GTM Sales

Wing Assistant

Sales Development Representative at Wing Assistant generating qualified meetings, supporting global workforce solutions. Engaging prospective customers to fill the sales pipeline with qualified opportunities.

Posted 7/4/2026full-timeRemote • 🇨🇦 CanadaJunior💰 $1,200 - $2,500 per monthWebsite

Tech Stack

Tools & technologies

Apollo

About the role

Key responsibilities & impact

Generate Qualified Opportunities
Identify 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 roles.
Use job postings, hiring signals, company growth signals, and account research to find strong-fit prospects.
Research target accounts to understand what they are hiring for, why they may need support, and where Wing could be a strong fit.
Reach out to prospective customers across email, phone, LinkedIn, and other outbound channels.
Run focused outbound campaigns around active hiring needs, operational pain points, and alternative workforce solutions.
Hold early discovery conversations to understand a prospect's hiring needs, pain points, urgency, and openness to remote talent or AI-enabled workforce solutions.
Communicate what Wing Assistant does and why it matters clearly enough to earn the next meeting.
Book qualified appointments with companies that have a clear hiring need, relevant business use case, or strong fit for Wing.
Turn Hiring Intent Into Conversations
Monitor companies that are posting roles Wing can service.
Understand what the company is likely trying to solve by hiring that role.
Position Wing as a faster, more flexible, and more scalable alternative to traditional hiring.
Educate prospects who may not have considered remote assistants, virtual assistants, offshore talent, or AI-enabled workforce support before.
Create curiosity with founders, executives, operators, HR leaders, recruiting teams, and department heads.
Support the Revenue Team
Work closely with the sales team to build and protect a healthy, well-qualified pipeline.
Hand off opportunities cleanly, with the context needed to move conversations forward.
Share 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 involved.
Keep activity, notes, and pipeline data accurate and current in our CRM.
Bring the Market Back In
Feed what you are hearing from prospects back to the Sales, Marketing, and Product teams.
Help refine messaging and outreach based on what is actually landing with companies.
Identify patterns in hiring demand, objections, industries, and roles where Wing is resonating.
Suggest new outbound angles based on job postings, hiring trends, and prospect conversations.

Requirements

What you’ll need

1 to 4+ years in sales, appointment setting, cold calling, recruiting, staffing, lead generation, outbound marketing, growth, or a comparable role.
A real 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; you can get to the point and make it 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 the ability to turn hiring signals into relevant outbound messaging.
Strong organization and the resilience to keep going when a day does not go your way.
The drive that comes from chasing clear goals, activity metrics, and booked meeting targets.
The ability to run your own desk while still collaborating well across teams.
A genuine eagerness to learn the product, the market, and the craft of go-to-market execution quickly.
Nice to Have
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.

Benefits

Comp & perks

Performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.
Appointment and Deal Bonuses
Earn a bonus for every qualified meeting that shows up.
Earn an additional bonus when a qualified meeting turns into a closed customer.
Weekly Competitions
Weekly bonus opportunity for top dial activity.
Weekly bonus opportunity for top meeting production.
These incentives are designed for people who are driven by targets, enjoy competition, and want direct upside from their effort.

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

Lead GenerationPipeline GenerationResearch SkillsHigh-Volume Outbound OutreachGo-To-Market Strategy

Soft Skills

Strong CommunicationOrganizationResilienceCollaborationEagerness to Learn