Regional Digital Transformation Advisor (12 Months 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.

JOB OBJECTIVES

South Asia, Middle East, and Africa (SAMEA) is the largest regional operation in Generation’s global network, supporting tens of thousands of young people into employment each year. As Generation scales its impact and increasingly leverages digital tools, data systems, and AI technologies to improve programme quality and operational efficiency, the need for dedicated, in-country digital transformation expertise has never been greater.

The Regional Digital Transformation Advisor is a member of the Generation SAMEA regional team and serves as the primary digital transformation resource embedded within the country team(s). This role provides expert advisory and facilitation support to drive measurable improvements in how Generation countries, in particular, Ghana and Kenya, operate: transitioning manual workflows to scalable digital solutions, building the team's AI literacy and capability, and acting as a critical bridge between the country teams and Generation's global functions on digital transformation and AI-related initiatives.

The Advisor will combine credible technical knowledge with strong facilitation and change management skills to ensure digital initiatives are prioritized & adopted effectively, sustainably, and in alignment with Generation's global standards and ethical principles.

This role will primarily focus on digital transformation for Ghana and Kenya but may support other countries digitization efforts in time.

12-month fixed-term contract, renewable subject to performance and funding, with strong potential for extension and long-term growth.

KEY ACCOUNTABILITIES & RESPONSIBILITIES

1. Digital Transformation Advisory & Workflow Improvement

Conduct assessments of current workflows and tools across country operations, identifying inefficiencies and prioritizing opportunities for digitization

Advise and support country team in transitioning from manual, Excel-based processes to more efficient, scalable solutions, leveraging existing Salesforce, Power BI, and Snowflake architecture

Lead or co-lead specific digitization initiatives from scoping through to implementation, ensuring local adoption and long-term sustainability

Support country team ensure digital transformation efforts remain in alignment with local and Generation Global policies, local regulations, and global best practices

2 . Discovery, Scoping & Prioritisation

Work with country leadership to identify new digitization opportunities beyond the initial defined portfolio, conducting process mapping and needs assessments as required

Develop business cases for new digital investments where needed

Maintain a living transformation roadmap for countries, tracking progress, milestones, and outcomes

3. AI & Digital Tool Adoption Coaching

Coach and empower country team members at all levels to adopt and use AI tools and agents effectively, responsibly, and confidently, including Microsoft Copilot and Claude

Develop practical, region-specific training resources, playbooks, and guidance materials

Champion ethical AI use across the country teams, ensuring adoption aligns with Generation's values, data privacy standards, Generation’s AI policy, local regulations, and global best practices

4. Global–Country Function Coordination

Serve as the primary connector between the country team and relevant global functions (especially Digital, Data & Impact, and Program Delivery Support) on digitization efforts, facilitating alignment and reducing duplication on digitization priorities

Represent country team needs and perspectives in relevant global forums, working groups, and planning processes

Support global functions in contextualizing and deploying initiatives effectively within the country setting

5. Stakeholder Engagement & Change Management

Build trusted, collaborative relationships with country team leadership and staff to secure genuine buy-in for digital change

Apply change management principles to support smooth transitions, minimise disruption, and embed new practices

Produce clear, accessible communications and documentation to support team adoption and institutional knowledge

QUALIFICATIONS

Education

Bachelor's degree required in a relevant field (e.g., information systems, computer science, business administration, social sciences)

Master's degree in a related discipline is an advantage but not required

Experience

7–10 years of professional experience, with a substantial track record in digital transformation, technology advisory, or change management roles

Demonstrated experience leading or supporting digital transformation in complex, matrixed, multi-stakeholder environments

Hands-on working experience with two or more of the following platforms: Salesforce, Power BI, Snowflake, Microsoft Copilot, Claude (or comparable AI tools)

Experience designing and delivering digital upskilling, training, or coaching programmes for non-technical audiences

Prior experience in or with the international development, social enterprise, or nonprofit sector is preferred

Experience working in SAMEA

Knowledge & Skills

Strong advisory and facilitation skills; able to translate complex technical concepts for non-technical stakeholders

Analytical mindset with the ability to diagnose process inefficiencies and design practical, proportionate solutions

Excellent interpersonal and stakeholder management skills; able to build trust and influence without formal authority across cultures

Robust understanding of data literacy, digital governance, and responsible technology frameworks

Familiarity with ethical AI principles and emerging best practices in responsible AI deployment

Comfortable operating in a global–local matrixed structure with competing priorities, including taking calls across timezones (working with India through to Mexico)

Outstanding written and verbal communication skills in English