Role Overview
As a Retail Sales Enablement Manager, you’ll partner closely with 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.
What You Will Do
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. Develop and maintain enablement content such as playbooks, cheat sheets, battle cards, frameworks, and sales tool resources.
Why It Might Be a Fit
You’ll need to thrive in a fast-changing environment, work independently, manage distributed teams, and pivot quickly. You’ll need to have a data-driven mindset, strong project management skills, excellent communication and presentation skills, and the ability to analyze performance metrics and identify strengths and areas for improvement in sellers.
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
Benefits
- Competitive compensation
- Benefits programs
- Flexible work arrangements
- Ongoing training and development opportunities
- Opportunities for growth and advancement
- Recognition and rewards for outstanding performance
- Paid time off (vacation, sick leave, etc.)
- Health insurance
- Retirement plan (401(k), etc.)
- Learning budget
- Parental leave
- Wellness programs
- Visa/relocation assistance
- Remote flexibility
- Stipends
- Bonus/commission
- Paid holidays
To apply for this job please visit careers.toasttab.com.

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