Jess Joss


A passionate connector of people, Jess brings 20 years of business experience in both entrepreneurial endeavours and not-for-profit organizations to York Angel Investors (YAI). With extensive business experience, as well as Board and volunteer management expertise, Jess became the Executive Director of York Angels in 2014, after years as an active angel with the group.

Leveraging her experience as a founder and her marketing acumen, Jess has worked with the YAI team to grow membership by over 220%, as well as increase deal flow, number of deals completed and amount invested.  This renewed focus earned York Angels the honour of being ranked Top 5 in Canada in 2015 and 2016. (Finger’s crossed for the 2017 results!) As well, York Angels is now has the largest membership in Ontario and second largest in Canada.  Jess has also been recently appointed to the National Angel Capital Organisation’s Board, as Marketing Chair; and is NACO World Summit Conference Chair.

Jess works closely with angels and ecosystem partners, to connect dedicated angels with game-changing young companies looking to grow! The goals? Mentorship, growth, exceptional exits and community development! Transparency of the angel investing process, community engagement and collaboration are paramount.

Jess is Executive Director of York Angel Investors Inc., and partner/co-founder of Insiteful Solutions. She is also on the AccelerateOTT Program Committee (startup conference in Ottawa) and advises several start-ups.

In her spare time, Jess enjoys spending time with her family. She is also an active community volunteer, whose roles have included International 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.