Jess Joss

With over 20 years of business expertise and almost a decade of investing experience, Jess Joss is Executive Director of York Angel Investors Inc. (YAI), 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 Insiteful Solutions, 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 has 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 and tied for 1st place in 2017, and in first place for 2018. Today, YAI has the largest membership in Ontario and second largest in Canada. Jess was appointed to the National Angel Capital Organisation’s Board, as Marketing Chair and was NACO World Angel Investment Summit (Conference) Chair 2018.

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.

In her spare time, Jess enjoys spending time with her family. She is also an active community volunteer, whose roles have included President of the Queen’s University Alumni Association and two terms as President of the local Rotary Club. Her hobbies include photography, Pilates, paddle boarding, cooking, and cottaging.

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