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Using Jira as a 1-to-2 person company

Kea Herron

How can I best use Jira as a small business? I'm the owner and don't have any employees, but may hire someone on a 1099 basis. What do you suggest?

Accepted answers

Anne Saunders

Hi, @Kea Herron! When you're using these tools for yourself, you have a lot more freedom. I like to think if it almost as a many-dimensional to-do list.

Without getting too in the weeds, I'd set up a small number of spaces grouped around the types of work you do (maybe a space per client or per service, but also one for operational / keep the lights on tasks). Once you have spaces, I'd think about building a couple of filters and maybe a dashboard to surface a broader Now / Next / Later, and I would recommend starting small, only adding more as you need it, so you can get your feet under you.

It will be a lot easier for a 1099 employee to know what to do (and to show you value!) if there's a clear framework of what needs to be done, and which parts are assigned to them - which you can absolutely do in Jira.

Anne Saunders

@Kea Herron The Community is a fantastic place to learn more and ask your questions - don't be a stranger!

All comments

Anne Saunders

Kea Herron

Hi, @Anne Saunders! I appreciate your nearly immediate response to my question! Although I've used a Trello board, this is much more elaborate or complex. My goal is to simplify and smooth my processes. I like your suggestions and will try them.

I also like what you said about the benefit of Jira for a potential 1099 employee.

I took a beginner training in Jira, so here we go… Thanks again!

Anne Saunders

@Kea Herron The Community is a fantastic place to learn more and ask your questions - don't be a stranger!

Kea Herron

Thank you for your kind encouragement! I'll ask away!

Anwesha Pan

Hi @Kea Herron

Welcome to the community! ✨

I would suggest you to do few things:

Leverage the free cloud plan for both Jira and Confluence for up to 10 users. Then you can invite a contractor directly with their own login without paying extra.
Choosing the right setup:
- Use Kanban —> easy to move and shift with the flow and progress.
- Use "Team-managed" project —> Simplified UI
You can start by keeping your workflows and fields simple and minimal:
- Workflows: To Do/Backlog —> In Progress —> In Review —> Done
- Issue types: Epic, Task & Subtask
For managing 1099 contractors:
- Restrict Access: Create a dedicated project for contractor-facing work (e.g., "Marketing Operations" or "Contractor Hub").
- In project settings under Access/ People, grant the 1099 contractor access only to that specific project. This keeps your company admin, financial tasks, or client-sensitive boards private.
- Ticket for each delivery to make tracking easy: Assign every freelance a ticket with:
  - Clear acceptance criteria in the description.
  - Attached assets, briefs, or Loom video walkthroughs.
  - Due dates tied to milestone payouts.
- Audit for invoice: When a contractor submits their invoice, you can simply pull up the Done column or filter by assignee = contractor AND status = Done to cross-reference every billable item they completed.
You can set up free automations like:
- Auto-Assign to Contractor:
  - Trigger: When an issue is moved to a specific list or given a component/label like freelance.
  - Action: Assign to the contractor and send an email/notification.
- Review Notification:
  - Trigger: When the contractor moves an issue to In Review.
  - Action: Reassign to you and add a comment "Ready for review".
- Overdue Task Alert:
  - Trigger: Scheduled daily.
  - Action: Flag any issue where the due date is in the past and status is not Done.
Combine Jira with Confluence: Use it for storage and documentation:
- Contractor Onboarding: You can add brand guidelines, system logins/passwords (via a password manager), tool instructions, and invoicing instructions.
- Standard Operating Procedures (SOPs): Document repeated business processes. When delegating to a contractor, simply embed the Confluence SOP link directly inside the Jira ticket.

I hope this helps. 🙂

Thanks,
Anwesha

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