Tutor Quality & Engagement Lead

Tutor Jackets is seeking a Tutor Quality & Engagement Lead to oversee the experience, performance, and development of our tutor team. This role is responsible for ensuring that tutors:

• Deliver high-quality, consistent sessions
• Feel supported and engaged
• Have the tools and guidance needed to succeed long-term

You will work closely with the Tutoring Operations Coordinator and Founder to maintain and scale tutor quality as the company grows.

• Conduct initial tutor interviews (first round screening)
• Lead new tutor onboarding sessions (small groups of 2-3 tutors)
• Guide tutors through:
  • Systems (Teachworks, Lessonspace, Google Drive)
  • Session expectations and structure
• Facilitate practice onboarding / demo sessions to ensure readiness
• Conduct 1-month check-ins with new tutors and provide initial feedback

• Conduct weekly session audits (3-5 tutors per week) to evaluate session structure, flow, student engagement, and teaching clarity and effectiveness
• Document audit notes and:
  • Send clear, actionable feedback to tutors
  • Identify trends or recurring issues
  • Escalate concerns when needed
• Lead occasional retraining sessions for tutors who need additional support

• Serve as the first point of contact for tutor questions (email / messaging)
• Ensure tutors:
  • Have access to the right resources
  • Feel confident in their sessions
  • Stay aligned with Tutor Jackets teaching & performance standards
• Facilitate and manage the Tutor Slack/Discord channel
  • Share announcements and updates
  • Answer questions
  • Encourage discussion and collaboration
• Host weekly or bi-weekly office hours for tutor support

• Conduct periodic tutor check-ins (mid-semester, end/start of semester, or as needed)
• Gather feedback on tutor experience, student progress, operational improvements
• Help maintain a strong tutor experience with goals of High engagement & 1-3 year tutor retention

• Maintain and improve tutor resources and training materials
• Share best practices and insights from session audits, tutor feedback, student outcomes

• Assist Coordinator in matching tutors to students using founder's consultation notes, schedules, student needs, and tutor strengths
• Support creation of SAT/ACT Prep Plans based on templates and Founder guidance
• Collaborate with Founder & Coordinator on final decisions

• Google Workspace (Drive, Docs, Sheets, Calendar)
• Teachworks / Lessonspace (session audits, reviewing schedules)
• Slack or Discord (tutor communication)
• Email & messaging tools (internal communication)

• 10 to 15 hours per week
• Primary availability: Tuesday - Thursday 5-8 PM EST (Some flexibility based on scheduling needs)

• Strong communication and leadership skills
• Experience in tutoring, teaching, or mentoring
• Ability to give clear, constructive feedback
• Organized and detail-oriented
• Comfortable working in a startup-style, evolving environment

This role focuses on tutor quality and internal team support.

• The Founder will continue to lead family consultations and oversee strategy and growth.
• The Tutoring Operations Coordinator will manage scheduling, daily operations, and client communication, escalating to the Founder or this role as needed. The team will align through a weekly stand-up meeting to review priorities, address challenges, and plan ahead.

$250 - $350 a month

• 100% REMOTE
• $50 birthday bonus
• $200 testimonial bonus
• $500 entry monthly raffle
• NO TRACKER. NO PROBLEM