GTM Sales

Wing AI Technologies, Inc.

Job Overview

Location

Calgary, Alberta

Job Type

Full-time

Full Job Description

📋 Description

• Serve as the first point of contact for prospective customers, representing Wing AI Technologies and introducing Wing Assistant as an AI-powered alternative to traditional hiring methods.
• Proactively identify and research companies that are actively hiring for roles aligned with Wing’s workforce solutions, using targeted outreach strategies to engage decision-makers.
• Craft and deliver personalized outreach messages via email, phone, and LinkedIn to generate interest and initiate conversations about AI-enabled talent acquisition.
• Qualify leads by assessing company needs, hiring timelines, and decision-making structures to ensure only high-intent prospects are passed to Account Executives.
• Consistently meet and exceed daily and weekly targets for outreach volume, qualified meetings booked, and pipeline contribution.
• Collaborate closely with Account Executives to understand customer pain points, refine messaging, and improve conversion rates through feedback loops.
• Maintain accurate and up-to-date records in CRM systems, documenting all interactions, lead statuses, and next steps to ensure seamless handoffs.
• Stay current on industry trends in AI, remote work, and global talent markets to speak knowledgeably with prospects and position Wing as a thought leader.
• Participate in regular training sessions to refine sales techniques, product knowledge, and objection handling skills in a fast-paced, evolving environment.
• Take ownership of your pipeline performance, using data and metrics to analyze what’s working and adapt outreach strategies accordingly.
• Work in a high-energy, target-driven culture where performance is recognized and growth opportunities are tied directly to results.
• Contribute to a team environment that values curiosity, resilience, and continuous learning as core traits for long-term success in sales.
• Represent Wing’s brand with professionalism, authenticity, and a customer-first mindset in every interaction.
• Adapt quickly to changes in product positioning, market demand, and sales tools to maintain effectiveness in a dynamic startup environment.

🎯 Requirements

• Proven ability to meet or exceed sales targets in a fast-paced environment
• Strong written and verbal communication skills with experience in cold outreach via email, phone, or LinkedIn
• High level of organization and ability to manage multiple outreach campaigns simultaneously
• Demonstrated curiosity about technology, AI, and the future of work
• Self-motivated with a competitive drive and resilience in the face of rejection
• Proficiency in CRM systems (e.g., Salesforce, HubSpot) or willingness to learn quickly

🏖️ Benefits

• Competitive base salary with uncapped commission structure
• Comprehensive health, dental, and vision insurance
• Generous paid time off and flexible work hours
• Access to professional development and sales training programs

Skills & Technologies

Remote

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Wing AI Technologies, Inc.

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About Wing AI Technologies, Inc.

Wing AI Technologies operates a phone and text-based concierge service that lets consumers outsource everyday tasks such as food ordering, courier requests, reservations, and customer-support inquiries to remote human agents supported by proprietary automation software. Users submit requests through the Wing app, WhatsApp, or SMS; agents coordinate with vendors, track orders, and handle payment, aiming to deliver results within minutes. The company monetizes via subscription plans and per-task fees while offering business-facing APIs that let restaurants and retailers receive and manage outsourced customer interactions. Headquartered in San Francisco, Wing serves individual and enterprise clients across the United States.

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