Seasonal Customer Success Training Facilitator & Supervisor

Are you a dynamic leader who thrives in fast-paced environments and can quickly master complex information to deliver engaging, impactful training? We are seeking a versatile and energetic Customer Success Training Facilitator & Supervisor to support a seasonal, premium product support team delivering exceptional white-glove customer experiences for design-forward, custom consumer products.

This critical, dual-focused seasonal role is built on a "train-and-follow" model to maximize team stability and performance. You will first absorb client-provided curriculum via an expedited Train-the-Trainer process, deliver a rigorous 2-week virtual onboarding program to a class of remote Customer Success Associates, and continue into production with that same class as their direct supervisor. By quickly building trust and keeping the team motivated from the start, you will play a key role in minimizing attrition and maximizing performance during a fast-paced peak season.

Essential Functions

Phase 1: Training Facilitation & Onboarding (August to October)

• Rapid Mastery: Build proficiency in complex product knowledge, custom print and design specifications, and software systems through client-led and internal train-the-trainer programs.
• Train-the-Trainer: Complete internal Train-the-Trainer workshops to refine delivery methods, master virtual classroom technology, and prepare lesson plans.
• Operational Readiness: Complete operational onboarding to develop proficiency with supervisory tools, quality assurance rubrics, scheduling systems, performance expectations, and escalation pathways.
• Class Rotations & Nesting: Rotate through the facilitation of four distinct training cohorts, each consisting of 25+ learners. Partner with a dedicated Subject Matter Expert (SME) to co-facilitate sessions and provide real-time learner support. The final two cohorts will transition into the trainer’s permanent production team.
• Engagement & Retention: Drive engagement and retention among remote learners by creating an inclusive, motivating learning environment, establishing trust early, and building strong team cohesion to minimize seasonal attrition.
• Administration & Readiness: Maintain accurate attendance records, assessment scores, and payroll inputs while evaluating individual learner readiness for transition to live production.

Phase 2: Production Supervision & Coaching (October to January)

• Operational Leadership: Manage daily workflow, queue volume, and performance for your dedicated associate team supporting a luxury, creative-focused customer base.
• Targeted Coaching: Analyze QA scores, operational metrics, and individual performance trends to deliver targeted coaching, close skill gaps, reinforce best practices, and improve resolution rates.
• Culture & Motivation: Maintain peak season morale through team engagement initiatives, recognition programs, and proactive support.
• Escalation & Support: Serve as a Tier 2 escalation point for complex order issues, custom project inquiries, and sensitive customer concerns, ensuring timely resolution while maintaining a high standard of customer experience.

Competencies

• The "Train & Follow" Mindset: A passion for teaching combined with a strong operational drive; an innate ability to build early dialogue and trust with learners.
• Resilience & Motivation: Ability to use creativity to develop an engaged, upbeat workforce and keep a team motivated through a fast-paced, high-pressure seasonal environment.
• Flexibility & Agility: A positive attitude with a strong ability to adapt quickly to rapidly changing operational priorities during peak season.
• Operational Organization: Highly organized with exceptional time management skills and a strong sensitivity to deadlines.

Required Education and Experience

• Contact Center Leadership (Weighted Heavily): 2+ years of supervisory/leadership experience in a high-volume contact center environment.
• Remote Training Facilitation: 1+ years of experience facilitating virtual onboarding and training classes for remote new hires.
• Agile Learning Ability: Proven track record of learning complex technical or regulated material quickly (e.g., via Train-the-Trainer) and successfully breaking it down for new learners.
• Industry Fit: Experience supporting high-end consumer brands, custom e-commerce, design/creative platforms, or white-glove retail support highly preferred.
• Performance Management: Strong experience interpreting performance data, managing team metrics, and coaching underperforming agents to success.
• Cross-Level Communication: Exceptional interpersonal skills with a proven track record of interacting confidently with people at all levels—from entry-level associates to senior leadership.
• Tech Proficiency: Highly tech-savvy with intermediate to advanced proficiency using Microsoft Office, Slack, Salesforce, and Learning Management System (LMS) software.

Preferred Education and Experience

• Associate’s or Bachelor’s Degree in a Training, Human Resources, or Business-related field.
• Familiarity with adult learning theory, instructional design principles, or remote team engagement strategies.

Position Details

• Pay Rate: $55,000-$58,000 /year (annualized and prorated for the duration of the contract)
• Project Length: September through December
• Schedule:
  • Training: Monday–Friday | 8:00 AM – 5:00 PM PST
  • Post Training Schedule: Schedule assigned upon completion of training. Working hours will fall between 8:00 AM and 8:30 PM PST.
• This is a BYOD (Bring Your Own Device) position!

What's in it for you?

• 100% remote

• Yuna Health
• EAP
• 401k
• Perkspot

Compliance & Eligibility

• Background & Screenings: Successful candidates must complete and pass a background check and drug screen prior to their start date
• Verification: In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification form upon hire. 
• Work Environment:  Because this is a remote work role, you must have a private, dedicated workspace that enables you to work independently and without interruptions. 

Location: Due to specific position requirements, we cannot hire from the following locations for this opportunity: California, Washington DC, Illinois, Iowa, Montana, North Dakota, Rhode Island, New Hampshire, OCONUS

EEO and Harassment Statement

Instant Teams provides equal employment opportunities (EEO) to all applicants, contractors, and employees without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. This policy applies to all terms and conditions of work, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training. 

Instant Teams expressly prohibits any form of workplace harassment based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. Improper interference with the ability of Instant Teams’ contractors and employees to perform their job duties may result in discipline up to and including discharge. 

Other Duties 

This job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee. Other duties, responsibilities, and activities may change or be assigned at any time with or without notice. 

From our military-connected to untapped talent communities, we welcome non-linear career paths and untraditional backgrounds and encourage applicants to apply even if they don't meet all the qualifications. If this role captivates you and speaks to your skills, apply away!