Full-Time

Sales Enablement Trainer

Updated on 9/4/2026

Wing Assistant

Wing Assistant

1,001-5,000 employees

Subscription-based virtual assistant services for businesses

Compensation Overview

$29k - $35k/yr

Tulsa, OK, USA

Remote

Remote role based in Tulsa, Oklahoma.

Category
Training (1)
Required Skills
HubSpot
Video Editing

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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.
Responsibilities
  • 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.
Desired Qualifications
  • 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)

Wing Assistant provides virtual assistant services for businesses, offering dedicated virtual assistants that work remotely on a full-time or part-time basis through a subscription model. Clients hire VAs who handle administrative tasks such as invoicing, payment tracking, and expense recording, while gaining complimentary access to the Wing Task Workspace App for communication, task management, file sharing, and screen recording. The service works by assigning a dedicated VA and, if needed, a Customer Success Manager plus thorough training for assistants to ensure consistent quality. This differentiates Wing Assistant through a strong emphasis on customer support and investment in VA training, with pricing tied to service level and hours required. The company’s goal is to help businesses run more efficiently by providing reliable, scalable administrative support via licensed remote assistants.

Company Size

1,001-5,000

Company Stage

Seed

Total Funding

$2.2M

Headquarters

Irvine, California

Founded

2018

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Simplify Jobs

Simplify's Take

What believers are saying

  • Wing reported 210% annualized growth after $1.4 million revenue-based financing in 2023.
  • Its 2026 careers pages show active hiring, suggesting demand and ongoing operational expansion.
  • 2026 content marketing around outsourcing and AI services strengthens lead generation against smaller rivals.

What critics are saying

  • Wing still relies on low-margin labor subscriptions, exposing it to price wars and churn.
  • 2026 job posts tie Wing to M32 AI, signaling uncertain strategic drift from core services.
  • The mandatory arbitration terms and security complaints raise client-trust risk before 2027 renewals.

What makes Wing Assistant unique

  • Wing bundles dedicated virtual assistants with customer success and task-workspace software.
  • Its 2026 hiring pages emphasize global remote coverage across hundreds of open roles.
  • Wing markets specialized vertical support, including medical scribing and customer service outsourcing guides.

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Benefits

Performance Bonus

Job Security

Paid Training

Inclusive Culture

Upskilling Opportunities

Remote Work Options

Exceptionally Supportive Team

Opportunities for Career Growth

Company Social Events

Holiday & Overtime Pay

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

0%

2 year growth

1%
FinSMEs
Mar 31st, 2022
Wing Assistant Raises $2.1M In Seed Funding

Wing Assistant, an Irvine, Calif. – based platform enabling companies to find remote talent for recurring work, raised $2.1m in seed funding. Backers included Surface Ventures, Brookstone Venture Capitaland UC BerkeleySkyDeck as well as angel investors. Co-founded by Karan Kanwar, CEO, Martin Gomez, COO, Saideep Gupta, CTO, and Roland Polzin, CMO, Wing Assistant provides business [] The post Wing Assistant Raises $2.1M in Seed Funding appeared first on FinSMEs.

Robotics and Automation News
Nov 5th, 2020
Wing Assistant partners with Kiwibot

Wing AI is partnering with KiwiBot to develop robotic delivery services.

Robotics and Automation News
Aug 18th, 2020
Wing Assistant is developing robotic delivery services

Wing AI is partnering with KiwiBot to develop robotic delivery services.