Retail Sales Enablement Manager

About the position

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.

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.

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.

Nice-to-haves

• Systems/Tools Proficiency: Google Sheets (or similar), CRM Systems (e.g. Salesforce), Conversational Intelligence tools, Google sites, Email engagement platforms.

Benefits

• Competitive compensation and benefits programs.
• Cash compensation (overtime, bonus/commissions if eligible), equity, and benefits.
• Flexibility to meet Toasters’ changing needs.