Retail Sales Enablement Manager - job 1 of 2

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 https://careers.toasttab.com/toast-benefits.

*Bread puns encouraged but not required