Learner Success Coach (Freelance / Contract-Based engagement aligned to allocate

MasterStart Proprietary Limited; United States; Remote; USD 83,000 - 131,000; Part time

Benefits offered by this job

Remote freelance engagement

Flexible scheduling

Job summary

MasterStart is seeking a hands-on Coach for a remote freelance engagement. You will design, develop and deliver engaging coaching sessions to support learners’ professional growth across virtual platforms.

The role requires facilitating knowledge sharing, mentoring at‑risk learners, and leveraging online tools to boost engagement. Ideal candidates will have 3+ years of facilitation experience, a relevant degree, and strong communication and interpersonal skills.

Qualifications

• A Diploma or Degree in Business, Education, HR, Psychology or equivalent.
• Professional certification in coaching, facilitation, or training is preferred.
• At least 3 years’ facilitation experience across in-person and online platforms.
• Proven track record of managing multiple learner cohorts and outcomes.
• Strong communication, facilitation and interpersonal skills.
• Self-managed, proactive and able to work independently as a freelancer.

Responsibilities

• Facilitate engaging coaching sessions to support learner growth in virtual environments.
• Drive Communities of Practice by sharing best practices and creating new knowledge.
• Develop strategies to encourage participation and engagement within the community.
• Organise meetings, forums and workshops to share insights and innovations.
• Create and maintain a central repository for resources and documentation.
• Onboard new members and ensure alignment with community goals and values.
• Support industry experts by guiding session delivery and using online tools to boost engagement.

Skills

Facilitation

Coaching

Online delivery

Communication

Interpersonal skills

Self-management

Education

Diploma or Degree in Business/Education/HR/Psychology

Tools

Online collaboration tools

Job description

This is a remote position.

MasterStart is a global learning consultancy that places human connection at the heart of our flexible and fully supported online courses. Our portfolio of courses empowers learners to grow, adapt and develop their careers in our fast-changing world. At MasterStart , we cultivate and champion competence, confidence, curiosity and character, equipping people not only with knowledge, but with the mindset and integrity required to apply it with impact.

We are looking for a hands-on Coach to engage with us on a freelance basis in a dynamic, fast-paced, and fast-growing environment. The Coach must have extensive training or facilitation experience (both in person and online) as they will be responsible for facilitating high-quality learning and development experiences through both in-person and virtual platforms on a contract basis. This role involves designing, developing, and delivering engaging coaching sessions to support the professional growth of learners. The Coach will also provide learner support, mentor at‑risk learners, and support industry experts in delivering interactive and impactful sessions using innovative online tools to enhance learner engagement. We are seeking a tech‑savvy and energetic individual who brings flexibility, initiative, and a results‑driven approach to delivery. As this is a freelance engagement, the role offers the opportunity to contribute meaningfully to specific programmes while working within defined delivery periods aligned to business needs.

Duties and Responsibilities

• Facilitate engaging and interactive coaching sessions to support learner success and professional growth through virtual environments.
• Drive and continuously interact on Communities of Practice by sharing best practices and creating new knowledge to advance a domain of learning and professional practice.
• Facilitate knowledge sharing and collaboration by developing and implementing strategies to encourage active participation and engagement within the community.
• Organise and moderate regular meetings, forums, and workshops to share best practices, insights, and innovations.
• Create and maintain a central repository for resources, tools, and documentation relevant to the community’s focus areas.
• Identify and onboard new members, ensuring alignment with the community's goals and values.
• Foster a sense of belonging and shared purpose by promoting networking opportunities and relationship‑building.
• Use a variety of facilitation techniques and formats within the different learning platforms (e.g., communities, one‑on‑one coaching, group facilitation, mentoring) to ensure learning objectives are achieved and learners are motivated to engage.
• Adapt coaching styles to meet diverse learning preferences and ensure an inclusive learning environment for all participants.
• Support industry experts in delivering interactive and impactful sessions, providing guidance on using online tools and techniques to enhance learner engagement.

Content and Resource Development

• Design, develop, and update training materials, facilitator guides, and resources to support effective delivery of learning content.
• Develop structured training plans and materials that are easily adaptable for different delivery methods, ensuring they are current, relevant, and aligned with business goals.
• Create digital content using innovative online tools to encourage participation and collaboration during virtual coaching sessions.

Learner Support and Engagement

• Provide hands‑on support to learners by addressing their academic, technical, and pastoral needs, ensuring a smooth and positive learning experience.
• Coach and mentor learners with poor attendance, lack of participation, or barriers to engagement, fostering their success and retention within the programme.

Assessment & Evaluation

• Facilitate learner assessments, providing constructive feedback and guidance to help learners achieve their developmental goals.
• Evaluate the effectiveness of coaching and facilitation sessions through participant feedback, assessments, and surveys, implementing continuous improvements as needed.
• Actively work to meet the throughput and success rate goals for learners as defined by programme and business objectives.

Session Facilitation & CLS Support

• Lead Collaborative Learning Sessions (CLS) and webinars, using online engagement tools such as polls, breakout rooms, interactive whiteboards, and community chats to enhance learning experiences.
• Lead group discussions and activities to reinforce learning and encourage active participation.

Stakeholder Engagement

• Collaborate with the Facilitation Manager to identify coaching and facilitation improvements and priorities.
• Support industry experts by offering advice and coaching on session delivery, ensuring sessions are well‑structured and learner focused.
• Liaise with key stakeholders to align session content with overall learning and development objectives.

Requirements

• A minimum of a Diploma or Degree in Business, Education, Human Resources, Psychology, or a related field (or equivalent relevant experience).
• Professional certification in coaching, facilitation, or training is preferred.
• A minimum of 3 years’ facilitation experience, preferably across both face‑to‑face and online platforms.
• Proven track record of successfully managing multiple learner cohorts and achieving positive outcomes.
• Strong communication, facilitation, and interpersonal skills.
• Self‑managed, proactive, and able to work independently within a freelance engagement model.

Engagement Terms

• Freelance, contract‑based engagement aligned to allocated course runs
• Hours vary depending on the number of course runs freelancers opt into; all live sessions scheduled on weekdays between 08:00 and 17:00
• Course runs offered month‑to‑month on an opt‑in basis, with allocations confirmed in consultation with freelancers