James Orsini: Q&A Session

Q&A Session: James Orsini

James Orsini Q&A Session is happening on November 11th 2021 at 10:00 AM PST (1:00 PM EST)

James Orsini is President of The Sasha Group a VaynerX company. Working alongside Gary Vaynerchuk, its CEO and serial entrepreneur, Orsini leads the group to help small businesses reach explosive growth potential. The Sasha Group provides educational, consulting and marketing services to help ambitious leaders build strong brands to flex with the times. Orsini held previous positions as Chief Operating Officer as well as Chief Integration Officer for VaynerMedia a digital agency with social at its core. Working alongside founder and CEO Gary Vaynerchuk James helped manage the agency for success. He was Chief Executive Officer and member of the Board of Directors of Sito Mobile Ltd., (NASDAQ: SITO) A proven leader and author of numerous business articles including Agency of the Future, and Let Leaders Lead and Practitioners Practice. Mr. Orsini has also penned white papers The Authentic Network, Reverse 360 Mentoring, Mastering Procurement and Procurements Evolution for Today’s Marketing Service Companies. He has appeared on more than 3 dozen podcasts including Second in Command with Cameron Herold and Self-made man with Mike Dillard. James has more than 35 years of finance and operations experience across a broad range of marketing and communications disciplines. 

James had been Executive Vice President and Director of Finance and Operations for Saatchi & Saatchi in New York, where he worked closely with the CEO to provide strategic and day-to-day direction of all financial and operational functions. Saatchi & Saatchi New York was the largest agency in the 153-office Saatchi & Saatchi global network, part of Publicis Groupe, the world’s third largest communications group (PUB.FR).

Before joining Saatchi & Saatchi Mr. Orsini was Chief Operating Officer of Interbrand North America, the world’s leading brand consultancy with 40 offices in 22 countries throughout the world. He has traveled extensively throughout Europe, Asia, and the Americas, and functions effectively in multi-cultural environments. Interbrand is a wholly owned subsidiary of Omnicom, which trades on the New York Stock Exchange. (NYSE:OMC)

Prior to joining Interbrand and serving first as its Global Chief Financial Officer, Mr. Orsini had enjoyed a great deal of success at various subsidiaries of Saatchi & Saatchi, KPMG Peat Marwick, and Goldman Sachs & Company. When first at Saatchi, Mr. Orsini was CFO of both their International Public Relations Division and later their B to B Advertising Unit. At Goldman Sachs, Mr. Orsini was selected from 30 analysts as the company’s primary liaison to Sumitomo Bank, in a new $500 million limited partnership. He was also one of four CPAs selected for a pilot program which changed the company’s hiring strategy, which is still in effect.


Mr. Orsini graduated Magna Cum Laude from Seton Hall University, with a Bachelor of Science in Business Administration. He received the University’s Presidential Academic Scholarship and still serves the University today. He is a licensed New York State Certified Public Accountant.


He is a Board member of Renovation House of New Jersey / New York, residential substance abuse rehabilitation programs. He has served as a member of the Board of Regents for Seton Hall University and has Chaired a Seton Hall advisory board for the Griffin Bridges foundation benefiting academically gifted and financially challenged inner city boys. James is a 40 over 40 honoree in 2020 Campaign US magazine

James Orsini – Transcript

AMA with James Orsini @ The Sasha Group

November 11th, 2021

Please give a warm OG welcome to James Orsini . Feel free to ask your questions below for James. James has an incredible background –  James is President of The Sasha Group a VaynerX company. Working alongside Gary Vaynerchuk, its CEO and serial entrepreneur, Orsini leads the group to help small businesses reach explosive growth potential. The Sasha Group provides educational, consulting and marketing services to help ambitious leaders build strong brands to flex with the times. Orsini held previous positions as Chief Operating Officer as well as Chief Integration Officer for VaynerMedia a digital agency with social at its core. He’s done so much more. We’re honored to have him here and excited to spend the next hour learning from him.

I’m here

Good morning James Orsini! Good to have you here!

Hey James, for marketers looking to jump into a leadership position—what are the 3-4 top skills they need to have to succeed?

Empathy, wisdom and experience

What’s the difference between Wisdom and Experience in your point-of-view?

Wisdom listens and experience talks in a room

Welcome James Orsini! What would be your framework to build an agency helping small businesses in 2022?

Absolutely have to have a business plan. A dream without a plan is nothing more than a wish. Dm me for an outline

What is the biggest skill gap you see with new hires?

I’ve been going outside my industry for some recent hires. Many lack patience

Hi James, thank you for joining.  I’m Janie in NYC.   What do you think the bigger growth channels — maybe 3-5 : ) on the horizon

Look  for where you can gain under-priced attention. Discord is rising fast

Discord for B2B software companies?”

for b2b we like LinkedIn. Can still get great organic reach

Nice, thanks for this James Orsini! How do you think a SaaS could leverage customer onboarding at a PLG strategy to grow his business?

Sorry I need more here to help?? What is PLG strategy?

What marketing channel will B2B buyers be using to make decisions in 10 years? Audio AI, Google, SMS? – Also welcome James Orsini and thank you!

Big fan of sms and we are driving our b2b clients to LinkedIn

hi James Orsini, how do you deal with entrepreneurs and Small Business owners who doubt/question your advice? I get that they’re personally invested but they would rather take the advice of their brother than the consultant they hired

By the time they get to me and sasha they have moved beyond the friends and family advice. Our tag line is entrepreneurial spirit infused with Fortune 500 experience

What suggestions would you like to give to someone who is starting his own digital agency?

There is a market for everyone. That said pick a lane to go deep in. Restaurant, construction etc. write about it, speak about it, post about it. give folks a reason to come to you

Hi James! I’m actually curious to hear more about the question David asked re: patience. Do you mean more in terms of patience to see payoff, or patience in internal relationship building, or something else?

When I came to Vayner I worked with 450 millennials. Most had a “semester” mentality. After 6 months ready to move on, try something new. Never rooted long enough in any spot to get really good at something

What would be your Advice to new agency owners?

Know what’s in front of you at each stage. Dm me and I will send you an article on what to expect when you are 25 people, 50 people, 100 people etc

James Orsini follow up question: they also try to nickel and dime your services to the point where you spend too much time negotiating

Yes we have moved to “productized” services. You want one of these it’s $10k you want one of those it’s $25k. We’ve tried to move away from hours and rates. Another solution could be to ask what’s your budget so I can explain what services I can provide for that

Hello James Orsini, thoughts on the best way to create “career paths” that can keep talent engaged and enthusiastic for longer?

Great question. We are now all in the staff retention business; just like our media 1 size does not fit all anymore. Need to get down from what Gary calls the clouds and get into the dirt. Even things like professional development need to move from classes to personal to keep talent. I have a creative in my south office who is interested in animation. I found a class in Atlanta. Told her if she was willing to drive I would pay for the class and hotel. You thought I bought her a car. She was so happy that as President I had her best interest in mind. This was a girl who prior to that had 1 foot out the door. Did this without a salary increase without a title change. Small personal gesture made the difference

Good Morning James Orsini always an honor to have someone like yourself here. Thank you for taking the time.What do’s and don’ts would you recommend to agencies who are trying to pivot from small/mid sized clients to more large/well known accounts?

I have an episode of STORK coming out soon. It talks about Using the Eisenhower matrix as a decision graph for client plotting it ranks clients in different tears and has different times of the year went to pursue them. DM me and I will send you my transcripts on this episode for free. Stork membership is $300 per year

Heya James, welcome and thanks for taking the time to share your expertise. What are your top 3 strategies for demand gen? Client is an AI automation platform

Really hard to find a silver bullet here. We at VAYNERX lean so much more into brand building rather than seo and sem. A great brand outsells the best salesman every time. It’s what we call and /and rather than and/or you need to do both simultaneously. Drive sales AND spend some $ on building brand. Brands are built on social now

Hey James – Welcome!
What quick advice would you give a person that runs his own tile business and he is a one man show? Looking for more phone calls/leads

Shameless plug  for our STORK product from the sasha group Found on our website $300 per year membership five minute tactical videos released every Monday how to find a local influencer for my business how to advertise on podcasting a real value here

What social media best practices you see business owners missing out on?

Volume trumps perfection. Too many folks not posting because they are trying to create the perfect social post

What’s the #1 thing young professionals should be focused on to continue growing as a digital creative/marketer?

Self awareness. Know what you are good at and play to your strengths. Too many folks “out of position “ on the field

What technique do you/your team apply for a fresh breath of inspiration for a new campaign?

We open it up to the entire agency. Good ideas can come from anywhere. Had a $250,000 campaign idea come from a research intern not from the creative department

Can you recommend a book that every young marketer should read?

Six fundamentals of success from Stuart Levine

How do you go about delegating responsibilities to your team?

I wrote an article on Medium. “Facilitate-don’t delegate”


What was the biggest mistakes you’ve made as a leader?

Trying to fix the problem before fully listening. It takes great restraint to sometimes just listen

It’s like jeopardy the game show in here 

If anyone is looking for the company website based on some answers it’s www.thesashagroup.com

Recommended podcasts?

Obviously Gary Vaynerchuk stuff is great. His interview today with mark zuckerberg is one of the best I’ve heard in awhile. For smaller entrepreneurs our podcast building while flying could be helpful

James- Thanks for taking time out of your busy day to answer questions for our community. We not only appreciate your wisdom but appreciate you spending time in our community. That concludes today’s AMA. 

Thank you  everyone

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