Senior Operations Systems Specialist

College Essay Guy LLC; United States; Remote; USD 70,000 - 80,000; Full time

Benefits offered by this job

20 days PTO / Flex Time

7 sick days

11 paid holidays

Medical, dental, vision, life coverage

401(k) + matching

Job summary

College Essay Guy LLC is seeking a technically fluent, hands‑on operator to run the day‑to‑day of the systems powering our programs and marketing. You will ensure clean systems, reliable automations, and healthy websites while supporting live events and marketing operations.

You will work closely with program leaders, automate recurring tasks with AI, and document processes to create durable, scalable operations for a growing organization.

Qualifications

• 6+ years in operations, marketing operations, or a technical operations role.
• AI‑fluent with ability to use AI tools to improve speed and output quality.
• Experience with HubSpot including workflows and data hygiene.
• Strong proficiency in Zapier for live workflows.
• Hands‑on Kajabi or LMS for course builds and automations.
• WordPress administration and basic site maintenance.
• Experience setting up and managing Zoom webinars.
• Excellent written communication and cross‑team coordination.
• Ability to work independently in a fully remote environment and contribute ideas.

Responsibilities

• Keep the operational systems clean and running day to day across HubSpot, Airtable, Zapier, Kajabi, and WordPress.
• Run the marketing operations: CRM hygiene, data quality, email scheduling and live event support.
• Own end‑to‑end build and delivery of live events, webinars, and online courses in Kajabi.
• Collaborate on infrastructure, design, build, and maintenance of automations.
• Be a thought partner to program leads with ideas, not just tasks.
• Automate recurring work using AI and help others do the same.
• Document SOPs and maintain up‑to‑date process guides.
• Website management and blog publishing in collaboration with Marketing.

Skills

HubSpot CRM

Zapier

Kajabi

WordPress

Zoom

Google Workspace

AI fluency

Remote work

Education

Bachelor's degree or equivalent professional experience

Tools

HubSpot

Airtable

Kajabi

WordPress

Zoom

Job 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.

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:

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

You will focus in three areas:

Operations Systems

Keep CEG's operational systems running cleanly day to day so Operations leadership can focus on infrastructure, revenue operations, and cross-functional strategy.

• 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 escape 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.
• Collaborate with the Head of Operations on systems improvements and new automation builds for our programs. You help design, build, test, and maintain; direction and architecture decisions sit with Operations leadership.
• Website management in partnership with Marketing: WordPress updates, plugin management, landing page maintenance, and hands-on support for the upcoming server migration.
• Publish approved blog content to WordPress, including final formatting and quality checks.
• Serve as a thought partner and operational collaborator to program Directors: recurring program tasks, scheduling coordination, systems improvements, and matching automation support.
• Build and maintain SOPs and process documentation so nothing in the function lives in one person's head.
• Use AI tools (Claude and others) to automate your own recurring work first, then help program leads do the same.

Marketing Operations

Own the operational side of marketing so marketing leadership can focus on strategy.

• CRM hygiene in HubSpot: contact records, lifecycle stages, segments, lists, and properties. Keep the data accurate and usable.
• Data hygiene across the connected systems (HubSpot, Airtable, Kajabi) so reporting and automations run on clean inputs.
• Manage the email marketing schedule in collaboration with Marketing. Marketing writes; you build, schedule, test links, and confirm sends and follow-up sequences deploy correctly.
• Coordinate with live event moderators and facilitators on logistics: discount codes, timing of what goes into presentations, links, and pre- and post-session details.
• Support marketing reporting by keeping system data accurate and helping pull recurring numbers.

Live Events & Courses

Own the build and delivery of CEG's live learning experiences so events feel seamless without heroics.

• End-to-end build of live events, webinars, and online courses in Kajabi: structure, content setup, registration, automations, and confirmation flows.
• Zoom webinar setup: configurations, registration workflows, links, and post-event automations.
• Registration-to-follow-up flow management: tagging, segmentation, reminder campaigns, and post-event sequences. Review accuracy before anything deploys.
• Webinar and course landing page creation and maintenance in partnership with Marketing.
• Collect attendance, feedback, audience type, and revenue across programs and turn it into clear observations for program leads, Marketing, and leadership.

Who You Are

• 6+ years in operations, marketing operations, or a technical operations role with a history of quantifiable improvements over time.
• AI-fluent, with a working habit of learning/using AI tools to improve speed and output quality.
• HubSpot or comparable CRM experience, including workflows, segmentation, and data hygiene.
• Strong Zapier proficiency, comfortable building, diagnosing, and improving live workflows.
• Hands-on Kajabi or LMS proficiency: course builds, registration flows, automations.
• WordPress administration: updates, plugins, page maintenance/hygiene.
• Zoom webinar setup and management.
• Google Workspace proficiency (Docs, Sheets, Drive).
• Strong written communication and comfort coordinating across teams and external partners.
• Demonstrated ability to work independently in a fully remote environment with minimal oversight, and to take direction well while bringing your own ideas forward.

Nice-to-Haves

Not required, but extra exciting if you have:

• Experience supporting a server migration.
• Email marketing platform experience (HubSpot Marketing Hub or similar) beyond basic sends.
• Experience inheriting or consolidating multiple operational scopes.
• Experience working in education, college access, student support, nonprofit, or mission-driven learning environments.
• Familiarity with the U.S. college admissions process, live online learning programs, webinars, or courses.
• Bachelor's degree or equivalent professional experience.
• Experience with volunteer management systems.

Compensation, Benefits, and Start Date

• Salary range: $70,000-$80,000/year, depending on experience and location.
• Benefits:
• 20 days of PTO/Flex Time Away
• 7 sick days
• 11 paid holidays
• Medical, dental, vision, life, and long-term disability coverage
• 401(k) + matching

We will follow-up with everyone who applies with an answer!

Questions?

Email Ashley at [e-mail].

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College Essay Guy is an equal-opportunity employer that seeks to hire those who represent the diverse communities we serve. All are encouraged to apply. We are a company of humans; our differences are our strengths. We bring all of ourselves to our jobs. That's what gives us our strength.