Retail Sales Enablement Manager

WinsAbove; Boston, Northern (MA, KY); Hybrid; USD 98,000 - 157,000; Full time

Job summary

Toast is seeking a Retail Sales Enablement Manager in the Boston area to partner with enablement peers and cross-functional teams to build and run programs that ramp new hires and equip Retail Account Executives with training and resources to sharpen their sales process.

You will design engaging training experiences, create playbooks and battle cards, align with product roadmap and GTM priorities, translate technical concepts into sales-ready messaging, and help drive performance metrics with

Qualifications

• 2+ years of direct sales experience with a track record of high performance.
• Proven ability to coach, mentor, and provide actionable feedback to sales professionals.
• Familiarity with sales methodologies (Sandler, SPIN, Challenger, MEDDPICC) and 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.
• 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, Google Sheets, conversational intelligence platforms, and email engagement tools.

Responsibilities

• Create, schedule, deliver, and sustain technical and sales enablement programs that accelerate new hire and ramping AE readiness on sales process, 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.
• 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.

Skills

Direct sales

Coaching

Sales methodologies

Project management

Communication

Data-driven

Decision making

Independent work

CRM tools

Tools

Salesforce

Google Sheets

Conversational intelligence

Email engagement tools

Job description

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

As a Retail Sales Enablement Manager, you'll partner closely with your enablement peers and cross-functional partners to build and deliver enablement programs that set new hires up to succeed and equip Retail Account Executives with the ongoing training and resources they need to sharpen their sales process and stay a step ahead in an evolving retail industry and competitive landscape.

A day in the life (Responsibilities)

• Create, schedule, deliver, and sustain technical and sales enablement programs that accelerate new hire and ramping AE readiness on sales process, 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.
• 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.

What you'll need to thrive (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)

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.

The starting pay rate for this role is below. Please note that there is no range for this role; the rate listed below is the only rate. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.

• Zone A: $98,000 – $157,000 USD
• Zone B: $85,000 – $136,000 USD
• Zone C: $76,000 – $122,000 USD

How Toast Uses AI in its Hiring Process

Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring.

Our Approach to Hybrid Working

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast.

People Are the Secret Ingredient in Our Recipe for Success

At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other.

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, 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 [e-mail].

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