Deborah Montaperto spent more than 20 years in a variety of investment banking roles at Dean Witter and Citigroup and its predecessor firms — and she loved it. Then, two years ago, she took a big leap, becoming a senior partner of the Polk Group, a wealth-management practice with Morgan Stanley Private Wealth Management. The risky move meant switching from a more-corporate culture to an entrepreneurial one. But, for Montaperto, it’s been a highly successful choice. “I’m now running my own business, in effect, and it’s very gratifying,” she says.

First Years in Financial Services

Montaperto didn’t start out bound for Wall Street. She graduated from college with a dual-degree in social sciences and art history and went on to get her M.A. in Art History from the Villa Schifanoia in Florence, Italy. Then she moved to New York, managed an art gallery briefly, and got an administrative job at what was then Dean Witter. She was quickly promoted and moved into an investment banking role.

When she gave birth to her second child in 1991 she took a couple of years off. Then, she got an offer from Dean Witter to work in a group that screened potential transactions for the investment bank. She took the job and went back to Wall Street. After that, she joined what was then Smith Barney to build out the business development group. It was an investment banking role in which she looked for transactions from non-traditional sources. In 2006, she was promoted to Managing Director in Citigroup’s Investment Bank. Her role was to build a platform aimed at cross-marketing different services for investment banking clients.

Moving to Wealth Management

But after that effort was disbanded, Montaperto had to decide what direction to take next. The platform had been a joint venture between Citigroup’s investment bank and private wealth management arm. Through that work, she had met many of the most successful wealth managers at the Firm. Why not sign on with one of those practices? She had offers to join four teams and chose the Polk Group.

It was a great opportunity—and a big change. For one thing, Montaperto had to build her book from scratch. Her role at the team was to be a rainmaker and then hand the servicing of those people to her team members. Her skill-set was in business generation. To that end, she made a plan, with a list of the many people she’d worked with throughout her career, what kind of business to go after and how to make it happen. Her timing was good. After the market upheaval of 2008, many disillusioned clients of wealth managers at other firms were looking to make a change.

In her first year, she opened 45 accounts, bringing in close to $300 million in assets. More recently, she won a $1 billion account from a contact she’d made in her investment banking days.

Then, there was the cultural change. For Montaperto, it was significant—going from a highly structured environment in which, she says “All things are taken care of for you,” to, in effect, running her own business. “I could have chosen a more traditional corporate lifestyle, what I had done for many years,” she says. “But I decided to take a risk and make a switch.”

The biggest surprise for Montaperto, was what it meant for her relationships with colleagues. “Your livelihood depends on your partners,” she says. As a result, because team members rely on each other for their success, according to Montaperto, the result is a particularly deep bond.

According to Montaperto, her profession is also well suited to women. “This is a relationship business,” she says. “And women are great at building and maintaining client relationships.”

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