About Jack Westin

Jack Westin is one of the most trusted names in MCAT preparation, helping thousands of pre-medical students each year reach their goal of getting into medical school. We are fully remote, mission-driven, and obsessed with student outcomes. Internally, we operate as a systems-first organization with clear roles, lightweight infrastructure, and modern automation tools so our team can stay focused on the work that matters most. We are in a period of rapid growth and are actively building our student support division to care for both new and continuing students.

The Role

The Student Progress Lead owns the lifecycle health of every tutoring student from onboarding through test day. You are not delivering MCAT content; you are making sure students stay engaged, progress on track, and feel supported. You will run proactive outreach and interventions across an active caseload of 200+ students, supported by a Student Progress Ops direct report and a team of MCAT experts who you can coordinate with on quality issues. Reports to the Senior Director of Services.

What You'll Own

• Daily monitoring of the active student dashboard to identify at-risk students and trigger interventions to ensure they don't fall through the cracks.
• Proactive outreach to flagged students to identify barriers and coordinate next steps (expect 15–25 student touchpoints per week).
• Tutor reassignments and escalations to the Lead Tutor or Lead Instructor when quality issues arise.
• Management and development of the Student Progress Ops direct report, including SOPs and daily task review.

What You Bring

• 3+ years in customer success, student services, account management, or a comparable student- or client-facing operations role.
• Communicates with both authority and empathy. Able to meet students where they are (happy, sad, scared, angry, and anywhere in between) while still providing necessary accountability.
• Proven ability to manage a large active caseload (100+) without losing the individual relationship.
• Google Sheets fluency and experience monitoring dashboards and data.
• Systems-thinker who builds checklists, spots patterns, and flags process gaps. Self-directed in a remote environment.
• Bonus: edtech or test-prep experience, familiarity with automation tools (Make, Zapier), or exposure to the pre-med journey.
• Not required: MCAT score or medical/content background. This role is student-facing, not instructional.

Logistics

• Location: Fully remote (United States)
• Hours: Monday to Friday. Available for student calls 10:00 AM to 6:00 PM Eastern, with responsiveness to email/messages as needed until 8:00 PM Eastern.
• Reporting Structure: Reports to Senior Director of Services  |  Direct report: Student Progress Ops.
• Compensation: Full-time salary, $50,000–$80,000/year.