Sales Learning and Development Specialist

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July 5

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Wing Assistant

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B2B • SaaS • Productivity

Wing Assistant is a company specializing in providing virtual assistant services to businesses worldwide. The company offers a wide range of services including general virtual assistant work, executive assistance, customer service, bookkeeping, and digital marketing. Wing Assistant aims to enhance productivity for startups and enterprise teams by delegating tasks to dedicated virtual assistants, reducing operational load, and enabling businesses to focus on core activities. Their services are accessible via a subscription model, providing flexible and cost-effective solutions compared to traditional hiring methods. Clients benefit from a dedicated assistant model where the assistant works solely for their business, gaining a deeper understanding of their processes over time.

501 - 1000 employees

🤝 B2B

☁️ SaaS

⚡ Productivity

💰 $2.1M Seed Round on 2022-03

📋 Description

• 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. • 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). • 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. • Deliver training sessions and workshops focused on improving key sales skills such as discovery, objection handling, negotiation, product knowledge, and closing techniques. • 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. • Partner with sales managers, sales enablement, and RevOps to identify gaps, set learning priorities, and evaluate program impact. • Keep learning materials, sales playbooks, talk tracks, and knowledge bases up to date and aligned with business goals and messaging. • Encourage continuous improvement and growth by facilitating peer-to-peer learning, coaching programs, and self-directed learning initiatives.

🎯 Requirements

• 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)