Retail Sales Enablement Manager

As a Retail Sales Enablement Manager joining the Retail Sales Enablement team, you’ll work closely with our retail sales, product, and marketing teams; responsible for building and expanding our retail line of business. This role will be part of Retail Sales’ dedicated enablement team - helping onboard new team members, supporting ramping AEs, and continuing to provide the whole team with ongoing training and crucial org-wise updates.

About this roll* (Responsibilities)

• Create, facilitate, and sustain technical and sales enablement programs to upskill our AEs on product functionality, roadmap insights, competitive differentiators, and use cases.
• Design classroom-style training, certifications, and interactive learning experiences (both live and on-demand) using Workramp LMS.
• Build technical playbooks, battle cards, and objection-handling frameworks to support sales conversations.
• Act as the bridge between Sales, Product, and Engineering to ensure AEs understand new feature releases, product enhancements, and technical integrations.
• Partner with Product Management to develop and deliver training content aligned with our product roadmap.
• Translate complex technical details into sales-friendly messaging.
• Provide ongoing technical coaching and feedback to new and tenured AEs to improve their ability to articulate product value.
• Support senior sales leadership in tracking and improving key performance metrics, conversion rates, and sales effectiveness.
• Reinforce the use of sales tools (e.g., CRM, demo environments, sales automation tools) to maximize AE efficiency.
• Conduct mock pitch sessions, role-plays, and real-time deal coaching to ensure training is put into practice.
• Comfortably provide direct feedback and hold AEs accountable for technical proficiency and sales execution.
• Create, facilitate, and sustain training to scale and develop the Retail Sales Team
• Develop classroom style training (both live and on-demand) and certifications leveraging our Learning Management System, Workramp
• Partner with cross-functional stakeholders to develop and deliver training content
• Provide Account Executives (both ramping and tenured) with the relevant feedback/coaching that will help to improve their individual performance
• Support senior sales leadership in driving key metrics to achieve overall sales goals and OKRs
• Execute training events and occasional onsite meetings
• Reinforce tools that will enhance Account Executive performance
• Maintain training and enablement materials
• Own and execute training events and occasional onsite meetings
• Provide live and virtual training to sales reps to ensure trainings are being put into practice; being comfortable providing direct feedback and holding your team accountable
  
  

Do you have the right ingredients*? (Requirements)

• 2+ years direct sales experience illustrating high performance and the ability to coach/mentor is ideal, with an interest in enablement/training; prior training or marketing experience a plus.
• Experience in mentoring, teaching, leading, and providing feedback
• Deep understanding of Toast's metric-driven goals and how to influence them
• Project management and content creation expertise (preferably of training materials)
• Clear & effective communication skills; ability to present & command an audience
• Ability to understand the sales process and ascertain strengths/weaknesses in sellers
• Ability to work independently and manage distributed teams to metric-driven programs
• Ability to be flexible and pivot quickly when needed
• Systems/Tools Proficiency:
• Google Sheets (or similar)
• CRM Systems (e.g. Salesforce)
• Conversational Intelligence tools
• Google sites
• Email engagement platforms
• Limited travel (roughly 4x/year)

Our Spread* of Total Rewards
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.

*Bread puns encouraged but not required