Senior Operations Systems Specialist

College Essay Guy; United States; Remote; USD 85,000 - 120,000; Full time

Job summary

College Essay Guy seeks a technically fluent, hands-on operator to manage the day-to-day systems powering our programs and marketing. You will keep HubSpot, Airtable, Zapier, Kajabi, and WordPress healthy, and act as a collaborator to program leads, ensuring reliable execution and automated workflows.

In time, you’ll cross-train across the full services lifecycle, supporting lead acquisition, onboarding, service delivery, and post-service activities.

Qualifications

• Experience operating day-to-day administration of core systems (HubSpot, Airtable, Zapier, Kajabi, WordPress).
• Ability to triage bugs, document issues, and maintain reliable infrastructure.
• Experience running live events end-to-end and coordinating marketing tech.

Responsibilities

• Keep systems clean, monitor automations, and triage issues across tools.
• Run marketing operations: CRM, data hygiene, email calendar, events prep.
• Build and run live events end to end from build to reporting.
• Collaborate on infrastructure and automate recurring work.
• Be a thought partner to program leads with proactive ideas.
• Automate own role and document SOPs for durability.

Skills

HubSpot

Airtable

Zapier

Kajabi

WordPress

Bug triage

Automation

Tools

HubSpot

Airtable

Zapier

Kajabi

WordPress

Job description

College Essay Guy

Senior Operations Systems Specialist

Remote · Full time

About College Essay Guy

College Essay Guy helps students tell their stories and find their way through the college admissions process. Founded by Ethan Sawyer, author of College Essay Essentials and College Admission Essentials, we reach more than one million students and counselors each year.

We offer free resources, including a blog, podcast, webinars, and resource centers for first-generation, low-income, and international students, alongside pay-what-you-can online courses. We also provide 1-on-1 essay coaching and admissions counseling, school workshops, and professional development for counselors and educators.

Our approach is practical and step-by-step. We give students clear tools to write essays that are honest, insightful, and their own. We're a Certified B Corp, and we're committed to making high-quality college guidance accessible to every student, regardless of background.

Description

College Essay Guy is hiring a technically fluent, hands-on operator to run the day-to-day of the systems that power our programs and our marketing, and to be a real collaborator to the people who lead them.

This role is the execution and maintenance layer underneath the technological direction: you keep the systems clean, the automations firing, the bugs triaged, the website healthy, and the live events built and running. You also carry the operational side of marketing, from CRM and data hygiene to the email calendar to what the moderators need in hand before a live event starts.

Over time, the person in this seat will be cross trained across the full 1:1 services lifecycle (lead acquisition, onboarding, service delivery, and post-service) and will take on more of the systems build-out as the org grows. In the near term, the priority is reliable execution, sharp collaboration, and a habit and comfortability of using AI to automate as much of your own recurring work as possible.

What You’ll Do

As a Senior Operations Systems Specialist, you will:

1. Keep the systems clean and firing. Own day-to-day administration, monitoring, and bug triage across HubSpot, Airtable, Zapier, Kajabi, and WordPress.
2. Run marketing operations. CRM, contact, segment, and data hygiene; the email schedule; and what moderators and facilitators need for live events.
3. Build and run live events end to end. Every webinar, course, and CEG Live event, from build to follow-up to reporting.
4. Collaborate on the infrastructure. Help design, build, and maintain automations and systems improvements under the direction of the Head of Operations.
5. Be a thought partner to the program leads. We need an operator who shows up with ideas, not just task completion.
6. Automate your own job. Lean on AI and automation to shrink recurring work, then help others do the same.
7. Document everything. SOPs stay current so the function is durable and nothing is single-threaded.

You will focus in three areas:

Operations Systems

• Day-to-day administration of HubSpot, Airtable, Zapier, Kajabi, WordPress, and the smaller tools around them.
• First-line bug triage across the stack: reproduce, resolve known issues, document, and elevate real infrastructure problems to the Head of Operations with a clear diagnosis.
• Monitor automations and workflows for accuracy and failures. Fix what is yours to fix, flag what is not, and bring recommendations with a plan rather than just a flag.