[Hiring] Seasonal Training Guide @Wayfinder

Role Description

Support our team of world-class Wayfinder trainers, or guides, as we like to call them. The ideal Wayfinder guide pairs an engaging and dynamic personality with a level of knowledge to facilitate professional learning experiences that leave educators feeling confident and excited to implement Wayfinder in their classrooms. We are looking for an enthusiastic, dedicated person who is excited to work in a fast-paced environment and has a proven track record of project management and an entrepreneurial mindset. You are extremely organized, have strong interpersonal and communication skills, and thrive off of the opportunity to solve real-world problems for educators.

Due to the regional needs and nature of this work, we require someone based on the West Coast, USA. Please note that this is a seasonal, contractor opportunity. If you are interested in full-time employment with Wayfinder, please see currently open opportunities on our Careers page. No agreement for full-time employment is indicated through your acceptance of this contracted position.

What We Expect You To Do

• Commit to and deliver virtual or on-site professional learning with school partners, as assigned by the Senior Director of Learning + Development. Please Note: Our highest volume of training is in August and September. As a result, availability during those months is critical.
• Efficiently manage, gather and share information.
• Develop and maintain expertise in specific training sessions from the Wayfinder Professional Learning catalog.

What We Expect You To Know

• How to use Zoom, Google Meets, Microsoft Teams, Google Tools For Education and Clever.
• How to efficiently manage your availability using Google Calendar.
• Effective teaching practices and learning strategies, particularly with future-readiness and how to connect it with Academic Achievement.
• How to lead dynamic and engaging sessions, ensuring participants leave with actionable takeaways.
• Knowledge of tools and methodologies for managing projects in a fast-paced environment (e.g., Slack, Google Drive, Spreadsheets etc.).

What You Will Need To Be Successful

• Strong, consistent internet bandwidth and your own computer.
• Leverage authentic experiences in training and facilitation.
• Strong stage presence for facilitating training while remaining approachable and relatable to educators.
• Genuine excitement for future-readiness education and the impact of Wayfinder’s curriculum.
• Manage independent tasks and assignments.
• Access to a quiet space for delivering virtual professional development.
• Ability to pivot with grace and comfort working in a startup-like environment where priorities and tasks may shift quickly.
• Willingness and ability to travel within the continental US 50-75% of the time.

Education and Experience

• Bachelor’s degree in Education or a related field.
• Experience delivering professional learning to educators in a virtual and in-person setting.
• Experience teaching in or supporting teachers in a school or district.
• Plus: Minimum of 1 year experience teaching or supporting Wayfinder in a school or district.
• Plus: Experience working directly with educators to ensure their success with a product or program.

Location

Due to the nature of this work, travel is required and frequent.

Compensation

• Virtual Facilitation: $100–$125/hour (facilitation), $50–$55/hour for prep & follow-up (up to 2 hours).
• In-Person Facilitation: $500–$550 flat rate.
• Travel expenses covered upfront by Wayfinder (no reimbursement needed).

Next Steps, If Interested

If you are interested, please fill out the application here. Applications will be reviewed on a rolling basis. Start date for the work will be July 2026, with Onboarding in June.

We strongly encourage people from traditionally underrepresented populations in tech - such as women, People of Color, People with Disabilities, and LGBTQ+ people, etc - to apply.

EEO Statement

At Wayfinder, we don’t just accept differences — we celebrate them, we support them, and we thrive on them for the benefit of our employees, our products, and our community. Wayfinder is proud to be an equal opportunity workplace.