Career Coach

Coaching ExperiencePart TimeVirtual Office

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Prosper provides advice for modern ambition. Our mobile app makes career development simple, fun, and accessible on-the-go. As a Prosper Coach, you will guide your members through their career - from discovery, the job search, getting a promotion and building leadership skills.

You'll get matched to your members and will coach in 30-minute video sessions, all on the Prosper app. Prosper coaching sessions follow a clear structure to ensure that members leave having built valuable skills to help them succeed..

You'll join a global coaching team and receive 1:1 training and feedback on your coaching skills. You are comfortable using mobile apps and easily communicate through both video calls and chat. You have proven expertise in supporting others though their career. You are familiar with what is required to land the next dream job; from finding the right career fit, to mastering the interview, to showing up on the first day of work.

If you're looking to build your coaching experience and work in a collaborative, learning environment, this role is for you.

What you'll do:

  • Coach your dedicated members through 30-minute video calls on the Prosper Coach app, coaching and teaching them the skills they need to succeed
  • Chat with your dedicated members through the Prosper Coach app - anytime, anywhere
  • Deliver additional services, such as, mock interviews via video-conferencing, and resumé and cover letter reviews
  • Encourage, motivate and guide your members through the key steps in their search

What you'll get:

  • Coach from anywhere, anytime - since all coaching happens on the Prosper Coach app, there is no need to commute to an office. You can coach anywhere, anytime through our easy-to-use mobile app. We are a global company with a global team of coaches.
  • Choose your own hours - we have a flexible service model that allows you to choose your own hours. All we ask is that you commit a minimum of 10 hours per week to provide the best possible experience to our members. All of our coaches are independent contractors, which allows you the freedom and flexibility to create your own schedule.
  • Fulfillment from helping others develop their career and their confidence - in our view, coaching others to accomplish their career goals is one of the most rewarding things in the world. The feeling you get when they land their first job or get promoted is amazing - when our members win, we all win!
  • Work with a dedicated, collaborative cohort of fellow coaches - At Prosper we are dedicated to creating a fantastic coaching community, providing learning and structure for our coaches. You will be supported and celebrated and we will take your professional and education goals seriously.
  • Build your brand - We'll help you build your coaching brand to stand out to new members in the matching process, including photography, and bio development


  • Excellent communication skills- both spoken and written facility in English. You will be guiding your members to improve their listening, speaking, and writing skills, which you will need to model
  • Confidence, curiosity, and gravitas
  • An active Linkedin page
  • A passion for helping people overcome obstacles
  • Proven experience helping people gain new skills
  • 3+ years of experience in career coaching, interview coaching, human resources or recruitment
  • Bachelor Degree or Diploma
  • An iOS mobile device

Nice to have:

  • Coaching certification
  • Experience in adult education
  • Volunteer experience with leadership responsibility

The details:

  • Independent Contractor Position
  • Company paid new hire training
  • Company paid ongoing training and support
  • We don't guarantee a minimum number of sessions each week



Prosper is the coaching app for job seekers to boost their confidence and performance through their job search. The app guides members with on-demand access to a career coach and interactive exercises, helping members gain the skills they need to get to what's next.

We started out as one person two years ago, and today we're a team of 25 coaches, designers, operators and engineers - working towards one core mission - to help people realize their full potential. We envision a world where it is easy and fun for young professionals to get better jobs through greater access to personalized coaching, any-time anywhere. We are headquartered in Toronto right by Union Station.

We are proud to be an equal opportunity workplace committed to building a team culture that celebrates diversity and inclusion. Learn more at

Hello Prosper Inc.

1 University Avenue

Toronto, ON

M5J 2P1