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About the Role

Wing Assistant is seeking a Go-to-Market Associate to identify companies with active hiring needs, engage them with a compelling alternative to traditional hiring, and book qualified meetings for the sales team. This is a high-energy, high-ownership role for an early-career professional eager to develop outbound skills and grow within sales, growth, or go-to-market strategy.

Responsibilities

• Identify companies actively hiring for roles Wing can support.
• Use job postings, hiring signals, company growth signals, and account research to find strong-fit prospects.
• Research target accounts to understand their hiring needs and Wing's potential fit.
• Reach out to prospective customers via email, phone, LinkedIn, and other outbound channels.
• Run outbound campaigns focused on hiring needs, operational pain points, and alternative workforce solutions.
• Hold early discovery conversations to understand prospect needs, pain points, and openness to remote talent or AI-enabled solutions.
• Clearly communicate Wing Assistant's value proposition to secure the next meeting.
• Book qualified appointments with companies that have a clear hiring need and relevant use case.
• Monitor companies posting roles Wing can service and understand their hiring challenges.
• Position Wing as a faster, more flexible, and more scalable alternative to traditional hiring.
• Educate prospects on the benefits of remote assistants, virtual assistants, offshore talent, or AI-enabled workforce support.
• Create curiosity with founders, executives, operators, HR leaders, recruiting teams, and department heads.
• Work closely with the sales team to build and protect a healthy pipeline.
• Hand off opportunities cleanly with necessary context for the sales team.
• Share key details from discovery calls, including hiring needs, process, pain points, timing, budget signals, and decision-makers.
• Maintain accurate and current activity, notes, and pipeline data in the CRM.
• Provide feedback from prospects to Sales, Marketing, and Product teams.
• Help refine messaging and outreach based on market feedback.
• Identify patterns in hiring demand, objections, industries, and roles where Wing resonates.
• Suggest new outbound angles based on job postings, hiring trends, and prospect conversations.

Requirements

• 1 to 4+ years in sales, appointment setting, cold calling, recruiting, staffing, lead generation, outbound marketing, growth, or a comparable role.
• Genuine interest in go-to-market strategy, pipeline generation, and B2B growth.
• Proven background in prospecting, cold calling, appointment setting, or high-volume outbound outreach.
• Strong written and verbal communication skills; ability to be concise and compelling.
• Comfort reaching out to companies that may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce solutions before.
• Strong research skills and ability to translate hiring signals into relevant outbound messaging.
• Strong organization and resilience to persevere through challenges.
• Drive fueled by clear goals, activity metrics, and booked meeting targets.
• Ability to manage individual responsibilities while collaborating effectively across teams.
• Eagerness to quickly learn the product, market, and go-to-market execution.
• Exposure to staffing companies, recruiting firms, BPOs, outsourcing companies, virtual assistant companies, digital agent companies, or high-ticket professional services organizations.
• Familiarity with CRM and sales engagement tools such as HubSpot, Salesforce, Outreach, Salesloft, Apollo, Instantly, Clay, Close, or LinkedIn Sales Navigator.
• Familiarity with auto dialers, power dialers, cold calling workflows, and high-volume outbound systems.
• Experience prospecting into founders, executives, operations leaders, HR leaders, recruiting teams, customer support leaders, sales leaders, or department heads.
• Awareness of business support workflows such as executive assistance, admin support, sales support, customer support, recruiting coordination, inbox/calendar management, and back-office operations.

Skills

• Prospecting
• Cold calling
• Appointment setting
• Outbound outreach
• Sales
• Lead generation
• Growth
• Go-to-market strategy
• Pipeline generation
• B2B growth
• Written communication
• Verbal communication
• Research
• Organization
• Resilience
• CRM
• Sales engagement tools
• Auto dialers
• Power dialers
• High-volume outbound systems

Experience Level

• Early in career
• 1 to 4+ years

Salary/Compensations

• $1,200 - $2,500 a month
• Performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.
• Appointment and Deal Bonuses for qualified meetings and closed customers.
• Weekly bonus opportunities for top dial activity and meeting production.

Benefits

• Performance-based incentives
• Appointment and Deal Bonuses
• Weekly Competitions with bonus opportunities

About the Company

• Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses.
• We help companies get high-quality support across various business functions.