Sam Sivarajan
Chair, Board of Trustees @Heartwood Investments
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WORK HISTORY
Chair, Board of Trustees @Heartwood Investments
Toronto, ON, CA
I serve alongside a mission-driven board to steward Heartwood Trust’s long-term vision and impact. Together, we provide governance, guide investment strategy, and ensure our decisions reflect our shared values.
EDUCATION
University of Toronto - Rotman School of Management
MBA, Banking, Corporate, Finance, and Securities Law
Alliance Manchester Business School
Doctor of Business Administration (DBA), Behavioural Finance
University of Toronto - Rotman School of Management
Small and Medium-Sized Enterprise Board Effectiveness Program
ESCP Business School
MBA, Finance
University of Toronto
J.D., Banking, Corporate, Finance, and Securities Law
Western University
BA, Honours Economics
Harvard Kennedy School
Investment Decisions and Behavioural Finance
SKILLS
ABOUT SAM SIVARAJAN
High-stakes decision-making rarely feels like a strategy.It feels like 3 AM.You’re staring at the ceiling, running mental scenarios:• The board wants answers.• Your team needs direction.• The data is inconclusive.• The risk is real.Move too fast—and it’s irreversible.Wait too long—and you’re accountable for doing nothing.That’s the trap between haste and hesitation.I help leaders move forward when certainty won’t come—and everything’s on the line. I’m Sam Sivarajan — keynote speaker, board chair, behavioral scientist, and author of The Uncertainty E.D.G.E.I’m Sam Sivarajan — keynote speaker, writer, board chair, behavioral scientist, and author. I write about these questions every week in two Substack publications — one on decision frameworks, one on the good life. Find the links here: https://linktr.ee/samsivarajanI’ve advised on $40B+ in M&A as a former investment banker—and built and led three wealth management firms overseeing $80B+ in assets, guiding them through market volatility, organizational change, and strategic transformation.I currently serve as Chair of the Board for Heartwood Trust, where I support executive teams in aligning risk, purpose, and decision clarity in their mission to deliver purpose-built rentals and close a significant market gap.My work blends decision science with real-world executive leadership—because impactful decisions aren’t made in theory.They’re made in the boardroom, the war room, and the sleepless nights in between.THE UNCERTAINTY E.D.G.E.™ FRAMEWORK• ESTABLISH your foundation — what you control, align priorities, balance present and future, and measure what matters• DIAGNOSE key drivers• GO — act with confidence, even without guarantees• EVOLVE your plan as markets changeEXPLORE→ Keynotes, consulting, and board advisory→ Get your free E.D.G.E. guide at: samsivarajan.comSUBSCRIBE→ The Uncertainty Edge – decision frameworks for high-stakes leaders: theuncertaintyedge.com→ The Good Human Practice – clarity and character in modern leadership: thegoodhumanpractice.comLISTEN→ Candid stories from leaders navigating high-pressure decisions If you\'re accountable for outcomes you can\'t fully control—let’s connect.
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