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Head of Technology - ‘Greenfield’ (New Startup)

The" Greenfield' Opportunity


We’re partnering with a brand new startup (yet to even be named!) that we’re referring to as ‘Greenfield’ for the time being. Tackling a big opportunity at the intersection of technology, insurance and agriculture in Canada, this company will drive innovation to impact the industry in a long-term and meaningful way. 


As a joint-venture between two established mutual insurance companies (Red River Mutual and The Commonwell Mutual Insurance Group), ‘Greenfield’ was created to be a standalone entity to drive innovation in Farm insurance (you can read the press release here).


The founding partners have funded this venture in order to invest in addressing a changing, complex and underserved market - insurance for the agriculture sector. These two partners recognized that in order to truly create something progressive for their industry they needed to establish an innovative MGA (managing general agent) model, operating with autonomy outside of their established organizations to innovate with an entrepreneurial startup development approach.


‘Greenfield’ will modernize the industry, become a vehicle for growth, expansion and innovation in the Canadian market. The business opportunity has been identified (and we’ll tell you much more once we’re connected!), the funding is secured, and with an innovation-focused and insurance industry expert CEO at the helm, we’re ready to help find the next member of this founding team.

How You Will Make An Impact? 


This is a unique opportunity to join a company from the very beginning. You will have influence over the business and technology strategy to leave your mark. 


You will also be making a difference in the industry - providing insurance solutions for Farmers in Canada.


This Head of Technology role will touch everything IT related at the company. You will work with the CEO to develop the technology strategy. From there, you’ll build and establish relationships with vendors, services providers and partners. You’ll be involved with developing all products from the ground up and building and managing your own team eventually as ‘Greenfield’ grows.

Does This Sound Like You?

  • You will develop the company’s strategy for using technology resources

  • Ensure technologies are used efficiently and securely

  • Evaluate and implement new systems, infrastructure and technologies (ie. the company might be exploring the use of  IoT, AI, etc)

  • Build relationships and integrations with external IT vendors, service providers and potential B2B partnerships

  • Actively participate in product development with the team

  • Build, manage and develop a team 


Skills We’re Looking For: 

  • Entrepreneurial, self-motivated and results-oriented with the innate ability to drive strategic opportunities from discovery to closure

  • Experience developing and managing third party managed services partnerships

  • Experience growing and managing a team using strong interpersonal skills to connect with leaders and employees

  • Strong analytical and critical thinking skills, plus a knack for creative problem solving and negotiation

  • Experience with the strategic management of and utilization of data

  • Experience with B2B integrations

  • Experience with web and mobile development

  • Experience with cloud platforms such as Microsoft Azure or AWS

  • Agile project management is an asset

  • 7+ years of experience leading IT functions, experience in a start up in a huge plus

  • Team player with a ‘roll up your sleeves’’s an early stage company after all!

We’d love to hear from you - even if you don’t meet 100% of the requirements! If this sounds interesting to you, send a note to


Does this sound exciting to you?
Get in touch with Leigh!

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