Head Coach

Virtual Office |Part Time|Coaching Experience

Share job posting:

  • Linkedin icon white
Apply Now

Prosper is the career coach in your pocket. Our mobile app makes career development simple, fun, and accessible on-the-go. As the Head of Coaching, you will directly lead our global, virtual team of coaches as they guide our users through major moments in their career - starting with the interview.

As the Head of Coaching you are a natural encourager that lives to motivate others to go after their dreams. You understand that everyone has potential for greatness and you are passionate about helping people build the confidence and skills to realize their potential.

While your focus is on supporting the coaching team and developing and promoting Prosper's coaching methodology, as the head of a growing team, you're organized and have an knack for process and structure. You'll report directly to the Chief Customer Officer who oversees the coaching team and is responsible for user growth.


  • Meet with Coach Leads to provide coaching and feedback on a regular basis
  • Evaluate the entire coaching team each quarter
  • Work alongside Prosper's product team to develop the coaching service design
  • Implement Prosper's coaching service design with the coaching team
  • Responsible for coaching team corporate objectives, focused on coach satisfaction, engagement and retention rates
  • Embody Prosper's values in order to model them to the coaching team


  • Flexibility - we have a flexible service model that allows you to choose your own hours, deciding when and where you work. While we may ask that you do come into Prosper's HQ once a week, the rest of your coaching hours are your own to schedule. Keep in mind, we're looking for a commitment of 15-20 hours per week.
  • Opportunity to lead a global coaching team - take your impact to another level. In this role, you'll touch thousands of users through the coaches you lead.
  • 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, your role will help coaches develop their skills and build their confidence.


  • Degree or Diploma in any field
  • 5+ years leadership experience in a corporate or not-for-profit environment
  • 7+ years of documented coaching experience
  • References from three clients
  • Optional: Coaching certification from an accredited organization


Prosper is the career coaching app for job seekers to boost their confidence and performance in the interview. The app guides users through their job search on-demand access to a coach and interactive exercises, proven to help you boost your interview performance. You may also think of Prosper as a “career coach in your pocket”.

We started out as one person a year 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 www.helloprosper.com