Temporary 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 the 2026 Medicare Annual Enrollment Period (AEP) season.

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 3-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.

Day in the Life

• Phase 1: Training Facilitation & Onboarding (late July – October 15, 2026)

  • Rapid Knowledge Acquisition: Successfully complete a rapid client Train-the-Trainer program to master Medicare AEP content and client systems.

  • Virtual Delivery: Facilitate the preparation, delivery, and assessment of client-provided training programs in a 100% remote environment.

  • Engagement & Motivation: Keep remote learners highly motivated, focused, and engaged through a rigorous, fast-paced learning environment.

  • Performance & Attendance Tracking: Meticulously track and log trainee performance metrics, assessment scores, and daily class attendance and payroll.

  • Adult Learning Support: Create a supportive adult learning environment, breaking down complex regulatory and system workflows into easily digestible concepts for new learners.

  • Readiness Evaluation: Evaluate training effectiveness and partner with leadership to identify gaps and confirm agent readiness for production launch.

  Phase 2: Production Supervision & Coaching (October 16 – mid December 2026)

  • Performance Supervision: Plan, prioritize, assign, and review the daily work of your team of remote Customer Success Associates during high-volume AEP operations.

  • Team Engagement & Culture: Maintain a highly engaged and motivated team throughout a demanding season by designing and executing team activities, contests, and interactive engagement initiatives.

  • Targeted Outlier Coaching: Review quality insights provided by a dedicated QA Specialist; take direct responsibility for coaching performance outliers, closing skill gaps, and implementing targeted performance improvement strategies.

  • KPI Management: Own team-wide performance against key operational metrics (Productivity, Compliance, and Customer Satisfaction).

  • Workforce & Schedules: Partner closely with workforce management to ensure proper operational coverage and review/approve employee timesheets.

  • Escalation Support: Act as a tier-2 resource to resolve complex customer inquiries, complaints, and account escalations.

  • Retention & Attrition Mitigation: Leverage relationships built during the training phase to foster a strong team culture, sustain engagement, and minimize seasonal attrition.

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.

Must Have's

• Contact Center Leadership: 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.

• 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

• Medicare AEP Experience: Prior experience working within or supporting a Medicare AEP contact center environment is highly preferred.

• 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: $60,000 / year (annualized and prorated for the duration of the contract)

• Project Length: Mid-Late July through December 8th

• Schedule:

  • Training: Monday–Friday | 8:00 AM – 5:00 PM EST

  • Post Training Schedule: Schedule assigned upon completion of training. Working hours will fall between 8:00 AM and 11:00 PM EST.

What's in it for you?

• 100% remote

• Equipment provided

• 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, District of Columbia, Illinois, Montana, Rhode Island

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!

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