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What to Expect When Working with a HubSpot Freelancer

So you’ve hired a HubSpot freelancer. Now what?

Whether it’s your first time outsourcing HubSpot work or you’ve worked with freelancers before, it’s helpful to know what to expect. Because let’s face it—working with someone external can feel a bit odd at first. Do they need access to everything? How often will they check in? Are they going to just disappear halfway through?

Let’s walk through how a great working relationship with a HubSpot freelancer should feel from day one to done.


1. A solid kickoff

A good freelancer won’t just dive in and start changing things. They’ll begin with some kind of kickoff or discovery session. This might be a 30–60-minute video call or a written onboarding doc.

Expect them to ask:

  • What’s working and what’s not?

  • What’s the main goal of this project?

  • Who’s involved on your side?

  • What does “done” look like?

They might also request access to your HubSpot portal (with the right permissions) and any other tools that connect to it.

Top tip: The more context you can give upfront—screenshots, reports, examples—the smoother the project will be.


2. A clear plan of action

After the kickoff, your freelancer should lay out:

  • What they’re going to do

  • When they’re going to do it

  • What they need from you to get it done

Depending on the size of the job, this might be as simple as a one-page outline, or it could be a full project plan in Google Docs, Notion, or Trello.

You should always know what’s happening next. If you feel left in the dark, don’t be afraid to ask for more structure.


3. Regular check-ins (but not micromanagement)

Most HubSpot freelancers will check in weekly (or more frequently if it’s a fast-moving project). These updates can be:

  • A quick Slack message

  • A short Loom video

  • An email summary

  • A 15-minute call

The goal here isn’t to flood you with updates—it’s to keep you in the loop and flag any blockers or questions.

You shouldn’t feel like you have to chase them. If you do, it might be time for a chat.


4. Flexibility (within reason)

Great freelancers are flexible. Need to shift priorities slightly? They’ll adapt. Need something urgent moved up the list? They’ll try to accommodate.

But keep in mind—they’re likely working with other clients too, so there’s a limit. Agree deadlines and turnaround times upfront, and you’ll avoid most issues.


5. Suggestions you hadn’t thought of

You’re not just paying for button-clicking. You’re paying for their experience.

Expect a good freelancer to spot things that you’ve missed—like automations that could save you hours, or ways to clean up your database, or simpler ways to track performance.

You want someone who brings ideas to the table, not just ticks boxes.


6. Deliverables you can use

By the end of the project, you should walk away with more than just a few workflows or a shiny dashboard. You should have:

  • Clear documentation of what was done

  • An understanding of how to maintain or use the work

  • Confidence that your team can build on it

If training is part of the project, it might include a walkthrough session, recordings, or even written guides for your team.


7. A clear wrap-up

Before they hit “done,” a good freelancer will recap:

  • What’s been delivered

  • Any recommendations for next steps

  • Any issues or open questions

  • Their availability for future work or questions

Pro tip: Ask them to record a short video showing you how things work if you’re worried you’ll forget it all later!


And what if it goes wrong?

Let’s be real—it doesn’t always go perfectly. Sometimes the fit isn’t right, or something slips through the cracks. The key is to communicate early. Most issues can be solved with a quick check-in.

If you feel stuck, ask:

  • Can we clarify expectations?

  • Can we simplify this?

  • Is there a better way to approach this?

Freelancers want the relationship to work too—it’s in their interest to keep you happy.