CHAPTER 1

The Über Product Manager

T
here was nothing particularly distinctive about the dozen
or so low-rise buildings in Seattle’s burgeoning South Lake
Union district that Amazon moved into over the course of
2010. They were architecturally ordinary and, on the insistence
of its CEO, bore no obvious signage indicating the presence of an
iconic internet company with almost $35 billion in annual sales. Jeff
Bezos had instructed colleagues that nothing good could come from
that kind of obvious self-aggrandizement, noting that people who
had business with the company would already know where it was
located.
While the offices clustered around the intersection of Terry Ave-
nue North and Harrison Street were largely anonymous, inside they
bore all the distinguishing marks of a unique and idiosyncratic corpo-
rate culture. Employees wore color-coded badges around their necks
signifying their seniority at the company (blue for those with up to
five years of tenure, yellow for up to ten, red for up to fifteen), and the
offices and elevators were decorated with posters delineating Bezos’s
fourteen sacrosanct leadership principles.
Within these walls ranged Bezos himself, forty-six years old at
the time, carrying himself in such a way as to always exemplify Ama-
zon’s unique operating ideology. The CEO, for example, went to great
lengths to illustrate Amazon’s principle #10, “frugality”: Accomplish

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 22 AMAZON UNBOUND

more with less. Constraints breed resourcefulness, self-sufficiency, and

invention. There are no extra points for growing headcount, budget
size, or fixed expense. His wife, MacKenzie, drove him to work most
days in their Honda minivan, and when he flew with colleagues on his
private Dassault Falcon 900EX jet, he often mentioned that he per-
sonally, not Amazon, had paid for the flight.
If Bezos took one leadership principle most to heart—which
would also come to define the next half decade at Amazon—it was
principle #8, “think big”: Thinking small is a self-fulfilling proph-
ecy. Leaders create and communicate a bold direction that inspires
results. They think differently and look around corners for ways to
serve customers. In 2010, Amazon was a successful online retailer, a
nascent cloud provider, and a pioneer in digital reading. But Bezos
envisioned it as much more. His shareholder letter that year was a
paean to the esoteric computer science disciplines of artificial intel-
ligence and machine learning that Amazon was just beginning to ex-
plore. It opened by citing a list of impossibly obscure terms such as
“naïve Bayesian estimators,” “gossip protocols,” and “data sharding.”
Bezos wrote: “Invention is in our DNA and technology is the funda-
mental tool we wield to evolve and improve every aspect of the expe-
rience we provide our customers.”
Bezos wasn’t only imagining these technological possibilities. He
was also attempting to position Amazon’s next generation of products
directly on its farthest frontier. Around this time, he started work-
ing intensively with the engineers at Lab126, Amazon’s Silicon Val-
ley R&D subsidiary, which had developed the company’s first gadget,
the Kindle. In a flurry of brainstorming sessions, he initiated several
projects to complement the Kindle and the coming Kindle Fire tab-
lets, which were known internally at the time as Project A.
Project B, which became Amazon’s ill-fated Fire Phone, would
use an assembly of front-facing cameras and infrared lights to con-
jure a seemingly three-dimensional smartphone display. Project C,
or “Shimmer,” was a desk lamp–shaped device designed to project

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 THE ÜBER PRODUCT MANAGER 23

hologram-like displays onto a table or ceiling. It proved unfeasibly ex-

pensive and was never launched.
Bezos had peculiar ideas about how customers might interact
with these devices. The engineers working on the third version of the
Kindle discovered this when they tried to kill a microphone that was
planned for the device, since no features were slated to actually use
it. But the CEO insisted that the microphone remain. “The answer I
got is that Jeff thinks in the future we’ll talk to our devices,” said Sam
Bowen, then a Kindle hardware director. “It felt a bit more like Star
Trek than reality.”
Designers convinced Bezos to lose the microphone in subsequent
versions of the Kindle, but he clung to his belief in the inevitability of
conversational computing and the potential of artificial intelligence
to make it practical. It was a trope in all his favorite science fiction,
from TV’s Star Trek (“computer, open a channel”) to authors like Ar-
thur C. Clarke, Isaac Asimov, and Robert A. Heinlein whose books
lined the library of hundreds of volumes in his lakefront Seattle-area
home. While others read these classics and only dreamed of alternate
realities, Bezos seemed to consider the books blueprints for an excit-
ing future. It was a practice that would culminate in Amazon’s de-
fining product for a new decade: a cylindrical speaker that sparked
a wave of imitators, challenged norms around privacy, and changed
the way people thought about Amazon—not only as an e-commerce
giant, but as an inventive technology company that was pushing the
very boundaries of computer science.
The initiative was originally designated inside Lab126 as Proj-
ect D. It would come to be known as the Amazon Echo, and by the
name of its virtual assistant, Alexa.

As with several other projects at Amazon, the origins of Project D

can be traced back to discussions between Bezos and his “technical
advisor” or TA, the promising executive handpicked to shadow the

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 24 AMAZON UNBOUND

CEO. Among the TA’s duties were to take notes in meetings, write the
first draft of the annual shareholder letter, and learn by interacting
with the master closely for more than a year. In the role from 2009
to 2011 was Amazon executive Greg Hart, a veteran of the company’s
earliest retail categories, like books, music, DVDs, and video games.
Originally from Seattle, Hart had attended Williams College in West-
ern Massachusetts and, after a stint in the ad world, returned home
at the twilight of the city’s grunge era, sporting a goatee and a pen-
chant for flannel shirts. By the time he was following Bezos around,
the facial hair was gone and Hart was a rising corporate star. “You
sort of feel like you’re an assistant coach watching John Wooden, you
know, perhaps the greatest basketball coach ever,” Hart said of his
time as the TA.
Hart remembered talking to Bezos about speech recognition one
day in late 2010 at Seattle’s Blue Moon Burgers. Over lunch, Hart
demonstrated his enthusiasm for Google’s voice search on his An-
droid phone by saying, “pizza near me,” and then showing Bezos the
list of links to nearby pizza joints that popped up on-screen. “Jeff was
a little skeptical about the use of it on phones, because he thought
it might be socially awkward,” Hart remembered. But they discussed
how the technology was finally getting good at dictation and search.
At the time, Bezos was also excited about Amazon’s growing cloud
business, asking all of his executives, “What are you doing to help
AWS?” Inspired by the conversations with Hart and others about
voice computing, he emailed Hart, device vice president Ian Freed,
and senior vice president Steve Kessel on January 4, 2011, linking the
two topics: “We should build a $20 device with its brains in the cloud
that’s completely controlled by your voice.” It was another idea from
the boss who seemed to have a limitless wellspring of them.
Bezos and his employees riffed on the idea over email for a few
days, but no further action was taken, and it could have ended there.
Then a few weeks later, Hart met with Bezos in a sixth-floor conference
room in Amazon’s headquarters, Day 1 North, to discuss his career op-

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 THE ÜBER PRODUCT MANAGER 25

tions. His tenure as TA was wrapping up, so they discussed several

possible opportunities to lead new initiatives at the company, includ-
ing positions in Amazon’s video streaming and advertising groups.
Bezos jotted their ideas down on a whiteboard, adding a few of his
own, and then started to apply his usual criteria to assess their merit:
If they work, will they grow to become big businesses? If the company
didn’t pursue them aggressively now, would it miss an opportunity?
Eventually Bezos and Hart crossed off all the items on the list except
one—pursuing Bezos’s idea for a voice-activated cloud computer.
“Jeff, I don’t have any experience in hardware, and the largest soft-
ware team I’ve led is only about forty people,” Hart recalled saying.
“You’ll do fine,” Bezos replied.
Hart thanked him for the vote of confidence and said, “Okay, well,
remember that when we screw up along the way.”
Before they parted, Bezos illustrated his idea for the screenless
voice computer on the whiteboard. The first-ever depiction of an
Alexa device showed the speaker, microphone, and a mute button.
And it identified the act of configuring the device to a wireless net-
work, since it wouldn’t be able to listen to commands right out of the
box, as a challenge requiring further thought. Hart snapped a photo
of the drawing with his phone.
Bezos would remain intimately involved in the project, meeting
with the team as frequently as every other day, making detailed prod-
uct decisions, and authorizing the investment of hundreds of millions
of dollars in the project before the first Echo was ever released. Using
the German superlative, employees referred to him as the über prod-
uct manager.
But it was Greg Hart who ran the team, just across the street
from Bezos’s office, in Fiona, the Kindle building. Over the next few
months, Hart hired a small group from in and outside the company,
sending out emails to prospective hires with the subject line “Join my
mission” and asking interview questions like “How would you design
a Kindle for the blind?” Then, just as obsessed with secrecy as his

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 26 AMAZON UNBOUND

boss, he declined to specify what product candidates would be work-

ing on. One interviewee recalled guessing that it was Amazon’s widely
rumored smartphone and said that Hart replied, “There’s another
team building a phone. But this is way more interesting.”
One early recruit was Amazon engineer Al Lindsay, who in a pre-
vious job had written some of the original code for telco US West’s
voice-activated directory assistance. Lindsay spent his first three
weeks on the project on vacation at his cottage in Canada, writing a
six-page narrative that envisioned how outside developers might pro-
gram their own voice-enabled apps that could run on the device. An-
other internal recruit, Amazon manager John Thimsen, signed on as
director of engineering and coined a formal code name for the ini-
tiative, Doppler, after the Project D designation. “At the start, I don’t
think anybody really expected it to succeed, to be honest with you,”
Thimsen told me. “But to Greg’s credit, halfway through, we were all
believers.”
The initial Alexa crew worked with a feverish sense of urgency
due to their impatient boss. Unrealistically, Bezos wanted to release
the device in six to twelve months. He would have a good reason to
hurry. On October 4, 2011, just as the Doppler team was coming to-
gether, Apple introduced the Siri virtual assistant in the iPhone 4S,
the last passion project of cofounder Steve Jobs, who died of can-
cer the next day. That the resurgent Apple had the same idea of a
voice-activated personal assistant was both validating for Hart and
his employees and discouraging, since Siri was first to market and
with initial mixed reviews. The Amazon team tried to reassure them-
selves that their product was unique, since it would be independent
from smartphones. Perhaps a more significant differentiator though
was that Siri unfortunately could no longer have Jobs’s active sup-
port, while Alexa would have Bezos’s sponsorship and almost mania-
cal attention inside Amazon.
To speed up development and meet Bezos’s goals, Hart and his
crew started looking for startups to acquire. It was a nontrivial chal-

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 THE ÜBER PRODUCT MANAGER 27

lenge, since Nuance, the Boston-based speech giant whose technol-

ogy Apple had licensed for Siri, had grown over the years by gobbling
up the top American speech companies. Doppler execs tried to learn
which of the remaining startups were promising by asking prospective
targets to voice-enable the Kindle digital book catalog, then studying
their methods and results. The search led to several rapid-fire acqui-
sitions over the next two years, which would end up shaping Alexa’s
brain and even the timbre of its voice.
The first company Amazon bought, Yap, a twenty-person startup
based in Charlotte, North Carolina, automatically translated human
speech such as voicemails into text, without relying on a secret work-
force of human transcribers in low-wage countries. Though much of
Yap’s technology would be discarded, its engineers would help de-
velop the technology to convert what customers said to Doppler into
a computer-readable format. During the prolonged courtship, Ama-
zon execs tormented Yap execs by refusing to disclose what they’d be
working on. Even a week after the deal closed, Al Lindsay was with
Yap’s engineers at an industry conference in Florence, Italy, where he
insisted that they pretend they didn’t know him, so that no one could
catch on to Amazon’s newfound interest in speech technology.
After the purchase was finalized for around $25 million, Amazon
dismissed the company’s founders but kept its speech science group in
Cambridge, Massachusetts, making it the seed of a new R&D office in
Kendall Square, near MIT. Yap engineers flew to Seattle, walking into
a conference room on the first floor of Fiona with locked doors and
closed window blinds. There Greg Hart finally described “this little
device, about the size of a Coke can, that would sit on your table and
you could ask it natural language questions and it would be a smart
assistant,” recalled Yap’s VP of research, Jeff Adams, a two-decade
veteran of the speech industry. “Half of my team were rolling their
eyes, saying ‘oh my word, what have we gotten ourselves into.’ ”
After the meeting, Adams delicately told Hart and Lindsay that
their goals were unrealistic. Most experts believed that true “far-field

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 28 AMAZON UNBOUND

speech recognition”—comprehending speech from up to thirty-two

feet away, often amid crosstalk and background noise—was beyond
the realm of established computer science, since sound bounces off
surfaces like walls and ceilings, producing echoes that confuse com-
puters. The Amazon executives responded by channeling Bezos’s re-
solve. “They basically told me, ‘We don’t care. Hire more people. Take
as long as it takes. Solve the problem,’ ” recalled Adams. “They were
unflappable.”

A few months after the Yap purchase, Greg Hart and his colleagues
acquired another piece of the Doppler puzzle. It was the technolog-
ical antonym of Yap, which converted speech into text. Instead, the
Polish startup Ivona generated computer-synthesized speech that re-
sembled a human voice.
Ivona was founded in 2001 by Lukasz Osowski, a computer sci-
ence student at the Gdan´sk University of Technology. Osowski had
the notion that so-called “text to speech,” or TTS, could read digi-
tal texts aloud in a natural voice and help the visually impaired in
Poland appreciate the written word. With a younger classmate, Mi-
chal Kaszczuk, he took recordings of an actor’s voice and selected
fragments of words, called diphones, and then blended or “concat-
enated” them together in different combinations to approximate
natural-sounding words and sentences that the actor might never
have uttered.
The Ivona founders got an early glimpse of how powerful their
technology could be. While students, they paid a popular Polish actor
named Jacek Labijak to record hours of speech to create a database
of sounds. The result was their first product, Spiker, which quickly
became the top-selling computer voice in Poland. Over the next few
years, it was used widely in subways, elevators, and for robocall cam-
paigns. Labijak subsequently began to hear himself everywhere and
regularly received phone calls in his own voice urging him, for ex-

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 THE ÜBER PRODUCT MANAGER 29

ample, to vote for a candidate in an upcoming election. Pranksters

manipulated the software to have him say inappropriate things and
posted the clips online, where his children discovered them. The
Ivona founders then had to renegotiate the actor’s contract after he
angrily tried to withdraw his voice from the software. (Today “Jacek”
remains one of the Polish voices offered by AWS’s Amazon Polly com-
puter voice service.)
In 2006, Ivona began to enter and repeatedly win the annual Bliz-
zard Challenge, a competition for the most natural computer voice,
organized by Carnegie Mellon University. By 2012, Ivona had ex-
panded into twenty other languages and had over forty voices. After
learning of the startup, Greg Hart and Al Lindsay diverted to Gdan´sk
on their trip through Europe looking for acquisition targets. “From
the minute we walked into their offices, we knew it was a culture fit,”
Lindsay said, pointing to Ivona’s progress in a field where research-
ers often got distracted by high-minded pursuits. “Their scrappiness
allowed them to look outside pure academia and not be blinded by
science.”
The purchase, for around $30 million, was consummated in 2012
but kept secret for a year. The Ivona team and the growing number of
speech engineers Amazon would hire for its new Gdan´sk R&D center
were put in charge of crafting Doppler’s voice. The program was mi-
cromanaged by Bezos himself and subject to the CEO’s usual curios-
ities and whims.
At first, Bezos said he wanted dozens of distinct voices to emanate
from the device, each associated with a different goal or task, such as
listening to music or booking a flight. When that proved impractical,
the team considered lists of characteristics they wanted in a single
personality, such as trustworthiness, empathy, and warmth, and de-
termined those traits were more commonly associated with a female
voice.
To develop this voice and ensure it had no trace of a regional accent,
the team in Poland worked with an Atlanta area–based voice-over stu-

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 30 AMAZON UNBOUND

dio, GM Voices, the same outfit that had helped turn recordings from
a voice actress named Susan Bennett into Apple’s agent, Siri. To cre-
ate synthetic personalities, GM Voices gave female voice actors hun-
dreds of hours of text to read, from entire books to random articles, a
mind-numbing process that could stretch on for months.
Greg Hart and colleagues spent months reviewing the recordings
produced by GM Voices and presented the top candidates to Bezos.
They ranked the best ones, asked for additional samples, and finally
made a choice. Bezos signed off on it.
Characteristically secretive, Amazon has never revealed the name
of the voice artist behind Alexa. I learned her identity after canvasing
the professional voice-over community: Boulder-based singer and
voice actress Nina Rolle. Her professional website contained links to
old radio ads for products such as Mott’s Apple Juice and the Volks­
wagen Passat—and the warm timbre of Alexa’s voice was unmis-
takable. Rolle said she wasn’t allowed to talk to me when I reached
her on the phone in February of 2021. And when I asked Amazon to
speak with her, they declined.

While the Doppler team hired engineers and acquired startups, nearly
every other aspect of the product was hotly debated in Amazon’s of-
fices in Seattle and in Lab126 in Silicon Valley. In one of the earliest
Doppler meetings, Greg Hart identified the ability to play music with
a voice command as the device’s marquee feature. Bezos “agreed with
that framework but he stressed that music may be like 51 percent, but
the other 49 percent are going to be really important,” Hart said.
Over the ensuing months, that amicable consensus devolved into
a long-standing tug-of-war between Hart and his engineers, who
saw playing music as a practical and marketable feature, and Bezos,
who was thinking more grandly. Bezos started to talk about the “Star
Trek computer,” an artificial intelligence that could handle any ques-
tion and serve as a personal assistant. The fifty-cent word “plenipo-

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 THE ÜBER PRODUCT MANAGER 31

tentiary” was used inside the team to describe what he wanted: an

assistant invested with full powers to take action on behalf of users,
like call for a cab or place a grocery order. With his science fiction
obsession, Bezos was forcing his team to think bigger and to push
the boundaries of established technology. But Hart, facing pressure
to actually ship the product, advocated for a feature set he dubbed
“the magical and the mundane” and pushed to highlight basic, reli-
able features like allowing users to ask for weather reports as well as
setting timers and alarms.
The debate manifested itself in endless drafts of the “PR FAQ”—the
six-page narrative Amazonians craft in the form of a press release at
the start of a new initiative to envision the product’s market impact.
The paper, a hallowed part of Amazon’s rituals around innovation,
forces them to begin any conversation about a new product in terms
of the benefit it creates for customers. Dozens of versions of the Dop-
pler PR FAQ were written, presented, debated, obsessed over, rewrit-
ten, and scrapped. Whenever the press release evolved to highlight
playing music, “Jeff would get really mad. He didn’t like that at all,”
recalled an early product manager.
Another early Doppler employee later speculated that Bezos’s fa-
mous lack of sophisticated musical tastes played a role in his reaction.
When Bezos was testing an early Doppler unit, for example, he asked
it to play one of his favorite songs: the theme to the classic TV show
Battlestar Galactica. “Jeff was pushing really hard to make sure this
product was more than just music,” said Ian Freed, Greg Hart’s boss.
“He wouldn’t let go of it being a more generalized computer.”
A related discussion centered around the choice of a so-called
“wake” word—the utterance that would rouse Doppler out of pas-
sive mode, when it was only listening for its own name, to switch into
active listening, where it would send user queries over the internet
to Amazon’s servers and return with a response. The speech science
team wanted the wake word to have a distinct combination of pho-
nemes and be at least three syllables, so the device wouldn’t be trig-

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 32 AMAZON UNBOUND

gered by normal conversation. It also needed to be distinctive (like

“Siri”) so that the name could be marketed to the public. Hart and his
team presented Bezos with hundreds of flash cards, each with a dif-
ferent name, which he would spread out on conference room tables
during the endless deliberations.
Bezos said he wanted the wake word to sound “mellifluous” and
opined that his mother’s name, Jacklyn, was “too harsh.” His own
quickly discarded suggestions included “Finch,” the title of a fantasy
detective novel by Jeff VanderMeer; “Friday,” after the personal assis-
tant in the novel Robinson Crusoe; and “Samantha,” the witch who
could twinkle her nose and accomplish any task on the TV show Be-
witched. For a while, he also believed the wake word should be “Ama-
zon,” so that whatever aura of good feeling the device generated would
be reflected back onto the company.
Doppler execs argued that people would not want to talk to a cor-
porate entity in their homes, and that spawned another ongoing dis-
agreement. Bezos also suggested “Alexa,” an homage to the ancient
library of Alexandria, regarded as the capital of knowledge. This was
also the name of an unrelated startup Amazon had acquired in the
1990s, which sold web traffic data and continued to operate inde-
pendently. After endless debates and lab testing, “Alexa” and “Amazon”
became the top candidates for the wake word as the device moved into
limited trials in the homes of Amazon employees at the start of 2013.
The devices employees received looked very much like the original
Echo that would be introduced by Amazon less than two years later.
The industrial designers at Lab126 called it the “Pringles can”—a
cylinder elongated to create separation between the array of seven
omnidirectional microphones at the top and the speakers at the bot-
tom, with some fourteen hundred holes punctured in the metal tub-
ing to push out air and sound. The device had an LED light ring at the
top, another Bezos idea, which would light up in the direction of the
person speaking, reproducing the social cue of looking at someone

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 THE ÜBER PRODUCT MANAGER 33

when they are talking to you. It was not an elegant-looking device,

Bezos having instructed the designers to let function dictate the form.
The experimental Doppler devices in the homes of hundreds of Am-
azon employees were not smart—they were, by all accounts, slow and
dumb. An Amazon manager named Neil Ackerman signed up for the
internal beta, bringing one home to his family in early 2013. Both he
and his wife had to sign several confidentiality agreements, promising
they would turn it off and hide it if guests came over. Every week they
had to fill out a spreadsheet, answering questions and listing what they
asked it and how it responded. Ackerman’s wife called it “the thing.”
“We were both pretty skeptical about it,” he said. “It would hardly
ever give me the right answer and the music coming out of it was
inconsistent and certainly not the family favorites.” Inexplicably it
seemed to best understand their son, who had a speech impediment.
Other early beta testers didn’t mince words either. Parag Garg,
one of the first engineers to work on the Fire TV, took home a device
and said it “didn’t work for shit and I didn’t miss it when it was gone.
I thought, ‘Well, this thing is doomed.’ ” A manager on the Fire Phone
recalls liking the look of the hardware, “but I could not foresee what it
was going to be used for. I thought it was a stupid product.”
Two Doppler engineers recall another harrowing review—from
Bezos himself. The CEO was apparently testing a unit in his Seattle
home, and in a pique of frustration over its lack of comprehension, he
told Alexa to go “shoot yourself in the head.” One of the engineers who
heard the comment while reviewing interactions with the test device
said: “We all thought it might be the end of the project, or at least the
end of a few of us at Amazon.”

Alexa, it was clear, needed a brain transplant. Amazon’s ongoing ef-

forts to make its product smarter would create a dogmatic battle in-
side the Doppler team and lead to its biggest challenge yet.

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 34 AMAZON UNBOUND

The first move was to integrate the technology of a third acqui-

sition, a Cambridge, England–based artificial intelligence company
called Evi (pronounced Evee). The startup was founded in 2005 as a
question-and-answer tool called True Knowledge by British entrepre-
neur William Tunstall-Pedoe. As a university student, Tunstall-Pedoe
had created websites like Anagram Genius, which automatically re­
arranged the letters in words to produce another word or phrase. The
site was later used by novelist Dan Brown to create puzzles in The Da
Vinci Code.
In 2012, inspired by Siri’s debut, Tunstall-Pedoe pivoted and in-
troduced the Evi app for the Apple and Android app stores. Users
could ask it questions by typing or speaking. Instead of searching the
web for an answer like Siri, or returning a set of links, like Google’s
voice search, Evi evaluated the question and tried to offer an immedi-
ate answer. The app was downloaded over 250,000 times in its first
week and almost crashed the company’s servers. Apple threatened
to kick it off the iOS app store for appearing “confusingly similar” to
Siri, then relented when fans objected. Thanks to all this attention,
Evi had at least two acquisition offers and a prospective investment
from venture capitalists when Amazon won out in late 2012 with a
rumored $26 million deal.
Evi employed a programming technique called knowledge graphs,
or large databases of ontologies, which connect concepts and catego-
ries in related domains. If, for example, a user asked Evi, “What is the
population of Cleveland?” the software interpreted the question and
knew to turn to an accompanying source of demographic data. Wired
described the technique as a “giant treelike structure” of logical con-
nections to useful facts.
Putting Evi’s knowledge base inside Alexa helped with the kind
of informal but culturally common chitchat called phatic speech. If
a user said to the device, “Alexa, good morning, how are you?” Alexa
could make the right connection and respond. Tunstall-Pedoe said
he had to fight with colleagues in the U.S. over the unusual idea of

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 THE ÜBER PRODUCT MANAGER 35

having Alexa respond to such social cues, recalling that “People were
uncomfortable with the idea of programming a machine to respond
to ‘hello.’ ”
Integrating Evi’s technology helped Alexa respond to factual que-
ries, such as requests to name the planets in the solar system, and it
gave the impression that Alexa was smart. But was it? Proponents
of another method of natural language understanding, called deep
learning, believed that Evi’s knowledge graphs wouldn’t give Alexa
the kind of authentic intelligence that would satisfy Bezos’s dream of
a versatile assistant that could talk to users and answer any question.
In the deep learning method, machines were fed large amounts
of data about how people converse and what responses proved sat-
isfying, and then were programmed to train themselves to pre-
dict the best answers. The chief proponent of this approach was an
Indian-born engineer named Rohit Prasad. “He was a critical hire,”
said engineering director John Thimsen. “Much of the success of the
project is due to the team he assembled and the research they did on
far-field speech recognition.”
Prasad was raised in Ranchi, the capital of the eastern India state
of Jharkhand. He grew up in a family of engineers and got hooked
on Star Trek at a young age. Personal computers weren’t common in
India at the time, but at an early age he learned to code on a PC at the
metallurgical and engineering consulting company where his father
worked. Since communication in India was hampered by poor tele-
communications infrastructure and high long-distance rates, Prasad
decided to study how to compress speech over wireless networks
when he moved to the U.S. to attend graduate school.
After graduating in the late 1990s, Prasad passed on the dot-com
boom and worked for the Cambridge, Massachusetts–based defense
contractor BBN Technologies (later acquired by Raytheon) on some
of the first speech recognition and natural language systems. At BBN,
he worked on one of the first in-car speech recognition systems and
automated directory assistance services for telephone companies. In

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 36 AMAZON UNBOUND

2000, he worked on another system that automatically transcribed

courtroom proceedings. Accurately recording conversation from
multiple microphones placed around a courtroom introduced him to
the challenges of far-field speech recognition. At the start of the proj-
ect, he said that eighty out of every hundred words were incorrect;
but within the first year, they cut it down to thirty-three.
Years later, as the Doppler team was trying to improve Alexa’s
comprehension, Bill Barton, who led Amazon’s Boston office, intro-
duced Prasad to Greg Hart. Prasad didn’t know much about Amazon
and showed up for the interview in Seattle wearing a suit and tie (a
minor faux pas) and with no clue about Amazon’s fourteen leadership
principles (a bigger one). He expressed reservations about joining a
large, plodding tech company, but by the time he returned to his hotel
room, Hart had emailed him a follow-up note that promised, “We are
essentially a startup. Even though we are part of a big company, we
don’t act like one.”
Persuaded, Prasad joined to work on the problems of far-field
speech recognition, but he ended up as an advocate for the deep
learning model. Evi’s knowledge graphs were too regimented to be
Alexa’s foundational response model; if a user says, “Play music by
Sting,” such a system may think he is trying to say “bye” to the art-
ist and get confused, Prasad later explained. By using the statistical
training methods of deep learning, the system could quickly ascertain
that when the sentence is uttered, the intent is almost certainly to
blast “Every Breath You Take.”
But Evi’s Tunstall-Pedoe argued that knowledge graphs were the
more practical solution and mistrusted the deep learning approach.
He felt it was error-prone and would require an endless diet of train-
ing data to properly mold Alexa’s learning models. “The thing about
machine learning scientists is that they never admit defeat because
all of their problems can be solved with more data,” he explained.
That response might carry a tinge of regret with it, because to the

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 THE ÜBER PRODUCT MANAGER 37

über product manager, Bezos himself, there was no question about

which way time’s arrow was pointed—toward machine learning and
deep neural networks. With its vast and sophisticated AWS data cen-
ters, Amazon was also in the unique position of being able to har-
ness a large number of high-powered computer processors to train
its speech models, exploiting its advantage in the cloud in a way few
of its competitors could. Defeated, Tunstall-Pedoe ended up leaving
Amazon in 2016.
Even though the deep learning approach won out, Prasad and his
allies still had to solve the paradox that confronts all companies devel-
oping AI: they don’t want to launch a system that is dumb—customers
won’t use it, and so won’t generate enough data to improve the service.
But companies need that data to train the system to make it smarter.
Google and Apple solved the paradox in part by licensing technol-
ogy from Nuance, using its results to train their own speech models
and then afterward cutting ties with the company. For years, Google
also collected speech data from a toll-free directory assistance line,
800-Goog-411. Amazon had no such services it could mine, and Greg
Hart was against licensing outside technology—he thought it would
limit the company’s flexibility in the long run. But the meager train-
ing data from the beta tests with employees amounted to speech from
a few hundred white-collar workers, usually uttered from across the
room in their noisy homes in the mornings and evenings when they
weren’t at the office. The data was lousy, and there wasn’t enough of it.
Meanwhile Bezos grew impatient. “How will we even know when
this product is good?” he kept asking in early 2013. Hart, Prasad, and
their team created graphs that projected how Alexa would improve
as data collection progressed. The math suggested they would need
to roughly double the scale of their data collection efforts to achieve
each successive 3 percent increase in Alexa’s accuracy.
That spring, only a few weeks after Rohit Prasad had joined the
company, they brought a six-page narrative to Bezos that laid out

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these facts, proposed to double the size of the speech science team
and postpone a planned launch from the summer into the fall. Held
in Bezos’s conference room, the meeting did not go well.
“You are going about this the wrong way,” Bezos said after reading
about the delay. “First tell me what would be a magical product, then
tell me how to get there.”
Bezos’s technical advisor at the time, Dilip Kumar, then asked
if the company had enough data. Prasad, who was calling into the
meeting from Cambridge, replied that they would need thousands of
more hours of complex, far-field voice commands. According to an
executive who was in the room, Bezos apparently factored in the re-
quest to increase the number of speech scientists and did the calcu-
lation in his head in a few seconds. “Let me get this straight. You are
telling me that for your big request to make this product successful,
instead of it taking forty years, it will only take us twenty?”
Prasad tried to dance around it. “Jeff, that is not how we think
about it.”
“Show me where my math is wrong!” Bezos said.
Hart jumped in. “Hang on, Jeff, we hear you, we got it.”
Prasad and other Amazon executives would remember that meet-
ing, and the other tough interactions with Bezos during the develop-
ment of Alexa, differently. But according to the executive who was
there, the CEO stood up, said, “You guys aren’t serious about making
this product,” and abruptly ended the meeting.

In the very same buildings in Seattle and Sunnyvale, California, where

the Doppler team was trying to make Alexa smarter, Amazon’s cam-
paign to build its own smartphone was careening toward disaster.
A few years before, Apple, Google, and Samsung had staked out
large positions in the dawning smartphone market but had left the
impression that terrain might remain for innovative newcomers. Typ-
ically, Jeff Bezos was not about to cede a critical strategic position in

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 THE ÜBER PRODUCT MANAGER 39

the unfolding digital terrain to other companies, especially when he

believed the ground was still fertile for innovative approaches. In one
brainstorming session he proposed a robot that could retrieve a care-
lessly discarded phone and drag it over to a wireless charger. (Some
employees thought he was joking, but a patent on the idea was filed.)
In another, he proposed a phone with an advanced 3D display, re-
sponsive to gestures in the air, instead of only taps on a touchscreen.
It would be like nothing else in stores. Bezos clung to that idea, which
would become the seed of the Fire Phone project.
The original designers settled on a handset with four infrared
cameras, one in each corner of the phone’s face, to track the user’s
gaze and present the illusion of a 3D image, along with a fifth cam-
era on the back (because it could “see” from both sides of its head, the
project was code-named Tyto, after a genus of owl). The custom-made
Japanese cameras would cost $5 a handset, but Bezos envisioned a
premium Amazon smartphone with top-of-the-line components.
Bezos met the Tyto team every few days for three years, at the
same time he was meeting the Alexa team as frequently. He was infat-
uated with new technologies and business lines and loved spitballing
ideas and reviewing the team’s progress. And while he was inordi-
nately focused on customer feedback in other parts of Amazon’s
business, Bezos did not believe that listening to them could result in
dramatic product inventions, evangelizing instead for creative “wan-
dering,” which he believed was the path to dramatic breakthroughs.
“The biggest needle movers will be things that customers don’t know
to ask for,” he would write years later in a letter to shareholders. “We
must invent on their behalf. We have to tap into our own inner imag-
ination about what’s possible.”
But many Tyto employees were skeptical of his vision for smart-
phones. No one was sure the 3D display was anything more than a
gimmick and a major drain on the phone’s battery. Bezos also had
some worrisome blind spots about smartphones. “Does anyone actu-
ally use the calendar on their phone?” he asked in one meeting. “We

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do use the calendar, yes,” someone who did not have several personal
assistants replied.
As in the Doppler project, the deadlines Bezos gave were unre-
alistic, and to try to make them, the team hired more engineers. But
throwing more engineers at failing technology projects only makes
them fail more spectacularly. Kindle was strategically important to
Amazon at the time, so instead of poaching employees internally, the
Tyto group had to look outside, to hardware engineers at other com-
panies like Motorola, Apple, and Sony. Naturally, they didn’t tell any-
one what they’d be working on until their first day. “If you had a good
reputation in the tech industry, they found you,” said a Fire Phone
manager.
The launch was perpetually six months away. The project
dragged on as they tried to get the 3D display to work. The original
top-of-the-line components quickly became outdated, so they de-
cided to reboot the project with an upgraded processor and cameras.
It was given a new owl-themed code name, Duke. The group started
and then canceled another phone project, a basic low-cost handset
to be made by HTC and code-named Otus, which would also use the
Amazon flavor of the Android operating system that ran on Amazon’s
new Fire tablets, which were showing promise as an economical al-
ternative to Apple’s iPad.
Employees on the project were disappointed when Otus was
scrapped because they quietly believed Amazon’s opportunity was
not in a fancy 3D display but in disrupting the market with a free
or low-priced smartphone. Morale on the team started to sour. One
group was so dubious about the entire project that they covertly
bought a set of military dogtags that read “disagree and commit,”
after Amazon leadership principle #13, which says employees who
disagree with a decision must put aside their doubts and work to
support it.
In his annual letter to shareholders released in April 2014, Bezos
wrote, “Inventing is messy, and over time, it’s certain that we’ll fail

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 THE ÜBER PRODUCT MANAGER 41

at some big bets too.” The observation was curiously prophetic. The
team was preparing to launch the phone at a big event that summer.
Bezos’s wife, MacKenzie, showed up for rehearsals to offer support
and advice.
On June 18, 2014, Bezos unveiled the Fire Phone at a Seattle event
space called Fremont Studios, where he attempted to summon some
of the charismatic magic of the late Steve Jobs and waxed enthusi-
astic about the device’s 3D display and gesture tracking. “I actually
think he was a believer,” said Craig Berman, an Amazon PR vice pres-
ident at the time. “I really do. If he wasn’t, he certainly wasn’t going to
signal it to the team.”
Reviews of the phone were scathing. The smartphone market had
shifted and matured during the painful four years that the Fire Phone
was in development, and what had started as an attempt at creating
a novel product now seemed strangely out of touch with customer
expectations. Because it did not run Google’s authorized version of
Android, it did not have popular apps such as Gmail and YouTube.
While it was cheaper than the forthcoming iPhone 6, it was more ex-
pensive than the multitude of low-cost, no-frills handsets made by
Asian manufacturers, which were heavily subsidized at the time by
the wireless carriers in exchange for two-year contracts.
“There was a lot of differentiation, but in the end, customers
didn’t care about it,” said Ian Freed, the vice president in charge of the
project. “I made a mistake and Jeff made a mistake. We didn’t align
the Fire Phone’s value proposition with the Amazon brand, which is
great value.” Freed said that Bezos told him afterward, “You can’t, for
one minute, feel bad about the Fire Phone. Promise me you won’t lose
a minute of sleep.”
Later that summer, workers in one of Amazon’s fulfillment cen-
ters in Phoenix noticed thousands of unsold Fire Phones sitting un-
touched on massive wooden pallets. In October, the company wrote
down $170 million in inventory and canceled the project, acknowl-
edging one of its most expensive failures. “It failed for all the reasons

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 42 AMAZON UNBOUND

we all said it was going to fail—that’s the crazy thing about it,” said
Isaac Noble, one of the early software engineers who had been dubi-
ous from the start.
Ironically, the Fire Phone fiasco augured well for Doppler. With-
out a smartphone market share to protect, Amazon could pioneer the
new category of smart speakers with unencumbered ambition. Many
of the displaced engineers who weren’t immediately snapped up by
Google and Apple were given a few weeks to find new jobs at Amazon;
some went to Doppler, or to a new hit product, Fire TV. Most impor-
tantly, Bezos didn’t penalize Ian Freed and other Fire Phone manag-
ers, sending a strong message inside Amazon that taking risks was
rewarded—especially if the entire debacle was primarily his own fault.
On the other hand, it revealed a worrisome fact about life inside
Amazon. Many employees who worked on the Fire Phone had seri-
ous doubts about it, but no one, it seemed, had been brave or clever
enough to take a stand and win an argument with their obstinate
leader.

After Jeff Bezos walked out on them, the Doppler executives working
on the Alexa prototype retreated with their wounded pride to a nearby
conference room and reconsidered their solution to the data paradox.
Their boss was right. Internal testing with Amazon employees was
too limited and they would need to massively expand the Alexa beta
while somehow still keeping it a secret from the outside world.
The resulting program, conceived by Rohit Prasad and speech sci-
entist Janet Slifka over a few days in the spring of 2013, and quickly
approved by Greg Hart, would put the Doppler program on steroids
and answer a question that later vexed speech experts—how did Am-
azon come out of nowhere to leapfrog Google and Apple in the race to
build a speech-enabled virtual assistant?
Internally the program was called AMPED. Amazon contracted

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 THE ÜBER PRODUCT MANAGER 43

with an Australian data collection firm, Appen, and went on the road
with Alexa, in disguise. Appen rented homes and apartments, initially
in Boston, and then Amazon littered several rooms with all kinds of
“decoy” devices: pedestal microphones, Xbox gaming consoles, televi-
sions, and tablets. There were also some twenty Alexa devices planted
around the rooms at different heights, each shrouded in an acoustic
fabric that hid them from view but allowed sound to pass through.
Appen then contracted with a temp agency, and a stream of contract
workers filtered through the properties, eight hours a day, six days a
week, reading scripts from an iPad with canned lines and open-ended
requests like “ask to play your favorite tune” and “ask anything you’d
like an assistant to do.”
The speakers were turned off, so the Alexas didn’t make a peep,
but the seven microphones on each device captured everything and
streamed the audio to Amazon’s servers. Then another army of work-
ers manually reviewed the recordings and annotated the transcripts,
classifying queries that might stump a machine, like “turn on Hunger
Games,” as a request to play the Jennifer Lawrence film, so that the
next time, Alexa would know.
The Boston test showed promise, so Amazon expanded the pro-
gram, renting more homes and apartments in Seattle and ten other
cities over the next six months to capture the voices and speech pat-
terns of thousands more paid volunteers. It was a mushroom-cloud
explosion of data about device placement, acoustic environments,
background noise, regional accents, and all the gloriously random
ways a human being might phrase a simple request to hear the
weather, for example, or play a Justin Timberlake hit.
The daylong flood of random people into homes and apart-
ments repeatedly provoked suspicious neighbors to call the police.
In one instance, a resident of a Boston condo complex suspected a
drug-dealing or prostitution ring was next door and called the cops,
who asked to enter the apartment. The nervous staff gave them an

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 44 AMAZON UNBOUND

elusive explanation and a tour and afterward hastily shut down the
site. Occasionally, temp workers would show up, consider the bizarre
script and vagueness of the entire affair, and simply refuse to partic-
ipate. One Amazon employee who was annotating transcripts later
recalled hearing a temp worker interrupt a session and whisper to
whoever he suspected was listening: “This is so dumb. The company
behind this should be embarrassed!”
But Amazon was anything but embarrassed. By 2014, it had
increased its store of speech data by a factor of ten thousand and
largely closed the data gap with rivals like Apple and Google. Bezos
was giddy. Hart hadn’t asked for his approval of the AMPED project,
but a few weeks before the program began, he updated Bezos with a
six-page document that described it and its multimillion-dollar cost.
A huge grin spread over Bezos’s face as he read, and all signs of past
peevishness were gone. “Now I know you are serious about it! What
are we going to do next?”
What came next was Doppler’s long-awaited launch. Working
eighty to ninety hours a week, employees were missing whole chunks
of their family’s lives, and Bezos wasn’t letting up. He wanted to see
everything and made impetuous new demands. On an unusually
clear Seattle day, with the setting sun streaming through his confer-
ence room window, for example, Bezos noticed that the ring’s light
was not popping brightly enough, so he ordered a complete redo. Al-
most alone, he argued for a feature called Voice Cast, which linked
an Alexa device to a nearby Fire tablet, so that queries showed up as
placards on the tablet’s screen. When engineers tried to quietly drop
the feature, he noticed and told the team they were not launching
without it. (Few customers ended up using it.)
But he was also right about many things. As launch neared, one
faction of employees worried that the device wasn’t good enough at
hearing commands amid loud music or cross talk and lobbied to in-
clude a remote control, like the one the company made for the Fire
TV. Bezos was opposed to it but agreed to ship remotes with the first

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 THE ÜBER PRODUCT MANAGER 45

batch of speakers to see if customers would use them. (They didn’t,

and the remote disappeared.)
He also headed off a near disaster when it came to what to actually
call the device. For four years there had been no consensus on that
topic. The team debated endlessly whether there should be one name
or two for the virtual assistant and the hardware. After opting for sep-
arate names, they cycled through various options for the speaker and
settled on . . . the Amazon Flash. The news updates would be called
“Flash briefings,” and packaging with the Flash brand printed on it
was ready to ship.
But then less than a month before the introduction, Bezos said in
a meeting, “I think we can do better.” Searching for a replacement,
they opted to pilfer the name of an Alexa feature, Echo, which allowed
a customer to ask Alexa to repeat a word or phrase. (The command
was then changed to “Simon says.”) There wasn’t enough time to print
new boxes or user manuals, so the Echo’s earliest buyers ended up re-
ceiving plain black boxes. Toni Reid, a director Hart hired to launch
the product, had to write the user manual without ever actually nam-
ing the product. “That’s a skill everyone should have,” she said.
The introduction of the Amazon Echo on November 6, 2014, was
molded by the failure of the Fire Phone only months before it. There
was no press conference or visionary speech by Bezos—he was seem-
ingly done forever with his halfhearted impression of the late Steve
Jobs, who had unveiled new products with such verve. Instead, Bezos
appeared more comfortable with a new, understated approach: the
team announced the Echo with a press release and two-minute ex-
planatory video on YouTube that showed a family cheerfully talking
to Alexa. Amazon execs did not tout the new device as a fully conver-
sational computer, but carefully highlighted several domains where
they were confident it was useful, such as delivering the news and
weather, setting timers, creating shopping lists, and playing music.
Then they asked customers to join a waiting list to buy an Echo
and reviewed the list carefully, considering factors like whether ap-

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 46 AMAZON UNBOUND

plicants were users of Amazon Music and owned a Kindle. Recogniz-

ing that it was an untested market, they also ordered an initial batch
of only eighty thousand devices, compared to a preliminary order of
more than three hundred thousand Fire Phones, and distributed them
gradually over the next few months. “The Fire Phone certainly made
folks a little cautious,” said Greg Hart. “It led us to revisit everything.”
After four years of development, more than one Doppler veteran
suspected that the Amazon Echo might leave another smoking crater
in the consumer technology landscape, right next to the Fire Phone’s.
On launch day, they huddled over their laptops in a “war room” from
their new offices in the Prime building, a few minutes’ walk from
Fiona, to watch as the waiting list swelled past even their most hyper-
bolic projections.
In the midst of the vigil, someone realized they were letting a sig-
nificant accomplishment slide by unappreciated. “It was our launch
moment and we weren’t ready for it,” said Al Lindsay. So, a hundred
or so employees headed to a nearby bar for a long-awaited celebra-
tion, and a few of the weary executives and engineers on the project
closed it down that night.

Over the next few weeks, a hundred and nine thousand customers
registered for the waiting list to receive an Echo. Along with some
natural skepticism, positive reviews rolled in, with quotes like “I just
spoke to the future and it listened,” and “it’s the most innovative de-
vice Amazon’s made in years.” Employees emailed Alexa executives
Toni Reid and Greg Hart, pleading for devices for family members
and friends.
After the Echo shipped, the team could see when the devices were
turned on and that people were actually using them. Bezos’s intu-
ition had been right: there was something vaguely magical in sum-
moning a computer in your home without touching the glass of a
smartphone, something valuable in having a responsive speaker that

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 THE ÜBER PRODUCT MANAGER 47

could play music, respond to practical requests (“how many cups are
there in a quart?”), and even banter with playful ones (“Alexa, are you
married?”).
Many Doppler employees had expected they could now catch
their breath and enjoy all their accrued vacation time. But that is not
what happened. Instead of stumbling ashore from choppy seas to
rest, another giant wave crashed over their heads. Bezos deployed his
playbook for experiments that produced promising sparks: he poured
gasoline on them. “We had a running success on our hands and that’s
where my life changed,” said Rohit Prasad, who would be promoted
to vice president and eventually join the vaunted Amazon leadership
committee, the S-team. “I knew the playbook to the launch of Alexa
and Echo. The playbook for the next five years, I didn’t have.”
Over the next few months, Amazon would roll out the Alexa Skills
Kit, which allowed other companies to build voice-enabled apps for
the Echo, and Alexa Voice Service, which let the makers of products
like lightbulbs and alarm clocks integrate Alexa into their own de-
vices. Bezos also told Greg Hart that the team needed to release new
features with a weekly cadence, and that since there was no way to
signal the updates, Amazon should email customers every week to
alert them to the new features their devices offered.
Bezos’s wish list became the product plan—he wanted Alexa to be
everywhere, doing everything, all at once. Services that had originally
been pushed to the wayside in the scramble to launch, like shopping
on Alexa, now became urgent priorities. Bezos ordered up a smaller,
cheaper version of the Echo, the hockey puck–sized Echo Dot, as well
as a portable version with batteries, the Amazon Tap. Commenting
on the race to build a virtual assistant and smart speaker, Bezos said,
“Amazon’s going to be fine if someone comes along and overtakes us,”
as part of the annual late-summer OP1 series of planning meetings,
the year after Alexa’s introduction. “But wouldn’t it be incredibly an-
noying if we can’t be the leader in creating this?”
Life inside the Prime building, and in the gradually increasing

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 48 AMAZON UNBOUND

number of offices around South Lake Union inhabited by the Alexa

team, became even busier. Many of the new features would be rushed
out the door, so that Amazon could start gathering customer feed-
back. Silicon Valley startups call this style of product development
“minimum viable product,” or MVP. At Amazon, Jeff Wilke had popu-
larized the idea of calling it “minimum lovable product,” or MLP, ask-
ing, “What would we be proud to take to the market?” It didn’t seem
to matter that many Alexa features, such as the voice calling, were ini-
tially half-baked and rarely used. Over the course of the 2015 holiday
season, Amazon sold a million Echo devices.
Alexa’s division-wide motto became “Get Big Fast,” the same slo-
gan used in the early years for Amazon. History was repeating itself.
An organization of a few hundred employees swelled to a thousand
in the first year after the launch, and then, incredibly, to ten thou-
sand over the next five years. Through it all, like a crazed pyromaniac,
Bezos kept spraying lighter fluid on the fire, promoting Alexa by pay-
ing an estimated $10 million for Amazon’s first ever Super Bowl ad in
January 2016, starring Alec Baldwin, Missy Elliott, and former Dol-
phins quarterback Dan Marino.
Despite all this attention, there was a sense inside Amazon that
the Alexa organization was not moving fast enough. Greg Hart, who
had produced the device out of nothing more than a Bezos email and
whiteboard drawing, left the division and moved over to help run
Prime Video. “The thing that I got up every day loving doing was the
creation of Alexa,” he said wistfully years later. But with the Alexa
group growing fast, “it was probably a better fit for another leader.”
In his place came a longtime Bezos favorite, Mike George, a bald,
charismatic, cowboy boot–wearing Amazonian with a penchant for
face paint, who liked to walk into meetings with an Amazon Tap
under his arm, blasting music.
Mike George had what Bezos called a “fungible” energy. Over
the years, Bezos deployed him like a firefighter to douse the flames
of chaos and instill order in divisions like human resources, market-

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 THE ÜBER PRODUCT MANAGER 49

place, payments, and later, Bezos’s private philanthropy, Day 1 Acad-

emies Fund. Various colleagues endearingly referred to him as a
“brute,” a “high school jock who never unjocked,” and “totally cleaved
from Jeff ’s rib.”
Mike George ran Alexa for a year, but the impact is still broadly
felt. The Alexa division couldn’t recruit fast enough to fulfill its hir-
ing needs, so Amazon instituted a sort of company-wide draft, giving
every new hire to other parts of Amazon—like AWS and retail—an al-
ternate job offer to join the Alexa division instead. Unhappy Amazon
managers suddenly lost sought-after engineers they thought they had
recruited.
George also instituted a dramatic change in the Alexa group’s
structure. It had been a functional organization, with centralized
engineering, product management, and marketing teams. But that
wasn’t growing smoothly or fast enough for Bezos’s liking. George in-
stead reorganized Alexa around the Amazonian ideal of fast-moving
“two pizza” teams, each devoted to a specific Alexa domain, like music,
weather, lighting, thermostats, video devices, and so on.
Each team was run by a so-called “single-threaded leader” who
had ultimate control and absolute accountability over their success
or failure. (The phrase comes from computer science terminology; a
single-threaded program executes one command at a time.) Alexa,
like Amazon itself, became a land of countless CEOs, each operat-
ing autonomously. To yoke them all together, George oversaw the
creation of a “north star” document, to crystalize the strategy of a
global, voice-enabled computing platform.
Meanwhile Bezos approved all these changes and stayed inti-
mately involved, attending product reviews and reading the Friday
night compilation of updates from all the various two-pizza teams,
and responding with detailed questions or problems that the groups
would then have to fix over the weekend. Alexa execs, like leaders
elsewhere in Amazon, became frequent recipients of the CEO’s esca-
lation emails, in which he forwarded a customer complaint accompa-

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 50 AMAZON UNBOUND

nied by a single question mark and then expected a response within

twenty-four hours. He was also the chief evangelist for Alexa within
the company. “What are you doing for Alexa?” he asked other execu-
tives, as he had for AWS years before. Everyone in the company had
to include Alexa in the OP1 documents they presented to the S-team,
describing their plans for the coming year.
At the end of 2016, after eight million U.S. households had pur-
chased an Echo or Echo Dot, device exec Dave Limp announced in-
ternally that Amazon had become the top-selling speaker company
in the world. It validated the entire crusade. But of course, Bezos
wanted to become the top AI firm in the world, and in that respect, he
was about to have significant competition.
That fall, Google introduced the Google Home smart speaker. It
looked considerably more stylish, “like something you might plant a
succulent in,” said Wired. It also had a crisper sound and, predictably,
searched the web and retrieved answers with aplomb. The Alexa team
had “gone into every holiday season just waiting for either Apple or
Google to announce something, and when they didn’t, we would just
high-five each other,” said former Alexa exec Charlie Kindel. Even
though those companies were allergic to what they considered copy-
cat products, eventually they couldn’t resist the fast-growing smart
speaker market.
That added to the pressure on the Alexa team to move faster and
stay ahead with new features and variations on the hardware. In early
2017, a Swedish customer emailed Bezos to ask why Amazon was
waiting to develop language-specific versions of Alexa before intro-
ducing the Echo in Europe. Why couldn’t they just sell it everywhere
in English first? This was actually on the product road map but wasn’t
a priority. According to one executive, Bezos got that email at 2 a.m.
Seattle time, and by the following morning there were a half dozen
independent groups working to sell Alexa in eighty new countries.
Later, Alexa execs would say that Bezos’s close involvement made
their lives more difficult but also produced immeasurable results.

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 THE ÜBER PRODUCT MANAGER 51

Jeff “gave us the license and permission to do some of the things we

needed to do to go faster and to go bigger,” Toni Reid said. “You can
regulate yourself quite easily or think about what you’re going to do
with your existing resources. . . . Sometimes, you don’t know what the
boundaries are. Jeff just wanted us to be unbounded.”

But there were drawbacks to the frenetic speed and growth. For years
the Alexa smartphone app looked like something a design student
had come up with during a late-night bender. Setting up an Echo, or
networking Echos throughout the home, was more complicated than
it needed to be. It was also difficult and confusing for users to phrase
commands in the right way to trigger third-party skills and special-
ized features.
The decentralized and chaotic approach of countless two-pizza
teams run by single-threaded leaders was manifested in aspects of
the product that had become overly complex. Basic tasks, like setting
up a device and connecting it to smart home appliances, had become
“painful, very painful to the customer,” agreed Tom Taylor, a sardonic
and even-keeled Amazon executive who took over from Mike George
as leader of the Alexa unit in 2017. He set out to “find all the places
that customers are suffering from our organizational structure.”
There was plenty of turmoil that Taylor and his colleagues couldn’t
quell. In March 2018, a bug caused Alexas around the world to ran-
domly emit crazed, unprompted laughter. A few months later, an
Echo inadvertently recorded the private conversation of a couple in
Portland, Oregon, and inexplicably sent the recording to one of the
husband’s employees in Seattle, whose phone number was in his ad-
dress book. Amazon said the device thought it had heard its wake
word and then a series of commands to record and forward the con-
versation. It was an “extremely rare occurrence,” the company said,
and that, “as unlikely as this string of events is, we are evaluating op-
tions to make this case even less likely.” After those incidents, em-

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 52 AMAZON UNBOUND

ployees had to write a “correction of error” report, which analyzes

an incident in detail and tries to get to its underlying root causes by
going through a series of iterative questions and answers called “the
five whys.” The memo went all the way to Bezos, describing what had
happened and recommending how the process that created the prob-
lem in the first place could be fixed.
Some errors could not be undone, such as Alexa’s penchant
for assassinating Santa Claus in the minds of younger users. One
such incident took place during the Alexa Prize, an Amazon contest
among universities to build artificial chatbots that could carry on a
sophisticated multipart conversation. When Alexa users said, “Alexa,
let’s chat,” they got to talk to one of the chatbots and rate its perfor-
mance. During the first competition in 2017, the chatbot from the
University of Washington was retrieving some of its answers from
Reddit, an online discussion board, and errantly informed a child
that Santa was a myth. The parents complained and the chatbot was
temporarily pulled from the rotation (but later won the $500,000
grand prize).
The periodic problems with Alexa underscored how far it had come
and how far it still had to go. By 2019, Amazon had sold more than 100
million Echo devices. In the span of a decade, a product spawned by
Bezos’s love of science fiction and infatuation with invention had be-
come a universally recognized product whose miscues and challenges
to conventional notions of privacy were widely covered by the media.
Yet Alexa still wasn’t conversational, in the way Bezos and Rohit
Prasad had originally hoped. And though it had spawned a small cot-
tage industry of startups and other companies pinning their hopes
on voice-enabled services and devices, not many people used Alexa’s
third-party add-ons or “Skills,” and developers still weren’t seeing
much revenue, compared to the way they did on the app stores of
Apple and Google.
Bezos fervently believed all that would come in the next few years.
Awed employees and Amazon fans who had watched him visualize

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 THE ÜBER PRODUCT MANAGER 53

Alexa and will it into existence believed the CEO could practically see
the future. But in at least one respect, he did not.
In 2016, he was reviewing the Echo Show, the first Alexa device
with a video screen. Executives who worked on the project recalled
that on several occasions when Bezos demoed the prototype, he spent
the first few minutes asking Alexa to play videos that ridiculed a cer-
tain GOP presidential candidate.
“Alexa, show me the video, ‘Donald Trump says “China,” ’ ” he
asked, or “Alexa, play Stephen Colbert’s monologue from last night.”
Then “he would laugh like there’s no tomorrow,” said a vice president
who was in the demos.
Bezos had no idea what was coming.

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