How to Hire an Online Business Manager (And What to Expect Once You Do)

You’ve decided you’re ready to hire an online business manager. You’ve done the research, read the reviews, maybe even had a few conversations. But now what? What actually happens after you say yes?

Most creative entrepreneurs put off hiring an OBM for one simple reason: they don’t know what to expect. It feels like a black box. You’re handing over the backend of your business to someone else, and that’s a big trust fall.

So let’s pull back the curtain. Here’s exactly what the process looks like from the moment you say “let’s do this” to the point where you finally feel real relief.

Note: I’m giving you a behind-the-scenes look at MY process, start to finish. Other OBMs may do it differently, and that’s okay too. But if you love the style…the call button is right here *wink wink*

Step #1: The Discovery Call

This is where it all starts, and it should feel like a real conversation, not a sales pitch.

On this call, I’m not just assessing whether I have the skills to support you. I’m paying attention to fit: your working style, your goals, your personality, and whether we’re going to communicate well together long term.

But you should be evaluating me just as much as I’m evaluating you. It’s a two-way interview.

A good OBM will lead the call and come prepared with thoughtful questions about your business. If you find yourself pulling teeth to get clarity on how someone works or what the next steps look like, that’s a red flag worth paying attention to. If you want a more detailed breakdown of what to look for, I put together a full vetting guide for creative CEOs hiring an OBM.

Step #2: Proposal and Agreement

Once we both feel good about moving forward, I’ll send over a proposal outlining scope of work, retainer structure, and communication norms.

I keep my proposals intentionally general because the actual work we do together is custom-tailored to your business, not a checklist of predetermined tasks. What I do want you to look for, though, is language.

Your proposal should talk about management, not admin. If your OBM’s proposal reads like a list of scheduling and task execution, that’s not an online business manager — that’s a virtual assistant.

Read the scope of work carefully, and never be afraid to ask questions before signing. If something feels unclear, a good OBM will welcome that conversation, not brush past it.

Step #3: The Getting Down to Business Call

Before we dive into any actual work, we get on a ninety-minute call together right after the contract is signed. This is where you tell me if any fires are happening in the business that need to be addressed immediately. This is also where we get honest about the biggest frustrations you’re facing so I can start working toward relief as quickly as possible.

This call sets the tone for everything that comes after it, and it’s probably one of the most important things I will ever do for your business. Getting this honest, this early, is exactly the kind of clear-headed, data-over-emotion decision-making I try to bring into every part of our partnership.

Step #4: The Business Audit

This is where I get into the backend of your business — current systems, team structure, recurring processes, and upcoming projects. You’ll need to have things like access, tools, and passwords ready to go, and I’ll warn you now: this phase can feel like a lot.

The business audit takes up the entire first thirty days of working together. I’m getting fresh eyes on everything in your business from a strategic standpoint, which means I’m often able to spot holes you might not even be aware of.

At the end of those first thirty days, we sit down and review the audit together and decide what to prioritize so we’re fully aligned before we move into action in month two.

Fair warning: Expect some questions during this phase that might seem random, or even a little odd. That’s just me poking holes in things and working to understand how everything fits together.

Patience is Key

I always encourage a lot of patience with clients during this stage. When you hire an online business manager, you’re usually looking for solutions fast. But this process is what allows those holes to actually get filled in a holistic way, instead of handing you a band-aid that falls off in six weeks. 

This is also usually where I start laying the groundwork for stronger SOPs and systems that let your business run without living entirely in your head.

Go into this knowing it will likely take the full first ninety days before you really start feeling the impact.

Step #5: 30-Day Integration

The business audit takes up month one in full, and by month two, we start implementing what we decided to prioritize coming out of that audit review.

This is also where the growing pains happen. And when they do, it’s important that you remember it’s completely normal to experience them. It doesn’t mean anything is wrong with your business or with you as a leader.

It’s as Much for Your Team as it is For You

It’s also important to remember that I’m building the systems that make everything smoother for everyone, not just you. And when a lot of things start shifting at once, it can create some friction on your team. 

But by the end, your team’s day-to-day will get so much easier. The messy middle won’t last forever. Getting communication norms right during this stretch matters, which is why I lean on the same strategies for leading remote teams without micromanaging that I coach my clients through.

Reporting Will Shift Significantly

This is also the month your team starts shifting from reporting to you, to reporting to me. You’ll start to feel some freedom in your day-to-day because of that, which is exciting. But since it’s still only month two, a lot of questions will likely still come back to you — just filtered through me instead of coming to you directly.

That’s intentional. It helps me learn what’s really happening in the business, and it trains your team over time to bring things to me instead of you.

Step #6: Ongoing Support

By month three, things really start to click. You’ll notice fewer and fewer questions coming your way, from both your team and me, because we’ve taken over most of the day-to-day communication by this point.

You may still see some restructuring happening on the backend as we finish implementing those initial priorities, but this is the month where you’ll finally start to feel meaningful, real relief.

This is also where you get a real sense of what working together long-term is going to look like. You’ll start to find your flow, and this is generally where both of us decide whether the partnership – and if current capacity – feels like a genuine fit.

What Makes a Great OBM Client

Hiring an online business manager works both ways. It’s not just about finding the right person — it’s about being ready to be a good partner to them too.

You need to be willing to let go of the reins, at least a little. Communication, trust, and honest feedback are critical to the relationship working. 

The best OBM partnerships I’ve had all share one thing in common: they treat it as a true partnership, not a hierarchy. That mutual trust is what allows the whole thing to actually work.

If you’re ready to stop carrying the weight of your business alone, I’d love to talk. Inquire about working with me and let’s figure out if we’re the right fit.