About the position

Generation is seeking experienced freelance Digital Marketing professionals based in South Africa, with Johannesburg preferred, to mentor graduates entering freelance and remote work. As a Super Agent, you will guide, coach, and support graduates as they build freelance careers, find clients, deliver quality work, and generate sustainable income. The role combines mentoring, technical guidance, accountability coaching, freelance business development support, and practical knowledge sharing. The ideal candidate has a successful freelance track record and is passionate about helping young people develop skills, confidence, and financial independence through freelancing and remote work. The role is part of Generation’s BOOST Project, which is expanding its network of freelance professionals to support Digital Marketing graduates as they transition into freelance and remote opportunities. Super Agents work with individual learners and groups, provide practical career and project guidance, and collaborate with Generation staff and other Super Agents to support learner success.

Responsibilities

• Provide ongoing one-on-one and group mentoring sessions for assigned graduates.
• Help graduates apply digital marketing skills in real-world client environments and build confidence, professionalism, and effective work habits.
• Give constructive feedback on portfolios, proposals, project work, and client communications; help graduates identify strengths, address challenges, and pursue professional goals.
• Share practical insights from personal freelance experience and support graduates in understanding the freelance marketplace and positioning themselves effectively.
• Help graduates identify income-generating freelance and remote work opportunities and build sustainable businesses and long-term client relationships.
• Advise graduates on sourcing work through networks, referrals, direct outreach, LinkedIn, and freelance platforms.
• Guide graduates in developing competitive, sustainable pricing and packaging and positioning their services.
• Review proposals and quotations and advise on client discovery, negotiation, project scoping, freelance income management, and client account growth.
• Assist graduates with creating and optimizing professional profiles on LinkedIn, Upwork, Fiverr, Contra, and other relevant marketplaces.
• Review portfolios and recommend improvements aligned with global recruitment standards; support personal branding, online presence, profile visibility, and client attraction.
• Guide learners on freelance and client projects, review outputs, and provide actionable quality-improvement feedback.
• Help graduates navigate client communications and project management challenges, and promote professionalism, strong client service, and continuous improvement.
• Conduct regular progress reviews to monitor graduate development and success.
• Share digital marketing resources, tools, templates, best practices, and real-world case studies; keep graduates informed about industry trends.
• Recommend improvements to the mentoring experience and program outcomes, and collaborate with Generation staff and other Super Agents.

Requirements

• At least 6 years of professional Digital Marketing experience, with hands-on expertise across disciplines such as social media marketing, content marketing, design, SEO, SEM, paid advertising, analytics, email marketing, and campaign management.
• At least 2 years of proven freelancing experience delivering Digital Marketing services to clients.
• Demonstrated success sourcing, securing, managing, and delivering freelance projects through networks, referrals, agencies, freelance marketplaces, or direct client acquisition.
• Strong understanding of freelance business development, pricing, proposal writing, client relationship management, and project delivery.
• Excellent communication, coaching, facilitation, and interpersonal skills.
• Strong organizational and time-management skills, including the ability to mentor multiple learners simultaneously.
• Ability and willingness to dedicate at least 10–15 hours per week to mentoring and learner support.
• Currently based in South Africa and open to remote work.
• Strong knowledge of the South African business environment, digital economy, and remote work ecosystem.
• Commitment to empowering young people from diverse backgrounds to achieve economic independence through freelancing and digital work.
• Passion for mentoring and developing emerging talent, sharing practical industry experience, motivating learners, and holding them accountable while providing supportive guidance.
• Understanding of the realities and challenges of freelancing and ability to provide practical advice to help graduates succeed.

Nice-to-haves

• Previous experience mentoring, coaching, teaching, or supporting people in career development or entrepreneurship.
• Experience helping freelancers secure clients and build sustainable freelance careers.
• Certifications in Google Ads, Google Analytics, Meta Blueprint, HubSpot, LinkedIn Marketing, SEMrush, or related Digital Marketing specializations.
• Experience sourcing gigs through Upwork, Fiverr, Contra, Freelancer.com, PeoplePerHour, or related platforms.
• Experience working with international clients and remote teams.
• Familiarity with online learning platforms, virtual collaboration tools, and community engagement approaches.