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Project Management

Get a ClickUp expert working in your account

You already know ClickUp can handle your projects, tasks, and team workflows. The problem is that building it out correctly, keeping it clean, and actually getting your team to use it takes consistent time you don't have. Trusty Oak's fractional specialists work inside your ClickUp account on a recurring basis, not just a one-time setup call. They handle the configuration, documentation, and upkeep so your workspace reflects how your business actually runs.

What our team does with ClickUp

Concrete work our fractional specialists take on inside your ClickUp account. No vague promises.

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Build and configure your ClickUp workspace from scratch

We set up your Space, Folder, and List hierarchy based on your team structure and project types. Custom fields, task statuses, and views (Board, Gantt, Calendar, Workload) are configured to match your actual workflows, not a generic template. You get a workspace your team can use on day one without a learning curve.

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Create and maintain Automations that reduce manual work

We build ClickUp Automations to handle recurring actions: assigning tasks when a status changes, moving items between Lists when conditions are met, and triggering notifications to Slack or email when deadlines shift. Each automation is documented so you know exactly what fires and why. We also audit existing automations regularly to catch broken triggers or outdated logic.

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Design reusable templates for repeating projects and processes

We build Task and List templates for any process your team runs more than once, whether that's client onboarding, content production, or sprint planning. Templates include pre-set custom fields, checklists, subtasks, and assignee placeholders so new projects spin up consistently. This eliminates the setup tax your team pays every time a new engagement starts.

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Audit and restructure an existing workspace that has grown messy

Over time, ClickUp workspaces accumulate duplicate Lists, inconsistent statuses, orphaned tasks, and Spaces nobody uses. We conduct a full structural audit, document what we find, and present a prioritized cleanup plan before touching anything. After your approval, we reorganize the hierarchy, archive stale content, and standardize naming conventions and field usage across the workspace.

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Connect ClickUp to your other tools via native integrations and Zapier

We configure ClickUp's native integrations with tools like Slack, Google Drive, Zoom, and HubSpot, and build Zaps to bridge gaps where native connections don't exist. A common example: a new deal closed in HubSpot automatically creates a project List in ClickUp with pre-populated custom fields and assigned tasks. We test each connection, document the data flow, and monitor for failures.

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Migrate tasks, projects, and data from another platform into ClickUp

If you're moving from Asana, Monday.com, Trello, or a spreadsheet-based system, we handle the migration so your history and structure aren't lost. We map your existing data to the right ClickUp objects, import in stages to reduce disruption, and validate that tasks, assignees, due dates, and attachments transferred correctly. We also document what was changed and why during the move.

How Trusty Oak supports ClickUp workflows

How the ClickUp handoff works

During onboarding, your dedicated Client Success Manager reviews your existing ClickUp workspace (or your goals if you're starting fresh) and works with you to build a Strategic Delegation Plan that prioritizes the highest-impact ClickUp work first. Your specialist is then matched based on experience with your industry and use case, not just general ClickUp familiarity. All work happens inside your account using your credentials or a guest seat you control, and every automation, template, or structural change is documented before it goes live. You approve the plan before we build, and you own everything we create. Ongoing support means your specialist is available each month for maintenance, updates, and new builds as your needs evolve.

Common ClickUp workflows we build

A few of the most common workflows our team has deployed with ClickUp.

1

New client signed → ClickUp project created → team notified in Slack

When a deal is marked Closed Won in your CRM (HubSpot or similar), a Zap creates a new List in your Client Projects Space using a pre-built template, assigns the account manager, and posts a Slack message to the delivery channel with the project link. The project is ready for kickoff before anyone has to touch ClickUp manually.

2

Task due date missed → status updated → manager alerted via email

A ClickUp Automation monitors tasks in designated Lists and triggers when a due date passes without a status change to Complete. The task status moves to Overdue automatically, a comment is added tagging the assignee, and an email notification goes to the project lead. This replaces manual follow-up chasing.

3

Content brief approved → subtasks assigned → Google Doc linked

When a content task moves to the Approved status in your Editorial List, an Automation creates a set of subtasks (draft, edit, design, publish) with default assignees and due dates staggered from the approval date. A Google Doc is created via Zapier and attached to the parent task so the writer has everything in one place.

4

Weekly team workload review → Workload view built → capacity flagged

We configure ClickUp's Workload view with accurate time estimates on recurring task types so your team's capacity is visible each Monday. We also set up a recurring task that prompts your project manager to review assignments before the week starts, with a checklist of rebalancing steps if anyone is over capacity.

5

Sprint planned in ClickUp → progress tracked → retrospective doc generated

We set up a Sprint folder structure using ClickUp's Sprint feature (or a List-based equivalent), configure velocity tracking via custom fields, and build a Gantt view for stakeholder reporting. At sprint close, we export a summary of completed versus incomplete tasks and populate a retrospective template in Notion or Google Docs, depending on your preference.

What ClickUp support costs

Drag the sliders to build a monthly plan that fits your workload.

Executive Assistants
~$35/hour
10 hours $350
Specialists
~$50/hour
20 hours $1,000
Fractional Executives
~$95/hour
0 hours $0
Your monthly budget
$1,350

Starting at $1,000/month. One-time $300 onboarding fee includes your Strategic Delegation Plan.

Book a Discovery Call

Frequently asked questions

You control access entirely. Most clients add their specialist as a member or guest with the permissions needed for the work in scope, and revoke or adjust access at any time. We never ask for more access than the current task requires, and we document every change made in your workspace so you have a full record.
Both are possible within the same monthly plan. Most clients start with a build or cleanup project in the first month, then shift to ongoing maintenance, new automation builds, and workspace updates as their team grows. Because unused hours roll over month to month, you can bank time during lighter periods and draw on it when a bigger project comes up.
Specialist work (which includes ClickUp configuration, automation builds, and integrations) is billed at $50 per hour. Monthly Talent Budgets start at $1,000 per month with a one-time $300 onboarding fee. The initial commitment is three months, after which the plan moves to month-to-month.
That's a fair question to raise on your discovery call. ClickUp is a strong fit for teams that need a single platform to handle task management, project tracking, and light documentation, but it has a steeper configuration curve than tools like Trello or Asana. If you're evaluating alternatives, your Client Success Manager can give you an honest read based on your team size, workflows, and how much admin overhead you're willing to manage long-term.
Your Client Success Manager acts as a consistent point of contact and can bring in a backup specialist if your primary is unavailable. Because we document all work inside your account, any specialist picking up the project has a clear record of what's been built and why. You're never dependent on one person's memory or undocumented setup.

Ready to get your ClickUp Workspace working?

Book a discovery call and we'll audit your current ClickUp setup (or your goals if you're starting fresh), identify the highest-priority work, and outline a 90-day plan before you commit to anything.