Sales Enablement Trainer

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Wing Assistant

WebsiteLinkedInAll Job Openings

501 - 1000 employees

🤝 B2B

☁️ SaaS

⚡ Productivity

💰 $2.1M Seed Round on 2022-03

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.

📋 Description

• Sit in the calls — live and recorded — and find exactly where deals are being lost. • Rewrite the copy, scripts, and sequences that aren't converting, and prove the new version works. • A/B test sales emails, call openers, demo pitches, and tactics like personalized video — keep the winners, kill the losers. • Build and tune outbound cadences so reps follow up at the right time, on the right channel, with the right message. • Coach reps one-on-one on real calls and build the objection-handling playbook for our market — then drill it until it's reflexive. • Produce a video training series and self-serve modules with assessments, so new reps ramp fast and tenured reps keep sharpening.

🎯 Requirements

• Have personally sold and closed — ideally outbound/high-volume B2B — and can show your numbers. • Write sales copy that converts and can explain *why* it works. • Are comfortable on camera and can produce clean training videos without a production team. • Can structure an A/B test, read the result honestly, and make the call. • Coach without crushing — you leave reps better and more confident. • Move fast: a diagnosis becomes a usable fix in hours, not weeks. • Know your way around a CRM (Hubspot plus) and a sales sequencing tool. • Nice to have: Experience in virtual staffing, BPO, or managed services · Pipedrive or CRM automations · video editing · sequencing tools (Apollo, Outreach, Salesloft, Instantly, Smartlead) · prior sales enablement assets (playbooks, battle cards, certification programs).