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Seasonal Training Guide - Midwest Contractor Role

3 weeks, 1 day ago
United States
Contract
Mid Level
Training Specialist
Project and Program Management
Apply Now
Wayfinder

Wayfinder

Wayfinder designs SEL + Life Readiness curriculum for K 12 schools that develops healthy self esteem, belonging, and purpose. Founded @stanforddschool to help students navigate their life with purpose. Build #SEL + future ready skills at your school wi...

Education Services
11-50
Founded 2017
$2M raised
View All Jobs 4

Description

  • Deliver virtual and on-site professional learning sessions for school partners as assigned by the Senior Director of Learning + Development.
  • Develop and maintain expertise in specific sessions from the Wayfinder Professional Learning catalog.
  • Manage, gather, and share information efficiently across assignments and training engagements.
  • Facilitate dynamic training experiences that leave educators with actionable takeaways.
  • Prepare for and support training during the highest-volume months of August and September.
  • Travel within the continental U.S. for in-person facilitation work, which may occur 50–75% of the time.
  • Work independently on assigned tasks while adapting to shifting priorities in a fast-paced environment.
  • Build confidence and excitement among educators implementing Wayfinder in their classrooms.

Requirements

  • Must be based in the Midwest, USA.
  • Availability during August and September is critical.
  • Bachelor’s degree in Education or a related field preferred.
  • Experience delivering professional learning to educators in both virtual and in-person settings.
  • Experience teaching in or supporting teachers in a school or district.
  • Minimum 1 year of experience teaching or supporting Wayfinder in a school or district is a plus.
  • Experience working directly with educators to support success with a product or program is a plus.
  • Strong internet bandwidth and access to a personal computer are required.
  • Access to a quiet space for virtual professional development is required.
  • Ability to use Zoom, Google Meet, Microsoft Teams, Google Tools for Education, Clever, Google Calendar, Slack, Google Drive, and spreadsheets.
  • Knowledge of effective teaching practices, learning strategies, future-readiness, and connecting future-readiness to academic achievement.
  • Ability to lead engaging sessions with strong stage presence while remaining approachable and relatable.
  • Ability to work in a startup-like environment where priorities can shift quickly.
  • Willingness and ability to travel within the continental U.S. 50–75% of the time.

Benefits

  • Virtual facilitation pay of $100–$125 per hour.
  • Prep and follow-up pay of $50–$55 per hour for up to 2 hours.
  • In-person facilitation paid at a $500–$550 flat rate.
  • Travel expenses are covered upfront by Wayfinder.
  • Seasonal contractor opportunity with onboarding in June and a July 2026 start date.
  • Rolling application review.
  • Opportunity to work with a mission-driven, purpose-centered team.
  • Wayfinder encourages applicants from traditionally underrepresented populations to apply.

Interested in this position?

Apply directly on the company website

Apply Now

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