Board Chair of Amperity, Former CEO of drugstore.com, Former Vice Chairman and CIO of Charles Schwab
When Dawn Lepore walked into meetings with male direct reports, visitors who didn't know her would automatically assume one of the men was the CEO. Her own name didn't help: Dawn, easily misheard as Don. So she started introducing herself first and handing over her business card before anyone could guess wrong.
In this episode of What Fuels You, host Shauna Swerland sits down with Dawn Lepore, the former CEO of drugstore.com who spent 21 years at Charles Schwab building its online trading business before Howard Schultz told her over dinner that she was ready to run a company. Dawn walks through the internet skepticism she faced at Schwab, the boardroom conversation about when to disclose her own cancer diagnosis as a sitting public company CEO, and the reading statistic out of Washington State that pulled her into Teach For America. She never thought she was the smartest person in the room. She built a career proving that didn't matter.
📋 Episode Chapters
| 00:00 | Cold open: opportunities for the next generation of women leaders |
| 02:15 | Introducing Dawn Lepore: drugstore.com, Charles Schwab, and a four time Fortune honor |
| 04:40 | Rapid fire: Dent Island, a shelved piano career, and a childhood misconception about MBAs |
| 09:30 | The helicopter blade story: what Chuck Schwab taught her about entrepreneurs |
| 14:00 | Growing up on the East Coast, transferring to Smith College, and a mother who went back to school |
| 18:45 | Eleven percent: Washington's low income reading crisis and Teach For America |
| 24:00 | Getting hired at Schwab, a husband's career tradeoff, and 21 years in technology |
| 29:30 | Building Schwab's online trading business against industry skepticism |
| 34:15 | Mistaken for the assistant: executive presence and the Dawn versus Don problem |
| 38:50 | Howard Schultz over dinner in Hawaii: you're ready to be a CEO |
| 43:30 | A cancer diagnosis, a public company board, and the question of when to disclose |
| 48:15 | Competing against Amazon and selling drugstore.com to Walgreens |
| 53:00 | Board lessons: getting talked over, picking the wrong boards, and becoming a better director |
| 58:30 | AI, fake resumes, and what fuels Dawn Lepore now |
The Helicopter Blade Lesson
Dawn Lepore spent 21 years at Charles Schwab, and she is direct about how badly her career there started. Early on, low level and green, she sat in a meeting with Chuck Schwab that went, in her words, really badly. Her boss left her a voicemail afterward with a verdict: she had hit a helicopter blade in that meeting, and she did not understand entrepreneurs. He sent her home for the weekend with a book about how entrepreneurs think, nonlinear, allergic to being told to choose between A and B, comfortable in white space other people could not see.
She does not remember the title of the book. She remembers what it changed in her.
"I just love the nonlinear thinking, the risk taking, seeing things people don't see and other people don't see in white space."
-- Dawn Lepore
That reframe became the foundation of her working relationship with Schwab for the next two decades, through the buildout of the company's early internet trading business and long after.
Mistaken for the Assistant
As drugstore.com's CEO, Dawn Lepore ran into a problem that had nothing to do with strategy. Her name, spelled D-A-W-N, sounds identical to Don. When she walked into meetings with male direct reports and a visitor who did not know the team, the assumption defaulted to one of the men being the CEO.
She did not let it play out.
"I started walking in, introducing myself and handing my business card so they would know I was the CEO."
-- Dawn Lepore
She is careful to separate that fix from any claim about her own presence. She does not model herself on the executives who own a room the moment they walk in, people like her early Schwab mentor Dave Pottruck. Her version of authority looked different, and she built it anyway.
You're Ready to Be a CEO
Dawn Lepore never set out to run a company. She rose to vice chairman at Charles Schwab under Dave Pottruck and later Chuck Schwab, and she credits two board seats, at eBay alongside Meg Whitman and Howard Schultz, with changing her own read on herself. The turning point came over dinner in Hawaii. Dawn and her husband were on vacation with their newborn daughter and four year old son when they ran into Howard Schultz, who invited them to dinner. Partway through the meal, he told her she was ready to be a CEO. She told him he was kidding.
He was not. Schultz made introductions. One of them led to drugstore.com in 2004.
"I've met so many people, men and women, who don't realize how good they are. They don't realize how talented they are."
-- Dawn Lepore
She calls Schultz one of three or four people in her career who believed in her before she believed in herself, and she has tried to be that person for others since.
A Cancer Diagnosis and a Board Meeting
About a year into the drugstore.com job, Dawn Lepore was diagnosed with a rare cancer of the appendix. As a public company CEO, disclosure was not a personal decision alone. She brought it to her board immediately, and together they worked through the timing: get the surgery first, then decide whether the outcome required a public statement.
"Let's get the surgery first and then see where things are."
-- Dawn Lepore
The cancer had not spread, and she never required chemotherapy, so the board did not disclose. A few years later, her family faced a second, more serious health crisis when her husband was diagnosed with a blood cancer requiring a bone marrow transplant, at a time when their household's health insurance ran entirely through her job. He was unequivocal that she keep working. Dawn describes getting her children into family counseling on the advice of her own doctor as one of the best decisions she made during that period.
Beating Amazon, Then Selling to Walgreens
Dawn Lepore led drugstore.com from 2004 through its sale to Walgreens in 2011, competing the entire time against a company with structurally lower costs and no branch network to support.
"We were competing against Amazon. That is not for the faint of heart."
-- Dawn Lepore
She calls a turnaround one of the hardest things a leader will do in a career, harder than building from scratch, because momentum is already moving against you. What she remembers most from the outcome is not the sale price. It is the team.
"I had an amazing team, Shauna, and I still stay in touch with my team, and they've gone on to do amazing things."
-- Dawn Lepore
Eleven Percent
Dawn Lepore now co-chairs the Washington chapter of Teach For America, an organization founded by Wendy Kopp that places new college graduates in low income classrooms. Her reason for getting involved is a statistic she repeats without softening it.
"We are failing our low-income children."
-- Dawn Lepore
Only 11 percent of low income students in Washington read at grade level, by her account, against a statewide average closer to 30 percent for all students. She points to third grade reading and eighth grade algebra as hinge points: students who miss algebra in eighth grade cannot reach STEM careers because the math never catches up. She cites John King, former U.S. Secretary of Education and author of Teacher By Teacher, whose line stuck with her: the country needs to want for other people's children what it wants for its own.
5 Key Takeaways
Frequently Asked Questions
Who is Dawn Lepore?
Dawn Lepore is the former CEO and Board Chair of drugstore.com, which she led from 2004 until its sale to Walgreens in 2011. She spent 21 years before that at Charles Schwab, rising to Vice Chairman and Chief Information Officer, where she helped build the company's early online trading business. She currently serves as Board Chair of Amperity and sits on the boards of loanDepot, Servco Pacific, and SecureSave. Fortune magazine has named her one of the 50 Most Powerful Women in American Business four times.
What did Dawn Lepore say about being mistaken for a man while running drugstore.com?
Dawn Lepore said that because her name, Dawn, sounds like the male name Don, visitors meeting her team for the first time would often assume one of her male direct reports was the CEO. Her response was practical: she started introducing herself and handing over her business card immediately in every new meeting so there was no ambiguity about who was in charge.
How did Dawn Lepore decide whether to disclose her cancer diagnosis as a public company CEO?
Dawn Lepore was diagnosed with a rare cancer of the appendix about a year into her tenure as CEO of drugstore.com. She brought the diagnosis to her board immediately, and together they agreed to wait for surgical results before deciding on public disclosure. Because the cancer had not spread and she did not require chemotherapy, the board ultimately determined disclosure was not necessary.
What is Dawn Lepore's view on hiring in the age of AI?
Dawn Lepore says AI has flooded hiring managers with resumes generated using AI tools, making it harder to distinguish candidates who can actually do the job from those who have simply produced a polished application. She also advises leaders to hire early career talent who have used AI tools natively throughout school, arguing that companies without that expertise will fall behind AI-native competitors.
Why does Dawn Lepore co-chair Teach For America Washington?
Dawn Lepore co-chairs Teach For America Washington because of a statistic she cites often: only 11 percent of low income students in Washington State read at grade level. She points to eighth grade algebra as a critical gate, since students who miss it cannot catch up to pursue STEM careers, and argues the country needs to want for other people's children what it wants for its own.
Board Chair of Amperity, Former CEO of drugstore.com, Former Vice Chairman and CIO of Charles Schwab
When Dawn Lepore walked into meetings with male direct reports, visitors who didn't know her would automatically assume one of the men was the CEO. Her own name didn't help: Dawn, easily misheard as Don. So she started introducing herself first and handing over her business card before anyone could guess wrong.
In this episode of What Fuels You, host Shauna Swerland sits down with Dawn Lepore, the former CEO of drugstore.com who spent 21 years at Charles Schwab building its online trading business before Howard Schultz told her over dinner that she was ready to run a company. Dawn walks through the internet skepticism she faced at Schwab, the boardroom conversation about when to disclose her own cancer diagnosis as a sitting public company CEO, and the reading statistic out of Washington State that pulled her into Teach For America. She never thought she was the smartest person in the room. She built a career proving that didn't matter.
📋 Episode Chapters
| 00:00 | Cold open: opportunities for the next generation of women leaders |
| 02:15 | Introducing Dawn Lepore: drugstore.com, Charles Schwab, and a four time Fortune honor |
| 04:40 | Rapid fire: Dent Island, a shelved piano career, and a childhood misconception about MBAs |
| 09:30 | The helicopter blade story: what Chuck Schwab taught her about entrepreneurs |
| 14:00 | Growing up on the East Coast, transferring to Smith College, and a mother who went back to school |
| 18:45 | Eleven percent: Washington's low income reading crisis and Teach For America |
| 24:00 | Getting hired at Schwab, a husband's career tradeoff, and 21 years in technology |
| 29:30 | Building Schwab's online trading business against industry skepticism |
| 34:15 | Mistaken for the assistant: executive presence and the Dawn versus Don problem |
| 38:50 | Howard Schultz over dinner in Hawaii: you're ready to be a CEO |
| 43:30 | A cancer diagnosis, a public company board, and the question of when to disclose |
| 48:15 | Competing against Amazon and selling drugstore.com to Walgreens |
| 53:00 | Board lessons: getting talked over, picking the wrong boards, and becoming a better director |
| 58:30 | AI, fake resumes, and what fuels Dawn Lepore now |
The Helicopter Blade Lesson
Dawn Lepore spent 21 years at Charles Schwab, and she is direct about how badly her career there started. Early on, low level and green, she sat in a meeting with Chuck Schwab that went, in her words, really badly. Her boss left her a voicemail afterward with a verdict: she had hit a helicopter blade in that meeting, and she did not understand entrepreneurs. He sent her home for the weekend with a book about how entrepreneurs think, nonlinear, allergic to being told to choose between A and B, comfortable in white space other people could not see.
She does not remember the title of the book. She remembers what it changed in her.
"I just love the nonlinear thinking, the risk taking, seeing things people don't see and other people don't see in white space."
-- Dawn Lepore
That reframe became the foundation of her working relationship with Schwab for the next two decades, through the buildout of the company's early internet trading business and long after.
Mistaken for the Assistant
As drugstore.com's CEO, Dawn Lepore ran into a problem that had nothing to do with strategy. Her name, spelled D-A-W-N, sounds identical to Don. When she walked into meetings with male direct reports and a visitor who did not know the team, the assumption defaulted to one of the men being the CEO.
She did not let it play out.
"I started walking in, introducing myself and handing my business card so they would know I was the CEO."
-- Dawn Lepore
She is careful to separate that fix from any claim about her own presence. She does not model herself on the executives who own a room the moment they walk in, people like her early Schwab mentor Dave Pottruck. Her version of authority looked different, and she built it anyway.
You're Ready to Be a CEO
Dawn Lepore never set out to run a company. She rose to vice chairman at Charles Schwab under Dave Pottruck and later Chuck Schwab, and she credits two board seats, at eBay alongside Meg Whitman and Howard Schultz, with changing her own read on herself. The turning point came over dinner in Hawaii. Dawn and her husband were on vacation with their newborn daughter and four year old son when they ran into Howard Schultz, who invited them to dinner. Partway through the meal, he told her she was ready to be a CEO. She told him he was kidding.
He was not. Schultz made introductions. One of them led to drugstore.com in 2004.
"I've met so many people, men and women, who don't realize how good they are. They don't realize how talented they are."
-- Dawn Lepore
She calls Schultz one of three or four people in her career who believed in her before she believed in herself, and she has tried to be that person for others since.
A Cancer Diagnosis and a Board Meeting
About a year into the drugstore.com job, Dawn Lepore was diagnosed with a rare cancer of the appendix. As a public company CEO, disclosure was not a personal decision alone. She brought it to her board immediately, and together they worked through the timing: get the surgery first, then decide whether the outcome required a public statement.
"Let's get the surgery first and then see where things are."
-- Dawn Lepore
The cancer had not spread, and she never required chemotherapy, so the board did not disclose. A few years later, her family faced a second, more serious health crisis when her husband was diagnosed with a blood cancer requiring a bone marrow transplant, at a time when their household's health insurance ran entirely through her job. He was unequivocal that she keep working. Dawn describes getting her children into family counseling on the advice of her own doctor as one of the best decisions she made during that period.
Beating Amazon, Then Selling to Walgreens
Dawn Lepore led drugstore.com from 2004 through its sale to Walgreens in 2011, competing the entire time against a company with structurally lower costs and no branch network to support.
"We were competing against Amazon. That is not for the faint of heart."
-- Dawn Lepore
She calls a turnaround one of the hardest things a leader will do in a career, harder than building from scratch, because momentum is already moving against you. What she remembers most from the outcome is not the sale price. It is the team.
"I had an amazing team, Shauna, and I still stay in touch with my team, and they've gone on to do amazing things."
-- Dawn Lepore
Eleven Percent
Dawn Lepore now co-chairs the Washington chapter of Teach For America, an organization founded by Wendy Kopp that places new college graduates in low income classrooms. Her reason for getting involved is a statistic she repeats without softening it.
"We are failing our low-income children."
-- Dawn Lepore
Only 11 percent of low income students in Washington read at grade level, by her account, against a statewide average closer to 30 percent for all students. She points to third grade reading and eighth grade algebra as hinge points: students who miss algebra in eighth grade cannot reach STEM careers because the math never catches up. She cites John King, former U.S. Secretary of Education and author of Teacher By Teacher, whose line stuck with her: the country needs to want for other people's children what it wants for its own.
5 Key Takeaways
Frequently Asked Questions
Who is Dawn Lepore?
Dawn Lepore is the former CEO and Board Chair of drugstore.com, which she led from 2004 until its sale to Walgreens in 2011. She spent 21 years before that at Charles Schwab, rising to Vice Chairman and Chief Information Officer, where she helped build the company's early online trading business. She currently serves as Board Chair of Amperity and sits on the boards of loanDepot, Servco Pacific, and SecureSave. Fortune magazine has named her one of the 50 Most Powerful Women in American Business four times.
What did Dawn Lepore say about being mistaken for a man while running drugstore.com?
Dawn Lepore said that because her name, Dawn, sounds like the male name Don, visitors meeting her team for the first time would often assume one of her male direct reports was the CEO. Her response was practical: she started introducing herself and handing over her business card immediately in every new meeting so there was no ambiguity about who was in charge.
How did Dawn Lepore decide whether to disclose her cancer diagnosis as a public company CEO?
Dawn Lepore was diagnosed with a rare cancer of the appendix about a year into her tenure as CEO of drugstore.com. She brought the diagnosis to her board immediately, and together they agreed to wait for surgical results before deciding on public disclosure. Because the cancer had not spread and she did not require chemotherapy, the board ultimately determined disclosure was not necessary.
What is Dawn Lepore's view on hiring in the age of AI?
Dawn Lepore says AI has flooded hiring managers with resumes generated using AI tools, making it harder to distinguish candidates who can actually do the job from those who have simply produced a polished application. She also advises leaders to hire early career talent who have used AI tools natively throughout school, arguing that companies without that expertise will fall behind AI-native competitors.
Why does Dawn Lepore co-chair Teach For America Washington?
Dawn Lepore co-chairs Teach For America Washington because of a statistic she cites often: only 11 percent of low income students in Washington State read at grade level. She points to eighth grade algebra as a critical gate, since students who miss it cannot catch up to pursue STEM careers, and argues the country needs to want for other people's children what it wants for its own.
