ABOUT HAWKER BOYS
Hawker Boys is a social enterprise in Singapore building a real pathway into hawkering for people rebuilding
their lives and returning to the community. The work is anchored in four pillars: Training, Placement, Aftercare
and Ownership.
ROLE SUMMARY
The Programme Lead (Retention & Aftercare) is responsible for strengthening trainee retention, supporting
day-to-day beneficiary stability and coordinating the practical aftercare structures that help individuals sustain
progress over time.
This role combines programme oversight, mentoring, case coordination and stakeholder engagement. The
focus is to ensure that trainees are supported with consistency, accountability and clear routines so that early
setbacks do not become dropouts.
KEY RESPONSIBILITIES
1. Retention and Beneficiary Support
• Build strong working relationships with trainees and graduates
• Monitor attendance, punctuality, engagement and overall adjustment
• Identify early signs of disengagement, instability or conflict and intervene promptly
• Provide steady mentoring, encouragement and practical accountability
• Support beneficiaries in maintaining discipline, consistency and workplace readiness
2. Aftercare Coordination
• Oversee the aftercare journey for trainees and graduates across training, placement and transition periods
• Conduct regular check-ins and follow-up conversations with beneficiaries
• Coordinate support plans for individuals who require closer monitoring or additional structure
• Maintain clear records of issues raised, interventions made and follow-up actions
• Work with partner agencies and relevant stakeholders to ensure continuity of support
3. Employer and Partner Liaison
• Serve as a key point of contact for partner hawkers, training partners and aftercare stakeholders on
beneficiary matters
• Support employer onboarding and help partners understand the profile and needs of trainees
• Address and help resolve workplace concerns, communication breakdowns or behavioural issues early
• Maintain professional communication with external partners to support retention and positive outcomes
4. Programme Operations and Safeguarding
• Help implement clear routines, expectations and escalation pathways for beneficiaries• Support the development and execution of SOPs related to attendance, conduct, mentoring and incident
management
• Escalate serious concerns appropriately and ensure issues are handled in a timely and responsible manner
• Contribute to a stable, structured and safe programme environment
5. Reporting and Continuous Improvement
• Track retention-related data, common drop-off points and recurring barriers to progress
• Prepare simple internal updates and reports on beneficiary progress, concerns and outcomes
• Support management in refining programme design, aftercare flows and retention systems
• Contribute practical insights from the ground to improve programme effectiveness over time
REQUIREMENTS
• Strong people skills with the ability to build trust while maintaining boundaries and standards
• Experience in mentoring, programme delivery, education, youth work, community work, social service,
coaching or related fields preferred
• Able to manage difficult conversations, conflict situations and emotionally charged circumstances with
maturity
• Organised and consistent in documentation, follow-up and case coordination
• Comfortable working with individuals rebuilding stability and returning to the community
• Strong sense of responsibility, discretion and professionalism
• Able to work independently and collaboratively in a start-up environment
• Belief in dignity, accountability and long-term progress
PREFERRED PROFILE
• Experience supporting individuals from challenging backgrounds
• Experience in programme management, pastoral care, education or structured mentoring
• Comfortable engaging both beneficiaries and external stakeholders
• Practical, calm and steady under pressure
• Able to balance empathy with firmness
REPORTING LINE
Reports directly to the Director / Founder of Hawker Boys.
KEY SUCCESS INDICATORS
• Trainee retention and follow-through across programme stages
• Improved attendance, punctuality and consistency among beneficiaries
• Reduction in preventable drop-offs and unresolved conflicts
• Strong communication and coordination with employers and support partners
• Clear documentation and timely escalation of issues
• Positive contribution to programme stability and beneficiary outcomes
WHY THIS ROLE MATTERS
This role is central to the Hawker Boys model. Training and placement only hold when people are supported well enough to stay the course. The Programme Lead (Retention & Aftercare) helps turn opportunity into something that can last - through steady support, practical accountability and consistent follow-through.