Toast
Overview
As a Retail Sales Enablement Manager, you’ll partner closely with enablement peers as well as retail sales, product, and marketing teams to accelerate the growth of our retail line of business. In this role, you’ll design and deliver high-impact enablement programs that prepare new hires for success, and provide Retail Account Executives with ongoing training, coaching, and resources that keep the sales team aligned with product updates, go-to-market priorities, and organizational goals during their ramping period. Responsibilities
Create, schedule, deliver, and sustain technical and sales enablement programs that accelerate new hire and ramping AE readiness on sales process, product functionality, competitive positioning, and retail-segment use cases. Design and facilitate engaging training experiences, including classroom-style sessions, certifications, role-plays, mock pitches, on-demand learning (Workramp LMS), and occasional onsite events. Develop and maintain enablement content such as playbooks, cheat sheets, battle cards, frameworks, and sales tool resources. Partner with cross-functional stakeholders to ensure training programs align with product roadmap, go-to-market priorities, and sales leadership goals. Translate complex technical concepts into clear, sales-ready messaging that improves AE effectiveness in customer conversations. Provide coaching, real-time deal support, and actionable feedback to drive technical proficiency, sales execution, and accountability. Reinforce best practices for sales tools (CRM, demo environments, automation platforms) to maximize AE efficiency. Support sales leadership in driving performance metrics, ensuring new hire cohorts achieve ramp milestones, sales targets, and OKRs. Maintain and evolve enablement resources, recurring programs, and training materials to ensure ongoing effectiveness and scalability. Requirements
2+ years of direct sales experience with a track record of high performance; prior enablement, training, or marketing experience a plus Proven ability to coach, mentor, and provide actionable feedback to sales professionals Familiarity with sales methodologies (e.g., Sandler, SPIN, Challenger, MEDDPICC) and demonstrated success in driving adoption Strong project management skills with experience creating enablement or training materials Excellent communication and presentation skills with the ability to command an audience and influence outcomes Data-driven mindset with the ability to analyze performance metrics and identify strengths and areas for improvement in sellers Strong decision-making, problem-solving, and execution abilities Ability to work independently, manage distributed teams, and pivot quickly in a fast-changing environment Systems/Tools proficiency: Salesforce (or similar CRM), Google Sheets, conversational intelligence platforms, and email engagement tools Willingness to travel occasionally (roughly 4x/year) Compensation & Benefits
The base salary range for this role is listed below. The starting salary will be determined based on skills and experience. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions, if eligible), benefits, and equity (if eligible). Pay Range: $85,000—$136,000 USD Legal & Inclusion
Toast is committed to creating an accessible and inclusive hiring process. We strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability. Additional
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As a Retail Sales Enablement Manager, you’ll partner closely with enablement peers as well as retail sales, product, and marketing teams to accelerate the growth of our retail line of business. In this role, you’ll design and deliver high-impact enablement programs that prepare new hires for success, and provide Retail Account Executives with ongoing training, coaching, and resources that keep the sales team aligned with product updates, go-to-market priorities, and organizational goals during their ramping period. Responsibilities
Create, schedule, deliver, and sustain technical and sales enablement programs that accelerate new hire and ramping AE readiness on sales process, product functionality, competitive positioning, and retail-segment use cases. Design and facilitate engaging training experiences, including classroom-style sessions, certifications, role-plays, mock pitches, on-demand learning (Workramp LMS), and occasional onsite events. Develop and maintain enablement content such as playbooks, cheat sheets, battle cards, frameworks, and sales tool resources. Partner with cross-functional stakeholders to ensure training programs align with product roadmap, go-to-market priorities, and sales leadership goals. Translate complex technical concepts into clear, sales-ready messaging that improves AE effectiveness in customer conversations. Provide coaching, real-time deal support, and actionable feedback to drive technical proficiency, sales execution, and accountability. Reinforce best practices for sales tools (CRM, demo environments, automation platforms) to maximize AE efficiency. Support sales leadership in driving performance metrics, ensuring new hire cohorts achieve ramp milestones, sales targets, and OKRs. Maintain and evolve enablement resources, recurring programs, and training materials to ensure ongoing effectiveness and scalability. Requirements
2+ years of direct sales experience with a track record of high performance; prior enablement, training, or marketing experience a plus Proven ability to coach, mentor, and provide actionable feedback to sales professionals Familiarity with sales methodologies (e.g., Sandler, SPIN, Challenger, MEDDPICC) and demonstrated success in driving adoption Strong project management skills with experience creating enablement or training materials Excellent communication and presentation skills with the ability to command an audience and influence outcomes Data-driven mindset with the ability to analyze performance metrics and identify strengths and areas for improvement in sellers Strong decision-making, problem-solving, and execution abilities Ability to work independently, manage distributed teams, and pivot quickly in a fast-changing environment Systems/Tools proficiency: Salesforce (or similar CRM), Google Sheets, conversational intelligence platforms, and email engagement tools Willingness to travel occasionally (roughly 4x/year) Compensation & Benefits
The base salary range for this role is listed below. The starting salary will be determined based on skills and experience. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions, if eligible), benefits, and equity (if eligible). Pay Range: $85,000—$136,000 USD Legal & Inclusion
Toast is committed to creating an accessible and inclusive hiring process. We strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability. Additional
We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
#J-18808-Ljbffr