People who turn insights into performance.
Second Order is a networked boutique. We assemble the right mix of strategy, operations, and pragmatic AI expertise for your goals—led by our principal and supported by trusted collaborators.
Core
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Darren McLennan
PRINCIPAL, SECOND ORDER
Strategy & Customer Insight • Performance & Process • Pragmatic AI
What he does: Makes strategy executable, simplifies processes, and embeds Copilot/ChatGPT in high-return knowledge workflows.
Credibility: Ex-Deloitte & CIBC; MBA (Rotman); Executive-in-Residence (TMU). Experience across corporate, non-profit, and government.
Focus sectors: Financial services, real estate, business services; light manufacturing/distribution.
Selected outcomes: Growth & margin programs; service cost reduction for a digital bank; enablement programs with NPS 60+.
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Jennifer Frees
PRINCIPAL, SECOND ORDER
Marketing • Partnerships • Non-Profit
Jenn has diverse executive leadership, marketing, business development, and strategic partnership experience in private, public and non-profit sectors. She has served on several leadership teams including in her current role as Chief Marketing & Business Officer at TIFF (Toronto International Film Festival). She has developed innovative, award-winning projects for top international brands, as well as leading the generation of over $180M for her non-profit clients globally.
She is an internationally sought-after business development speaker and has trained business leaders from over 20 countries. Jenn is passionate about working with organizations dedicated to the authentic pursuit of total equity, and is proud to support an array of related charitable causes.
Network
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Chloë Wade
Chloë is a respected business development and client service leader, an architect of revenue strategy and partnerships that deliver tangible impact. She is known for her calm, collaborative and empathetic approach to coaching and engaging clients and teams. Chloë’s experience spans leadership roles at TIFF, Ottawa Sports & Entertainment Group, with FIFA and Luminato International Arts Festival early in her career. She has smoothly secured and managed tens of millions of dollars in sponsorship revenue, and is fluent in English, French and Spanish.
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Richard Lee
Richard retired as a Partner in Deloitte’s Consulting practice in Canada in 2014 after a career of 29 years. While at Deloitte, Richard worked with his clients’ senior leadership teams to facilitate the development of their business, customer and product strategies and to plan the implementation transformational change. After leaving Deloitte, Richard worked for Aequitas Innovations for two years on an online platform to facilitate the capital formation process for private companies. He is currently an Executive in Residence at the Ted Rogers School of Management where he coaches MBA students and an Advisor at the DMZ at Ryerson (a tech business incubator). In his spare time, Richard enjoys travel and he is an avid student of British history.
Get to Know Us
Darren McLennan
Principal, Second Order
Darren is a strategy and operations specialist with a focus on strategic planning, organic revenue growth, client experience, and operational improvement. Darren has recently been leveraging generative AI for revenue generation and service improvement.
His background includes roles at CIBC and Deloitte Consulting, where he has guided non-profit organizations, modernized technology & processes, and developed customer strategies for SMBs, government, and multibillion-dollar organizations.
Darren holds an MBA from the University of Toronto's Rotman School of Management and a B.Sc. in Industrial Engineering from the University of Manitoba, supplemented by certifications in areas such as Digital Product Management, Agile Design Thinking, and Generative AI. Darren is currently enrolled in “Competing in the Age of AI” at Harvard Business School Executive Education.
Darren is also an Executive-in-Residence at Toronto Metropolitan University, where he advises startup companies on Strategy, Operations, and Generative AI.
Jennifer Frees
Principal, Second Order
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