Training Facilitator - AI - Freelance (Hawaii)

Training Facilitator - Artificial Intelligence (AI) - Freelance

Location: On-Site, Hawaii (The Big Island)

Who We Are

At SweetRush, we believe that when you put people at the center of business, magic happens. As a global leader in learning and development, we blend high-end storytelling, emerging tech like AI and VR, and deep psychological insights to help organizations—from iconic global brands to essential nonprofits—flourish. We are a remote-first, tight-knit community built on a foundation of radical empathy and creative excellence. Our work isn’t just about the awards we win with incredible partners such as Hilton, Google, Bridgestone, Adidas, SHRM, and numerous others; it’s about balancing profit with a genuine desire to spread good in the world. If you are a caring innovator who believes work should be life-centered and impactful, then this is where you come in…

About the Role

We are seeking an experienced facilitator to deliver a 90-minute AI training session(s) to small businesses on the Big Island of Hawaii.

SweetRush has created the Instructor-Led Training (ILT) for a business association advocacy client, and we are hiring a facilitator to train small business owners in Hawaii. Facilitators will work with the local association point of contact, who will handle logistics, marketing, and participant recruitment.

Key Responsibilities

Training Delivery

• Conduct 1-4 AI training sessions this year in the assigned location (The Big Island)
• Adapt presentation style to diverse business owners with varying levels of technical and AI expertise
• Facilitate hands-on learning experiences using participant-provided laptops and digital training materials
• Local travel within your assigned region is expected and will be reimbursed.

Assessment & Feedback

• Encourage participants to complete an electronic survey form after training session(s)
• Gather insights on how participants plan to utilize AI in their businesses
• Identify areas where businesses intend to implement AI solutions
• Submit session report(s) and recommendations to program leadership

Qualifications

Required

• Proven experience (minimum 5 years preferred) as a corporate facilitator, trainer, or workshop leader in both virtual and in-person settings.
• Exceptional communication skills, both written and verbal. You must be able to communicate effectively both orally and in writing, and speak effectively before large and small groups.
• Demonstrated active listening skills to draw out insights and encourage participation.
• Outstanding interpersonal skills with a natural ability to build rapport and connect with diverse audiences.
• Strong questioning and active listening skills to draw out insights and encourage participation.
• Demonstrated ability to manage group dynamics, handle challenging discussions, and keep sessions on track and within timeframes.
• Ability to synthesize and summarize key points from discussions.
• Self-motivated, highly organized, and detail-oriented with excellent time management skills.
• Must demonstrate AI knowledge exceeding that of a typical small business audience
• Experience with Google AI tools and platforms
• Bachelor's degree in a related field (e.g., Adult Education, Organizational Development, Human Resources, Communications) or equivalent practical experience.
• Ability to drive or take public transit for in-person facilitation as required by client.

Experience Facilitating the Following Subjects is Preferred:

• Competency/Soft Skill Development: Formal skill development to support soft skills (i.e., communication, collaboration, emotional intelligence).
• Leadership Competencies: Development in areas such as coaching, delegation, strategic thinking, and team leadership.
• Technical Skills: Facilitation of subjects like Artificial Intelligence (AI), Project Management, Design Thinking, and other specialized technical areas.

Program Timeline

• Session Frequency: 1-4 training sessions for the remainder of 2026

Support Structure

• Local staff provide logistical support, venue, marketing, advertising, and participant recruitment
• Digital training materials accessible via QR code for participants

Interested candidates should submit:

• Resume highlighting relevant training and AI expertise
• Examples or descriptions of previous training delivery experience
• You must be located on the Big Island and be able to commute to the delivery location.
• If we are interested in your candidacy, we will request a 2-3 minute video work sample that demonstrates your facilitation skills

SweetRush is an Equal Opportunity Employer

We are committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. All employment decisions are based on business needs, job requirements, and individual qualifications, without regard to race, color, religion or belief, national, social, or ethnic origin, sex (including pregnancy), age, physical, mental or sensory disability, HIV Status, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate. SweetRush will not tolerate discrimination or harassment based on any of these characteristics. We encourage applicants of all ages.

Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.

Call-To-Action: Submit Your Resume!

Team chemistry is everything to us, so our ultimate goal is to find the right fit. If the above describes your interests and experience, and you believe this will be a dream job, please submit your resume. We are excited to hear from you!