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

Some of 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



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?



TECHNICAL MARKETING LEAD – Fixed Term – Updated Jun 2nd 2019

We are building the world’s leading platform for private lending and investing

Boss Insights predicts private company performance in real time. The smart portfolio manager offers private investors the same access to company data that public investors have, and in addition verified artificial intelligence models that predict private company performance.  Offering debt and equity capital to private companies is a science and an art. The science is the data insight and the art is the investor’s professional expertise. Boss Insights takes care of the data to let investors focus on what they do best: helping companies get to where they need to go. Boss Insights gathers from private companies in real-time by connecting directly to cloud-based software enabling lenders, investors and exchanges to create KYP (know your product) on every company they engage with.

Our team is very close-knit, each department works together to tackle new challenges and opportunities. You will be working closely with the Founders and other departments, providing you with exposure to every aspect of the company.

You have an uncanny ability to put yourself in the shoes of your readers: speak their language and understand their motivations. You enjoy educating and guiding people to solve real world problems with creative solutions and technology.


We’re based at Dundas Square in Downtown Toronto.  We’re part of a co-working space with great entrepreneurs. We are results based. In practice, this means that if you have requirements to make your days better, let us know and if we can accommodate, we will!   As a startup – it’s all hands on deck, and you’ll be immersed in all areas of the business through regular meetings and learn more as a result.
What do we ask in return? We’re building game changing technology and want your authentic self to enable the best work of your life.
Competitive salary/commission structure commensurate with experience
35 hours/week
Family flexible

  • Prior digital marketing and technology content writing experience
  • Attention to detail
  • Using digital media (SEO/Social) to increase, automate and optimize the flow of inbound customer leads to Boss Insights website
  • Monitor sales funnel and increase conversion to active paid customers
  • Encourage existing customers to actively use the system and monitor usage and satisfaction levels
  • Respond to customer issues and identify future improvements
  • Identify partner websites/companies
  • Create and measure organic and paid ad campaigns
  • Writing blog articles on the business topics of scaling your business using Boss Insights – illustrate the problem, quantify the pain, discuss manual solution vs Boss Insights and where the value is. Example topics: HR administrative burden, mixed customer service signals, inconsistently trained staff
  • Ability to establish Boss Insights as a knowledgeable and trusted expert in the field and to grow organic SEO (and social media) based sales leads
  • Create user guides and tutorials to accomplish common tasks

Candidate Must Be Canadian Citizen/Permanent Resident

To Apply send the following to :

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

No Recruiters please