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. 

Wanna Learn Watercolor?

i wrote some books



How to Make the Right Hire

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Disclaimer: This post contains affiliate links, which means that if you click on one of the links and make a purchase, I may receive a small commission at no extra cost to you. Don't you worry—I only share products/services I absolutely love. This just helps to support my work so that I can continue to make valuable free content for you on this podcast. Thank you for the support!


Thinking about hiring? Is your biz ready to expand? Or maybe you think you can do it all and you’ve found yourself strapped to your desk 24/7…

Whether you’re ready to hire or not, this post will give you some of the best tips for hiring the RIGHT team member for your brand at the right time (Yes, hiring too soon can cost you. Trust me. I did this!).


My Current Team

Here's the crew that makes up my small but mighty team:

  1. JohnContent Producer and Videographer (and sexy husband). He heads up our YouTube Channel, IGTV videos, and edits the episodes for my podcast.
  2. KellyVA (Virtual Assistant). She does ALL the things. She's the organization, strategy brain behind launching our courses, managing the podcast, answering emails, etc.
  3. Blake & DerekFacebook Ads and Marketing Strategy. These guys head up my launch campaigns and ad strategy for courses and products.
  4. YeseniaBookkeeper. She tracks and labels all of the business' income and expenses.
  5. ColleenAccountant. She does the tax strategy working with our financial advisor on funding for retirement, donating money, and paying taxes.
  6. JulieLicensing Agent and Co-Instructor for Brand Plus Brand.
  7. KimberlyLiterary Agent. Kimberly helped me sign contracts for my books with Ten Speed Press
  8. Grant – IP Attorney. You can read about all the things Grant manages in this post—things like trademarks, copyright, compliance, contracts, etc.
  9. I have more part time contractors on hand that I regularly use for things like writing launch campaign emails, a website developer who can help with site updates, etc.


The Remote Office

In the past, I’ve gone through a couple in-person assistants, a junior calligrapher and designer, but have now shifted my business to have mostly (with the exception of John), remote employees. This has been HUGE for my business. If your business can swing it, I highly recommend working with remote employees. OBVIOUSLY, some businesses require in-person employees because of shipping products, meetings, etc.

But when I made the transition from having a physical office (where I felt like I always needed to be *on*) to a remote office with skilled specialized employees that I didn't need to micro-manage, it took the weight off of my shoulders. 


Getting Traction

Here's the thing with me guys… I am a 100% creative person. I am a visionary—a term from two books called Traction by Gino Wickman and Rocket Fuel by Gino Wickman and Mark Winters. If you are a business owner thinking about growing your team, I highly recommend these books.

What's a visionary? I'm a creative problem-solver, I come up with the big ideas, and I execute those big ideas and create the courses or the products. I'm also the sales and the marketing leader and I know how to talk to people. I have the vision for my brand.

I knew that the biggest downfall that I had was in the integration side of the business—the operations. And I'm not just talking about answering emails and doing the admin stuff (while that's still valuable and something to hire out). I knew there was a better way to effectively execute our process and systems so that we were saving—not wasting—time.

With this awareness, I knew I was ready to hire.


My Best Hiring Tips

Everyone who is currently on my team was vetted during the hiring process. I was very clear on the specific skills I wanted with each person, which has made it incredibly seamless in being a leader/boss. I want the people working for me to have their own leadership qualities, to not have to “wait for Jenna's direction” on things to execute on small decisions. This ultimately saves me SO much time, and allows my employees, contractors, etc. to do their best work. 

Want this for your business? Here are my tips:


Write down your company values and your vision for your company

This will inform the hiring process and bring laser focus to the entire hiring process. It will inform the right people for the right job which precedes everything else. You can't have the wrong people working for you and also succeed. The details about how to determine your values and vision are outlined in Traction.

Let's look at some examples:

Nordstrom: Never being satisfied
Phillip Morris: Hard work and continuous self-improvement
Sony: Encouraging individual ability and creativity
Disney: Fanatical attention to consistency and detail

To achieve sustained growth and success, an organization has to place a strong emphasis on its greatest resource—its people.  Don't just hire an extra pair of hands. Managing people in a task rabbit culture is time-sucking. Fill your organization with people who understand your core values and are gifted in a specific skill set you need.


Acknowledge that your time is more valuable than doing all the things just because you can

This is the first step in getting the RIGHT help with your business. Full disclosure: This is something I still struggle with—giving up control. A lot of solopreneurs think they can do it all, and have a hard time giving up the reins. Just because you can do it, doesn't mean you should. Maybe someone else can do it more efficiently. And that time you SAVE you can pour back into the business to GROW it!

Related: What No One Tells You About Being Your Own Boss


Trust your gut instincts

I know this sounds basic, but it's easily overlooked. And let's be real—you can't solely go off of your gut. You should also be clear on your core values, write down your business needs, identify your 90-day/1-year/3-year/10-year goals, vet your candidates. THEN…listen to what your gut is telling you. Should you hire a team member to recoup your time? Or is it too soon?


LinkedIn is awesome

I love to use LinkedIn for hiring. The whole process of sending out an application and you can see a candidate's previous experience, skill sets, and more all in one snippet!

When I listed the VA position last fall, there were hundreds of people that applied, but I was able to narrow it down to less than 10 people very quickly. I knew I wanted someone with experience in operations. I knew I wanted someone who understood the nuances of a small entrepreneurial business and who deeply understood my brand.

I saw Kelly had taken courses from Marie Forleo so I knew she got that whole online marketing and online course space. She immediately stood out to me with that experience and she's been amazing.

Bottom line: Get clear on what's really important to you. What will help elevate your brand and achieve your goal? And then look for clues in candidates' profiles that check those boxes for you.


Be really thorough with your job listing

Be diligent in the front end of the hiring process, so you don’t attract applicants who don’t qualify. Be picky! It’s your brand! List all the critical traits and experience in your post.


Have processes and systems in place before hiring, so onboarding a new employee isn’t as time consuming

Record your conversations with various team members or contractors. Use Google docs/sheets with steps and notes on a process (ie. template email responses, directions on how to make changes on the website, etc.). Track EVERYTHING so if after training, that new team member still has quesitons, they can review the notes rather than continuously ask you.

We also use LastPass for login/password information. I'm terrible at keeping track of passwords and bank account info. LastPass keeps every password, login, etc. in one place AND you're able to securely share it with team members! 

Finally, I want to share one last bonus tool my team and I use to stay organized. This Master Marketing Calendar keeps up to date with all launch and promo schedules in the show notes! If you're looking to get your team on the same page with promo dates, launches, etc., this calendar is the BEST for planning all your launches, deadlines and MORE!


So what do you think? Are you feeling inspired to let go of some things, free up your time, and plan your next hire? Remember, get clarity on these things first: your company vision, your wins, your failures, your goals, your needs, your strengths, your weak links, etc. Be honest with yourself. Then, when you're ready, go find your people.


Comment below and tell me: What has been your best hiring experience? Or what has been your biggest hiring challenge? 

by Jenna Rainey 

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