Sales Learning & Development Specialist

Role Summary

We are looking for a Sales Learning & Development Specialist to join our growing sales team. In this role, you will be responsible for designing, delivering, and optimizing learning initiatives that enhance the performance and effectiveness of our sales representatives. You’ll play a critical role in creating a customized training curriculum, developing engaging learning modules, and implementing long-term skill-building strategies that directly contribute to increased close rates and revenue growth.

Develop and Implement Training Programs

Create scalable and tailored sales training programs that address different stages of the sales funnel and rep seniority levels (onboarding, ramp-up, ongoing L&D).

Customize Curriculum and Modules

Design role-specific, relevant learning paths using a mix of formats (e.g., live sessions, e-learning, shadowing, and simulations). Customize based on team needs, market dynamics, and performance data.

Upskill Sales Team

Deliver training sessions and workshops focused on improving key sales skills such as discovery, objection handling, negotiation, product knowledge, and closing techniques.

Collaborate with Sales Leadership & Enablement

Partner with sales managers, sales enablement, and RevOps to identify gaps, set learning priorities, and evaluate program impact.

Maintain Sales Content & Resources

Keep learning materials, sales playbooks, talk tracks, and knowledge bases up to date and aligned with business goals and messaging.

Foster a Learning Culture

Encourage continuous improvement and growth by facilitating peer-to-peer learning, coaching programs, and self-directed learning initiatives.

Requirements

Track Learning & Skills Adoption

Build systems and processes to measure training engagement, knowledge retention, and the long-term incorporation of skills in daily workflows. Track KPIs like ramp time, conversion rate, and close rate improvements.

• 3+ years of experience in sales training, sales enablement, or a similar L&D role supporting a sales team (required)
• Experience designing and executing training programs that improved measurable sales performance (required)
• Strong understanding of B2B sales methodologies (e.g., SPIN, MEDDIC, Challenger, etc.) - (Preferred)
• Excellent facilitation, presentation, and communication skills (required)
• Comfortable using LMS platforms, e-learning tools, and sales tech stacks (CRM, enablement tools, etc.) - (Required)
• Data-driven mindset with the ability to assess training effectiveness and impact - (Required)
• Self-starter with a passion for developing people and driving performance - (Required)

About the Company

Wing connects the world's best talent with winning teams, high-growth businesses, startups, executives, and enterprises that move fast and refuse to settle. We provide top-tier remote talent that takes ownership of the operational work weighing teams down, so leaders can focus on the strategic work that actually moves the business forward.

By embedding skilled, cost-effective operators into our clients' workflows, we help companies scale without the overhead, driving productivity, sharpening execution, and unlocking capacity at every level of the organization. We're digitizing talent and building a global workforce without borders.