Learning & Development Specialist

About Boundless Life

Boundless empowers remote workers to experience—with their families—the nomadic lifestyle many people without children have been enjoying for years. We create a complete "live abroad" immersive experience for families looking to get the most out of what the digital age and the world can offer.

Through premium kid-friendly lodging and a cutting-edge education system that follows children wherever they go, Boundless brings together a community of like-minded families who want to explore the planet while working remotely and having a positive impact on their lives and the world.

Since our founding in 2021, we have quickly grown to 6 locations across two continents and over 135 team members of different nationalities. We’re continuing to grow at a fast pace—next year, we’re opening two new locations (hello LATAM!) and have ambitious goals to empower people to live more fulfilling lives by designing a lifestyle that enables balance, growth, and deeper connections with ourselves, our families, nature, and the world.

The Role

We are looking for a Learning & Development Specialist to build our function from the ground up and drive impactful learning programs across Boundless Life. In this high-impact role, you will shape our learning strategy, design and implement key development initiatives, and create a culture of continuous learning that enables our team members to thrive.

You will identify learning needs, develop training solutions, and oversee the end-to-end execution of learning programs to foster growth and development across all levels of the organization. This is a temporary position for 6 months, with the possibility of extending.

Your work will focus on four key pillars:

• Onboarding Excellence – Creating seamless and engaging onboarding experiences that accelerate productivity and integration for new team members.

• Education Certification Programs – Establishing structured training pathways to ensure our educators are equipped with the skills to deliver high-quality learning experiences.

• Hospitality Training – Developing training programs that empower our hospitality teams to deliver exceptional guest experiences for Boundless families.

• Leadership Development – Designing impactful programs that drive behavioral change, strengthen leadership capabilities, and enhance business results.

Your Day-to-Day

• Partner with leadership to assess learning needs and design a comprehensive strategy aligned with company goals, focusing on professional development at all levels

• Develop and deliver engaging, scalable training programs in multiple formats (in-person, virtual, and blended) using best practices in adult learning and instructional design.

• Build and continuously refine our onboarding programs to enhance the new hire experience and accelerate ramp-up time.

• Design and lead customized team-building sessions (virtual and in-person) to foster stronger collaboration, communication, and alignment among teams.

• Develop structured certification programs for educators and potential candidates.

• Design leadership upskilling programs – identify leadership effectiveness gaps and design targetted interventions to improve leadership skills

• Develop clear project documentation, including learning program standards, templates, and guidelines to ensure consistency and scalability.

• Leverage AI-driven tools and digital learning technologies to streamline program administration, personalize learning experiences, and reduce manual workload.

• Oversee scheduling and logistics for all L&D programs and events, ensuring smooth execution across virtual and in-person settings.

• Provide administrative support for learning programs, including Learning Management System (LMS) administration, intranet communications, and content repository management.

• Evaluate and iterate – Measure program effectiveness and continuously improve offerings based on data and feedback.

Your Success Will Be Measured By:

• On-time execution of key learning initiatives

• Improved onboarding efficiency and time-to-productivity

• Engagement and satisfaction scores from learning programs

• Retention and internal mobility rates

• Positive feedback from managers and team members

Your Manager

You will work directly with Lilian, Head of People and Culture. Lilian brings over 15 years of experience in People and Culture, leading teams across multiple countries and company stages. Most recently, she has worked with startups and scale-ups, building People functions from scratch, setting scalable processes, and growing teams.

About you

To be successful in this role, you should bring expertise in learning and development, a passion for helping people grow, and a strategic mindset to build an L&D function from the ground up. You will be valued for:

• 5 years of experience in designing, launching and scaling L&D programs in a high-growth, global, startup environment.

• Having designed and implemented learning programs for hybrid companies from scratch

• Your background in the Education or hospitality industry

• A product development mindset, ensuring learning programs meet real employee needs.

• Expertise in adult learning principles, instructional design, and facilitation.

• Your track record leveraging AI, digital learning technologies and modern L&D tools and methodologies to create innovative learning solutions.

• Your project management skills with experience handling multiple priorities and stakeholders.

• Ability to thrive in a fast-paced, remote-first environment with a high degree of autonomy.

• Strong facilitation skills, with the ability to engage learners effectively across different levels and channels.

• A strategic yet hands-on approach, comfortable driving both high-level strategy and execution.

• Exceptional collaboration and communication skills, with the ability to influence across the organization.

• A data-driven approach to measuring program effectiveness and continuous improvement.

What's Next?

• Video interview – Answer 4-5 key questions about your experience.

• First call (30 min) – Chat with our Recruiter.

• Interview with the Head of People and Culture (45 min) – Deep dive into your experience and approach.

• Interview with a key business stakeholder (45 min) – Discuss L&D needs within the organization.

• Team meeting (45 min) - get to know how we work as a team and validate cultural fit

• Final check-in with the Head of People and Culture (30 min) – Wrap-up conversation before the offer.

The process might change slightly as we go along, but we’ll keep you informed at all times. 

Want to know more about working at Boundless Life? Check out our story!