Jason Bacon

Go-getter
DISC Type : d

CEO and Co-Founder at Sidekick Digital

Northern Sunrise County, Alberta, Canada

Overview

Jason Bacon is the CEO and Co-Founder of Sidekick Digital, where he focuses on making technology accessible for Canadian organizations. With a background as an Entrepreneur Strategist at ATB Financial and a Bachelor of Management, he has extensive experience guiding businesses from startup to sale. People who have worked with him describe him as a strategic thinker, master collaborator, and a positive guide.

Jason is deeply committed to the entrepreneurial community, dedicating his time to advising, training, and mentoring founders. He finds fulfillment in helping those around him become the best versions of themselves, both personally and professionally. His work with organizations like Firecircle highlights his passion for supporting innovators and fostering growth within the business ecosystem.

He has directly coached and advised thousands of entrepreneurs across the province of Alberta.

Personality Overview

Vision Oriented

Direct & Candid

Challenger

They don’t always try to control the conversation but neither do they like yielding it fully.  They care equally about the product and its potential impact. They focus on objectivity in a pitch and pay little attention to bells and whistles.

Topics They Care About

Entrepreneurial Coaching
His entire career is built around advising and training entrepreneurs on strategy, business planning, and growth, working with thousands of business owners.
Impactful AI
He is focused on helping businesses implement AI and automation in a way that generates a tangible impact on their financial statements, not just for the sake of technology.
Team Dynamics
As a certified Working Genius Facilitator, he is actively involved in helping teams improve collaboration and productivity by leveraging individual strengths.

Media Appearances

Jason has no verified media appearances

Work History

1-2026
CEO and Co-Founder at Sidekick Digital
1-2021
Founder at Sunstone Strategic
5-2020 - 3-2021
Senior Manager, Entrepreneur Education at ATB Financial
2-2018 - 5-2020
Entrepreneur Strategist at ATB Financial
8-2015 - 2-2018
Business Analyst / Project Coordinator at Community Futures Lethbridge Region

Education

2020 - 2020
Inclusion at Work Certificate from NorQuest College
2009 - 2013
Bachelor of Management from The University of Lethbridge

More Information

Social Presence :

Prographics :

Exp : 12 Location : Northern Sunrise County, Alberta, Canada Job Level : Leadership Designation : CEO and Co-Founder at Sidekick Digital
URL has been copied!

Insights For Selling To Jason

During A Call Or A Meeting

DO's

  • Be crisp while making the pitch
  • Ask them questions confidently while doing discovery, don’t be apologetic
  • Make sure that you you respond to any queries from them quickly

DONT's

  • Don’t expect them to change their mind quickly if they say no once
  • Don't try too hard to get friendly, let it happen with time
  • Avoid long winding pitches, stay objective

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jason is

  • Belief in the product plays an important role, followed by objective proof and testimonials.
  • Will you ever get a clear answer from Jason

  • They may hesitate slightly, but if they are not convinced, they will say no.

Insights For Deal Planning

    How fast (or slow) will Jason move?

  • They are neither the fastest decision makers nor the slowest.
  • Can Jason take some risk or not?

  • They can take risks only after they have analyzed the advantages and disadvantages.

You And Jason

Personality Compatibility


More Profiles

Discover additional public profiles from our index.

Search more profiles

Looking for someone else? Search here for anyone.

Or visit Humantic AI to know more.