Master Trainer

TwentyEighty

Master Trainer Contractor facilitating training experiences in-person and virtually for Crucial Learning. Managing training calendar and delivering high-quality training experiences.

Posted 6/30/2026contractRemote • 🇺🇸 United StatesMid-LevelSeniorWebsite

About the role

Key responsibilities & impact

Facilitate exemplary training experiences both in-person and virtually.
Manage a Crucial Learning-calendar using our tools to accurately reflect the training availability on your schedule
Foster relationships with Sr. Client Advisors and Crucial Learning employees to showcase your facilitation skills
Prepare and plan for upcoming speeches, training events, and client interactions
Attend and lead pre-event calls with Sr. Client Advisors and Clients to understand organizational barriers and the need/reason for training
Deliver high-quality speeches and facilitate impactful training on each of the Crucial Learnings products (Crucial Conversations, Crucial Accountability, Crucial Influence, Getting Things Done, and The Power of Habit) both in-person and virtually
Conduct email and phone post-event follow-up that includes a summation of the event, identifies potential next actions, and support needed for training sustainability
Submit communication and invoices in a timely manner with customer service in mind
Engage in a variety of Master Trainer Community support activities including quarterly support and informational communication as well as occasional opportunities for professional development

Requirements

What you’ll need

Bachelors degree
3+ years of experience delivering training overall (some experience needed both in-person and virtually)
A minimum of 7 courses taught with Crucial Learning content strongly preferred
Crucial Conversations Trainer Certification (achieved prior to application) preferred
The ability to take on a minimum of 12 events per year should the event needs arise
Experience with psychometric tools and assessments is also a plus
The ability to work as an independent contractor
The ability to provide independently the technical resources for facilitation (i.e. in accordance with US law a contractor is to provide their own laptop, email, reliable internet service, conducive physical office space, etc.)
Efficient and effective communication skills both written and verbal
Quickly learn company tools and internal processes
Must be detail oriented and well organized, have the ability to work independently, exercise good judgment, and respond quickly to a variety of requests
Familiarity with learning and development in a variety of industries
Cognitive understanding of the Crucial Learning content
An understanding of the intention of the content and the ability to align with Crucial Learning delivery directions
Ability to apply relevant business examples to the content
Ability to handle tough questions from participants and clients and use those questions as a learning opportunity
Ability to relate training content to real-life examples for a variety of clients
Ability to effectively engage learners across training modalities
Exemplary training, facilitation, engagement, and public speaking skills

Benefits

Comp & perks

Access to some of the richest professional development programs.
Access to a variety of resources to support your facilitation success from speech decks to training materials.
Access to a community of practice focused on honing their facilitation skills and changing the world for good.
Ongoing internal support from Crucial Learning

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Training DeliveryFacilitationEvent PlanningContent PreparationPost-Event Follow-UpLearning and DevelopmentCognitive Understanding of ContentEngagement TechniquesTechnical Resource ProvisionIndependent Contractor Skills

Soft Skills

Effective CommunicationDetail OrientedOrganizational SkillsJudgmentAdaptability

Certifications

Crucial Conversations Trainer Certification