VaynerX’s First Retiree Marks a New Milestone for the Company

If you’d have told a young James Orsini – sitting at account behemoth KPMG or crunching numbers on Wall Street – that he’d one day retire from a global advertising agency, he would have “laughed out loud”.

And yet, after 35 years in the business, that unlikely journey is exactly what has brought James to this moment – stepping into retirement as the first-ever retiree from Gary Vaynerchuk’s VaynerX organisation.

Trained as an accountant (he estimates he took one marketing class his entire life), James began his career in finance, moving through senior roles across public companies and Wall Street. But he “possessed strong client instincts” – imperative in the client-driven world of advertising.

One of those clients was Omnicom agency Siegel+Gale. “I remember sitting in the office and just soaking in the atmosphere,” he says, speaking with LBB. “Even though I was there for an audit, I caught myself looking around and thinking, 'I really like this creative environment. I could see myself in a place like this someday.' That was the spark that eventually led me away from auditing and into this industry.”

Prior to joining Vayner in 2015, James held leadership roles at Saatchi & Saatchi and Interbrand. And while his eventual shift into advertising wasn’t necessarily driven by a love of ads, his reputation for making complex organisations work – combining operational rigour, financial discipline and an instinctive ability to spot the right people and solutions – proved pivotal.

“When I finally crossed over into this world, I never looked back,” he says. “It allowed me to tap into a different skillset, capitalise on my operational mindset, and ultimately deliver value to the agencies I worked for and the clients we served.”

Over the course of a decade at Vayner, James would play a central role in scaling the business, serving as chief integration officer and chief operating officer of VaynerMedia, as well as president of The Sasha Group and president of startup operations. Across each chapter, he helped guide Vayner’s evolution from a social-first shop into a growing global independent agency.

“It all clicked during my very first interview,” says James of his decision to join Vayner in those early days. “Gary shared his vision with crystal clarity. He looked at me and said, 'James, I want to build an independent, integrated, international company. Can you help me do that?'

“I didn’t have to think about it. I looked him in the eye and said, 'Yes. I can.' And we’ve been building toward that ever since.”

At Vayner, James became known within leadership for blending financial discipline with a people-first approach, without treating the two as opposing forces. So, how does that balance actually work in practice?

“It comes down to mindset,” he says. “I spend a lot of time educating the team on the idea that we are 'purposing to make profits’.”

That means being intentional. “Many agencies run on momentum and then look in the rearview mirror at the end of the year to ask, 'How did we do?' That’s too late. I practice people-first leadership by giving my team the financial tools to look forward, so they can control the outcome rather than just reacting to it.”

James’ approach is simple: don’t delegate tasks, facilitate solutions. By doing that, he says he removes “the fear”. Instead of hiding problems, the creative teams are more inclined to bring them to him so they can solve them together. “No spreadsheet can teach you how to manage the creative need for variety,” he says.

“The trick is providing freedom without chaos. I give them room to explore, but not total 'boxlessness’. Creativity actually thrives on having a few constraints – it gives them something to push against.”

It’s a philosophy that’s present in the moments that James looks back on with the most pride. “One of the decisions I’m most proud of is leading the launch of The Sasha Group with key leaders I’d worked with previously at VaynerMedia,” he says. “By starting with a team that already had deep trust and chemistry, we bypassed the usual startup growing pains.”

The Sasha Group was named after Gary’s father, Sasha, and is an homage to the roots of their family wine business. “Being trusted to launch this company was a huge responsibility, and I take great pride in the fact that we honored that trust by delivering results, consistently achieving year-over-year growth,” says James.

More broadly, James points to scale itself – and how carefully it was managed – as a defining achievement of his time at Vayner. “One challenge when it comes to scaling is ensuring you’re growing, and not swelling,” he says. “Both get you big, but one is healthy and one is not. I’m proud that we built the operational muscle to support our speed.”

When James first entered the world of advertising, he says the strategy was ‘one size fits all’ – one message used to reach a variety of audiences. Today, that strategy is no longer viable. “Effective advertising now requires a rigorous strategic approach,” he says. “We have to target specific cohorts and tailor the message to a wide swath of consumers.”

With that in mind, he advises fellow industry outsiders debating stepping into the advertising industry to bring their unique perspectives with them. “Because that difference is your competitive advantage,” he adds. “The industry needs outside voices to evolve.

He points to Vayner’s founder and leader as a prime example. “After all, Gary was a retailer and a wine connoisseur, not an ad executive. Now he is a leading voice in the advertising industry.”

In retirement, James will be keeping a toe or two in the corporate world with plans to launch his own in-home advisory firm. “After all, there are still people who want to hear what I have to say,” he jokes.

“Maybe [I’ll] write a book. I’ll always pick up the phone for the Vayner Family. I’ll help my friends and colleagues at [Vayner-incubated] vYve and reunite with some ex-Saatchi folks from London in their work with small businesses. I always enjoy time with my growing family and look forward to more of that as well.”

So, what does it feel like to be Vayner’s first-ever retiree?

“It feels incredible,” says James. “After 11 years, four titles, and five different roles, I truly feel a sense of 'Mission Accomplished’.

“But beyond my personal journey, it represents a milestone for the company. Having a retiree is a sign of VaynerX’s evolution.”

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