Seasonal Training Guide - Contractor Role

Wayfinder; United States; On-site; USD 50,000 - 70,000; Part time

Benefits offered by this job

Travel expenses covered

Flexible working hours

Job summary

An educational organization is seeking a dedicated individual to support professional learning experiences for educators as a Wayfinder guide. This contractor role demands an engaging personality, project management skills, and strong communication abilities. Responsibilities include managing training sessions and delivering content using various digital tools. Ideal candidates will have a background in education, with a passion for future-readiness curricula. This position requires flexibility and travel across the continental US, making it suitable for individuals excited about impactful teaching methods.

Qualifications

• Strong and consistent internet bandwidth and a personal computer.
• Experience facilitating training for educators both virtually and in-person.
• Genuine excitement for future-readiness education.

Responsibilities

• Deliver virtual or on-site professional learning with school partners.
• Efficiently manage and share information.
• Maintain expertise in Wayfinder training sessions.

Skills

Project management

Interpersonal skills

Communication skills

Dynamic presentation

Adaptability

Education

Bachelor's degree in Education

Tools

Zoom

Google Meets

Microsoft Teams

Slack

Google Drive

Job description

Overview

The Organization: What if K-12 education were designed to help all students develop lives of meaning and purpose? Wayfinder was founded at the Stanford d.school to answer this question. Our goal is to double our impact each year for the coming years. Our vision is to become the preeminent future-ready skills curriculum company in the world — leading the global movement of purpose, meaning, and belonging-based education worldwide.

What We Value: In this contract work, you'll be supporting a team of incredibly motivated and dedicated staff members committed to living our organization's values. We work collaboratively across teams, and we feel and act like a purpose-driven organization. To the best of our abilities, each person's role aligns with their own sense of purpose, which feeds into Wayfinder's larger sense of purpose. We value equal access, inclusive community, and belonging, and these values are represented in our product, our team, and our school partners. Product: We develop our learning tools using human-centered design principles. We work with grade-level experts to ensure our curriculum is developmentally appropriate and engaging at all levels. Every Wayfinder lesson is supported by relevant research, prototyped in classrooms, and vetted by teachers over rounds of feedback and iteration. We use Universal Design for Learning principles to give every student an equal opportunity to succeed. Team: Our team is composed of people from all different backgrounds and walks of life. We intentionally recruit, hire, and work with people of diverse identities + experiences. We focus on belonging: being connected, accepted, and valued by the people around us. School Partners: We intentionally target a wide array of educational partners, from traditional to non-traditional, that work with a range of students from different socioeconomic groups. We\'ve taught our curriculum in high-need schools in the Bronx, independent schools in Silicon Valley, and after-school programs in San Antonio.

The Role: 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. 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.

Responsibilities

• Commit to and deliver virtual or on-site professional learning with school partners, as assigned by the Senior Director of Learning + Development. Availability during August and September is critical due to high training volume.
• 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)

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

We want you to have these but still apply if you believe you can get the job done!

• 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.

Benefits

Compensation

• This role is paid at $100/hour for virtual facilitation and $50/hour for up to two hours of preparation and follow-up time.
• In person rates are paid at a $500/ flat rate.
• Wayfinder covers all travel expenses up front. Reimbursement is not required.

Next Steps

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.