The Woman Who Broke the Code

THE SIL­I­CON VAL­LEY GEN­DER NAR­RA­TIVE IS FIRMLY EN­TRENCHED: WOMEN DON’T GET COM­PUTER SCI­ENCE DE­GREES AND DON’T START SUC­CESS­FUL TECH COM­PA­NIES. DON’T TELL THERESE TUCKER ANY OF THAT

Inc. (USA) - - FEATURES CONTENTS - By Maria As­pan

Sil­i­con Val­ley's gen­der nar­ra­tive was firmly en­trenched— un­til Black­Line’s Therese Tucker, one of the only fe­male founder-CEOs run­ning a pub­lic tech com­pany, changed it.

ONE EVENING IN MAY, a team of Gold­man Sachs bankers helped a founder-CEO raise some se­condary money for in­vestors in Black Line, a fast-grow­ing soft­ware com­pany now worth more than $1.5 bil­lion. Af­ter the deal priced, as they ush­ered the hoodie-clad founder and the be­suited CFO into an el­e­va­tor, the bankers ran into a se­nior Gold­man guy: “Hey, you should meet the CEO of Black Line. They’re rais­ing $115 mil­lion.” The ex­ec­u­tive looked right past Therese Tucker, in her black hoodie and flower-printed blue jeans and pas­tel-pink hair, and di­rected his praise to her male fi­nance chief: “Great job.” Tucker is laugh­ing about this a few min­utes later, hu­mor loud and in­fec­tious, ethe­real hair swing­ing along. It’s been a good year for Black­Line, a nine-time Inc. 5000 hon­oree that an­a­lysts credit with in­vent­ing a new mar­ket for ac­count­ing soft­ware. The Los An­ge­les com­pany, which had $123 mil­lion in 2016 rev­enue and went pub­lic a year ago, has seen its stock out­per­form buzzier re­cent tech IPOs, in­clud­ing Nu­tanix’s and Snap’s. So for Tucker, a blaz­ingly in­tel­li­gent and imp­ish 56-year-old, this

evening wasn’t the first time in her long ca­reer as a tech founder—or her rel­a­tively short one as a pub­lic com­pany CEO—that she’s been un­der­es­ti­mated. But such dis­missals barely give her pause.

“Why have a mod­est am­bi­tion?” she shrugs. “Be­cause then you ac­com­plish it, and it’s bor­ing.”

Tucker has rarely been bored over the past 17 years, as she’s faced vir­tu­ally ev­ery en­tre­pre­neur­ial ob­sta­cle. Af­ter cash­ing out her re­tire­ment sav­ings to fund her startup, she came per­ilously close to fail­ing with its first prod­uct, piv­oted her way out, and then spent sev­eral white-knuckle years try­ing to per­suade big cor­po­ra­tions to buy her tech­nol­ogy. De­ter­mined to be­come a sort of Sales­force for ac­coun­tants— drag­ging an­ti­quated busi­ness book­keep­ing from paper into the cloud—Tucker grit­ted her way through ev­ery dark pe­riod.

Even to­day, Black Line isn’t a house­hold name (un­less your house­hold con­tains an ac­coun­tant). But it does busi­ness with plenty of them: Coca- Cola, Un­der Ar­mour, United Air­lines, and eBay are all cus­tomers. Black Line was so early into the mar­ket that the prod­uct de­scrip­tion it coined, “con­tin­u­ous ac­count­ing,” is now used by es­tab­lished en­ter­prise-soft­ware gi­ants, in­clud­ing Black Line part­ner SAP. What the term ac­tu­ally means: Tucker’s soft­ware-as-a-ser­vice won’t crunch your num­bers, but it will pull in the data through pro­grams that do—let­ting you see ex­actly what’s af­fect­ing those num­bers, at any time and from any­where, rather than mak­ing you wait for your ac­coun­tant to email you the lat­est month’s Ex­cel spread­sheets. Black- Line sells this ser­vice mostly to com­pa­nies with more than $50 mil­lion in rev­enue, and counts al­most 2,000 cus­tomers. Ac­cord­ing to a Frost & Sul­li­van re­port it com­mis­sioned, Black Line’s po­ten­tial global mar­ket could be $20 bil­lion by next year.

“A lot of prod­uct founders don’t make the tran­si­tion to be­ing the CEO of a big­ger com­pany, but Therese has a knack for fig­ur­ing out when she needs to drill down and when she needs to run with things,” says Hol­lie Moore Haynes, who led Sil­ver Lake Sumeru’s ini­tial 2013 pri­vate equity in­vest­ment in Black Line and re­mains on its board. “She kept hit­ting num­bers—and she’s the heart of the com­pany.”

Tucker, in many ways, re­sem­bles a stereo­typ­i­cal tech founder, with her di­rect, some­times im­pa­tient ques­tions; her in­tense fo­cus on de­tails; and her small, clut­tered of­fice tucked be­hind her pro­gram­ming team. Ex­ter­nally, of course, she stands out: The IPO turned her into one of the only fe­male founder- CEOs run­ning a pub­lic tech com­pany.

While women formed the back­bone of the early tech in­dus­try (see “When Women Ruled Com­put­ing,” be­low), their ero­sion there is star­tlingly grim. The likes of Ap­ple, Face­book, and Google now em­ploy tech­ni­cal work forces that are more than 75 per­cent male. Among growth-minded fe­male founders, the num­bers are worse: While roughly 30 per­cent of all small busi­nesses are woman-owned, only 10 per­cent of the Inc. 500 fastest-grow­ing pri­vate com­pa­nies in Amer­ica have fe­male founders, and ac­cord­ing to Cata- lyst, only 5.2 per­cent of the S&P 500 have women in charge.

For those women who do make a ca­reer in Sil­i­con Val­ley, the past year has un­veiled plenty of ex­am­ples of the ram­pant misog­yny and sex­ism they must over­come. In Fe­bru­ary, engi­neer Su­san Fowler pub­lished a vivid ac­count of the ha­rass­ment she ex­pe­ri­enced at Uber, one that pre­ceded the ouster of its CEO, Travis Kalan­ick. In June, sev­eral women re­ported years of un­wel­come sex­ual ad­vances from high-pro­file ven­ture cap­i­tal­ists, in­clud­ing 500 Star­tups’ Dave McClure and Light­speed Ven­ture’s Justin Cald­beck (see page 75). And in Au­gust, Google fired a 28-yearold male engi­neer for a memo claim­ing that women are less bi­o­log­i­cally suited to com­puter pro­gram­ming than men.

“Tech is male-run,” says Tucker, who stud­ied com­puter pro­gram­ming in the early 1980s. “I kept think­ing, ‘I know this could be a great ca­reer, if I can just get through this pro­gram,’ but it was not wel­com­ing to­ward women.” Since then, she has faced all of the now-fa­mil­iar af­fronts, from the col­lege pro­fes­sors telling her that she was ex­pected to fail to grop­ing male bosses to in­vestors as­sum­ing that she couldn’t fi­nance her own com­pany with­out sup­port from a hus­band.

Yet Tucker, a farmer’s daugh­ter with a “no-bull­shit” rep­u­ta­tion (ac­cord­ing to se­rial entrepreneur and au­thor Sra­mana Mi­tra), has man­aged to defy these statis­tics. Now this founder, who nei­ther dwells on nor dis­misses the chal­lenges fac­ing women in tech, is keep­ing her fo­cus on what she can

di­rectly af­fect: con­tin­u­ing her com­pany’s decade-plus of fast growth.

“I still have these mas­sive goals. I just want to change how ac­count­ing works,” Tucker re­flects in late June, at her com­pany’s Wood­land Hills head­quar­ters. “I’ll be ready to re­tire once ev­ery­body does it my way.”

SEV­EN­TEEN YEARS AGO, a seed of that am­bi­tion is what started Black-Line. Di­vorced, par­ent­ing two small chil­dren, and burnt out af­ter leav­ing her job at soft­ware com­pany Sun Gard, Tucker de­cided to re­turn to what had made her happy—if broke— soon af­ter col­lege: start­ing her own pro­gram­ming busi­ness.

It’s not a very rad­i­cal choice for some­one who self-iden­ti­fies as an entrepreneur. Yet it made Tucker an out­lier: a woman who built a ca­reer, and a hard- core tech­nol­ogy busi­ness, at the very time that women in gen­eral were drop­ping out of the in­dus­try.

Many early com­puter pro­gram­mers were fe­male when Tucker was grow­ing up milk­ing cows in ru­ral Illi­nois, the youngest of four girls. She be­came the first in her fam­ily to go to col­lege, study­ing busi­ness and French—un­til she took an early Ap­ple pro­gram­ming class and fell in love. “It was like, ‘You’re kidding—peo­ple will pay me to ac­tu­ally sit and make a list of in­struc­tions for the com­puter to ex­e­cute? That’s su­per cool.’ ”

Still, she had to face down male pro­fes­sors telling her she wasn’t cut out for pro­gram­ming. For­tu­nately, as she de­scribes it, she had “an un­rea­son­able amount of con­fi­dence.” She grad­u­ated in De­cem­ber 1983—just as the per­cent­age of women earn­ing com­puter sci­ence de­grees peaked at 37 per­cent. (It now hov­ers around 18 per­cent.) Af­ter grad­u­at­ing, she found an en­gi­neer­ing job that would move her to Cal­i­for­nia, work­ing for Hughes Air­craft on sur­face-ship sonar fault de­tec­tion firmware. Then, in 1985, Tucker started her first com­pany, sell­ing her pro­gram­ming ser­vices to small busi­nesses. That even­tu­ally led to work cre­at­ing soft­ware for a mort­gage com­pany and then a pro­gram­ming job at a firm later pur­chased by Sun Gard, where she be­came CTO of its trea­sury sys­tems de­part­ment.

While start­ing her first busi­ness in the mid-’80s, Tucker met her fu­ture hus­band, then a Ma­rine and now a hos­pi­tal chap­lain, at a laun­dro­mat. They got mar­ried and had two chil­dren, a son and a daugh­ter; but by 2000, both con­sumed by their ca­reers and the de­mands of par­ent­ing, they had split up.

The di­vorce, co­in­cid­ing with her rest­less­ness at Sun Gard, ul­ti­mately gave Tucker the space she needed to take a gam­ble and set up her own com­pany. “My hus­band is very risk-averse. I put ev­ery­thing into this com­pany, and he never would have been com­fort­able with that,” she says. “It was like, my kids and my com­pany and that was it. Ab­so­lutely noth­ing else.”

Rather than try to raise money from ven­ture cap­i­tal­ists, Tucker cashed out her re­tire­ment ac­counts and her Sun Gard op­tions and took out a sec­ond mort­gage on her house. At 40, with more than 15 years of ex­pe­ri­ence pro­gram­ming for fi­nan­cial com­pa­nies, she had both the con­tacts and the pro­fes­sional sea­son­ing, yet she still had to prove her qual­i­fi­ca­tions. In meet­ings with early clients or po­ten­tial in­vestors, Tucker of­ten heard “re­marks like, ‘Oh, well, your hus­band’s sup­port­ing you, right?’ ” re­calls Char­lie Gaulke, a woman Tucker hired as Black Line’s fifth em­ployee and who is now vice pres­i­dent of devel­op­ment. “She did so much of it with her own fi­nan­cial back­ing, her own sheer will, and de­ter­mi­na­tion.”

Dur­ing those early years fight­ing for sur­vival, the com­pany ended up chang­ing ev­ery­thing from its core prod­uct to its name. In June 2001, Tucker dubbed her busi­ness Os­aba, Span­ish for “I was

dar­ing.” A few months later, the Septem­ber 11 ter­ror­ist at­tacks made any name sim­i­lar to “Osama” ra­dioac­tive.

There were big­ger prob­lems than nomen­cla­ture. Tucker’s first prod­uct was wealth man­age­ment soft­ware, a mar­ket dom­i­nated by bet­ter-es­tab­lished Thom­son Reuters. Within a few years, Tucker was run­ning out of cash to keep the lights on—un­til one day, an ex­ist­ing cus­tomer asked for help au­tomat­ing its ac­count rec­on­cil­i­a­tion process: “As a boot­strapped com­pany, if some­one will pay you to do some­thing, you say, ‘Hell, yeah,’ ” she ex­plains.

In that re­quest, Tucker rec­og­nized a big­ger op­por­tu­nity: to cre­ate soft­ware that would dig­i­tize what was still a very paper-bound mar­ket. Cor­po­rate ac­coun­tants at the time re­lied heav­ily on three-ring binders. What if Tucker’s pro­gram­mers could take all of that data, put it on a server some­where, and let any­one in your com­pany look at it, at any time of day or night? What if you could see the real-time ef­fect that for­eign ex­change rates were hav­ing on your fi­nances? What if Tucker could cre­ate a mar­ket for sim­pli­fy­ing and ac­cess­ing your busi­ness data?

“What she went af­ter is an area of soft­ware that’s his­tor­i­cally not been well served,” says Terry Till­man, an equity an­a­lyst for Sun Trust Robin­son Humphrey. Black Line “was first to mar­ket with a cou­ple of ma­jor prod­ucts to cre­ate au­to­ma­tion in an area where there hadn’t been au­to­ma­tion … and now I think they’re reap­ing the ben­e­fits of be­ing an early innovator.”

The com­pany—rechris­tened Black- Line—started its pivot in 2004. But Tucker still had a few tense years be­fore her bet paid off. Among the most painful set­backs was her sales chief’s leav­ing to start a ri­val prod­uct, which was sold to what be­came Trin­tech, now one of Black Line’s big com­peti­tors. To­day, Tucker claims to be grate­ful for the de­fec­tion: “When you’re a ven­dor, you need a com­peti­tor” to le­git­imize the prod­uct.

But you also need re­lent­less cold­call­ing. “I called a girl­friend from Sun Gard and said, ‘My com­pany is fail­ing and I can’t pay you much. Come work for me?’ ” Tucker says. The friend did—and landed Costco and eBay as two of Black Line’s first big-name clients.

Mean­while, Tucker was feel­ing suc­cess­ful enough to re­turn some fo­cus to her per­sonal life. She and her ex-hus­band, Brian, had re­mained po­lite co-par­ents dur­ing her startup’s most un­cer­tain years. Even­tu­ally, the exes went from co­or­di­nat­ing their kids’ sched­ules to laugh­ing about their lat­est dat­ing hor­ror sto­ries, and “we got to be best friends again,” says Tucker. She re­mar­ried Brian in 2005; their chil­dren were best man and maid of honor at the sec­ond wed­ding. (Their son, Isaac, is also now VP of prod­uct at Black Line.)

Within a cou­ple of years, Tucker made another cru­cial de­ci­sion: em­brac­ing the cloud-based soft­ware model pi­o­neered by the likes of Sales­force. That helped Black Line ap­peal to smaller cus­tomers, for whom an in­ter­nal server in­stal­la­tion was too ex­pen­sive. Tucker’s com­pany gained a rep­u­ta­tion among clients for stel­lar cus­tomer ser­vice. Rev­enue con­tin­ued to grow, by about 50 per­cent ev­ery year; Black Line landed on the Inc. 5000 list of the fastest­grow­ing pri­vate com­pa­nies in Amer­ica nine con­sec­u­tive times, from 2008 to 2016, when it went pub­lic.

The road to the IPO started in 2013, when Tucker was con­sid­er­ing re­tire­ment. She went look­ing for a buyer and wound up feel­ing rein­vig­o­rated when pri­vate equity firm Sil­ver Lake de­cided to take a bet on her and took a ma­jor­ity in­vest­ment. (Tucker kept what is now a roughly 12 per­cent stake.)

“It didn’t mat­ter to me that she hadn’t done this be­fore,” says Haynes, who’s since started her own pri­vate equity firm, Lu­mi­nate Cap­i­tal. “We just want com­pa­nies that have re­ally great prod­ucts.”

LAST DE­CEM­BER, af­ter her com­pany’s IPO raised $152 mil­lion, Tucker cel­e­brated by buy­ing her­self a Tesla. She wound up with a tech founder’s ul­ti­mate first­world prob­lem: The car was a dud. The cruise con­trol wouldn’t kick on, the mu­sic-stream­ing ser­vice kept crash­ing, the air con­di­tioner stalled out. And when Tucker quickly re­turned it, the Tesla deal­er­ship kept her $2,500 de­posit.

That’s chump change for a woman worth some $180 mil­lion on paper. But Tucker, for whom cus­tomer ser­vice is a mantra, says she wanted to prove a point: She hired a lawyer and paid him $3,000 in fees to sue the deal­er­ship, which ul­ti­mately set­tled the law­suit this sum­mer. Tucker got her de­posit back—

and got to cri­tique one of Sil­i­con Val­ley’s fa­vorite sta­tus sym­bols—for only $500. “It was worth ev­ery penny,” she says. “This is sup­posed to be the amaz­ing car of the fu­ture … and the tech­nol­ogy was not as ad­vanced as my three-year-old Dodge Du­rango’s.” (A Tesla spokesper­son says that Tucker’s “de­mands and com­plaints were very un­rea­son­able” and the next buyer of the re­turned ve­hi­cle “has had zero com­plaints.”)

Still, Tucker is thought­ful about her provo­ca­tions: She got Sil­ver Lake’s sig­noff be­fore fil­ing the law­suit. She also got her board’s per­mis­sion, “in a low-key way,” be­fore dy­ing her hair pink.

To be a woman at the helm of a com­pany is to be con­stantly, tire­somely, judged by your ap­pear­ance. “When you have gray hair, you could die on the floor and no­body would no­tice,” Tucker says. “Mid­dle-aged, gray-haired woman—who cares?” So three years ago, she de­cided to re­claim that sig­ni­fier.

It hap­pened dur­ing what Tucker calls a “game of chicken” with Black-Line’s mar­ket­ing de­part­ment. The pub­li­cists begged the CEO to film a staid cor­po­rate video, one that would re­quire her to be “this older woman, with a bun and a suit and a scarf, go­ing ‘blah blah blah,’ ” she re­calls. Fi­nally, she agreed—but only if, she added, “‘I dye my hair pink.’ It just popped out.”

She booked an ap­point­ment at a Bev­erly Hills sa­lon, and hasn’t looked back. “It has changed how I in­ter­act with the world at large,” she re­flects. “Now it’s al­most like a weird trade­mark.”

That car­toon­ishly fem­i­nine hair is also a bit of an open chal­lenge to tech’s boys’ club, and all who pre­sume that a tech­ni­cal founder- CEO of a soft­ware com­pany would be male. It’s another de­lib­er­ate provo­ca­tion—es­pe­cially this year.

Dur­ing in­ter­views over the past sev­eral months, Tucker ex­pressed both frus­tra­tion and fa­mil­iar­ity with the re­lent­lessly de­press­ing head­lines out of Sil­i­con Val­ley. Early in her ca­reer, when faced with sim­i­lar ha­rass­ment, she chose the path of prac­ti­cal­ity: “You avoided cer­tain peo­ple, you made sure there was a ta­ble be­tween you and so-and-so, and you just dealt with it,” she re­calls.

One of her fe­male co-work­ers, who did re­port a grop­ing boss, be­came “a pariah. Her ca­reer dead-ended,” Tucker says. But “my ca­reer suc­ceeded. Noth­ing ever re­ally ter­ri­ble hap­pened. It was just kind of gross and an­noy­ing and aw­ful.”

That’s not a crit­i­cism of any of the women who have re­cently come for­ward. “If you don’t ever say any­thing, how do you get change to hap­pen?” re­flects Tucker. “I still don’t know if putting up and shut­ting up was the right thing to do.”

As she and other women founders have dis­cov­ered, of­ten it’s eas­i­est to avoid those be­hav­iors by start­ing (and fi­nanc­ing) your own thing—one where “you make sure that your en­vi­ron­ment does not have any bias or dis­crim­i­na­tion built in,” Tucker says.

Black Line would not dis­close its racial or gen­der di­ver­sity statis­tics, and Tucker says she’s found it dif­fi­cult to re­cruit as many qual­i­fied fe­male pro­gram­mers as she would like. Two of her six top lieu­tenants are fe­male, slightly bet­ter than the per­cent­age of se­nior- level ex­ec­u­tive po­si­tions at S&P 500 “in­for­ma­tion” com­pa­nies. Many days at 6 a.m., you can find Tucker and her top women ex­ec­u­tives at the gym across the street, lift­ing weights with a trainer.

But fight­ing for some big­ger ideal of gen­der equity is an over­whelm­ing task, and one that Tucker—or any founder— doesn’t have time for. She is still work­ing through the grow­ing pains that all high­growth star­tups ex­pe­ri­ence. The com­pany, which had 600 em­ploy­ees when it went pub­lic a year ago, has more than 700 now. There’s been some turnover among top ex­ec­u­tives, in­clud­ing the chief tech­nol­ogy of­fi­cer, a not-in­signif­i­cant role for a tech com­pany. The firm is still not prof­itable, and the de­mands of pub­lic in­vestors are only mount­ing. Now that Tucker has opened up a lu­cra­tive mar­ket, might bet­ter-funded, big­ger play­ers even­tu­ally push her out of it?

Not if she can help it. On a sun­drenched sum­mer day in June, Black-Line’s chief rev­enue of­fi­cer, Chris Mur­phy, swings by Tucker’s of­fice, which is dec­o­rated with a re­li­gious print op­pos­ing the death penalty. Mur­phy wants to talk num­bers, but first gets sucked into a con­ver­sa­tion about pol­i­tics, re­li­gion, and how to help the home­less pop­u­la­tion in Los An­ge­les. Which brings the dis­cus­sion back around to Black Line’s am­bi­tious goals, and how quickly its founder wants to achieve them. “You’re not al­ways easy to work for, Therese,” Mur­phy half-teases his boss.

Tucker grins back, un­apolo­get­i­cally in charge: “You’d be so bored if I were easy.”

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