Sales Deal Desk Manager

About the role

We lose deals every month not because clients don't want our service, but because deals stall, go cold, or fall through cracks in the pipeline. In January 2026 alone, premature and misqualified sales accounted for over $27,000 in lost MRR from accounts that were signed but never started. Beyond that, qualified leads are dying in the pipeline before they ever reach a close because follow-ups are delayed, momentum is lost, and nobody intervenes when a deal starts going sideways. The Sales Pipeline Lead exists to maximize every deal in the pipeline. You are both a player and a coach. You personally jump into stalling deals to rescue them, while also holding AEs accountable for pipeline hygiene, follow-up cadence, and deal progression. Your default orientation is to push deals forward and help AEs close more - but you also serve as the last line of defense against deals that will create problems downstream, such as selling the wrong plan or closing a client who has no internal buy-in to use a VA. This is not a back-office analytics role. You are in the pipeline every day, on the phone with prospects, reviewing deals with AEs, and personally intervening when a deal needs to be saved.

Requirements

• WHAT YOU'LL NEED
• 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.
• NICE TO HAVE
• 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.

Additional Information

About Wing AI Wing AI is a technology-enabled talent platform helping businesses scale with high-quality global talent and AI-powered support. We manage the full talent lifecycle from sourcing and onboarding to training and performance so companies can focus on what matters most. Trusted by thousands of teams worldwide, Wing AI combines human expertise with smart systems to deliver fast, reliable, and scalable execution for modern businesses.

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