We are Hiring!

About The Courage Chapter

The Courage Chapter is a Singapore-based organisation that helps experienced professionals transition into meaningful second chapters of work and life.

As life expectancy increases, many professionals in their 40s, 50s and 60s are rethinking what the next stage of their careers could look like. Rather than traditional retirement, we see many seeking what we call the four Fs: fulfilment, flexibility, fitness (across physical, mental and social wellbeing), and finances. Through our community and partnerships with companies, charities and institutions, we create opportunities for experienced professionals to contribute through projects, fractional roles, advisory work, and purposeful employment.

Our mission is simple but ambitious: to build a society where experience continues to matter.

We believe deeply that when experience meets opportunity, individuals thrive, organisations benefit, and society becomes stronger.

Role Overview

We are looking for a Freelance Recruiter to support the growing number of opportunities across our ecosystem of corporate partners, social sector organisations, and impact initiatives.

Unlike traditional recruiting roles, this position involves working with experienced professionals who are exploring second chapters, and helping organisations rethink how talent can contribute in more flexible and meaningful ways.

You will play an important role in identifying strong candidates from our community, understanding organisational needs, and facilitating thoughtful matches that create value for both individuals and organisations.

This role is well suited for someone who enjoys connecting people, understanding motivations, and facilitating meaningful opportunities.

Key Responsibilities

Talent Matching & Recruitment

• Identify suitable candidates from The Courage Chapter’s community for available opportunities
• Conduct screening conversations to understand candidates’ skills, experience, motivations, and second-chapter aspirations
• Recommend strong candidates to hiring organisations
• Coordinate interview processes between candidates and hiring organisations
• Support both parties throughout the recruitment and decision-making process

Candidate Engagement

• Build relationships with experienced professionals in the Courage community
• Help candidates articulate their transferable skills and value proposition
• Support candidates in navigating career transitions into new sectors or types of work
• Provide feedback and encouragement where needed

Employer Partnership Support

• Work closely with the Courage team to understand employer needs and job scopes
• Help translate employer requirements into clear candidate profiles
• Advise on candidate fit based on experience, motivations, and organisational culture

Recruitment Operations

• Maintain candidate notes and progress updates
• Track interview processes and outcomes
• Support coordination of offers and onboarding where relevant

Requirements

• Experience in recruitment, HR, talent acquisition, or people advisory is strongly preferred
• Strong interpersonal and communication skills
• Ability to assess candidate suitability and motivations thoughtfully
• Comfortable working independently in a freelance or project-based arrangement

Regulatory Requirement

Under Singapore regulations, individuals performing recruitment activities with The Courage Chapter must hold the Certificate for Employment Intermediaries (CEI) – Non-MDW

Candidates should either:

• Already hold a valid CEI (Non-MDW) certification, or
• Be willing to attend the CEI preparatory course and pass the CEI exam

The Courage Chapter will cover the cost of the first exam attempt and the licence application for suitable candidates who do not yet hold the certification.

Our Values

At The Courage Chapter, how we work matters as much as what we do.

• Respect for Experience - We believe experience carries deep wisdom and value.
• Courage to Redesign Careers - We encourage people to rethink traditional career paths and create new possibilities.
• Human-Centred Work - Behind every CV is a person, a story, and a season of life.
• Contribution Over Titles - We care less about hierarchy and more about how people contribute meaningfully.
• Community First - We believe progress happens when people support one another.

Working Arrangement

• Freelance / contract basis
• Remote-friendly with occasional in-person meetings or events
• Flexible hours depending on recruitment needs

Compensation will be project-based or placement-based, depending on the nature of the role.

Why Join Us

This is more than a recruiting role.

You will be helping experienced professionals find renewed purpose, while helping organisations unlock the value of experience.

You will also gain exposure to a wide ecosystem of corporates, charities, social enterprises, and mission-driven initiatives that are experimenting with new ways of working.

If you believe that careers should not be defined by age, and that experience should continue to matter — we would love to hear from you.