Smarten Transport Inc

ClickUp Systems Architect & Automation Engineer

Remote | Paid Project First | Long-Term or Full-Time Potential

We are a U.S.-based trucking company building a scalable operations system around ClickUp.

We need a senior specialist who can understand business processes, design the ClickUp architecture, build working workflows, connect external platforms through APIs and automation tools, and document the complete system.

This is not a normal Project Manager or basic ClickUp administrator position.

Main objective

Build ClickUp as the company’s central work-management, coordination, documentation, and automation layer.

Specialized platforms such as DataTruck, Fleetio, Samsara, Netradyne, RingCentral, and QuickBooks may remain the authoritative systems for their specific data. ClickUp should receive the operational information employees need, trigger the correct work, track responsibility, and send updates between systems.

Responsibilities

Business-process discovery

• Review existing workflows across Dispatch, Safety, Fleet, Recruiting, HR, Accounting, and management.
• Identify manual work, duplicate entry, missing ownership, weak handoffs, and disconnected systems.
• Decide what should be automated and what should remain a controlled human decision.
• Define which platform owns each type of data.

ClickUp architecture

• Design Spaces, Folders, Lists, task types, statuses, Custom Fields, relationships, permissions, views, Forms, templates, Docs, dashboards, and reporting.
• Create a scalable structure that remains understandable as the company grows.
• Design role-based permission models.
• Prevent duplicate records and conflicting sources of information.
• Establish naming, documentation, version-control, and change-management standards.

Workflow and dashboard development

• Build workflows for departments and recurring business processes.
• Create task templates, intake Forms, recurring processes, reminders, dependencies, and escalation logic.
• Build operational and management dashboards.
• Connect SOPs and training materials to real tasks and responsibilities.

Integrations and automation

Build and maintain integrations between ClickUp and systems such as:

• DataTruck
• Fleetio
• RingCentral
• Google Workspace, Gmail, and Drive
• Samsara
• Netradyne
• Jotform
• Recruiting and driver-application systems
• Other trucking platforms

Use:

• ClickUp native automations
• ClickUp API
• Webhooks
• n8n
• Make
• Zapier
• Python or JavaScript when appropriate
• AWS or middleware services when necessary

AI agents and skills

• Design practical ClickUp AI agents and reusable skills.
• Connect agents to approved company knowledge, SOPs, tasks, messages, and documents.
• Build workflows that summarize calls or messages, identify the related employee, driver, load, or task, and create the correct follow-up.
• Add controls so AI-generated actions can be reviewed when human approval is required.
• Document agent instructions, sources, limitations, and escalation rules.

Reliability and documentation

• Build monitoring for failed integrations and automations.
• Prevent silent failures, duplicate task creation, and incorrect field updates.
• Maintain technical documentation, system diagrams, data maps, credential ownership, change logs, and recovery procedures.
• Test changes before production deployment.
• Train the Technical Systems Administrator and ClickUp Coordinator to operate and maintain completed workflows.

Initial paid project

The engagement begins with a small paid project.

The candidate will be asked to:

1. Review one real company process.
2. Identify current problems and data sources.
3. Design the ClickUp structure.
4. Define statuses, fields, relationships, permissions, views, and dashboards.
5. Define integrations and automation logic.
6. Build a working prototype.
7. Document the design and explain how it should be maintained.

Successful work may lead to a larger project, fractional cooperation, or a full-time position.

Must-have experience

• Building advanced ClickUp systems from scratch
• ClickUp workspace and permission architecture
• Custom Fields, relationships, Forms, templates, dashboards, and automations
• ClickUp API and webhooks
• n8n, Make, Zapier, or equivalent platforms
• REST APIs, JSON, authentication, and data mapping
• Business-process and SaaS integration design
• Automation testing, monitoring, and error handling
• Technical documentation and system handoff
• Ability to communicate with a non-technical business owner

Strong advantages

• AI agents, LLM workflows, RAG, or knowledge-connected assistants
• RingCentral call or message automation
• Google Workspace integrations
• Python or JavaScript
• Transportation, trucking, logistics, fleet, safety, or dispatch systems
• Experience designing systems for small or medium-sized businesses

Talent Acquisition & Recruitment Marketing Coordinator

Full-Time | Remote | U.S. Trucking Company

We are a growing U.S.-based trucking and logistics company with approximately 25 drivers and an international remote team.

We need a hands-on coordinator who will execute recruiting from vacancy publication through candidate preparation for management review, while also creating professional recruitment graphics, videos, and presentations without relying on a separate designer.

This is not an HR Manager, Recruitment Manager, or marketing-strategy position.

Responsibilities

Recruiting Operations

• Publish and manage vacancies on Djinni, LinkedIn, Facebook groups, and other approved platforms.
• Complete all vacancy settings, screening questions, salary fields, locations, schedules, and application instructions.
• Actively source candidates instead of relying only on applications.
• Review résumés, profiles, portfolios, and screening answers.
• Conduct structured initial screening calls in English.
• Verify employment dates, titles, experience, portfolios, links, and other candidate claims.
• Prepare factual candidate summaries for management review.
• Schedule interviews, tests, reminders, follow-ups, and approved rejection messages.
• Maintain complete candidate records, stages, documents, and follow-up dates in ClickUp.
• Build reusable candidate pipelines for future positions.

You will not make final hiring decisions, approve compensation, or conduct final management interviews.

AI Content and Recruitment Marketing

The company will provide the job requirements, facts, and main message. You will turn them into finished materials, including:

• LinkedIn and Facebook recruitment posts.
• Professional vacancy graphics.
• Short recruitment videos and reels.
• Presentations and candidate-facing materials.
• Stories, carousels, and reusable vacancy templates.
• Multiple versions of advertisements for different platforms.

You will independently manage layout, image selection, typography, subtitles, branding, platform sizing, and final presentation quality.

This is a core part of the role. We do not plan to hire a separate designer for everyday recruitment materials.

Required Experience

• At least one year of hands-on recruitment coordination, sourcing, recruitment assistance, or recruitment marketing.
• Previous experience posting vacancies and actively sourcing candidates.
• Previous experience conducting initial candidate screening calls in English.
• Professional experience creating social-media graphics.
• Professional experience creating or editing short videos.
• Regular use of AI tools for graphics, videos, presentations, or social content.
• Experience with Canva or an equivalent design tool.
• Experience with CapCut or equivalent video-editing software.
• Experience with ClickUp, an ATS, CRM, or another structured candidate-management system.
• Minimum B2 spoken and written English.

Required Portfolio

Please provide work that you personally created:

• At least two graphics.
• At least one short video.
• At least one presentation, carousel, or multi-page visual.
• A short explanation of which tools you used and what you completed personally.

Applications without creative examples will not proceed.

Preferred but Not Required

• Experience supporting a U.S.-based company.
• Experience recruiting international remote employees.
• U.S. trucking, transportation, or logistics experience.
• Employer-branding experience.
• ClickUp experience.

Work Schedule

• Full-time, Monday through Friday.
• Eight working hours with a one-hour break.
• At least six hours of daily overlap with 7:00 a.m.–4:00 p.m. Chicago Central Time.
• Long-term position.

Compensation

• $1,200–$1,600 per month after taxes.
• Up to $1,800 for an exceptional candidate with strong recruiting and creative-production experience.

Hiring Process

1. Application and portfolio review.
2. Initial screening call.
3. Paid practical assignment combining recruiting and creative production.
4. Final interview.
5. Professional-history verification when appropriate.

Please Apply With

Include:

• Summary of your recruitment and sourcing experience.
• Examples of positions you supported.
• Required graphics, video, and presentation portfolio.
• AI, design, video, ATS, and project-management tools used.
• Availability during Chicago Central Time.
• Expected monthly compensation.
• Confirmation that you are seeking full-time, long-term work.

Technical Operations & ClickUp Governance Coordinator

Full-Time | Remote | $1,500/month

We are a U.S.-based trucking company looking for a practical systems coordinator who can support employees with technical issues, administer company SaaS accounts, keep ClickUp organized, follow up on incomplete work, and maintain clear technical documentation.

This is a combined technical support, SaaS administration, ClickUp governance, and documentation role.

It is not an advanced software-development, API-automation, DevOps, HR, or Operations Manager position.

Work Schedule

Monday through Friday
7:00 a.m.–4:00 p.m. Chicago Central Time
One-hour break

The employee must consistently work this schedule without another overlapping full-time position.

Main Systems

You may support:

• ClickUp
• Google Workspace, Gmail, and Google Drive
• RingCentral
• DataTruck
• Fleetio
• Samsara
• Netradyne
• Jotform
• ManageEngine MDM
• Vaultwarden
• RustDesk
• Basic AWS, Ubuntu, Docker, and Kasm environments
• Other trucking and business SaaS platforms

Prior experience with every system is not required. You must be able to learn unfamiliar software independently.

Responsibilities

Technical Support

• Serve as the first point of contact for internal technical questions.
• Troubleshoot login, access, browser, application, email, phone, file-sharing, device, and basic system problems.
• Reproduce technical problems and collect screenshots, error messages, logs, and examples.
• Resolve problems internally when possible.
• Contact SaaS technical-support teams when vendor assistance is required.
• Open, follow up on, test, and close vendor-support cases.
• Confirm that the issue is fully resolved before closing the task.
• Document recurring problems and confirmed solutions.

Accounts, Access, and Permissions

• Create, update, suspend, and remove employee accounts.
• Manage basic roles, permissions, MFA, phone extensions, groups, and shared inboxes.
• Maintain a list showing which employees have access to each company system.
• Review access regularly and remove unnecessary permissions.
• Track active accounts, paid licenses, and unused subscriptions.
• Complete technical onboarding and offboarding checklists.
• Make sure former employees and contractors lose access promptly after authorization.

ClickUp Governance

• Review active, overdue, and recently completed tasks.
• Check assignees, due dates, statuses, Lists, descriptions, checklists, updates, and required proof.
• Identify misplaced, duplicate, incomplete, unclear, or incorrectly closed tasks.
• Follow up with employees regarding overdue work and missing updates.
• Return or reopen incomplete tasks.
• Escalate repeated failure to follow the approved process.
• Help employees use the correct Spaces, Folders, Lists, statuses, Custom Fields, templates, and views.
• Maintain recurring tasks, task templates, filters, saved views, and simple dashboards.
• Identify permission problems and incorrect workspace access.
• Test new workflows created by the ClickUp Systems Architect.

Documentation and Training

• Create and update technical SOPs, troubleshooting guides, checklists, and internal instructions.
• Convert meetings, recordings, voice messages, screenshots, and rough notes into clear documentation.
• Maintain the company knowledge base.
• Organize technical training for ClickUp, RingCentral, DataTruck, Fleetio, and other systems.
• Assign training tasks and track completion.
• Follow up on overdue training.
• Identify outdated, duplicate, conflicting, or missing instructions.
• Maintain document owners, review dates, and current versions.

Basic Technical Administration

• Use remote-support tools such as RustDesk.
• Perform approved basic troubleshooting for AWS, Ubuntu, Docker, or Kasm.
• Check service status and basic logs.
• Restart approved services when documented procedures allow it.
• Escalate advanced server, security, networking, coding, or infrastructure problems to a specialist.

Must-Have Experience

• Frequent hands-on ClickUp experience.
• Experience monitoring tasks assigned to other employees.
• Experience following up on overdue or incomplete work.
• SaaS account, access, or permission administration.
• Internal technical support or software troubleshooting.
• Experience communicating with vendor technical-support teams.
• Google Workspace administration or strong practical experience.
• SOP, technical-instruction, or process-documentation experience.
• Strong written English.
• Ability to work independently and follow problems through to completion.
• Availability during the required Chicago schedule.

Strong Advantages

• RingCentral administration
• DataTruck, Fleetio, Samsara, or other transportation software
• ManageEngine or another MDM platform
• Vaultwarden or Bitwarden
• RustDesk, AnyDesk, or TeamViewer
• Basic AWS, Ubuntu, SSH, Docker, or Kasm experience
• Training-material or knowledge-base administration
• Ukrainian or Russian language

This Role Does Not Own

• Advanced ClickUp architecture
• Complex API integrations
• Make, n8n, Zapier, Python, or JavaScript development
• ClickUp AI-agent architecture
• Advanced AWS or DevOps administration
• Formal HR discipline
• Departmental operational management
• Deciding whether specialized Safety, Dispatch, Fleet, or Accounting work is operationally correct

Hiring Process

• Automatic screening questions
• Short interview
• Live screen-sharing technical and ClickUp test
• Paid practical task
• Final decision