Retail Sales Enablement Lead

WinsAbove

Boston, Northern (MA, KY)

Hybrid

USD 98,000 - 157,000

Full time

14 days+

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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.