Senior Trainer, Customer

About this roll* (Responsibilities)

Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love.

As a Customer Success Trainer, you’ll organize and lead the facilitation of our new hire, enablement, and upskilling programs for agents and managers both internal and through our Business Process Outsourcing (BPO) partners around the globe. Your training will set learners up for success in a rapidly evolving, dynamic environment of AI assisted design.

You will not only lead the facilitation of our new hire and upscaling programs for internal and BPO teams but also serve as an innovator in our AI-assisted enablement ecosystem. You will be at the forefront of transitioning the standard training cycle into a closed-loop system that leverages autonomous AI role-play, hyper-personalized coaching, and automated curriculum management.

Delivery of additional enablement programs will position you to expand business knowledge, establish clear expectations, and grow Toast employees to expertise. This position will work closely with CS Enablement, Field Operations Leadership, learning design, and business leaders to ensure our agents and managers (internal & BPO) have the knowledge, confidence, and skills to provide an exceptional experience for all our customers during their journey at Toast.

About this roll* (Responsibilities)

• Create and facilitate comprehensive training agendas in-person and virtually—including new hire, upskilling, and process change enablement—across diverse internals and BPO teams through multiple campaigns and channels in a fast-paced, self-directed environment.
  Guide AI enabled blended facilitation delivery, integrating AI voice role-play tools into the "practice arena" to simulate high-complexity customer interactions, ensuring agents are proficient before interacting with live customers.
• Create hyper-personalized learning experiences leveraging AI analytics and transcription engines to glean performance insights, identifying specific opportunities to assess training needs based on real-time agent performance and customer friction points, and driving curriculum design, maintenance, and iterative improvement.
• Partner with Enablement Program Managers to coordinate all aspects of new hire and ongoing enablement initiatives, including content updates, scheduling, transition to their in-line managers, evaluations, and more

• Provide observational, and Train-the-Trainer/Mentor needs to support programmatic needs
• Evaluate and assess post training impact measurement through innovative AI optimization and provide input to enhance and improve the learning experience.
  Problem-solve for technology, learner, and environment needs, often with minimal support and in new environments leading with an AI-first methodology.
• Support ad hoc enablement projects as needed.
  

Do you have the right ingredients*? (Requirements)

• 5-8 years of direct classroom training/facilitation/design experience as part of a learning delivery team, delivering a variety of effective learning solutions in a fast-paced, ever-changing tech environment
• As needed, travel to national and international destinations to provide in-person support to our Toasters around the globe.
• Exceptional facilitation and classroom management skills, with a history of success driving measurable results by delivering modern, innovative, and interactive learning solutions in both virtual and in-person settings  
• Skilled at navigating ambiguity in an autonomous setting while representing Toast, cultivating relationships, and creating meaningful learner experiences 
  Ability to manage and prioritize multiple projects, deliverables, and competing priorities with a proven record of success with limited managerial oversight
• Broad expertise in learning design methodologies (ADDIE, SAM) and adult-learning best practices, specifically applied to microlearning and autonomous AI coaching, and familiarity with common learning tools (i.e. Zoom, Articulate, LMS, engagement tools, NotebookLM, etc.).
• Passionate about the learner experience and how to make it better (always looking for ways to improve skills and learn new things), with a bias to action
  

• Experience developing curriculum and delivery of nuanced customer experience interactions.
• Proven experience in the technical evaluation, piloting, and scaled implementation of third-party AI training tools (e.g., AI voice role-play agents, LLM-based content creation platforms).
• Ability to leverage AI technology to deliver and measure proven learning impact, moving beyond traditional completion rates to deep performance insights.
• Proven ability to leverage AI to analyze learning opportunities, recommend and gain buy-in on the right solutions for complicated business needs, and follow through to completion.
  

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.