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Retail Sales Enablement Manager

2 weeks ago

Boston, Massachusetts, United States Toast Full time $85,000 - $136,000 per year

As a Retail Sales Enablement Manager, you'll partner closely with your 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.

About this roll* (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.

Do you have the right ingredients*? (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)

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

  • Bread puns encouraged but not required

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

*Diversity, Equity, and Inclusion is Baked into our Recipe for Success*
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

We Thrive Together
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 restaurant community. To learn more about how we work globally and regionally, check out:

Apply today
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

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.