Amy Webber stays in for the long haul

For all the talk of job-hopping one’s way to the top, continually trading loyalty for a better title, it’s worth noting that sometimes sticking around and displaying one’s skills pays off. And handsomely, too.

Just ask Cambridge Investment Group CEO Amy Webber.

Webber was hired as Cambridge’s 22nd associate in 1998 and rose up the ranks until she was named CEO in 2016, succeeding founder Eric Schwartz. Over those nearly three decades in the same old place, she’s seen Cambridge grow into an industry powerhouse most recently boasting $267 billion in assets under advisement and more than 4,100 producing financial advisors nationwide.

To be clear, she’s done far more than simply watch Cambridge snowball over that time. She’s helped lead the charge.  

“What has kept me here is the combination of independence, entrepreneurship, and a deeply people-centered culture. Cambridge has always believed advisors should have the freedom to serve clients in the way that best fits their business, while also having the support of a strong, values-driven firm behind them,” Webber says.

Adds Webber: “That has always been a natural fit for me because I care deeply about building something durable – a firm that can grow, evolve, and still do the right thing, even when no one is looking.”

CAMBRIDGE THEN AND NOW

The size and scale of Cambridge may have changed since Webber started (and Bill Clinton was president, for the record), but she maintains that the core of the firm has remained both sound and consistent. For her, that means employees staying focused on supporting advisors as both partners and clients, preserving choice, and creating a culture where advisors and associates feel they are part of something bigger than themselves.

“That is only possible because of our long-standing commitment to organizational longevity through internal control,” Webber says.

What has changed significantly in Webber’s view is the complexity of the overall business. The regulatory environment, cybersecurity and fraud risks, technology and platform expectations, client needs, and the competitive landscape are all far more sophisticated than they were in 1998. As a result, she’s pushed the Cambridge team to become more disciplined, efficient, and continuously innovative.

Put simply: the tools, infrastructure, and scale may have evolved, but Webber’s commitment to independence, internal control, service that earns unwavering client loyalty, and long-term partnership has remained the same.

And when Cambridge finally crossed the $2 billion annual revenue mark for the first time last year, it provided Webber with a clear confirmation that “the model works.” Or, as Webber puts it, that Cambridge’s advisors are growing and thriving, and that the investments they have made in strengthening relationships, elevating service, building flexible technology, supporting and developing their people, and enhancing their platform capabilities are creating real momentum.

“Most of all, though, I felt gratitude. I am deeply grateful for the trust and confidence of our advisors, the commitment of our associates, and the foundation Eric and so many others worked so hard to build,” Webber says.

A BRAVE NEW M&A WORLD

Cambridge has not only been building on its foundation under Webber’s leadership but it has also been buying. Yes, like many of its competitors, Cambridge is also a major participant in the private equity-fueled M&A battles taking place in the wealth management arena.  

Cambridge acquired Georgia-based Dempsey Lord Smith last year, adding roughly 75 financial professionals. It also brought over Ameriflex Group, which was affiliated with Osaic, representing $11.9 billion in client assets and 129 advisors.

“What differentiates us in this space is how we apply our core value of flexibility to every opportunity. We understand that no two firms, advisors, or succession plans are exactly alike. Our goal is not simply to complete a transaction – it is to create long-term alignment that supports advisors, their clients, and the long-term health of the business,” Webber says.

She adds that M&A at Cambridge is not limited to transactions at the corporate level. Equally important to her is the work they do supporting succession and acquisition opportunities between advisors, or between advisors and one of its Office of Supervisory Jurisdiction business executives.

Last year, Cambridge supported nearly 180 succession and acquisition transactions across its network, in addition to executing eight transactions directly with Cambridge representing more than $20.6 billion in invested or acquired assets under advisement. In six of those transactions, Cambridge established 100 percent ownership.

Still, Webber is quick to concede that private equity has radically changed the competitive landscape, particularly as more private equity-backed firms have entered the independent and mid-sized firm space.

“There is significantly more capital competing for quality businesses, which has driven higher valuations across the industry. Recent industry reporting showed record levels of RIA M&A activity in 2025, and while valuations continue to rise for high-quality firms, we believe the highest price is not always the best outcome,” Webber says.

ORGANIC AND AI GROWTH

Despite this heightened M&A environment, Webber is quick to point out that organic growth remains a major focus for Cambridge. She notes that a firm Cambridge’s size must rely heavily on organic growth to create meaningful enterprise value over time. That means supporting their existing advisors as they continue to grow and scale their businesses through deeper practice management support, more effective lead generation, succession and continuity planning, family office capabilities, and more specialized engagement strategies.

And, of course, better technology. As in AI. The question is, How does Webber expect AI to impact the associate and advisor experience over time?  

“Roles will change. Skill sets will continue to evolve. But we believe the strongest model is human associates and digital capabilities working together. At the same time, I am not naive about the risks. AI brings both known and unknown challenges, and firms must approach implementation thoughtfully and responsibly with proper due diligence and a clear understanding of return on investment,” Webber says.

Her advice to firms is to explore and implement AI responsibly, but with urgency.

“As I have shared with our teams, we cannot allow fear to impede progress,” Webber says.

SUCCESS NOT SUCCESSION

With all the talk about succession planning in the financial industry, the questions regarding Webber’s future at Cambridge naturally arise. Seriously, she has been with the firm since Bill Clinton was impeached (once again, for the record).

“I am here for the long haul. I love what I do and truly enjoy the people I am fortunate enough to work with. Leaders, particularly at the highest levels, can sometimes stay in their roles beyond the point where they are contributing at the level they once did. I spend a significant amount of time making sure I am focused on where I can provide the highest and best value for the greater good of Cambridge,” Webber says.

Going forward into the next – however many – decades, Webber says her focus is on making sure Cambridge is built to last well beyond any one person, including herself. That means recruiting and developing leaders, and team members overall, who are fully aligned with Cambridge’s culture and values.

I do not view succession as a single event. I view it as an ongoing responsibility. One of the most important jobs of a CEO is to make sure the organization is stronger, more resilient, and better prepared for the future than it was when you stepped into the role,” Webber says.