Digital Marketing Super Agent (Freelance Mentor) (6Months Fixed Term/Remote)

ABOUT GENERATION

At Generation, we believe in the power of employment to change lives. We are a global nonprofit organization that supports adults to achieve economic mobility through employment. Generation trains and places adult learners of all ages into careers that are otherwise inaccessible, working in partnership with governments, employers, and other system actors. We also conduct original research and share data insights on high-priority global workforce transition topics to inform decision-making by workforce system stakeholders. Launched in 2015, Generation comprises a global hub (Generation You Employed, or GYE) and a network of in-country affiliates. To date, the network has 150,000+ graduates and 23,000+ employers across 50 professions and 17 countries.

When learners join Generation, 91% are unemployed, of which nearly half are long-term unemployed.  Three months after completing our program, graduates have a 78% job placement rate, rising to 88% within six months. Of our employed graduates, 79% are hired by repeat employers who have previously hired Generation graduates, and 89% are in jobs directly related to the profession for which we have trained them. Employed graduates immediately earn an average of 3-4X their previous earnings.  Two to five years after graduation, 77% of our alumni from upper-middle income countries continue to meet their daily financial needs and 63% can save for the future. To date, Generation’s global graduates have earned more than $1.9 billion in wages. Generation graduates typically have a secondary school background, 52% are female, 28% have dependents, and the majority identify with underrepresented communities in their country.

As part of the BOOST Project, Generation is expanding its network of experienced freelance professionals to support and mentor Digital Marketing graduates as they transition into freelancing and remote work opportunities. Through expert mentorship, practical guidance, and industry connections, Super Agents play a critical role in helping graduates build sustainable freelance careers, secure income-generating opportunities, and achieve greater financial independence.

JOB OBJECTIVES

Generation is seeking experienced freelance Digital Marketing professionals based in South Africa (Johannesburg preferred) to serve as Super Agents and mentors for graduates entering the freelance/gig economy.

As Super Agent, you will play a critical role in guiding, coaching, and supporting graduates as they build freelance careers, secure clients, deliver quality work, and generate sustainable income. This role combines mentoring, technical guidance, accountability coaching, freelance business development support, and practical knowledge sharing.

The ideal candidate is an experienced Digital Marketing freelancer with a successful track record of delivering client work, building freelance income streams, and supporting others to grow professionally.

Most importantly, we are looking for individuals who are passionate about helping young people build skills, confidence, and financial independence through freelancing and remote work.

KEY ACCOUNTABILITIES & RESPONSIBILITIES

Mentorship & Coaching

• Provide ongoing one-on-one and group mentoring sessions for assigned graduates.
• Support graduates in applying digital marketing skills in real-world client environments.
• Guide graduates in building confidence, professionalism, and effective work habits.
• Provide constructive feedback on portfolios, proposals, project work, and client communications.
• Help graduates identify strengths, overcome challenges, and achieve their professional goals

Freelance Career Development

• Share practical insights from your own freelance journey and professional experience.
• Support graduates in understanding the freelance marketplace and how to position themselves effectively.
• Help graduates identify opportunities for income generation through freelance and remote work.
• Guide graduates in building sustainable freelance businesses and long-term client relationships.
• Advise graduates on sourcing opportunities through personal networks, referrals, direct outreach, LinkedIn, and freelance platforms.

Pricing Strategy & Business Development Support

• Guide graduates in developing competitive and sustainable pricing strategies.
• Support graduates in packaging and positioning their services effectively.
• Review proposals and quotations and provide recommendations for improvement.
• Help graduates understand client discovery, negotiation, and project scoping processes.
• Provide practical advice on managing freelance income and growing client accounts.

Profile Setup & Optimization

• Assist graduates in creating and optimizing professional profiles on platforms such as LinkedIn, Upwork, Fiverr, Contra, and other relevant marketplaces.
• Review graduate portfolios and recommend improvements in line with global recruitment standards.
• Support graduates in developing compelling personal brands and professional online presence.
• Advise graduates on improving profile visibility and attracting potential clients.

Project Support & Quality Assurance

• Provide guidance and support to learners working on freelance and client projects.
• Review project outputs and provide actionable feedback to improve quality.
• Help graduates navigate client communications and project management challenges.
• Encourage high standards of professionalism, client service, and continuous improvement.
• Conduct regular progress reviews to monitor graduate development and success.

Knowledge Sharing & Community Building

• Share relevant digital marketing resources, tools, templates, and best practices.
• Present practical case studies and examples from real-world client engagements.
• Keep graduates informed about trends and developments within the digital marketing industry.
• Contribute ideas and recommendations to strengthen the mentoring experience and overall program outcomes.
• Collaborate with Generation staff and other Super Agents to support learner success.

QUALIFICATIONS

Desired Experience & Qualifications

• A minimum of 6 years of professional experience in Digital Marketing, with hands-on expertise across key disciplines including social media marketing, content marketing, Design, SEO, SEM, paid advertising, analytics, email marketing, and campaign management, etc...
• At least 2 years of proven freelancing experience, successfully delivering digital marketing services to clients.
• Demonstrated success in sourcing, securing, managing, and delivering freelance projects through personal networks, referrals, agencies, freelance marketplaces, or direct client acquisition.
• Strong understanding of freelance business development, pricing strategies, proposal writing, client relationship management, and project delivery.
• Excellent communication, coaching, facilitation, and interpersonal skills.
• Strong organizational and time management skills, with the ability to mentor multiple learners simultaneously.
• Ability and willingness to dedicate a minimum of 10–15 hours per week to mentoring and learner support activities.
• Must be currently based in South Africa and open to remote ways of working.
• 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.

Preferred Qualifications

• Previous experience mentoring, coaching, teaching, or supporting individuals 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 using freelance platforms such as Upwork, Fiverr, Contra, Freelancer.com, PeoplePerHour, or related job platforms to source gigs.
• Experience working with international clients and remote teams.
• Familiarity with online learning platforms, virtual collaboration tools, and community engagement approaches.

What We’re Looking For

We are looking for a successful freelance Digital Marketing professional who:

• Has built a credible and sustainable freelance career.
• Is passionate about mentoring and developing emerging talent.
• Enjoys sharing knowledge, practical insights, and industry experience.
• Can motivate, inspire, and hold learners accountable while providing supportive guidance.
• Understands the realities and challenges of freelancing and can provide practical advice to help graduates succeed.
• Believes in the power of freelancing and remote work to create economic opportunities for young people across Africa.
• Is committed to helping graduates build confidence, secure income-generating opportunities, and achieve long-term financial independence.

To apply, please submit:

• An up-to-date CV/Resume.
• A brief cover letter highlighting:
  • Your Digital Marketing experience.
  • Your freelancing experience and achievements.
  • Your experience coaching, mentoring, or developing others.
  • Why you are passionate about supporting young people pursuing freelance careers.
• Links to your LinkedIn profile, portfolio, freelance profiles, website, or other relevant work samples.

*Generation is committed to diversity, equity, and inclusion and welcomes applications from qualified candidates across South Africa who are passionate about creating opportunities for young people through digital work and freelancing.*