We're here for you

Let's get to know each other


We believe that you can share your passion with the world and build your business without being run into the ground. And you can do it while eating all the doughnuts and drinking all the coffee along the way.

Values we stand for

01. be yourself

Your personality is your greatest asset. Be your authentic self! People buy from people, not brands. The biggest advantage you have in business is being you!

02. experiment

Try new things that’s the whole point in this entrepreneur thing! They teach us so many valuable lessons! So take the leap, you’ll be able to get back up if you fall. We promise!


03. balance

This is supposed to be fun! Not a test to see how long you can sit at your computer. We want you to love what you’re doing and have time for the rest of your life!

Our Story

We want to help you because we’ve been there too


business experiments not ending in disaster


Happy clients


Work fuelled by coffee

The story of what becomes Pilot Solutions starts in 2010 when Katherine and Callum meet.

Callum had a steady government job that he hated (really, really hated). Katherine was just about to graduate with a Master’s in political science and big dreams to work in the government.

Katherine convinced Callum to quit his job so they could go backpacking around Europe together. It was the first glance that we wanted a life together that wasn’t a stable job and climbing the corporate ladder.

But going against what you’re told you should do is big and scary so we didn’t listen to our intuition and went back to life as usual.

Callum took the big leap though. He left working at an NGO to start his photography business, Callum Pinkney Photography, in 2014. Callum’s experience running his photography business is what inspired us to help other creative entrepreneurs.  

Katherine spent the next 7 years climbing a corporate ladder that she wasn’t even sure she wanted to be on – working at a small publishing company. She worked her way up from admin assistant to running marketing and operations. It was a great lesson in how to run a small business and the struggles facing small businesses with limited people and resources. 

In 2016, we got married and had the perfect excuse to go on an adventure we always wanted to go on. We sold our belongings, gave up our apartment, and lived in a 1994 Roadtrek camper van for 6 months while driving across the USA. This trip solidified that we wanted to live on our terms and use our skills to help other entrepreneurs. This time we were ready to make a plan and go for it.

We decided that we’d figure out a way to both work for ourselves so we could in charge of our time. We wanted to opportunity to work with clients that we love and knew we could help.

And that’s when we started Pilot Solutions. Pilot has taken a few iterations since we opened in late 2018 but the purpose has remained the same – to help entrepreneurs with marketing so they have the skills to succeed!

Your Business Consultants

Those who build together, stay together.

Callum Pinkney

Systems, Tech & Strategy

Callum worked with marketing small businesses in the sports sector, before starting his own photography business in 2014. He uses his experience of growing a successful business as a solopreneur to help other entrepreneurs through Pilot.  

When Callum’s not finding solutions to modern business systems, you may catch him out photographing the world, playing a video games, or running the trails near their house.


Katherine yager

Marketing & Strategy

Katherine’s background in marketing comes from the better part of a decade working with B2B companies to find solutions to digital marketing issues.

Katherine loves finding creative marketing solutions for small business owners. 

When she isn’t planning out how to wow your next client, she may be running trails, petting all the dogs, or trying to find the best cappuccino.


Benefits of working with us

What we do best. Everytime.

The Big Picture

Take advantage of our multi-industry experience to create the big picture with you that builds your success.

we're part of your team

Being an entrepreneur is tough but you don’t have to do it alone! We’re here for you and will be there by your side for as long as you need us. 

Targeting the important Metrics

Numbers matter in business but all numbers don’t have the same weight. We will identify the numbers that matter the most and create a roadmap of how to get there. Paving the road to success!

creating little wins

Remember when you learned how to ride a bike? Or how to swim? You broke it into little pieces. Those little wins when taken together make the big wins. Planning for little wins is the best way to create your success.

Identifying areas for success

We’ll ask the tough questions to find out what is holding you back and where you are you succeeding. Together, we’ll create a plan that highlights your strengths and pushes the needle forward.

Put in the work

Together, we will outline the plan to get you where you want to go. Then it’s time to put in the work. All good plans need muscle. We can be your muscle or teach you how to do it!

Located in Hamilton, ON.