Operations and Automation Specialist

Role details: This is a 100% remote contractor role open to applicants worldwide.

The role

TailWerks runs on ClickUp, Google Workspace, GoHighLevel, n8n, documented SOPs, and a growing set of supervised automations. This role keeps the operating record clean and builds leverage without turning the agency into a pile of fragile workflows.

You will maintain task hygiene, reports, templates, onboarding and offboarding handoffs, system documentation, backups, and approved automations. You will investigate failures, keep costs and dependencies visible, and make sure a human approval remains in the loop where client, financial, or public actions require it.

This is not a build-it-and-forget-it role. An automation is useful only when its purpose is clear, its owner is known, its failures are monitored, its output is verified, and someone can maintain or disable it safely.

What you will own

• Maintain ClickUp structure, required task fields, templates, operational reporting, and cross-department handoffs.
• Keep current SOPs, system inventories, owners, dependencies, credentials locations, and recovery notes documented in approved systems.
• Build and maintain approved workflows in GoHighLevel, n8n, ClickUp, and related tools.
• Test automations with controlled data, obtain required approval before production use, and verify the live result.
• Monitor scheduled workflows, backups, errors, stale jobs, and cost or usage concerns.
• Investigate failures and communicate the impact, containment, owner, and recovery plan.
• Support onboarding, offboarding, access changes, and vendor follow-through through the approved checklists.
• Identify recurring manual work and propose automation only when the process and risk boundaries are understood.

How our core values show up in this role

Own It

You own the reliability and documentation of assigned systems. A failed workflow or stale operating record does not stay invisible because someone else may notice it.

Over Communicate

You report incidents, access gaps, cost changes, dependencies, and rollout risks early with the facts and a recovery plan.

Understand Before Doing

You map the real process, source of truth, approval boundary, failure mode, and rollback path before automating it.

Checked In

You review the agreed health checks, keep operational records current, and respond to system issues during the coverage window.

Results Over Activity

More automations are not automatically more leverage. You focus on reliable time savings, fewer errors, clear ownership, and maintainable systems.

Only Client Energy

Clients receive dependable workflows and calm communication. Internal failures are caught, contained, and resolved before they create avoidable client chaos.

Talk Is Cheap

A workflow is not complete because it ran once. It needs verified output, monitoring, documentation, ownership, and a tested way to recover.

What good looks like

• ClickUp and operational reports reflect reality and required fields stay clean.
• Automations have a named purpose, owner, source of truth, approval boundary, monitoring path, and recovery notes.
• Failures are found by our monitoring rather than by a client or missed commitment.
• Manual recurring work decreases only where reliability and control are preserved.
• Onboarding, offboarding, access, and cross-department handoffs follow current checklists.
• Documentation is current enough for another qualified operator to understand and maintain the system.

You may be a strong fit if

• You enjoy making a process boring, visible, and reliable before making it automatic.
• You can move between ClickUp administration, workflow logic, documentation, and incident response.
• You test edge cases and failure behavior instead of stopping after the happy path works.
• You can explain technical systems to nontechnical teammates without hiding the risk.
• You prefer a small maintainable system over a clever pile of tools.

This role is probably not a fit if

• You automate unclear processes before deciding what the correct process is.
• You consider a workflow complete after one successful test.
• You build side systems that hide work from ClickUp or create a second source of truth.
• You make production, billing, credential, or client-facing changes without the required approval.
• You leave monitoring, documentation, cost, and recovery for someone else.

Required experience

• Experience running operations, systems, or automation for a small team, agency, or comparable service business.
• Hands-on work with workflow tools such as n8n, GoHighLevel, ClickUp automations, or comparable platforms.
• Comfort with APIs, webhooks, structured data, troubleshooting, and clear technical documentation.
• Process discipline around testing, approvals, monitoring, backups, access, and incident communication.

Helpful, not required

• Python or JavaScript.
• Linux or macOS administration.
• Docker and self-hosted tools.
• AI workflow operations, model routing, or cost monitoring.

Your first 90 days

First 30 days

Learn the operating systems, owners, approval rules, recurring reports, current automations, documentation, and health checks. Complete supervised maintenance and small fixes.

By 60 days

Own routine audits, reporting, documentation, monitoring, incident follow-through, and low-risk approved workflows with less review.

By 90 days

Own the assigned operations scorecard, catch failures before users do, reduce at least one recurring manual burden safely, and improve the documentation or recovery path for a critical workflow.

Hiring process for this role

1. Apply on this page. Fill out the form and include your 2 to 3 minute intro video.
2. Application review. We review your video, relevant experience, availability, and schedule fit. Allow 2 to 5 days.
3. Initial interview. A conversation about the role, your experience, how you work, and whether the expectations fit both sides.
4. Written offer, then onboarding. Terms approved and in writing, then tool access, role documentation, SOPs, supervised work, and clear first-month expectations.