Sales Supervisor / Trainer

WM•Chicago, IL

16h•Remote

About The Position

The Sales Training Supervisor supports the execution and continuous improvement of sales training and development initiatives for WMHS, operating within an integrated WM environment. This role focuses on supervising and delivering training programs, monitoring training effectiveness, conducting evaluations and gap analyses, and supporting sales performance through observations, coaching, and reinforcement of standardized sales processes. The Supervisor works closely with Sales Leadership, Sales Training leadership, and cross-functional partners to ensure training programs are effectively implemented, consistently delivered, and aligned with broader WM sales methodologies, tools, and systems (including SFDC and related applications).

Requirements

50% TRAVEL required
Bachelor’s degree or equivalent work experience required.
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.
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.

Nice To Haves

Degree in Education, Marketing, Management, Training, or a related field preferred.
Instructional Design or Sales Training certification preferred.

Responsibilities

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.