Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses. We help companies build high-performing teams across executive assistance, administrative support, customer support, sales support, recruiting, operations, and other critical business functions.
We are looking for an energetic and disciplined Outbound Appointment Setter to help grow our sales pipeline by connecting with decision-makers at software and SaaS companies.
Your primary responsibility will be to start conversations, qualify prospective customers, and book high-quality sales meetings for our Account Executives.
This is a performance-driven role for someone who is comfortable making cold calls, communicating with senior business leaders, and consistently working toward clear activity and appointment targets.
Salary: $950 USD to $1300 USD + OTE
Schedule: Pacific Time
What You'll Own
Outbound Prospecting
- Make high-volume outbound calls to targeted software and SaaS companies.
- Connect with founders, executives, sales leaders, operations leaders, and other relevant decision-makers.
- Introduce Wing's services clearly and generate interest in a sales conversation.
- Use account research and prospect information to personalize outreach.
- Follow structured call scripts while adapting naturally to each conversation.
Appointment Setting
- Book qualified sales meetings for Account Executives.
- Confirm the prospect's needs, authority, interest, and potential fit before scheduling.
- Clearly communicate the purpose and value of the scheduled meeting.
- Coordinate calendars and ensure accurate meeting details are entered into the CRM.
- Reduce meeting no-shows through confirmation and reminder outreach.
Lead Qualification
- Ask effective discovery questions to understand the prospect's current hiring, staffing, or operational needs.
- Identify companies that may benefit from remote talent, sales support, customer support, executive assistance, or other workforce solutions.
- Properly categorize qualified, unqualified, and nurture-stage prospects.
- Maintain detailed notes so Account Executives have the context needed for each meeting.
Pipeline Management
- Keep prospect records, call outcomes, and follow-up activities updated in the CRM.
- Follow up consistently with prospects who express interest but are not ready to schedule immediately.
- Manage callbacks and future follow-up dates with discipline.
- Work closely with sales leadership to improve messaging, targeting, and conversion rates.
Qualifications
- At least 3 years of experience in outbound appointment setting, cold calling, business development, or sales development.
- Experience prospecting into software, SaaS, technology, or B2B companies is strongly preferred.
- Strong spoken and written English communication skills.
- Comfortable speaking with founders, executives, managers, and other decision-makers.
- Ability to handle objections and continue conversations confidently.
- Strong listening, questioning, and qualification skills.
- Comfortable working with activity targets, appointment goals, and performance metrics.
- Highly organized and disciplined with follow-up.
- Experience using a CRM such as HubSpot, Salesforce, or a similar platform.
- Experience using sales engagement, calling, or prospecting tools is an advantage.
- Reliable internet connection and a professional remote-working environment.
What We're Looking For
- Confident, persuasive, and professional on the phone.
- Competitive and motivated by measurable results.
- Persistent without sounding aggressive or scripted.
- Coachable and willing to continuously improve.
- Able to communicate value quickly and clearly.
- Comfortable working in a fast-moving sales environment.
- Consistent, accountable, and dependable.
- Curious about software, SaaS, AI, remote work, and modern workforce solutions.
