Full-Time

Sales Deal Desk Manager

Wing Assistant

Wing Assistant

1,001-5,000 employees

Subscription-based virtual assistant services for businesses

Compensation Overview

₱50k - ₱70k/mo

Tulsa, OK, USA

Hybrid

Category
Sales & Account Management (1)
Required Skills
Cold Calling
Data Analysis
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.

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

Simplify Jobs

Simplify's Take

What believers are saying

  • Achieved $1.3M GSV in under one year post-launch, demonstrating strong market demand.
  • Founder team from UCI with pandemic-driven pivot attracted $2.1M seed from tier-one VCs.
  • Subscription model with $699–$7,999/month pricing captures diverse customer segments profitably.

What critics are saying

  • AI automation platforms eliminate invoicing and expense tracking demand within 12–24 months.
  • Agentic AI founders render human VAs obsolete as startups adopt zero-cost automation.
  • Four-year funding drought since 2022 prevents AI integration while VC-backed competitors scale.
  • BELAY and Time Etc capture vertical markets through superior domain expertise and budgets.
  • Philippine VA providers undercut pricing by 50–70%, compressing margins or losing clients.

What makes Wing Assistant unique

  • Managed marketplace model pairs VAs with dedicated CSMs and Wing Workspace App.
  • 25+ specialized plans across sales, marketing, healthcare, real estate, e-commerce.
  • Software-augmented VA service with expert-level assistants managing projects independently.

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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

-2%

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.

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