Senior Associate, Training & Onboarding

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