Jenna Rainey


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hey friend!

I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.



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A highly creative nerd with a unique breed of humor and the proud earner of a self-bestowed award for being the world’s most curious and driven human.

Hey I'm Jenna!

(with me)


It’s like Netflix-binging Bob Ross videos, but with a dose of dry + quirky humor and fewer happy little tree references. 

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How to Hire Your Dream Team



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If you follow me on Instagram, then you may have seen my stories about my Operations Manager, Kelly. Every time I mention Kelly or what she does for me, I always get responses like:

Where did you find her?
How do you onboard people?
What does she do for you?

Now that I’m nearly 10 years into running this business, I’ve learned a thing or two about hiring—specifically, what NOT to do. When I hired Kelly, I was shown what hiring the right people can do for your business!

So, first, let’s talk about how to know if you’re ready to hire someone. When I was about 2 years into my business, I hit a season of complete overwhelm. I was swimming in deadlines, teaching workshops every weekend and barely keeping up. I needed help answering emails, packing kits for my workshops and staying on task. And I definitely wasn’t prepared for the extra time it’d take me to hire someone. You have to consider the onboarding, training, and the day-to-day managing. I thought if I just snapped my fingers and hired someone—anyone—my problems would go away.

I was dead wrong.

Just because you’re overwhelmed and insanely busy doesn’t mean you’re ready to hire someone!

Read that again and try this exercise.


Are you ready to hire?

#1: Consider the status of your business

Ask yourself these questions:

  1. Do you have a good record of your profit and loss within your business?
  2. Have you raised your prices in the last 6 months?
  3. If you had 15 hours of time freed up, where would your priorities be?


#2: Reflect on your task preferences

Take out a pen and paper and write down the answers to these questions: 

  1. What do you LOVE doing in your business? (For me it’s painting, designing, creating course content and teaching.)
  2. What do you prefer not to do, but you’re pretty good at and okay with doing? (For me that’s writing copy for sales pages, blogs, and emails, and creating handouts/templates for courses.)
  3. What tasks do you absolutely hate doing, avoid doing and dread doing? (Mine are bookkeeping, filing taxes, troubleshooting customer issues, uploading course content, etc.)


#3: Assign time estimates to your tasks

Once you make a really thorough list of tasks, estimate the weekly hours each task takes you to complete—even the ones you love doing! For the third list of tasks above (you know, the ones you hate), how many hours per week could you free up if you didn’t have to do these tasks? Are there tasks that you could automate or streamline before hiring someone?

Note: If you don’t keep track of your time now and how long it takes you to do it, start now! There are loads of apps like Toggl and Everhour out there to help. Oftentimes we seriously underestimate this number!


#4: Review your P&L

Next, take a good hard look at your profit and loss reports and break even points in your business. If your eyes just glazed over, don’t worry. I get it. Talking finances actually makes me want to throw up sometimes, too, but this is so important! If you don’t have a good template for your profit and loss and break even points, we’re coming out with some amazing resources for this soon!!

For now, just get some rough numbers on how much you made the past few months vs. how much you spent (business stuff, not personal stuff). Is there any wiggle room? If you were to hire a virtual assistant, let’s say, for 20 hours per week at $35/hour, how much extra work would you be able to accomplish in your business? Could you book an extra job each month? If so, would that be able to cover the new hire and then some?


Hiring the Right Person

When you’ve completed the above exercise and the time is right to hire, it's important to find someone who is RIGHT for your business.

I’ve gone through many assistants over the years, but no one (besides myself and my husband, John, who works for me, too) loves my business as much as Kelly does.

She treats this business like it’s her own. She’s invested in every big decision, spearheads some of the biggest breakthrough discussions and helps me execute all of my crazy visionary ideas for the business. She works Asana like nobody else and makes sure everyone on my team is on the same page, on task and ready for what’s ahead.

Related: What It's Really Like Working for Jenna Rainey with Kelly Martin


How I Hired Kelly

I used LinkedIn! (with a side of Instagram…)

I’ve hired in the past only using Instagram and I was nervous to do it again. I just got bombarded with DMs from people who were looking to start businesses just like mine. I didn’t want to hire them and then say goodbye a few months later because they were short-term people who wanted to learn all the things and then leave to get their own business up and running.

What I needed was someone who was going to take my business to the next level, be my protector and integrator of ideas, and be around long-term. So I decided to focus the candidate search on LinkedIn with just one small shout out on my Instagram story for a couple of hours.

After I posted the job description and application on LinkedIn, I had hundreds of applicants within days. 

My hiring process wasn’t super thorough, I’ll be honest. After seeing Kelly's application on LinkedIn, I had a casual phone conversation with her and KNEW she was the person I needed. She seemed very Type A (I’m so not Type A and needed that), professional, and her previous work experience covered all the things I needed. I knew I wouldn’t have to spend tons of time training!



I was so unorganized at the time Kelly started. I really wish I had more of a process for her onboarding. But honestly, that’s what she was there to help me with. She created a huge SOP (Standard Operating Procedures) spreadsheet with links to screen recorded videos of how each task within my business gets done. For example: how to upload podcast episodes, where to put certain files in our Dropbox, how to respond to customer support questions, and more. That way, every new hire we have in the business has videos to watch of how to complete certain tasks, instead of me having to walk them through each step! 


Before you make a hire…

So, if you’re thinking you’ll want to hire someone soon, start recording yourself doing every task in your business! Save these videos in a spreadsheet or folder that you can then send to your new hire for homework/training!! Brilliant, right?!

Even if you aren’t ready for hiring just yet, all of these questions are good to consider. As a business owner, we take on SO much in the beginning—from taxes to creating design work, emailing clients, etc. It’s overwhelming! I’m so grateful I’ve been able to hire the right people on my team and watch the business grow beyond anything I could’ve imagined! 

by Jenna Rainey 

add a comment

  1. Josette says:

    Geez Jenna. Amazing info. You’re a business coach and artist. A true gem.

    Myself, I’m a exercise coach and artist.

    Could your gift here be all I need to
    become “unstuck” and free?

    Yes! A step towards more of that anyway.

    Don’t know you Jenna but love you already.

  2. Pamela says:

    thank you! you answered all my questions!

  3. Nabeelah says:

    Such a great idea to have pre-recorded videos when onboarding a new hire!

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