After 25 years as the head of EMILY’s List, Ellen Malcolm’s last month on the job was perhaps her worst.

Attorney General Martha Coakley’s (D) stunning special election loss in overwhelmingly Democratic Massachusetts was far from the crescendo Malcolm had hoped for as she transitions from being president to chairwoman of the board at the abortion-rights group.

Still, in an interview just days after the Massachusetts race, Malcolm reflected on the many highs that have offset the lows during her career as president of the pre-eminent women’s group in politics, which she famously founded in her basement in 1985.

“I think the low point was this week,— Malcolm said with a chuckle when asked about her tenure. “The high points? Oh my gosh, we’ve had so many hard-fought victories that we’re so proud of. Obviously, the year of the woman in 1992 was historic.—

But as Malcolm gets set to hand the reins of the organization over to seasoned operative Stephanie Schriock, the challenge of bridging the generational divide between EMILY’s List’s female donors and voters has never been more obvious.

Some Mass. Regrets

EMILY’s List had a banner year in 2008, when the group helped elect 12 new female House Members and two new female U.S. Senators, and all of their endorsed incumbents won re-election.

But in the early weeks of 2010, Massachusetts seemed to overshadow much of that success.

“It’s all hindsight,— Malcolm said in a wide-ranging interview three days after Coakley’s 5-point loss to Sen.-elect Scott Brown (R) on Jan. 19. “When there was a 19-point lead on Dec. 22, did we think it was going be in free fall in the second week of January? Absolutely not. And nobody else did, either. And anybody who says it is blowing smoke.—

She was quick to add: “When we did see the problem, we were the first off the mark trying to solve it. We were the first independent group on our side to go up with a media buy.—

Even with the blame game among Democratic leaders and their allies still ricocheting in the aftermath of the loss, Malcolm appeared relaxed as she approached her last week in her 11th-floor corner office. There’s a photo of her grandson with then-Sen. Barack Obama (D-Ill.) on her desk, which she confessed she hid during the 2008 White House race until the EMILY’s List-backed candidate, Hillary Rodham Clinton, ended her campaign.

At close to 6 feet tall, Malcolm is somewhat imposing, both physically and in personality.

A self-described professional marketer, she has been known for her entrepreneurial style at EMILY’s List. In many different words, colleagues have described her as a pragmatic businesswoman who has expanded EMILY’s List — the name is an acronym for Early Money Is Like Yeast — to include a variety of programs and adapted the organization beyond just a fundraising powerhouse to include strategic advice for candidates.

“She invented EMILY’s List, she went around the country and she marketed the hell out of it,— said Ann Liston, a Democratic media consultant and former EMILY’s List employee.

The Gold Standard

It’s hard to find a campaign or a candidate who could utter a single complaint about EMILY’s List. After all, the organization swoops in — hopefully sooner rather than later — and bundles cash for abortion-rights women candidates. But over time, the organization has stepped up its role in advising campaigns on strategy.

“A lot of the function is general consultants without getting paid,— said Julia Piscitelli, a Democratic strategist who has worked with several candidates endorsed by EMILY’s List.

Some candidates report fundraising numbers to EMILY’s List on a daily or weekly basis, almost as frequently as they report their fundraising progress to the House and Senate campaign committees. One endorsed candidate recalled that an EMILY’s List finance director would sit in during her call time and give suggestions as she dialed for dollars.

Rep. Niki Tsongas (D-Mass.) received an EMILY’s List endorsement early on in a five-way primary, where she was one of two women. Even though her husband, the late Sen. Paul Tsongas (D-Mass.), was a seasoned politician, Tsongas was a first-time candidate when she ran in the 2007 special election. As part of her endorsement, Tsongas received debate training from EMILY’s List early on.

“I’d never participated in debates, and there was much I had to learn, and they were helpful with that,— Tsongas said in a recent phone interview.

Of all the services that EMILY’s List provides candidates, many campaign managers and party officials hail their staffing support. As one of its many services, EMILY’s List provides training for young, inexperienced future staffers and circulates their résumés to campaigns. Some top EMILY’s List alumni have risen to high ranks in national campaigns and politics: Rep. Rosa DeLauro (D-Conn.), Secretary of Commerce Chief of Staff Ellen Moran and Sen. John Kerry’s (D-Mass.) presidential campaign manager, Mary Beth Cahill, all served as executive director of the organization.

“Their campaign training is really the gold standard so far,— Piscitelli said. “That’s been consistent for a while.—

However, many operatives have grumbled that often EMILY’s List focuses too much on abortion and women’s issues when strategizing with candidates. While a trademark issue with their donors, operatives say it’s not always the most politically advantageous point in many races.

One party official commented that EMILY’s List perhaps does not always appreciate how the abortion issue is received across the spectrum of House districts as well as they could.

“When you take choice out of it, some of their [independent expenditures] are very strategically run and some of their mail is very good and helpful,— said one Democratic party official. “I think that’s why the party committees have been so successful these past two years. There are different ways to do it. You have to tailor a similar message, you have to tailor a similar frame to a different district.—

Passing the Baton

A quarter-century after Malcolm started EMILY’s List, the organization’s membership has grown to more than 100,000 — according to a group official — and they donated $43 million to candidates in 2008.

But like many political groups and especially progressive organizations, fundraising has become more difficult as the economy sagged. Many organizations, including EMILY’s List, are largely supported by an aging fundraising base that has diminished means. Additionally, national Democratic donors were fatigued at the end of the 2008 presidential campaign.

“We’re not in as good of shape as we were, but we’re doing fine,— Malcolm said. “We haven’t laid anybody off because of the economy, which I’m very proud of. We’ve had, as we do every election cycle, people who have moved on and we haven’t filled those jobs … but it’s been a tough environment, no question.—

What’s more, money isn’t going as far as it used to in politics and campaigns. EMILY’s List could make a much bigger impact in House races in the 1990s, when a campaign only needed to raise upward of $1 million to be competitive. With political campaigns and outside groups spending $3 million or more on a competitive House race, it’s harder for third-party organizations to really pack a financial punch.

“The popular perception is that EMILY’s List can throw money at you,— said one 2006 campaign manager for an EMILY’s List candidate. “But at the end of the day, it wasn’t even 10 percent of our haul. But in terms of political strategy, advice and staff training, they were great.—

Although EMILY’s List keeps mum on the demographics of its donor base, several sources described its core base as women who heeded the call during Supreme Court Justice Clarence Thomas’ sexual harassment hearings on Capitol Hill or witnessed the “Year of the Woman— in 1992.

In contrast, Liston points out that many female donors coming of age now philosophically see reproductive choice as a given right instead of something for which they personally fought. She said the types of fundraising activities that made EMILY’s List so successful in its early years, such as coffees and dinners, are not as popular with donors.

“Fundraising is changing and much of that is happening at the Internet, and much less of it is event-driven,— Liston said. “How does an organization that ended up being event-driven use these new techniques and networks?—

As Malcolm, 62, is the first to point out, the generational gap between donors in the Democratic Party is reflected in the passing of the baton to her successor, Schriock. A fundraiser for former Democratic National Committee Chairman Howard Dean and the well-respected lead operative on two winning Senate campaigns, the 36-year-old Schriock has firm roots in the new generation of female operatives.

“I think Stephanie is going to be a very exciting addition to the EMILY’s List mix because I think she understands the way younger women communicate,— Malcolm said. “She did Dean’s fundraising. She used the Internet a lot in [Minnesota Democratic Sen. Al] Franken’s campaign. She has the same life experience as a lot of women that we’re trying to reach out to.—