Experienced Remote Appointment Setter (Sdr) for Career Coaching Program

About Win at Work
Win at Work helps professionals land better jobs faster through workshops, coaching, and online programs. We work with motivated people navigating career decisions and looking for clarity, confidence, and direction. As we continue to grow, we’re expanding our enrollment team to support outreach, follow-up, and appointment scheduling.

About the Role
We’re hiring an Appointment Setter who is confident on the phone and fluent in English.

In this role, you’ll speak with prospective clients by phone to build rapport, understand their situation, and help qualified people schedule a coaching conversation. Some leads will be warm, others will require consistent follow-up and proactive outreach over time.

This role requires strong spoken English, emotional intelligence, and comfort initiating conversations with professionals.

Key Responsibilities
Call prospective clients to follow up, reconnect, and schedule coaching calls.

Communicate clearly and professionally in English with U.S.-Based professionals.

Build trust and rapport quickly over the phone.

Ask thoughtful questions to understand goals, challenges, and hesitation.

Guide conversations toward booking an appointment when appropriate.

Track all calls, notes, and outcomes accurately in our CRM (GoHighLevel).

Follow up via phone, text, and email as needed.

Track daily and weekly activity metrics such as calls, conversations, and bookings.

Required Skills & Experience
Excellent spoken English with a clear, natural tone and strong listening skills.

Prior experience as an appointment setter, SDR, enrollment assistant, or similar role.

Confidence initiating phone conversations.

Strong relationship-building and follow-up skills.

Comfortable handling objections and uncertainty calmly.

Organized and reliable in a remote work environment.

Experience using a CRM (GoHighLevel, HubSpot, or similar is a plus).

This Role Is a Great Fit If You
Enjoy talking to people and starting conversations.

Sound warm, professional, and natural in English.

Know how to listen for what actually matters.

Are comfortable with outreach and follow-up.

Want a long-term role with growth potential.

Compensation
Paid trial: $4/hour to start (potential to make a lot more after the trial)

Ongoing hourly pay based on performance and experience.

Performance-based bonuses tied to booked and completed appointments.

Full-time team members receive paid time off, paid holidays, and advancement opportunities.

How to Apply (Required)
Please submit all items below. Incomplete applications will not be reviewed.

1. Voice Recording
Submit a 60–90 second voice recording (Google Drive or Loom audio is fine).

Prompt:
“You’re calling someone who showed interest in career coaching but hasn’t booked a call yet.
How would you start the conversation and learn what’s holding them back?”

2. Short Written Response
In 3–6 sentences, answer:

Describe a time you successfully booked a call with someone who was hesitant or unsure.
What did you do that worked?

3. Experience Snapshot
Please list:

Previous appointment-setting or call-based roles

Types of leads you’ve worked with (inbound, outbound, follow-up, mixed)

Tools used (CRM, dialers, Google Sheets, messaging tools)

4. Availability & Setup
Please confirm:

Your time zone and availability during U.S. Business hours

Reliable internet connection

Quiet environment suitable for phone calls

Comfort being on the phone for a significant portion of the day

Optional (Strong Plus)
You may submit a second short voice recording answering:

“What do you enjoy most about talking with prospective clients?”

Why Work With Win at Work
Meaningful conversations with professionals making important career decisions.

Clear agreements, systems, and support.

Remote-first, respectful, and collaborative culture.

Opportunity to grow into senior enrollment or closing roles as we scale.