---
title: 'Sales Learning & Development Specialist at Wing Assistant'
canonical: 'https://feeny.ai/job/sales-learning-development-specialist-wing-assistant-united-states-v47re0erpns7'
type: 'job'
last_seen: '2026-09-08'
---

# Sales Learning & Development Specialist at Wing Assistant

- **Company:** Wing Assistant
- **Location:** United States
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2025-06-16
- **Last confirmed live:** 2026-09-08
- **Apply:** https://jobs.lever.co/getwingapp/8a0716d2-f4fd-43eb-862d-4500802181ff

## Job description

Overview: 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.

Key Responsibilities:

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. 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. 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.

Qualifications:

- 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 Wing Assistant

## Company Overview
- **One-liner**: Wing Assistant provides fully managed, vetted virtual assistants from the top 1% of global talent to handle recurring business tasks for small businesses, startups, executives, and enterprises.
- **Entity Type**: Private (funded: Seed & Pre-Seed)
- **Headquarters**: Berkeley, California, United States
- **Founded**: 2018
- **Founders**: Not explicitly listed in available sources; co-founders include Sai G. (Co-Founder & CTO) per LinkedIn.

## Core Business
- **Primary industry**: Internet Marketplace Platforms / Virtual Assistant Services
- **Target customers**: B2B – small businesses, startups, executives, and enterprises across multiple verticals (e.g., healthcare, real estate, sales, marketing)
- **Mission or purpose statement**: "Reinventing the future of work for companies worldwide" by providing elite virtual assistants so clients can focus on core business activities.

## Products & Services
- **General Virtual Assistant (GVA) Full-Time**: Dedicated assistant, 160 hours/month, $999/month – includes free training, onboarding, free replacement, Customer Success Manager, quality control, Wing Workspace app, month-to-month.
- **General Virtual Assistant (GVA) Part-Time**: 80 hours/month, $699/month – same features with limited file storage.
- **Healthcare Assistant**: Specialized VA for patient intake, EHR updates, insurance verification (HIPAA compliant).
- **Other Specialty Roles**: Executive Assistant, Sales Development Representative, Digital Marketing Assistant, Bookkeeper, Real Estate VA, and more – sourced and managed by Wing.
- **Enterprise Services**: SOC 2 certified, HIPAA compliant, managed devices/VDI support, access controls and auditability for regulated industries.

## Market Standing
- **Valuation/Market Cap**: Not publicly available (private company)
- **Key Metric**: Annual revenue estimated $5M–$25M (based on employee count of 445 and industry benchmarks); Total funding $2.2M.
- **Notable Investors/Partners**: Surface Ventures (led Seed round of $2.1M in March 2022), SkyDeck Berkeley (Pre-Seed $105k in March 2020).
- **Growth Signals**: 445 employees (+20.7% YoY, +209 people), 177,516 LinkedIn followers (+34.9% yearly), 10,000+ companies supported, 2M+ applicants screened annually (hires <1%), active job postings across multiple roles.

## Competitive Advantages
- **Top 1% talent pool**: Vetted, trained, and managed assistants from a global applicant base of 2M+ annually.
- **Free replacement guarantee**: If an assistant isn’t a fit, Wing replaces them at no cost, monitored by a Customer Success Manager.
- **Managed service model**: Wing handles training, supervision, quality control, and security compliance (SOC 2, HIPAA) – reducing client hiring overhead.
- **Month-to-month contracts**: No long-term commitment, with plans starting at $699/month for part-time support.
- **Security-first**: SOC 2 certified, HIPAA compliant, managed devices, and VDI support for regulated workflows.

## Strategic Focus
- **Current priorities**: Expanding AI solutions (e.g., hiring a Product Manager, AI Solutions) and deepening specialization (healthcare, real estate, sales enablement).
- **Growth direction**: Scaling global talent pool across 23+ countries (Philippines, India, Mexico, US, Nigeria, etc.) and increasing enterprise adoption through compliance certifications.
- **Operational efficiency**: Automating vetting, training, and quality processes to maintain high service consistency while growing headcount.

## Why Work Here
- **Culture**: Inclusive, fun work environment with opportunities for career growth, upskilling, and paid training. Rated 3.7/5.0 on employer reviews (356 reviews) with work-life balance at 3.9, culture at 3.8.
- **Remote/hybrid policy**: Fully remote (100% work-from-home) with US work hours for most roles; positions available across multiple time zones (e.g., US, Philippines, India, Latin America).
- **Notable perks**: Performance incentives, job security and stability, holiday & overtime pay, supportive team, opportunities for advancement.
- **Engineering culture**: Mobile and engineering leaders are present (e.g., Mobile Engineer Leader, Head of Engineering); React Native Developer roles indicate modern tech stack.

## Sources
1. [linkedin.com](https://linkedin.com/company/wingassistant)
2. [get.wingassistant.com](https://get.wingassistant.com/)
3. [leadiq.com](https://leadiq.com/c/wing-assistant/5a1daaf52300005b009fbca2)
4. [wingassistant.com](https://wingassistant.com/careers/us/executive-assistant-us-columbus/)
5. [linkedin.com](https://linkedin.com/company/wing-india)

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