Retail Sales Enablement Manager

Toast•Boston, MA

7h•$76,000 - $157,000•Hybrid

About The Position

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.

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)

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.