Sider Road

New Home Test

Clarity. Power. Legacy.

Your partners for business transformation

From mess to momentum. We cut through the chaos and build clear systems so every decision is smarter—whether you’re scaling, selling, or just staying sane through a transition.

Clarity. Power. Legacy.

Your partners for business transformation

From mess to momentum. We cut through the chaos and build clear systems so every decision is smarter—whether you’re scaling, selling, or just staying sane through a transition.

From boardrooms to boutiques, the world’s founders trust us.

Masterminds and Masterclasses

Business

Strategic Advisory
The truth, with a plan attached.

Efficiency Audits
Find it. Fix it. Fast.

Scalability Plans
Systems built to grow.

Family Business

Family Dynamics
Fewer fights, smarter decisions.

Family Business Succession Strategy
Smooth transitions, no fireworks.

Exit Prep
Max value, zero surprises.

Masterminds

Power Partners: Women Behind the Family Business ➜

Stop guessing, start knowing. Learn how to ask the smart questions that move the business-and your voice-forward

Power Partners: Men Behind the Family Business ➜

Redefine partnership by leading with insight, curiosity, and the questions that keep business-and family-on track.

The Family Transition Table ➜

Family businesses don’t fail from lack of effort-they fail from chaos. This is where confusion turns into clarity, operations get smart, and everyone knows their role

Masterclasses

Business Reputation RX  ➜

Diagnose your risks. Prescribe the fixes. Protect your most valuable asset: your business reputation,

Charisma ➜

Average leaders talk. Winning leaders captivate. Charisma can be learned-and this is where you get it.

Generational Fluency ➜

Operations don’t break from lack of talent-they break from generational misfres. Learn to speak fluently across six generations (yes, military included).

Are these thoughts that keep circling in your head?

Why do strategy talks get hijacked by side arguments?

Why does a five-minute decisions always take five hours ?

Why does every decision require three debates and a referee?

Why is our growth plan basically 'Hope and argue'?

Reach out here to make time to discuss how to overcome issues driving you mad!

Are these thoughts that keep circling in your head?

Why do strategy talks get hijacked by side arguments?

Why does a five-minute decisions always take five hours ?

Why does every decision require three debates and a referee?

Why is our growth plan basically 'Hope and argue'?

Reach out here to make time to discuss how to overcome issues driving you mad! ​

Masterminds and Masterclasses

Business:
  • Strategic Advisory—The truth, with a plan attached.
  • Efficiency Audits—Find it. Fix it. Fast.
  • Scalability Plans—Systems built to grow.
Family Business:
  • Family Dynamics—Fewer fights, smarter decisions.
  • Family Business Succession Strategy—Smooth transitions, no fireworks.
  • Exit Prep—Max value, zero surprises.
Masterminds:
Masterclasses:
  • Business Reputation RX:  Diagnose your risks. Prescribe the fixes. Protect your most valuable asset: your business reputation.
  • Charisma:  Average leaders talk. Winning leaders captivate. Charisma can be learned—and this is where you get it.
  • Generational Fluency:  Operations don’t break from lack of talent—they break from generational misfires. Learn to speak fluently across six generations (yes, military included).

New: Sider Road Kids

Leadership isn’t just for boardrooms. It starts in classrooms.

In a world shaped by AI, the ability to communicate with confidence and presence matters more than ever.

Sider Road Kids brings Jocelyn’s signature lessons to students — inspiring the next generation of leaders.

Are these thoughts that keep circling in your head?

Why do strategy talks get hijacked by side arguments?

Why does a five-minute decisions always take five hours ?

Why does every decision require three debates and a referee?

Why is our growth plan basically 'Hope and argue'?

Reach out here to make time to discuss how to overcome issues driving you mad!

If your business feels messy, stalled, or stuck in family drama — stop spinning. Office Hours is where we cut through the noise and fix what’s holding you back.

Charisma Masterclasses

“ You don’t need to be the loudest person to be the most powerful. ”

However, you NEED the tools. Join a curated, high-trust group where presence becomes practice—and results follow.

Jocelyn Greenky, MBA
Business Transformation Expert

Meet the leadership team

We are all passionate and committed to delivering high-quality services to our clients.

Jocelyn Greenky Underwood

Founder

Jocelyn is a renowned keynote speaker and business strategist with a wealth of experience in 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, Jocelyn has worked with Fortune 500 companies, mid-sized businesses, and startups, and her expertise extends to her roles as an Adjunct Professor and published author.

Her award winning notable book, The Big Sister’s Guide to the World of Work: The Inside Rules Every Working Girl Must Know, has garnered widespread recognition, and her insights have been featured on CNBC, FOX, CNN, and in prominent publications like The New York Times, USA Today, and the Washington Post among many others.

Jocelyn’s diverse background includes serving as the Digital Global Editorial Director at Hachette Filipacchi, where she managed prestigious titles such as ELLE, Car and Drive, Road & Track, Eating Well, Women’s Day and 20+ other titles. She led Broadcasting and Event Marketing for Wenner Media, overseeing the brands Rolling Stone and Men’s Journal, and worked as an event manager for Philip Morris with brands including Virginia Slims, Marlboro and Cartier. Additionally, Jocelyn has been COO of Colin Cowie Lifestyle and CEO of BriteBean Technology, CEO of Ortho Marketing and has served as a consultant to Material Bank, Wall St. Journal, HBO, iNDEMAND among many others.

She holds an MBA in Organizational Leadership (with distinction) and a B.S. from Syracuse University. Jocelyn was honored with the first grant awarded to an adjunct business school professor and woman in the master’s business program to research psychological safety in the global workplace.

Residing in Greenwich, CT, Jocelyn enjoys the company of her three dogs and husband, and their six blended children cherish their visit for home-cooked meals and family warmth.

Dr. John Power

Dr. John Power is a proven senior executive whose career has encompassed many industries and roles. He is currently involved in three start-up businesses as a founder; a robotics company where he serves as COO, a marketing technology company where he serves as CEO, and a financial technology company where he serves as CFO.

Prior to these endeavors, John was the Chief Financial Officer and Chief Administrative Officer of DS Healthcare Group, Inc, a Nasdaq listed company where he helped the company avoid bankruptcy and be sold saving shareholder value.

 Previously, John was the CEO and Founder of Mark My Media, an education technology company providing pathways to the finance industry for students in universities across the US. Other roles include, COO and CFO of Mantara, a venture-backed technology firm focused on high frequency/low-latency trading platforms. John was Chief Administrative Officer at Mellon Investor Services and President of Mellon Securities through their acquisition by Bank of New York and was part of the integration team.  Prior to Mellon, John was the Director of Finance for E*Trade Financial.  During his tenure, John was involved in sixteen acquisitions by E*Trade including Harrisdirect purchased from BMO Financial Group and BrownCo purchased from JPMorgan Chase & Co.  Prior to E*Trade, John was Controller/Chief of Staff for Bank Julius Baer’s US Private banking unit.  John started his management career in finance at Spear, Leeds & Kellogg.

John serves on the faculty of Mercy University’s College of Business. He is currently the Director of the MBA Program and the Chair of Graduate Business program. John has a B.S. in Finance from Manhattan College, an M.B.A. from Dowling College and has completed his Doctoral degree in business at Wilmington University. His dissertation was Exploratory Analysis of Artificial Intelligence (AI) Impact and Opportunities for Financial Services Compliance. He was a contributing author to 97 things about Ethics that Everyone in Data Science Should Know.

John lives in Bayside, NY with his wife and two sons. He enjoys mentoring his current and former students and volunteers for the Boy Scouts.

Paige Herman-Axel

Writer Extraordinaire

Mechle Wenceslao, MBA

Executive Assistant

Jade Herz

Social Media Guru

Gilda

Chief Vibe Officer (aka The Queen)

Gilda doesn’t work at Sider Road — she rules it. With a keen eye for comfort and an unmatched ability to detect snacks in a 5-mile radius, she ensures the team stays grounded (and well-cuddled). She specializes in strategic lounging, morale boosting, and silently judging your outfit choices during Zoom calls. Every empire needs a queen. Gilda is ours.

Aunt Cece

Barketing Boss

Cece brings big energy and even bigger opinions. As our unofficial security chief and master of side-eye, she keeps the squirrels out and the standards high. Known for her no-nonsense attitude and occasional zoomies, Cece ensures we don’t take ourselves too seriously. Just don’t touch her chew toy unless you're ready for a performance review.

Finn Lucky

Director of Distraction & Joy

Finn may be the newest hire, but don’t let the puppy face fool you — he’s all about chasing goals (and tennis balls). Between accidental naps and strategic tail wags, he keeps the team on track with calendar reminders disguised as enthusiastic barks. Still learning the ropes, but already stealing the show (and everyone’s lunch). Lucky us.

Jocelyn Greenky Underwood

Founder

Jocelyn is a renowned keynote speaker and business strategist with a wealth of experience in 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, Jocelyn has worked with Fortune 500 companies, mid-sized businesses, and startups, and her expertise extends to her roles as an Adjunct Professor and published author.

Her award winning notable book, The Big Sister’s Guide to the World of Work: The Inside Rules Every Working Girl Must Know, has garnered widespread recognition, and her insights have been featured on CNBC, FOX, CNN, and in prominent publications like The New York Times, USA Today, and the Washington Post among many others.

Jocelyn’s diverse background includes serving as the Digital Global Editorial Director at Hachette Filipacchi, where she managed prestigious titles such as ELLE, Car and Drive, Road & Track, Eating Well, Women’s Day and 20+ other titles. She led Broadcasting and Event Marketing for Wenner Media, overseeing the brands Rolling Stone and Men’s Journal, and worked as an event manager for Philip Morris with brands including Virginia Slims, Marlboro and Cartier. Additionally, Jocelyn has been COO of Colin Cowie Lifestyle and CEO of BriteBean Technology, CEO of Ortho Marketing and has served as a consultant to Material Bank, Wall St. Journal, HBO, iNDEMAND among many others.

She holds an MBA in Organizational Leadership (with distinction) and a B.S. from Syracuse University. Jocelyn was honored with the first grant awarded to an adjunct business school professor and woman in the master’s business program to research psychological safety in the global workplace.

Residing in Greenwich, CT, Jocelyn enjoys the company of her three dogs and husband, and their six blended children cherish their visit for home-cooked meals and family warmth.

Dr. John Power

Dr. John Power is a proven senior executive whose career has encompassed many industries and roles. He is currently involved in three start-up businesses as a founder; a robotics company where he serves as COO, a marketing technology company where he serves as CEO, and a financial technology company where he serves as CFO.

Prior to these endeavors, John was the Chief Financial Officer and Chief Administrative Officer of DS Healthcare Group, Inc, a Nasdaq listed company where he helped the company avoid bankruptcy and be sold saving shareholder value.

 Previously, John was the CEO and Founder of Mark My Media, an education technology company providing pathways to the finance industry for students in universities across the US. Other roles include, COO and CFO of Mantara, a venture-backed technology firm focused on high frequency/low-latency trading platforms. John was Chief Administrative Officer at Mellon Investor Services and President of Mellon Securities through their acquisition by Bank of New York and was part of the integration team.  Prior to Mellon, John was the Director of Finance for E*Trade Financial.  During his tenure, John was involved in sixteen acquisitions by E*Trade including Harrisdirect purchased from BMO Financial Group and BrownCo purchased from JPMorgan Chase & Co.  Prior to E*Trade, John was Controller/Chief of Staff for Bank Julius Baer’s US Private banking unit.  John started his management career in finance at Spear, Leeds & Kellogg.

John serves on the faculty of Mercy University’s College of Business. He is currently the Director of the MBA Program and the Chair of Graduate Business program. John has a B.S. in Finance from Manhattan College, an M.B.A. from Dowling College and has completed his Doctoral degree in business at Wilmington University. His dissertation was Exploratory Analysis of Artificial Intelligence (AI) Impact and Opportunities for Financial Services Compliance. He was a contributing author to 97 things about Ethics that Everyone in Data Science Should Know.

John lives in Bayside, NY with his wife and two sons. He enjoys mentoring his current and former students and volunteers for the Boy Scouts.

Paige Herman-Axel

Writer Extraordinaire

Mechle Wenceslao, MBA

Executive Assistant

Jade Herz

Social Media Guru

Gilda

Chief Vibe Officer (aka The Queen)

Gilda doesn’t work at Sider Road — she rules it. With a keen eye for comfort and an unmatched ability to detect snacks in a 5-mile radius, she ensures the team stays grounded (and well-cuddled). She specializes in strategic lounging, morale boosting, and silently judging your outfit choices during Zoom calls. Every empire needs a queen. Gilda is ours.

Aunt Cece

Barketing Boss

Cece brings big energy and even bigger opinions. As our unofficial security chief and master of side-eye, she keeps the squirrels out and the standards high. Known for her no-nonsense attitude and occasional zoomies, Cece ensures we don’t take ourselves too seriously. Just don’t touch her chew toy unless you're ready for a performance review.

Finn Lucky

Director of Distraction & Joy

Finn may be the newest hire, but don’t let the puppy face fool you — he’s all about chasing goals (and tennis balls). Between accidental naps and strategic tail wags, he keeps the team on track with calendar reminders disguised as enthusiastic barks. Still learning the ropes, but already stealing the show (and everyone’s lunch). Lucky us.

Testimonials

“Jocelyn, Thomas Dean here. We connected on LinkedIn after your beyond fabulous CEPA Preso last week. Some presentations certainly can be banal, yours was informative and exciting. Amid my world of ongoing growth mindset, your excellence has inspired me to very consciously sharpen the charisma and communication axes. I guess that’s why God invented AI! Again, huge gratitude for such a wonderful, wonderful, wonderful hour. And BTW, I thought I was the only person struggling with that AI butterfly in the lower right corner. Hope our paths cross professionally in value creation and EPI, very good people hopefully working together.”

THOMAS DEAN Founder of Relentless Value

“I thought the session with Jocelyn went really well, and I just wanted to say how much I enjoyed it. Our team truly values this type of insight—it’s incredibly relevant and actionable for our CEPA community. Thanks again Jocelyn for sharing your expertise with us!”

RYAN BELTZ Account Manager Exit Planning Institute

“Jocelyn is the consummate professional, extremely smart and dedicated. She goes above and beyond to assist her clients and aid them in achieving their goals. Her level of knowledge and expertise is unparalleled and she genuinely cares significantly. I had the opportunity to work with Jocelyn on a family business matter. She approached the delicate situation with a unique perspective and a calm demeanor. Needless to say, she solved the matter with aplomb!”

SAMANTHA REISS

“I’ve been working with Jocelyn for almost 20 years. Her ability to understand the issues that need to be addressed and implementing a roadmap to move forward have been instrumental in achieving success”

STUART BROWNSTEIN President of Colin Cowie

“We can’t thank Jocelyn and her team enough for developing our branding, social media and training our employees within our grocery stores. She worked tirelessly and went over and above our requests.”

NANCY D’AGOSTINO Co-CEO, D’Agostino’s Supermarket

“Jocelyn is one of the funniest, most insightful, and creative brand strategists I’ve had the pleasure of working with. My nickname for her is the ‘inceptionator’ because she has sprouted so many ideas. She understands what motivates people and how to inspire and expand their global impact.”

JENN HALWEIL CEO, #GoBeyond

“After hearing Jocelyn speak at Villanova, I knew that students, faculty, and staff at Drexel would love her, and more importantly, what she had to share! Her insight is laser-point accurate to the realities of being successful in the work environment, and her interactive delivery was keenly in touch with the wide demographics of our audience.”

ANN WILSON Booking client, Drexel University

“Jocelyn Greenky is an outstanding guest speaker. She engages students with equal parts humor, candor, and insight, and always delivers a thoughtful presentation on office politics and generational challenges in workplace. Jocelyn advises students that the real work comes after they get the jobs – in building and managing personal brands throughout their careers.”

ANDREW GOLDMAN Adjunct professor NYU/Tisch School of the Arts

“Sider Road is a Change Agent. By being present in our day-to-day activities, she re-constituted the support staff, trained long-term employees on operational execution, reworked all workflow, and trained us with effective communication skills. Sider Road has given us a sense of relief now that we have a clear structure.”

DEAN STEINMAN Presentation Multimedia

Jocelyn doesn’t just talk about innovation—she embodies it. Her ability to blend executive presence with AI-powered clarity is something rare. Every conversation with her feels like a masterclass in modern leadership.

TERRY WHINSTON Executive Coach, NYC

We brought Jocelyn in to streamline our messaging and bring focus to our leadership team. She not only delivered — she used her AI assistant to track insights, action items, and even preempt what we needed next. Efficiency meets insight — that’s her edge. 

MILEY CRAWFORD Partner, Mid-size Consulting Firm
Previous
Next

Jocelyn & The Sider Road Team

Accessibility Toolbar