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EPISODE 011 · FINTECH → LEGAL TECH

Amy Kugali McWilliams has spent nearly twenty years in marketing, most of it in technology. South by Southwest, Chipotle, software, finance, and now legal technology at Epiq. She is also a former roller derby blocker who teaches marketing inside Texas men's prisons. This episode is about the thing that reorganized everything: being laid off at twenty-eight, and what she learned from the people who picked up the phone afterwards.
Full disclosure, which Sondra makes in the first minute. The two of them worked together years ago. This is a reunion as much as an interview, and it sounds like one.
Sort of, and not in the way she planned. She studied psychology and communications, then took a master's in advertising, and has never worked in advertising a day in her life.
“I knew I liked communications, even though I couldn't figure out what that means.”
Amy Kugali McWilliams, Women IN episode 11
What she had instead was a direction and a pile of internships. One of them was at a PR firm she hated immediately, which she counts as useful rather than wasted. Her advice to students is that an internship earns its keep as much by ruling things out as by ruling them in. You are not only finding the work you want. You are finding the work you now know you will never do again.
She was living in New York for her undergraduate degree when September 11th happened. The economy fell apart, she did not know what to do next, and graduate school became the answer by default rather than by plan. It led to an internship at South by Southwest that turned into a job, and to the people who made technology look interesting. Austin was not a technology hub yet. It is now.
That is the part worth sitting with. The first job out of school did more to set her direction than the degree did, and she did not choose it so much as arrive at it after a detour she never wanted to take.
She was a few years into a technology company, newly married, newly back in Houston, and certain things were going well. The company needed to slim the books before a funding round and cut thirty percent of its staff.
“I did everything right and I got laid off. It was a huge blow to the ego.”
Amy Kugali McWilliams, Women IN episode 11
The chief marketing officer told her directly that it had nothing to do with her work. She could not hear it. She went home and cried for two days, worse, she says, than any breakup. The money worry came second. The first blow landed on a self-image built entirely on having always done the right thing, and a layoff does not care about that.
This is the part most layoff advice skips. The spreadsheets and the severance calculators assume the problem is arithmetic. For her, for the first forty-eight hours, it was not.
Talking to people, including people she barely knew. The ones who had been around longer kept telling her the same thing, which nobody had ever told her before. Everyone gets laid off at some point. Her mother was a teacher. Layoffs were not part of the culture she grew up in, and so the event arrived with no frame around it at all.
Then she went to interviews braced for the shame of explaining it, and nobody blinked.
“No one batted an eye. It wasn't even a conversation topic.”
Amy Kugali McWilliams, Women IN episode 11
She put it on LinkedIn, had lunch with everyone she had ever known, and was interviewing quickly. The second ego hit, she says with some amusement, was discovering that nobody cared. She had spent two days certain her record was ruined and then watched hiring managers move straight past it to the next question.
Almost none of hers are in her field. A former professor. A former boss she has not worked with in twelve years. Her father-in-law, the only man on the list, who spent long enough in business to be the one who told her that everyone gets laid off. A friend in Los Angeles who works in music and was the receptionist at South by Southwest when Amy worked there.
“Somebody who thinks you're awesome. Someone who is rooting for you.”
Amy Kugali McWilliams, Women IN episode 11
The test is not seniority and it is not industry. It is whether they have a vested interest in you. A current colleague fails that test more often than people expect, because a current colleague is also inside the thing you need perspective on. And if you do not have anybody like that, she adds, get a therapist. That helps too.
Teaching marketing, through the Prison Entrepreneurship Program. She got there through the same chief marketing officer who laid her off, reconnected on LinkedIn years later. Circle of life, as Sondra puts it.
The men in the program are in the last three months of their sentences. Entry is competitive. Professors from Rice and around Houston teach entrepreneurship, and each man builds a business plan for something he could run after release, when being a felon makes finding a job very hard. Amy advises on the marketing. Food trucks, lawn services, laundromats. Direct to consumer work she has never otherwise done in a twenty year career spent selling software to businesses.
One man she worked with had been inside for thirty-six years. He went in before people had computers. He has never held a smartphone, and he is building a business plan for a world that reorganized itself entirely while he was away.
She also got turned away at the gate once for wearing a sleeveless top in July, and had to buy a replacement shirt at a Family Dollar around the corner. Both halves of that are true at the same time, which is most volunteer work honestly described.
She saw a flyer in Houston, went to a bout, signed up for the free skating lessons and was hooked. She skated as a blocker until a concussion retired her.
“You should do hard things sometimes because it's good for your brain.”
Amy Kugali McWilliams, Women IN episode 11
It was the strongest she has ever been, and she was covered in bruises the whole time. The point is not the sport. It is that she took up something physically difficult as an adult, in public, badly at first, and it did something for her that nothing at a desk was going to.
Being everyone's cup of tea. She describes herself as someone who wants everyone to get along and wants to be well liked, and she is clear that the shift was not rejecting that so much as loosening her grip on it. A job, an activity, a person. If it is not a fit, it no longer bothers her the way it used to.
Work is the exception, and she knows it.
“It could be said that I have too much of my self-worth wrapped up in my work.”
Amy Kugali McWilliams, Women IN episode 11
She has a stop time. But while she is there, she is locked in. That is a more honest account of work-life balance than most people give, because it does not pretend the wiring changed. It just has a boundary around it.
“It's going to be fine. It might not always be ideal. In fact, it might be crappy sometimes, but it's going to be fine.”
Amy Kugali McWilliams, Women IN episode 11
Maintain your connections. If there is a friend you have not spoken to in a while, send the text, get the lunch. The people who care about you want to support you, so keep them in your life even if it is once a year. The support system she leaned on at twenty-eight was built years before she needed it, which is the only time it can be built.
Listen to Women IN episode 11 with Amy Kugali McWilliams wherever you get your podcasts.
Who is Amy Kugali McWilliams?
Amy Kugali McWilliams is a marketing leader at Epiq, with nearly twenty years across technology, finance, healthcare and legal technology. She began at South by Southwest's Interactive Festival in Austin and has since worked in fintech, healthcare technology, risk management and, for the past decade, legal technology and eDiscovery. She holds a master's in advertising from the University of Texas at Austin and a Leadership Principles certificate from Rice, and she volunteers with the Prison Entrepreneurship Program in Texas. She is also a former roller derby blocker.
Does being laid off hurt your chances at the next job?
In Amy Kugali McWilliams' experience, no. She was laid off at twenty-eight when her company cut thirty percent of staff ahead of a funding round, and she went into every interview braced to explain it. Nobody treated it as a topic worth pausing on. The second blow to the ego, as she puts it, was discovering that nobody cared.
What should you do first after a layoff?
Talk to people, including people outside your field and outside your company. The thing she most needed to hear, that everyone gets laid off eventually, came from someone who had simply been working longer than she had. She then put it on LinkedIn, had lunch with everyone she had ever known, and was interviewing quickly.
Who should be in your professional support system?
Not necessarily colleagues. Amy Kugali McWilliams' list includes a former professor, a former boss she has not worked with in twelve years, her father-in-law, and a friend in the music industry who was the receptionist at South by Southwest when Amy worked there. The qualification is not seniority or industry. It is whether they have a vested interest in you. If you do not have anyone like that, she says, get a therapist.
What is the Prison Entrepreneurship Program?
A Texas program for men in the final three months of their sentences. Entry is competitive. Professors from Rice and around Houston teach entrepreneurship, and each participant builds a business plan for something he could run after release, when a felony record makes finding a job very hard. Amy Kugali McWilliams volunteers as a marketing advisor on food trucks, lawn services and laundromats.