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# Cold Calling & Sales Role-Play Coach — 1-on-1 Training

Confidential employer

Posted 10/5/2026Rate visible after sign-upSource: Curated from source
Coaching
Cold Calling
Sales
Appointment Setting
About the Role

I am looking for an experienced Sales Coach / Sales Trainer / Cold Calling Trainer to work with me one-on-one.

I am not looking for someone to make cold calls for me. I am looking for someone who will personally train and coach me so I become much better at cold calling and selling.

The right person should be comfortable actively coaching me, challenging me, correcting me, and doing realistic role-plays with me.

What I Want to Learn

I want to become confident and effective on the phone, including:

  • How to start a cold call confidently
  • How to create and deliver a strong pitch
  • What exactly to say and how to say it
  • How to sound confident, natural, and conversational
  • How to avoid sounding nervous, robotic, or overly scripted
  • How to ask good questions
  • How to keep the prospect engaged
  • How to identify the prospect's needs
  • How to transition naturally into the offer
  • How to ask for the appointment or sale
  • How to handle rejection
  • How to handle difficult prospects
  • How to overcome common objections
  • How to think on my feet when the prospect says something unexpected
  • How to become more comfortable and confident through repeated practice

I Want REAL Role-Playing

This is extremely important.

I want you to actually play the role of the prospect while I practice calling you.

For example, you might act like a prospect who says:

> "I'm not interested."

Then I respond.

You challenge me again.

You might say:

> "Just send me an email ."

Or:

> "We already have someone."

Or:

> "How much does it cost?"

Or:

> "Where did you get my number?"

Or give me another realistic objection.

I want you to challenge me instead of making the role-play easy.

After the role-play, I want you to explain:

  • What I did well
  • What I did poorly
  • Where I sounded uncertain
  • What I should have said instead
  • How I could improve my wording
  • How I could sound more confident
  • Where I talked too much
  • Where I should have asked a question
  • Where I should have pushed back
  • How I could have moved the conversation toward an appointment or sale

Then I want to do the role-play again and apply your corrections.

I Want a Coach Who Will Push Me

Please don't simply tell me that everything sounds good.

I want someone who will respectfully challenge me and point out my weaknesses.

If my pitch is weak, tell me.

If I sound nervous, tell me.

If I'm talking too much, stop me.

If I'm asking the wrong question, explain what I should ask.

If I'm avoiding asking for the sale, challenge me to actually ask.

The goal is for me to improve through repetition, feedback, and realistic practice.

Help Me Build My Pitch

I would also like help developing and improving my actual sales pitch.

You should be able to help me:

1. Understand the product/service I'm selling
2. Create a strong opening
3. Develop the pitch
4. Create good discovery questions
5. Prepare responses to common objections
6. Practice the entire conversation
7. Adjust the script so it sounds natural rather than memorized
8. Practice until I can deliver it confidently

Experience I'm Looking For

You should have significant experience in one or more of the following:

  • Cold calling
  • B2B sales
  • B2C sales
  • Sales training
  • Sales coaching
  • Sales management
  • SDR/BDR training
  • Business development
  • Appointment setting
  • Closing
  • Objection handling
  • Phone sales
  • Sales role-playing
  • Sales performance coaching

Teaching/coaching ability is very important.

Being a good salesperson alone is not enough. You need to be able to teach another person how to sell.

Sample Video — VERY IMPORTANT

If you have a video showing yourself doing any of the following, please send it with your application:

  • Sales coaching
  • Cold-call training
  • Role-playing a sales call
  • Teaching someone how to sell
  • Demonstrating a cold call
  • Handling objections
  • Training salespeople

It does not have to be a professionally produced video.

I mainly want to see how you actually teach and coach.

If you don't have an existing video, you may record a short sample explaining how you would coach someone through a cold call.

Please Include Your Desired Rate

Please tell me how much you are asking per hour for this type of one-on-one coaching.

Do not simply write "negotiable."

Please provide your actual requested hourly rate.

Please Answer These Questions

1. How many years of sales experience do you have?
2. How many years of sales training/coaching experience do you have?
3. Have you personally trained people to cold call?
4. Have you done live sales role-play with students or salespeople?
5. What types of products/services have you sold?
6. What type of sales were you involved in — B2B, B2C, high-ticket, appointment setting, closing, etc.?
7. How do you normally structure a one-on-one sales coaching session?
8. How do you teach someone to sound more confident on the phone?
9. How do you teach objection handling?
10. Are you comfortable challenging the student rather than simply giving encouragement?
11. Do you have a sample video? Please provide the link.
12. What is your desired hourly rate?

Top 3 Skills

Please make sure your profile/application highlights these three skills:

1. Cold Calling & Sales Training

2. Sales Role-Play & Objection Handling

3. Sales Pitch, Confidence & Communication Coaching

I am looking for someone interested in ongoing one-on-one coaching, not just a one-time session.

Please apply with your experience, sample video if available, and desired hourly rate.

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