Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses. We help companies get high-quality support across roles like executive assistance, admin support, customer support, sales support, recruiting support, operations support, and other business functions.Our growth depends on a steady flow of qualified opportunities, and we are hiring a Go-to-Market Associate to help create them. This person will sit at the front line of our revenue motion: identifying companies with active hiring needs, reaching out with a compelling alternative to traditional hiring, and booking qualified meetings for our sales team.This is a high-energy, high-ownership role for someone early in their career who wants to learn fast, build real outbound skills, and grow into bigger roles across sales, growth, revenue, or go-to-market strategy over time.It is a great fit for someone who is competitive, well-organized, motivated by clear targets, and genuinely curious about how AI, remote talent, and global workforce solutions are changing the way companies build teams.What You'll DoGenerate Qualified OpportunitiesIdentify companies actively hiring for roles Wing can support, such as Executive Assistants, Admin Assistants, Customer Support, Sales Support, Recruiting Support, Operations Support, and other business support rolesUse job postings, hiring signals, company growth signals, and account research to find strong-fit prospectsResearch target accounts to understand what they are hiring for, why they may need support, and where Wing could be a strong fitReach out to prospective customers across email, phone, LinkedIn, and other outbound channelsRun focused outbound campaigns around active hiring needs, operational pain points, and alternative workforce solutionsHold early discovery conversations to understand a prospect's hiring needs, pain points, urgency, and openness to remote talent or AI-enabled workforce solutionsCommunicate what Wing Assistant does and why it matters clearly enough to earn the next meetingBook qualified appointments with companies that have a transparent hiring need, relevant business use case,



or strong fit for WingTurn Hiring Intent Into ConversationsMonitor companies that are posting roles Wing can serviceUnderstand what the company is likely trying to solve by hiring that rolePosition Wing as a faster, more flexible, and more scalable alternative to traditional hiringEducate prospects who may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce support beforeCreate curiosity with founders, executives, operators, HR leaders, recruiting teams, and department headsSupport the Revenue TeamWork closely with the sales team to build and protect a healthy, well-qualified pipelineHand off opportunities cleanly, with the context needed to move conversations forwardShare key details from discovery calls, including the role the company is hiring for, their current hiring process, pain points, timing, budget signals, and decision-makers involvedKeep activity, notes, and pipeline data accurate and current in our CRMBring the Market Back InFeed what you are hearing from prospects back to the Sales, Marketing, and Product teamsHelp refine messaging and outreach based on what is actually landing with companiesIdentify patterns in hiring demand, objections, industries, and roles where Wing is resonatingSuggest new outbound angles based on job postings, hiring trends, and prospect conversationsWhat We're Looking ForCore Requirements1 to 4+ years in sales, appointment setting, cold calling, recruiting, staffing, lead generation, outbound marketing, growth, or a comparable roleA real interest in go-to-market strategy, pipeline generation, and B2B growthProven background in prospecting, cold calling, appointment setting, or high-volume outbound outreachStrong written and verbal communication; you can get to the point and make it compellingComfort reaching out to companies that may not have considered remote assistants, virtual assistants, offshore talent,



or AI-enabled workforce solutions beforeStrong research skills and the ability to turn hiring signals into relevant outbound messagingStrong organization and the resilience to keep going when a day does not go your wayThe drive that comes from chasing clear goals, activity metrics, and booked meeting targetsThe ability to run your own desk while still collaborating well across teamsA genuine eagerness to learn the product, the market, and the craft of go-to-market execution quicklyNice to HaveExposure to staffing companies, recruiting firms, BPOs, outsourcing companies, virtual assistant companies, digital agent companies, or high-ticket professional services organizationsFamiliarity with CRM and sales engagement tools such as HubSpot, Salesforce, Outreach, Salesloft, Apollo, Instantly, Clay, Close, or LinkedIn Sales NavigatorFamiliarity with auto dialers, power dialers, cold calling workflows, and high-volume outbound systemsExperience prospecting into founders, executives, operations leaders, HR leaders, recruiting teams, customer support leaders, sales leaders, or department headsAwareness of business support workflows such as executive assistance, admin support, sales support, customer support, recruiting coordination, inbox/calendar management, and back-office operationsWe may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.In addition to base compensation, this role includes performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.Appointment and Deal BonusesEarn a bonus for every qualified meeting that shows upEarn an additional bonus when a qualified meeting turns into a closed customerThis means you are rewarded not just for booking activity, but for creating real opportunities that move through the revenue process.Weekly CompetitionsWeekly bonus opportunity for top dial activityWeekly bonus opportunity for top meeting productionThese incentives are designed for people who are driven by targets, enjoy competition, and want direct upside from their effort.

📌 Gtm Associate (Ottawa)
🏢 Wing Assistant
📍 Ottawa