Senior Trainer & Curriculum Specialist / Head of Training

ABOUT SKILLSEED

Skillseed is a Singapore-based social enterprise that designs and delivers experiential programmes to transform how organisations engage communities - from transactional interactions to trust-based relationships that enable collective action. Grounded in Asset-Based Community Development (ABCD) and over a decade of practice, we work with public agencies, corporates, and community partners to build capabilities in dignity, empathy, and relational engagement.

THE ROLE

We are hiring a senior practitioner-educator to lead Skillseed’s training, curriculum, and learning products. This is not just a trainer role — you will own the design, delivery, and evolution of learning experiences across:

• Workshops (senior leaders, professionals, youth)
• Curriculum & case studies
• Digital learning tools
• Multi-session programmes with facilitator teams

You will work closely with the Directors to shape our trust-building and community-building frameworks, while building our ability to deliver at scale. This role is suited for someone who can step in with confidence and operate at a senior level quickly, while working collaboratively within a team-based environment.

Key Responsibilities

• Lead Training (Senior Stakeholders)
  • Independently teach and facilitate workshops for adults, including senior management and professionals from the Singapore Public Service, private, people and fourth sector organisations
  • Handle complex group dynamics and questions with confidence and credibility
  • Analysing, consolidating and reporting learning impact, for reporting and improvement purposes
  • Represent Skillseed in high-level engagements where required
• Curriculum & Case Development
  • Create and refine real-world, locally grounded case studies
  • Co-develop new trust-building and community-building curriculum
  • Translate field practice into structured, high-quality learning experiences
  • Design experiential learning approaches beyond lecture-style delivery
• Client Partner & Stakeholder Engagement
  • Support proposal design and solutioning, translating client needs into training approaches
  • Engage client partners across sectors with professionalism and credibility
  • Contribute to strong, long-term working relationships with both community and client partners
• Training Product & Programme Management
  • Manage training-related products (e.g. AI-enabled learning tools)
  • Work with tech/design partners to translate content into digital learning experiences
  • Oversee end-to-end project delivery, including managing timelines, engaging stakeholders, and ensuring quality outputs are delivered
  • Integrate digital tools, guidebooks, and workshops into cohesive learning journeys
• Facilitator Development & Deployment
  • Train, mentor, and deploy associate facilitators
  • Ensure quality and consistency across multi-session programmes
  • Work closely with internal teams to coordinate facilitator deployment
• Youth Programmes
  • Lead and deliver, or deploy associates when needed, all youth-focused workshops, adapting frameworks for accessibility and engagement

WHO WE ARE LOOKING FOR

• Core Experience
  • 5-8 years in training, facilitation and/or community/public sector work where training was a core part of your portfolio, 2 years in a leadership/managerial role preferred
  • Recent experience teaching and facilitating adult learners, such as in soft skills, leadership, OD, communication and teamwork skills
  • Strong experience in curriculum design and experiential learning
  • Experience working within a structured organisation or team environment
  • Ability to translate experiences from the ground and theoretical research into curricula
  • ACTA, ACLP, DACE, or equivalent adult-learning qualification helpful but not mandatory
  • Singaporeans and Permanent Residents preferred
• Core Capabilities (Non-Negotiables)
  • Strong Facilitation Presence
  • Intellectual & Practical Depth
  • Strong Written Communication & Point of View
  • Fast Learner & Adaptable
  • Independent Operator (within a team context)
  • High Ownership & Initiative
  • Independent Thinking & Problem Solving
  • Strong Project & Stakeholder Management
  • Meticulousness & Attention to Detail
  • Professional Discipline & Work Ethic

Additional Strengths (Preferred)

• Exposure to digital or blended learning formats
• Experience engaging public sector or cross-sector stakeholders
• Active interest in community, social, or environmental issues

What Success Looks Like (within 6 months)

• Independently leading senior-level workshops with confidence
• Upgraded curriculum with strong, locally grounded case studies
• Equipped a reliable bench of trained associate facilitators
• Effective rollout and improvement of digital learning tools
• Strong client feedback and repeat engagements

Role Fit (Important)

This role is best suited for someone who:

• Has both facilitation and design depth
• Has recent, hands-on experience teaching adult learners
• Is comfortable operating with high autonomy and accountability
• Works well within a collaborative, team-based environment
• Wants to build and shape, not just deliver

Projected Start Date

We are looking for a candidate who is available to start latest by August 2026.

WHAT WE OFFER

• Contract Terms – A 2-year full-time contract (renewable) with competitive remuneration (between $5.5 to $7k), commensurate with experience.
• Work-Life Balance – Hybrid working arrangements (in-person and remote work), with 2 days WFH, 3 days WFO, and adjustable start/end times daily, with occasional evening/weekend commitments to engage with community activities (with Time-off provided).
• Centrally located work venue on WFO days @Waterloo Centre.
• Meaningful Work – An opportunity to contribute to the development of capabilities in our social sector ecosystem and across sectors.
• Professional Growth – Exposure to cross-sector collaboration with community leaders, subject matter experts, and social impact stakeholders.
• Supportive Environment – A values-driven team that emphasises learning, empathy, and collaboration.
• Positive Office Culture – A fun, non-stuffy, and relaxed workplace where professionalism is balanced with warmth, authenticity, and humanness.

HOW TO APPLY

If this role excites you, we’d love to hear from you! Please share the following with us in this Google Form: Your CV – highlighting relevant experiences. Please also include a link to your Linkedin Profile. A Cover Letter – sharing why you’re interested in this role, how your experiences and strengths align with Skillseed’s work, and what excites you about facilitating learning experiences. A little about you – please include your MBTI profile and your Gretchen Rubin Tendency so we can better understand your working style and how you thrive in a team. References/referral letters - Please include at least one reference from previous employers who can attest to your capabilities in this particular area. We are less concerned with perfect resumes and more interested in understanding who you are, how you work, and what motivates you. Due to limited bandwidth, we regret that only shortlisted candidates will be notified. Please ONLY apply using our Google form above. But know that we appreciate every candidate who takes the effort to apply. Thank you!