Welcome
Jocelyn Greenky
Founder, Sider Road · Business Transformation Expert
Jocelyn is a renowned keynote speaker and business strategist with a wealth of experience tackling complex business challenges.
Expertise
- Family Business Advisory
- Fortune 500 Experience
- Interim / Fractional CEO
"Structure beats talent. Every single time."
Business Transformation Expert
Jocelyn is a renowned keynote speaker and business strategist with a wealth of experience tackling complex business challenges. She specializes in revitalizing and launching companies, earning the trust of both family-owned businesses and global CEOs. With a career spanning over 40 years, she has worked with Fortune 500 companies, mid-sized businesses, and startups.
Her notable book, The Big Sister's Guide to the World of Work, has garnered widespread recognition, and her insights have been featured on CNBC, FOX, CNN, The New York Times, USA Today, and the Washington Post. She holds an MBA in Organizational Leadership (with distinction) and a B.S. from Syracuse University.
Known as a no-nonsense business “fixer,” she helps leaders cut through chaos, navigate succession, and build credibility that lasts. From Fortune 500 giants to family-run firms, she serves as strategic advisor, Interim / Fractional CEO, keynote speaker, and professor, often all at once.
The Operator's Chair
Over four decades in the operator's chair — the roles behind the work.
Current
Founder, Sider Road
From Fortune 500 giants to family-run firms, she serves as strategic advisor, Interim / Fractional CEO, keynote speaker, and professor, often all at once.
Adjunct Professor
Queens College, CUNY
Currently an Adjunct Professor at Queens College, CUNY, where her research on psychological safety in the global workplace is IRB sanctioned.
Co-Founder
BriteBean
She co-founded BriteBean, a technology company connecting recipe websites to grocery stores, which she built to a successful exit through its acquisition by D'Agostino's.
C-Suite & Leadership Roles
Media, Technology & Lifestyle Brands
Jocelyn held C-suite and leadership roles across media, technology, and lifestyle brands — ELLE, Rolling Stone, Car and Driver, Men's Journal, HBO, and Material Bank.
Grounded, funny, and fearless, Jocelyn brings clarity to complexity and a serious edge to leadership.
The Story Behind the Name
Why this business is named after
a farm road in Canada.
Jocelyn spent summers on a multigenerational Mennonite farm called Sider Road — run by Emma, the family's beloved housekeeper. Emma held an entire family's life and livelihood together with no title, no fanfare, and no ask for credit.
"The most important work is never the loudest."
Emma never gave a keynote. She led anyway — completely, quietly, without ever needing the room to notice. Those summers are why Jocelyn sees every client not as an engagement, but as a legacy in progress.
Featured In
Recognized by the world's most trusted media outlets
Education & Expertise
She holds an MBA in Organizational Leadership from Mercy University and is currently an Adjunct Professor at Queens College, CUNY, where her research on psychological safety in the global workplace is IRB sanctioned.
MBA in Organizational Leadership (with distinction)
Mercy University.
Mercy UniversityB.S.
Syracuse University.
SyracuseAdjunct Professor
Queens College, CUNY — teaches and researches psychological safety in the global workplace.
CUNYPsychological Safety in the Global Workplace
At Queens College, CUNY, her research on psychological safety in the global workplace is IRB sanctioned.
Trusted by Leading Organizations
From boardrooms to boutiques, the world's founders trust us
Ready to Unlock Strategic Clarity?
Whether you're navigating a transformation, planning a succession, or preparing for what's next — let's talk about what's possible.