The Flynn Collaboration

Your pop-in business partner, serving Collingwood Ontario and beyond.

Ready to get the support you need to thrive?

the flynn col-lab-o-ra-tion

/THe flin ke, laberaSH(e)n/

  1. Gets every detail of your project done well

  2. The answer to your small business problems

Entrepreneurship, Community and Lifelong Learning

As a result of my uniquely diverse background, my brand pillars are both important concepts and really adaptable across industries. I'm a passionate entrepreneur, an educator with a creative spirit, held up by an intense drive to ACTION ideas and implement solutions.

How can we collaborate?

Up to 2 hours of my eyes and ears on your business

Unlimited email access and up to 4 hours of 1:1 calls

When you need a project done, and done well.

"Jessica is so knowledgeable in all things business. She knows the ins and outs from her wealth of experience that can save you time and money. She really listens to what's at the heart of your business and/or project to ensure that is at the root of everything that is completed. She is one of my favourite people to collaborate with because she leads with confidence and you can truly sense how much joy and pride she has in what she does. Passion drives excellence and it could not be more true when working with Jessica Flynn! She is a local gem!"

Lindsay Earle

Founder, Mountain Movie Fest.


"Jessica's innovation mindset, amazing problem-solving skills and strategies plus her creative genius, all come together when orchestrating any social and/or event. These assets aside, working with Jess is pure fun. She has the ability to elevate your own thinking and take you out of your comfort zone, with the purpose to create magic for the audience you serve. It has been a dream to collaborate with Jess and be a witness to her growth and sparkle."

Ashley Lougheed

CEO of Girl Time Inc.


"Jessica is a great listening ear. She really tries to understand what your struggles are and where you can grow and expand. She comes from the perspective of your ideal client. She has so many practical ideas and suggestions for how to execute them. After a conversation with Jessica, I'm always pumped up and ready to take on the world. Her insight has helped me see what my clients are needing and how to give it to them."

Michelle McVittie

Child Life Specialist, TV Host, and author @momthemanager and

Meet your pop-in business partner!

Hi there, I'm Jess Flynn!

Like so many of us, Georgian Bay drew me in and in 2011 I put down roots here in Collingwood. I met my partner here and we are raising our two small children just down the street from the GB shoreline. There's something so special about living in a place rich with natural beauty that also buzzes with entrepreneurial energy. This area has become the backdrop to a life I'm so in love with.

I've worked in education for the past decade while also pursuing my entrepreneurial interests (and helping countless others pursue theirs). To name a few I've helped launch the Oxford Learning Centre in Collingwood, served as Operations Manager for a staff of over 40 at IWA Spa, and have built and run three of my own successful businesses in the event planning, construction and event rental spaces.

My background is diverse, and that's why I love living in the world of entrepreneurs. It's a community of dreamers AND problem solvers. I absolutely love helping other small business owners identify their challenges and then create ACTION PLANS to overcome them. Let's see how I can help you.

You're a small business owner with big important goals

You just need a strategic consultant to help you clarify your vision and create an action plan to get you where you want to be.