Small Business Coach

"You are the key to your small business’s success."

My passion has always been helping small business owners. I’m a third generation small business owner myself , and I know first hand about all the ups and downs which occur as you start and scale your business for long-term sustainability.

Throughout the years of working with Small Business Owners, I’ve noticed one thing they all have in common. They don’t know how to build strategies for their business sustainable for longterm growth.

That’s why I use the Enneagram as a base for my small business coaching. With this approach, we start by finding out who you are as a person FIRST, then we build your business strategies around who you are as a small business owner. Let’s be real: you directly affect how your business operates and grows. If your strategies aren’t sustainable for you, the business owner, then they won’t be sustainable for your business.


1 on 1 Ongoing Coaching Programs



What's Holding You Back?

I mean really, let’s lay it all out there. What’s keeping you from taking the next step toward developing yourself and growing your business?

Here are the common objections I hear:

1. Time. I’m already so busy. I don’t have time for another thing to be added to my plate. Well, let me ask you this? Can you afford to keep taking the time doing things like you’re doing now that aren’t moving yourself or business anywhere? Let’s work together to identify those time obstacles for a more sustainable strategy.

2. Money. I can’t afford to invest. But what does it look like if you don’t? Will you be burnt out and your mental health shot? Will you have to shut down your business because you’re not growing? You have to invest to grow. Invest in yourself and invest in your business.

3. Not sure if it’s a right fit. This is the easiest obstacle to overcome. Let’s talk to each other and find out! Schedule a free 30 min needs analysis call with me. I’ll give it to you straight. Schedule on my calendar HERE.



As Small Business Owners, sometimes you just need an extra set of professional eyes and ears on an aspect of your business.  Call on me for hour consulting sessions anytime you need to talk things out.

About Hillarie Kay

Hey Small Business Owner! I’m so pumped you’re here. I’m a third generation small business owner, so when I say #smallbusinesslove, I MEAN IT!

At the beginning of my career I sought out a PR and Marketing Management degree, and found myself working in agencies and in corporate America for the first 5 years out of college, but it became very clear to me that being an entrepreneur and small business owner myself was the key to my happiness and fulfillment in life.

I’ve made it my mission to to help small business owners no matter where they are at in their business. I help small business owners identify who they are as a person and business owner, and then coach them on forming the business strategies and tactics most sustainable to their personality type using the enneagram.

When I’m not working with Small Business Owners, I’m a wife, mom of two boys and stepmom to three boys. I split my time between Southeast Missouri and the Durham area of North Carolina.  I’m obsessed with the 60s and 70s and you can often finding me thrifting around vintage shops on the weekends.

I can’t wait to meet and learn all about YOU and your business!

What people say?

I always look forward to my coaching calls with Hillarie. I know she will bring me the clarity and confidence I need to move forward with my goals! She always delivers - above and beyond - with great ideas, exceptional editing, thoughtful insight, and detailed follow ups that keep me motivated and on track.
Gina Warner
Founder, Badass Women's bookclub
I have a small u-pick orchard in eastern Washington. I first worked with Hillarie on a very short basis to help me think through my social media campaign. She was so insightful and fun to work with that I hired her as my small business coach. We communicate largely through Marco Polo and regular zoom calls. It’s wonderful to be able to just quickly ask her a question about anything and receive a prompt response. Whether I’m frustrated, stuck on how to go forward, needed a second opinion or just need to vent—Hillarie’s positive, up-beat, creative personality and business sense takes a lot of stress off of me. I was burned out with my small business and she’s helped me reorganize it and make it manageable again.
Ronda Bosma
Cherry hill orchard and market
Amazing! That's all I can say. I hired HIllarie to help me with setting up a marketing strategy and sales funnel for my Interior Design Services and online course. I'm amazed with how she grasped the way I run my business and how I showcase my brand personality. The amount of value that Hillarie provided me with far exceeded my expectations. I'm so incredibly thankful for her help and can't wait to implement all of her ideas. I highly recommend her services and will definitely be using her again. Thank you, Hillarie, for all you've done. You don't even know the amount of relief I feel right now!
Val Malnar
Orangetree Interiors
With a passion and skill for growing small businesses, HIllarie recognizes the value of YOU before the value of your business. She is your source for helping you to recognize your value, and understand how to brand and market yourself- not just your business- helping you and your business to truly GROW exponentially.
Teresa Gaikema
Young Living Distributor
Marketing has always been one of the areas I have struggled in my business and I never understood why. Hillarie helped me realize it was because I don't find it fun or fulfilling, and as an Ennegaram 7 finding things fun or fulfilling is key to our success. She coached me on ways to overcome this obstacle in my business, so I can continue growing my business in a sustainable way. I have also seen Hillarie use the Enneagram to coach other business owners. She is able to see where business owners are getting hung up and helps them to see ways to improve based on their Enneagram type.
Cheree Saur
Heartfelt Mamas
I just got off the best coaching call I’ve ever had. It wasn’t me coaching, it was me getting coached! Hillarie’s heart truly is in it for small businesses. She helps empower me and remind me who I am in order to best serve my clients and grow my business!
Heather Winston
Women's Functional Health Coach
Working with Hillarie has not only taken my business to the next level, but has opened my eyes to what makes me tick. Applying her knowledge, and application of my enneagram type, has helped me be a better communicator, relate to my clients and give myself grace. If you want to understand yourself better and take your business to the next level, look no further.
Sarah Kellogg
Oola Life Coach
© All Rights Reserved 2020