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Wing Assistant

Subscription-based virtual assistant services for businesses

Sales Deal Desk Manager

Full-Time
₱50k - ₱70k/mo
Mid, Senior
Tulsa, OK, USA
Hybrid
Sales & Account ManagementAccount Executive

About the job

Requirements
  • 3-5 years of experience in B2B sales, sales management, or sales operations in a services, staffing, or subscription business. You have personally closed deals and you understand what it takes to push a deal across the finish line.
  • Willingness and ability to pick up the phone and engage directly with prospects. This role is at least 50% hands-on deal work, not just pipeline review and reporting.
  • Strong coaching instinct — you can review an AE's deal and quickly identify what's missing, what objection isn't being addressed, or what the next best action is.
  • Deep comfort with CRM systems (Pipedrive preferred). You should be able to look at a pipeline and immediately spot which deals are at risk and why.
  • Assertiveness balanced with collaboration. You need to hold AEs accountable without creating an adversarial relationship. You are their partner in closing more deals, not a police officer.
  • Analytical ability to identify patterns in deal data and translate them into actionable process improvements for the sales team.
  • High energy and urgency. Deals die from delay. You operate with a bias toward action and speed.
Responsibilities
  • Monitor the active sales pipeline daily in Pipedrive. Identify deals that are aging, stalling, or at risk of falling through. Proactively intervene on at-risk deals before they die — this includes calling prospects directly, coaching AEs on next steps, or joining calls to help move deals forward.
  • Hold AEs accountable for follow-up cadence and pipeline progression. If a qualified lead has not received a follow-up in 48 hours, flag it and ensure it gets actioned. Review each AE's pipeline weekly to identify patterns — which deals are stuck, which need a different approach, which AEs are consistently losing deals at the same stage.
  • Personally rescue stalling deals. When an AE has exhausted their approach or a prospect has gone cold, step in with a fresh angle. Re-engage prospects through phone calls, re-frame the value proposition, address objections the AE couldn't resolve, or loop in the Solutions Expert to do early work extraction that builds client confidence before the close.
  • Catch deals that are being sold incorrectly before they close. Review job descriptions against the plan being sold — if an AE is selling a bookkeeping plan for tasks that clearly require a GVA Expert, flag it and correct the plan before the contract is signed. Work with the Talent Advisor to validate that staffing can deliver what sales is promising.
  • Coordinate with the Solutions Expert to warm uncertain prospects. For high-value deals where the client is interested but hesitant, introduce the Solutions Expert to begin mapping out workflows and tasks before the close. This gives the client confidence that they'll know what to do with their VA on day one and reduces post-sale ghosting.
  • Track and report on pipeline metrics weekly: conversion rates by stage and by AE, average deal cycle time, deals rescued, deals lost and why, and recurring patterns in deal fall-through. Use this data to recommend process improvements to sales leadership.
  • Identify systemic issues in the sales process and recommend fixes. If multiple deals are dying at the same stage, or if a specific objection keeps coming up, bring it to leadership with a proposed solution — whether that's a new talk track, a process change, or a resource the sales team needs.
  • Support AEs during complex or high-value sales cycles. Join calls when needed, help structure proposals, and provide coaching in real time. The goal is to make AEs better at closing while also ensuring deal quality.
Desired Qualifications
  • Experience in the virtual staffing, BPO, or managed services industry.
  • Familiarity with common objections and sales cycles in outsourced staffing or VA services.
  • Track record of personally rescuing or saving at-risk deals in a previous role.
  • Experience working directly alongside or managing SDR/AE teams.

About the company

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

Berkeley, California

Founded

2018

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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

6 month growth

1%

1 year growth

0%

2 year growth

0%
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.