Jess Joss


With over 20 years of business expertise and almost a decade of investing experience, Jess Joss is CEO of 3 angel investing groups, co-founder of Insiteful Solutions and partner in Spyder Capital Corp.

Jess’s passion for entrepreneurship began shortly after university when she founded a web development firm which continues to thrive today. Jess grew the business, scaling it to an integrated online marketing firm, eventually adding partners. In 2011, with a structure in place, devoting her time to Insiteful Solutions pivoted to investing in the future of start-ups. With extensive business experience, as well as Board and volunteer management expertise, Jess became the Executive Director of YAI in 2014, following many years as an active angel investor with the group.

Leveraging her entrepreneurial, business, and marketing acumen, Jess worked with the YAI team to grow membership by over 450%, as well as increase deal flow, the number of deals completed and amount invested. This renewed energy and motivation earned YAI the honour of being ranked Top 5 in Canada in 2015 and 2016, tied for 1st place in 2017, and solely in first place in 2018. YAI now has the largest membership in Ontario and second largest in Canada. Jess completed her work with York Angle Investors at the end of June 2019.

And starting this summer Jess is transitioning into a new role, as CEO of an alliance of three angel groups; Angel One, GTAN and SWO. This new joint venture (yet to be named) will provide streamlined screening, presenting and Due Diligence for founders who are raising equity funding. And for the almost 200 angels it will provide and opportunity to see the best companies, negotiate the best deals, and nimbly invest. Jess is eager to learn about the local innovation ecosystems in Kitchener-Waterloo, Burlington-Hamilton, and London. This will be an exciting and challenging new role, and jess looks forward to working closely with the local partners.

Jess is also active in the ecosystem and believes in supporting early stage innovation through mentoring, speaking on panels and judging pitch competitions. She was also elected to the NACO Board in Oct. 2017, as Marketing Chair, was NACO World Angel Investment Summit (Conference) Chair 2018 and is also currently Board rep on the Team Enhancement (HR) Committee.

A passionate connector of people, and driven by entrepreneurship, Jess works closely with ecosystem partners, to connect dedicated angels with game-changing young companies looking to grow. The goals? Mentorship, growth, exceptional exits and community development! Throughout all of this, maintaining transparency of the angel investing process, building community engagement and collaboration are paramount.


Mon, Sept 23

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Wed, Sept 25

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Thurs, Sept 26

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