Michaele James, CSAA

Digital Insurance - - CONTENTS - By Elliot M. Kass

Michaele James grew up in Colorado with a strong in­ter­est in math and a desire to build things — per­haps un­sur­pris­ing, com­ing from a fam­ily of ac­coun­tants and en­gi­neers.

Orig­i­nally, she en­rolled in the Uni­ver­sity of Den­ver think­ing she would be­come a civil en­gi­neer, and when she grad­u­ated it was with a de­gree in quan­ti­ta­tive meth­ods and statis­tics. But it was her first job that re­ally set the course for her fu­ture ca­reer in com­puter science.

“I went to in­ter­view with Elec­tronic Data Sys­tems, and that was kind of like sign­ing up for the mil­i­tary,” she re­calls. Founded by Ross Perot, a for­mer naval of­fi­cer and fu­ture bil­lion­aire and pres­i­den­tial can­di­date, EDS pro­vided James with “phe­nom­e­nal” train­ing.

“It was my first foray into IT,” she says, “and I haven’t looked back since.”

As CSAA’s CTO, James is charged with up­grad­ing its ap­pli­ca­tions — in­clud­ing nine legacy sys­tems. She says when she orig­i­nally ac­cepted the job, she didn’t re­al­ize that the in­dus­try-wide suc­cess rate for pol­icy-ad­min­is­tra­tion re­place­ments was dis­mal. “I had ab­so­lutely no idea there was a 60% fail­ure rate,” she laughs.

De­fy­ing the odds, James and her team suc­cess­fully moved four of the nine sys­tems onto CSAA’s new dig­i­tal plat­form on time and on bud­get. They also con­sol­i­dated sev­eral dif­fer­ent claims sys­tems into one. The re­main­ing five PAS up­grades are sched­uled to be com­pleted by 2020.

“There we were in the heart of Sil­i­con Val­ley,” James re­counts, “and we had ab­so­lutely no web pres­ence,” along with a great many other tech­no­log­i­cal deficits. How­ever, her IT acu­men forged over a long ca­reer has helped her pull off the dif­fi­cult task.

Go­ing back to her ex­pe­ri­ence at EDS, James has tack­led chal­lenges re­lated to her gen­der with grace and suc­cess.

“I have a bias for ac­tion and some­times can be a lit­tle pushy in mak­ing things hap­pen,” she says, not­ing that “peo­ple aren’t al­ways used to hav­ing a se­nior woman in IT.”


A stand­ing pol­icy at EDS was to trans­fer new re­cruits to an un­fa­mil­iar part of the coun­try. In James’ case, that meant leav­ing Den­ver to work out of an of­fice in Colum­bus, Ohio, that was over­whelm­ingly male. About eight months in, she was ap­proached by a man­ager in the data cen­ter, who told her that she was fre­quently the topic of con­ver­sa­tion at his man­age­ment meet­ings.

“There I was,” she says, “a 22-yearold fresh out of col­lege, and I felt like some­body had just punched me in the stom­ach.” When she asked him why, he told her, “’You’re not sup­posed to wear col­ored ny­lons and open-toed shoes. You’re not sup­posed to paint your nails.’

“Well,” she re­mem­bers, “I just looked at him and thought, ‘No, I don’t know any of that. And if none of you have the guts to tell me, then I’m just go­ing to go on my merry way!’”

But it was also a huge les­son: “If there’s an is­sue about some­one and they don’t know it, then shame on man­age­ment for not shar­ing it with them. I feel that way to­day, with my staff, and I ex­pect the same from my man­ager.”

James’ pro­file grew over her ca­reer to the point where Steve O’Con­nor, a for­mer col­league who was the CIO at CSAA, said he wanted her to help over­haul the com­pany’s legacy en­vi­ron­ment. She at­tributes her suc­cess to learn­ing how to bal­ance her bi­ases to ac­tion with the need to lis­ten to em­ploy­ees’ pain points and find the right way to di­rect projects— cru­cial with a team of more than 300.

“I take the long view, and I love fram­ing prob­lems in terms of the mar­ket and the com­pany’s over­all ob­jec­tives.” Paus­ing, she adds, “I ask a lot of ques­tions, and I try to hear. I want peo­ple to feel like they’re heard and that they are hav­ing an im­pact and con­tribut­ing to what we’re try­ing to achieve.”

Michaele James CTO, CSAA In­sur­ance Group

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