Careers at Boss Insights

Get ready to teach, to learn and to do the best work of your life.

Welcome to Toronto

We are located in the stunning heart of downtown Toronto, Canada – North Americas fastest growing technology hub.

Some things to know about us:

  • We are constantly updating our product and looking for more innovative ways to solve our customer’s problems
  • Speed matters, as a startup one of our core advantages is being able to move quicker than the big guys
  • We like to offer the right mix of autonomy and teamwork to ensure you can both own your work and learn from your peers.
  • Be the change you seek – not happy with something? change it, have the courage and resourcefulness to bring change

If you think you’d be a good fit for the team drop us an email (, we are growing fast and have built something of a reputation for finding roles for talented people

The things that make Boss Insights a special place to work

Continuous Learning

We are building the world’s leading platform for private lending and investing which means innovation is at our core, to meet this goal we need to provide you with more than just on the job experience, we take an active role in your growth by providing experiences to help stretch your capabilities and ensure you are learning new skills all the time.

Convenient Location

Leave the car at home, We are located right on the subway line at Dundas Station making it one of the easiest locations to get to. When lunch time rolls around we are spoilt for choice being situated in the middle of an eclectic mix that you'll never be bored of.

Everyones a Boss

Of course the best benefit of working with us are the people! We are a diverse collection of smart finance and technology enthusiasts united in the belief that our technology can empower and measure vision

Current Openings


  • Technical Marketing Lead
  • UI/UX Designer

When someone shows you who they are, believe them the first time. - Maya Angelou

when all is said and done have you said more than you’ve done?



Boss Insights is hiring for the Technical Marketing Lead and the UI/UX Designer positions.

What is Boss Insights?

Awarded Canadian Lender Association’s Top 25 Executive Leaders in Lending, Boss Insights, opens the door to customer arbitrage enabling FIs to acquire new business borrowers without taking additional risk.  By developing a universal API platform, Boss Insights provides 360⁰ insights on business borrowers, integrating all of their data and streamlining the borrower and lender journey. Our big data and AI platform accelerates loan qualifications and approvals from months to minutes and provides real-time alerts to drive post-loan origination profitability.  This digital lending functionality takes only 8 weeks to adopt.

How do our teams work?

“It doesn’t make sense to hire smart people and tell them what to do; We hire smart people so they can tell us what to do.” – Steve Jobs

If you’re hired at Boss Insights, it’s because you’re exceptional at your craft. That’s why we adjust your role to suit you rather than the other way around. The company performs best when everyone involved is doing work that they care about and are more capable of than anybody else. You’ll get the daily opportunity to have your say in the direction of the business. The entire team works closely with each other and with the founders to drive results – So if you have an idea that will help the company, you’re not just encouraged to speak up, we consider it your duty.

To apply, send the following to

  • Resume
  • Transcript
  • Why do you want to join Boss Insights?
  • What’s a product or app you love, and why?