The folks at National Discount Brokers pride themselves as innovators. In 1994, the company launched the first flat-fee brokerage service on the Internet-a move since mimicked by dozens of rivals. Now they're trolling investor waters for upscale female clients via an alliance with Women's Connection Online (WCO).

Chairman and CEO Dennis Marino hopes the marketing relationship with the popular Web site will give NDB an inside track on one of the fastest- growing segments in the fiercely competitive world of on-line trading.

Female professionals "represent a really vibrant market that has not been recognized in any meaningful sense by the brokerage community," Marino says. "We saw this alliance as a very natural strategic fit for what we're trying to accomplish."

Let's be clear: These aren't the Beardstown Ladies we're talking about (although nearly two-thirds of investment club members are women). Nor are they mothers concerned with parenting issues or recent female college grads looking for jobs.

NDB's target is a new breed of wealthy, Internet-savvy women who increasingly want to manage their own investments, but lack some of the basic knowledge they need to get started and often feel slighted by financial firms.

In a 1997 study commissioned by mutual fund giant OppenheimerFunds, Inc., 38 percent of women said they were "not very knowledgeable" about investing, while 58 percent said brokers and financial planners treated women with less respect than men.

"What I hear a lot is, 'I'm making the decisions in the household, but financial services firms aren't showing me any respect'," says Susan Williams Defife, CEO of WCO. "It's incredibly frustrating for many women."

These things are slowly changing. The OppenheimerFunds study found that 64 percent of women are more interested in investing today than five years ago. Thirty-six percent said they had read something on investing in the previous month.

For Marino's marketing money, there's no place better to pursue this segment than WCO. The four-year-old enterprise seeks to capture the on-line essence, if not the pocketbooks, of computer-literate female professionals and business owners with a menu of news, bulletin boards and practical tools aimed at empowering women to make their own decisions. "We're not just a content site. We're creating a community where women can interact with each other and guest experts," Defife says. "That's the glue that holds everything together."

The alliance, touted as the first between an on-line brokerage and a women-oriented Web site, is straightforward in structure. NDB provides custom-made educational pages to the WCO site, and helps arrange for financial experts to appear in WCO's personal finance chat rooms.

In exchange, NDB gets a link to its own trading site and the ability to leverage WCO's reputation with professional women who frequent the site. "Women can say, 'This is coming from someone I know and trust already, so I'm a bit more receptive to the message'," says Paul Miller, managing director of marketing for NDB. "Everything in financial services marketing- especially with remote relationships like ours-is about developing trust. After all, it's their money."

NDB also pays an unspecified fee to WCO, which observers say is most likely based on the number of new accounts the relationship generates. The site-www.womenconnect.com-generated about 2.5 million hits in March, up sharply from just 80,000 last May.

There's no denying the appeal of professional women for on-line investment services. According to Defife, women account for 47 percent of Americans with assets of at least $500,000, and hold 48 percent of all professional jobs.

Yet they are much more conservative than men, and often timid, when it comes to investing. While the OppenheimerFunds study found that 62 percent of women in married households manage the checkbook, only 15 percent manage investments. They also are far more likely to put money in a savings account than in stocks or bonds.

To Defife, it's a matter of education. "Women want to invest their money, and they are willing to take risks when they feel informed. But as a group they are maybe a little unsure about what to do and how to do it," she explains.

WCO, she adds, wants to "partner with companies that are willing to link education with execution, and empower our audience to make their own decisions. NDB fit that profile."

Indeed, it was WCO, not NDB, that initiated the relationship. Last year, NDB launched an advertising campaign that featured male and female actors discussing investments. Tag line: "For those who have a passion for trading." Defife saw the ads, did some additional research and concluded that NDB had the commitment her site's visitors demanded. NDB took the bait, and less than three months later a deal was struck.

For NDB, which presently manages about $5 billion in assets for 115,000 customers, the effort marks the first in what officials expect will be a growing array of affinity marketing relationships, as it seeks to subsegment the mass market into easier-to-digest bites.

The number of on-line trading accounts is projected to explode to over 12 million by 2002, from about 3 million today. As many as half of those new customers could be women, NDB officials say.

The trick for NDB is how to take advantage of that growth," says Miller, who arrived at NDB in February from Citibank's credit card unit, where he managed affinity marketing. "You can't reach every single American. You need to find more targeted audiences, where you can craft meaningful messages."

NDB, with a flat $14.75 trading commission and goodies like free research and real-time quotes, has positioned itself between high-price, high-service firms like Charles Schwab & Co., and lower cost operators such as AmeriTrade.

Marino asserts that affinity relationships are a lower cost way to acquire customers. "We think it makes sense to wrap ourselves in third- party endorsements, and have somebody who has established a level of loyalty and trust with their existing customer base introduce NDB to them."

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