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step by step guide to hire an obm

How to hire an Online Business Manager

Your Online Business Manager. She’s your right hand. Your Jill-of-all-trades. Your utility player.

She’s the perfect cross between a COO & a VA.

She’s going to know and run your business BETTER than you will.

She’s gotta be perfect.

So, how do you hire her?

It can feel overwhelming to find such a unicorn, so Prowess Project has pulled together a step-by-step guide on how to hire an Online Business Manager. Enjoy! 


1. Define your Needs

Assess Business Requirements:  What areas do you need support?  Is it Ops, CRM management/ Tech? Automation? Pulling it all together? Growth Strategy.  Get clear on that.

Remember – You will need to delegate control. It’s natural to feel unsure about that – especially with SUCH important aspects of the business.  “If you really want to grow as an entrepreneur, you have to learn to delegate” – Richard Branson


2. Set Clear Expectations

Job Description: WRITE ONE.  Put everything on there and then come back and rate how important it is to you.  Sure you won’t get EVERYTHING you need, but let’s try to get as close as possible, right? 

PRO TIP – Make expectations clear on the JP, ex. “Reduce time to deliver by 20% by leveraging automation”

3.  Source Candidates 

Time to tell people about the OBM that you’re seeking.  Start with the people you already know by leveraging your network.  Then check out groups on social media.  Lastly, explore specialized OBM placement company *ahem* Prowess Project to find the right candidates who fit your needs.


4. Evaluate Candidates

Do the OBM candidates have the experience, enthusiasm or knowledge that is relevant or transferrable to your business?

If so, make sure that you interview.  Be sure to ask scenario-based questions to understand how they handle challenging situations, times they have failed, who they give credit to, etc.  This tells you A LOT.  Be specific 🙂 

5.  Gauge Emotional and Social Add 

Work-style match: Make sure that they jive with your sense of humor, how you like to work, tone, etc.  Also, take into consideration how the OBM will work with others on the team.   Will she be compatible with them and the culture of the business as a whole?

Tease out examples of her emotional intelligence ie. empathy, communication skills, ability to handle stress etc.  That’s more telling than the hard skills most of the time.


6. Confirm Professional Compatibility 

Are the two of you aligned on the vision of the business? Since she will be your right hand, is she excited to be along for the ride – for the long haul?  Does she have the skills to grow with you? 

Ask about her leadership skills, if she’s helped a business scale, or what her 5-year vision for your business could be. You’re not listening if she gets it right. You’re listening to how she thinks 🙂 

7. Trial Period 

Consider implementing a 90-day trial period to test each other out and re-evaluate. 

Also keep in mind how many hours she’s working for you.  If 5 hrs a week, then within a month, she’s worked 20 hours. That’s half of a full-time role. 

Create and stick to checkpoints, benchmarks and what progress you’d like to see by when.  

8. Finalizing the Hire 

Be very clear on terms. Is this a full-time hire or an independent contractor? Are you providing benefits or sick days? When will the OBM be paid? etc. 

We suggest creating an onboarding plan so that your OBM can hit the ground running and start making progress. 


9. Ongoing Support and Development 

Your OBM is the backbone of your business. Your investment in her professional growth is a force multiplier for your business.  Suggest courses, ask her what she’s interested in.  Remember, most of the time training is a tax write-off 🙂 

Set aside time for monthly check-ins about her role and growth as a whole. 

10. Evaluate and Adjust 

Instill MANDATORY performance review.  Feedback is critical.  As good as OBMs are, they aren’t mind readers.  This is your chance to give and get feedback on how the business and people can approve.

Then do something about it.  You can adjust.  Does the statement of work need to change? Has the role changed? Should the compensation change?  All of this will evolve as your business evolves.

And Viola! You have your OBM and your business is rockin’ and rollin’!  As long as you are true to the above AND keep the communication open, clear, and often – you’re setting yourself up for success. 

And if you need help defining, sourcing, managing, growing, etc your OBM – Prowess Project is the place 🙂 

Hope you enjoyed our how to hire an online business manager guide. 

Until next time, 



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