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Sales Supervisor – Trainer
WMSales Training Supervisor overseeing sales training and effectiveness for WMHS in collaboration with sales leadership. Focused on coaching, evaluations, and continuous improvement initiatives.
Posted 4/24/2026full-timeChicago • Illinois • 🇺🇸 United StatesMid-LevelSenior💰 $96,690 - $117,150 per yearWebsite
Tech Stack
Tools & technologiesSFDC
About the role
Key responsibilities & impact- Deliver and facilitate sales effectiveness courses, new hire training, certifications, and ongoing development programs using a variety of delivery methods (virtual, in-person, blended)
- Conduct observations, ride-alongs/shadowing, and coaching sessions with sales managers and representatives to reinforce sales process adherence and skill development
- Evaluate training effectiveness through assessments, observation, feedback, and performance metrics; identify skill gaps and recommend targeted improvements
- Support sales managers by providing guidance, tools, and coaching resources to improve individual and team performance
- Supervise the execution of assigned sales training programs and initiatives, ensuring consistency, quality, and alignment with Sales Leadership and WM standards
- Manage and administer certification processes and training progression for new hires and transitioning team members
- Coordinate logistics and scheduling for training sessions, onboarding cohorts, certifications, and sales enablement events
- Maintain and update training materials, leader guides, and participant resources to reflect current products, services, processes, and systems
- Partner with Sales Leadership, Sales Operations, Marketing, Customer Service, and WM stakeholders to support revenue-generating activities and sales effectiveness initiatives
- Provide input into training needs based on field observations, performance data, and feedback from sales leaders
- Support integration efforts by aligning Stericycle sales training content and delivery with WM tools, platforms, and learning methodologies
- Analyze sales performance data, training outcomes, and sales process adoption to identify trends and improvement opportunities
- Conduct follow-up reviews of completed training programs and assist in updating content or delivery methods as needed
- Track participation, completion, and certification metrics and provide regular updates to Sales Training leadership
- Develop and manage assigned project timelines and priorities to support training deliverables
- Assist with planning and coordination of sales training events and activities, including materials and supplies
- Monitor assigned spending and resources in alignment with departmental guidelines
- Perform other related duties and responsibilities as assigned by the Senior Manager and Sales Training leadership
Requirements
What you’ll need- 50% TRAVEL required
- Bachelor’s degree or equivalent work experience required
- Degree in Education, Marketing, Management, Training, or a related field preferred
- Demonstrated understanding of adult learning principles and effective training facilitation methodologies
- 3–5+ years of experience in sales training, sales enablement, sales operations, or related field
- Working knowledge of sales processes, CRM systems (SFDC preferred), and sales-supporting applications
- Instructional Design or Sales Training certification preferred
- Strong facilitation, coaching, and presentation skills
- Ability to analyze performance data and translate insights into actionable training support
- Strong collaboration, organization, and time-management skills
Benefits
Comp & perks- Medical
- Dental
- Vision
- Life Insurance
- Short Term Disability
- Stock Purchase Plan
- Company match on 401K
- Paid Vacation
- Holidays
- Personal Days
ATS Keywords
✓ Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
sales trainingsales enablementsales operationsadult learning principlestraining facilitation methodologiesperformance data analysisinstructional designCRM systemssales processescoaching
Soft Skills
facilitationcoachingpresentationcollaborationorganizationtime managementcommunicationleadershipfeedbackproblem-solving
Certifications
Instructional Design certificationSales Training certification