Senior Manager, Global Live Training & Enablement

WinsAbove; Northern (KY); Hybrid; USD 130,000 - 210,000; Full time

Job summary

Toast is seeking a Senior Manager of Live Training to lead a high-volume, 1:many live training program for SMB and Core customers across the US and international markets. Reporting to the Director of Customer Enablement, you will scale the program while ensuring quality and adherence to facilitation standards across virtual offerings, tying training to improved product adoption.

You will partner with Learning Design, Customer Success, GTM, and Product teams to evolve training amid AI tools and

Qualifications

• Minimum of 8 years of experience in B2B Customer Training, Enablement, Instructional Program Management, Learning Design or related discipline.
• 4+ years of people management experience.
• Experience managing a live/virtual training calendar and team capacity at scale.
• Deep expertise in instructional strategy and curriculum design to address customer proficiency gaps.
• Experience influencing senior stakeholders and driving cross-functional alignment.
• Strong data analytics skills guiding prioritization and design.
• Familiarity with AI tools in training delivery or development.

Responsibilities

• Own the strategic vision and operational excellence of the SMB/Core training team and scale as Toast grows.
• Lead evolution of training programs to align with company initiatives including international expansion.
• Oversee training schedules, delivery logistics, and quality standards for live trainings.
• Collaborate with GTM, Marketing, Customer Success, and Product to support cross-functional goals.
• Define and pilot AI-enabled training tools and content development.

Skills

B2B Training

People Management

Curriculum Design

Data Analysis

AI in Training

Cross-functional Collaboration

Tools

Zoom

Articulate

LMS

Job description

Toast is seeking a Senior Manager of Live Training to lead a high-volume, 1:many live training program for SMB and Core customers across the US and international markets. Reporting to the Director of Customer Enablement, you will scale the program while ensuring quality and adherence to facilitation standards across virtual offerings, tying training to improved product adoption.

You will partner with Learning Design, Customer Success, GTM, and Product teams to evolve training amid AI tools and