Ready for the next chapter.
From the board room to the pickle courts, Chris dominates any terrain he steps foot on.
Chris Jensen is a seasoned entrepreneur and executive known for building values-driven companies, scaling global teams, and helping founders turn ideas into reality.
Originally from the UK, he built a successful early career in banking before moving to Canada and stepping fully into entrepreneurship, ultimately co-founding multiple award-winning technology companies and shaping global teams across Canada, Bangladesh, Costa Rica, Thailand, Sri Lanka, and beyond.
Now “retired” but more active than ever, Chris offers his experience to boards, founders, innovators, and anyone committed to building meaningful companies that last.
1981–1984
Early Academic Foundation
Chris completed his Bachelor of Science with Honours in Economics and History at Queen Mary University of London, building the analytical grounding that would shape his future leadership roles.
2004-2018
Early Executive Leadership at CWH Group
Chris spent fourteen years as CEO of CWH Group, guiding multiple companies through organizational transitions and helping teams evolve their capabilities and market positions. His work focused on helping talented people and passionate teams move through pivotal periods of change.
2009-2015
Supporting Innovation at ConnectionPoint
He served as a Director at ConnectionPoint Systems Inc., supporting the success of FundRazr and contributing to the rise of social commerce technologies.
2010-2020
Founding and Leading Left
In 2010, Chris co-founded Left and served as its CEO for a decade. Under his leadership, Left grew into an award-winning global organization recognized for innovation, culture, and technical excellence, earning distinctions such as Canada’s Top 100 Employers and Deloitte’s Technology Fast 50.
2016-Present
Co-Founder of TravelAI
In 2016, Chris co-founded TravelAI, an applied AI company building technology across the travel ecosystem. His work supports a suite of interconnected brands dedicated to improving the entire travel journey and redefining how people experience mobility and movement.
2020-Present
Co-Founder of UpNext Ventures
In 2020, Chris helped launch UpNext Ventures, a venture studio building and accelerating travel-related brands. UpNext extends his passion for technology, social impact, and founder mentorship, cultivating new companies with the potential to reshape global travel.
ABOUT THE JOURNEY
Chris Jensen
Board Advisor, Venture Mentor & Growth-Driven Tech Leader
With over three decades of experience building, scaling, and guiding high-impact companies, Chris Jensen has helped shape some of the most innovative brands in travel technology and digital commerce. As Co-Founder of TravelAI™, UpNext Ventures, and Left, he has led teams through rapid growth, breakthrough innovation, and award-winning company culture.
His leadership has earned national recognition, including Deloitte’s Technology Fast 50 and Canada’s Top 100 Employers. Chris’s approach blends strategic clarity, operational excellence, and a deep understanding of how technology and humanity intersect. He has advised founders, guided executive teams through complex transitions, supported global product launches, and helped build companies that make a lasting mark on their industries.
Now in his retirement, Chris is opening his expertise to the world — serving on boards, mentoring early-stage founders, speaking at events, and occasionally dominating a pickleball court.;
CONNECT WITH CHRIS
Advisory & Mentorship
Chris works with founders at all stages, offering:
- Fundraising and capital strategy guidance
- Go-to-market refinement
- Founder decision-making support
- Culture-building for fast growth teams
- Strategic partnerships + operational clarity
Board
Roles
With over 30 years in business, Chris brings valuable insights:
- 30+ years of executive leadership
- Deep experience in tech, travel, finance, and global tea
- Corporate governance insig
- Profitability and operational optimization
- AI transformation oversight
Speaking Engagements
Some of the topics that Chris is passionate about:
- AI and the future of the travel industry
- Entrepreneurship and the founder’s journey
- Building distributed global teams
- Culture as strategy Technology for social good
SEE YOU ON THE COURTS
When Chris isn’t advising founders, shaping companies, or sitting in boardrooms, there’s a good chance he’s holding a paddle. Pickleball has become one of his favourite arenas — a place where competitiveness, strategy, and good humour meet on the court. Known for sharp reflexes, a tactical mind, and a healthy respect for a well-placed dink, Chris plays the game the same way he builds companies: with focus, patience, and just enough fire to keep things interesting.
He enjoys singles for the challenge, doubles for the camaraderie, and tournaments for the thrill of seeing skill and chaos collide. If you’re ever looking for a partner, opponent, or someone who plays like he’s still pitching to investors, Chris is always game.
Ready for the next chapter.
CHRIS JENSEN
Advisor • Innovator • Mentor • Speaker
ACHIEVEMENTS
3× Deloitte Technology Fast 500 Winner
- Left — Ranked #101 (2018)
- Left — Ranked #92 (2019)
- TravelAI — Ranked #187 (2025)
2× Canada’s Top Employer Winner
- Canada’s Top 100 Employers
- Canada’s Top Small & Medium Employers (and also BC’s Top Employers)
2× BC Tech Association TIA Winner/Community Engagement
- First-ever consecutive & two-time winner (2015 & 2016)
Best For The World: Workers — Top 10% of All B Corps
- Global recognition for employee impact (2019)
Multiple Innovation & Culture Awards
- High Impact Hero Award (BambooHR)
- Metabridge Top 15 + People’s Choi
- Finalist in multiple Canadian HR Awards
Growth, Impact & Innovation
- Built companies achieving >400% growth periods
- Pioneered socially impactful technologies