About Jack Westin

Jack Westin is a leading Medical College Admissions Test (MCAT) preparation company which is known for crafting high quality, but free, practice materials. The MCAT tests students on the scientific reasoning skills and scientific knowledge which can be learned during typical undergraduate coursework.

Our Three Principles

As we continue to grow and help students, we are guided by three major principles that we believe are vital to our community.

Attention to quality

We only create courses and practice questions that we would use. That means having the best, first-class teaching content that can possibly exist. We're not satisfied with mediocrity. We don't care about the amount of time or money it takes to get something done right. If it's not perfect, we won't stop until we believe it is. This ethos runs deep within our company.

Excellence in support

We're obsessed with our students. Their well-being and success drives us each day. Great customer service is not an afterthought. It is the most important service we can offer. We understand that our students come from different learning backgrounds. It's our mission to ensure that each one has an amazing experience.

Learn from anywhere at anytime

We are committed to building the future of education on the internet so that it is easily accessible to all students from around the world. Our dedication is to all students who want to learn, regardless of their pace, and no matter what time of the day it is.

About the Role

Position: Lead Support Agent

Department: Student Support

Reports To: Senior Director of Operations

Direct Reports: Customer Support Agents (functional lead)

Schedule: Shift coverage incl. some evenings/weekends

Salary: $1,800 – $2,500 per month

The Lead Support Agent is an experienced, trusted member of our Student Support team who does everything a Customer Support Agent does — and then helps the rest of the team do it well. You still work directly with students across email, phone, and text, but you also train new recruits, set the standard for what great support looks like, and own the judgment calls on the harder cases.

Like everyone on the team, you hold the line on our core principle: every communication is courteous, respectful, human, and written for the individual student. Templates and the guidebook are tools, never shortcuts — and a big part of your job is making sure that standard holds across the whole team, especially as new agents come on board.

What You’ll Do

Everything a Customer Support Agent Does

• Handle student inquiries and requests across email, phone, and text — course questions, guarantee claims, technical issues, billing, and account matters.
• Read each ticket in full, answer every part, and personalize every reply so it speaks directly to the student. Templates are a starting point, not a finished message.
• Apply guarantee, refund, and product policies accurately and consistently, and keep clean records in the help desk and CRM.

Train and Onboard New Recruits

• Onboard new Customer Support Agents: walk them through our products, policies, tools, templates, and the guidebook.
• Model the Jack Westin voice and show new hires how to turn a template into a genuine, student-specific reply.
• Run shadowing and reverse-shadowing sessions, review early tickets, and give specific, constructive feedback.
• Help build and keep training materials, onboarding checklists, and guidebook content current as products and policies change.
• Serve as the day-to-day go-to person for agents’ questions about how to handle a situation.

Own the Hard Cases and Decisions

• Act as the escalation point for complex, sensitive, or high-stakes tickets that fall outside the standard playbook.
• Make the judgment calls. Decide on edge-case guarantee claims, exceptions, sensitive refund situations, and upset-student conversations — balancing fairness to the student with company policy.
• Know when to decide independently, when to loop in a manager, and when to involve billing, technical, or other teams; document the reasoning either way.
• Step in directly on escalations, de-escalate tense situations, and bring them to a clean resolution.

Uphold and Raise Quality

• Review a sample of the team’s communications for accuracy, completeness, tone, and personalization, and coach toward improvement.
• Help maintain and refine the call/email quality standards and grading rubric for the support team.
• Spot recurring issues, policy gaps, and workflow problems, and partner with the manager on fixes.
• Help triage and balance the team’s ticket load during busy periods so response and resolution targets stay on track.

What We’re Looking For

Required

• Proven experience in customer or student support, with a track record of excellent, personalized communication.
• Outstanding written and verbal English; you set the example for clear, warm, courteous, and complete replies.
• Sound judgment and composure under pressure — comfortable making decisions on ambiguous or sensitive cases.
• A natural coach: patient, specific, and encouraging when training and giving feedback.
• Deep attention to detail and strong ownership; you follow through and you hold a standard.
• Fluency with support tooling (help desk/ticketing, CRM, phone systems) and the ability to teach others to use it.

Nice to Have

• Prior experience as a senior agent, team lead, or trainer in a support environment.
• Familiarity with the MCAT, the medical school application process, or pre-health advising.
• Experience with HubSpot and contributing to SOPs, knowledge bases, or quality rubrics.

How Success Is Measured

• New agents ramp quickly and reach a high, consistent quality bar in their communications.
• Escalated and complex cases are resolved fairly, promptly, and in line with policy.
• Team-wide quality stays high — replies are accurate, complete, personalized, and on-brand.
• Students on escalated cases come away feeling respected and well cared for.
• The team consistently meets response, resolution, and satisfaction targets.