enhance delivery and learner engagement.
- Assist with light content design or updates in partnership with Learning Experience Designers—this may include refining facilitation decks, updating job aids, or contributing feedback to improve learner materials.
- Foster a culture of growth, inclusion, and positivity, modeling adaptability, collaboration, and customer-centric thinking.
- Champion an inclusive learning environment where all employees feel represented, respected, and supported.
- Travel as needed for in-person training, facilitation, workshops, and stakeholder engagement.
What You’ll Bring
- 2–4 years of experience in training, onboarding, sales enablement, or adult learning (sales or contact center environment preferred)
- Strong facilitation and presentation skills with experience leading adult learners across various levels and roles
- Confidence navigating ambiguity, adapting quickly to change, and managing multiple programs simultaneously
- A learner-first mindset with a bias for action and continuous improvement
- Excellent communication, collaboration, and organization skills
- Comfort working in a fast-paced, high-growth environment
- Familiarity with virtual facilitation platforms (e.g., Google Meet, Slack) and LMS tools
Nice-to-Haves
- Experience supporting both B2C and B2B sales teams
- Experience in performance coaching or onboarding program design
- Familiarity with content authoring tools (e.g., Articulate, Rise, or similar)
- Experience designing or editing learning content, such as slide decks, facilitator guides, or learner-facing materials
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.
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.
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