Sales Deal Desk Manager

Wing Assistant•Ottawa, ON

43d

About The Position

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 â 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

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 â 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 Haves

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.

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 â 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 â 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 â 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 â 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.