Two Ways to Fail: Give Up or Die." How Sigma Software CEO Katherine Built a Foreign Office, Completed a Half Ironman, and Learned to Lead on One Rule

"There are only two ways to fail: give up or die. And neither is a reasonable option."

That is the saying Katherine's team uses to remind themselves who they are. She means it literally. When she was trying to open Sigma Software Group's first Latin American office, she tried recruiting agencies, acquisition targets, universities, and different countries for an entire year. Nothing worked. Then in a brainstorming session, someone mentioned speaking at a developer conference. She found one in Brazil, submitted a paper, got accepted to one of the most selective conferences in the region, went, fell in love with the community, and pivoted the entire Latin American strategy to Brazil on the spot.

Then she went back to the same conference the following year and gave her talk in Portuguese. She had submitted the paper in December, in Portuguese, with a translator. The conference was in March. She did not speak Portuguese. She had three months to learn.

Katherine rose from junior software developer to CEO of Sigma Software Group Americas in 16 years. In this episode, she is completely direct about how she actually did it — not as a philosophy, but as a series of specific situations where she refused to stop.

You'll learn:

• How she spent a year hitting walls trying to open a Latin American office, the random brainstorming idea that changed everything, and why resolve in the goal combined with total flexibility in the approach is what finally broke through.
• Why she submitted a conference paper in a language she couldn't speak, learned Portuguese in three months with 15 minutes a day of consistent practice, and used the speech itself to encourage Brazilian engineers not to be afraid of making mistakes in English.
• The grandmother she is named after: a high-level judge described by everyone as tough, smart, and fair. Never nice or sweet. And why Katherine wants to invoke strong opinions rather than be universally liked.
• Why she believes being perceived as aggressive is an acceptable trade-off for being decisive and authentic — and where she draws the line between assertive and actually offensive.
• Her father's career advice that drives her decisiveness: "A wrong direction is better than no direction." Make the call, correct fast, keep moving.
• What she learned from completing a Half Ironman — 1.2 miles of swimming, 56 miles on a bike, then a half marathon. She was terrified of the bike, had crashes, had scars, genuinely questioned whether to continue. She finished. She signed up for another one.
• How she managed a solo transatlantic flight from Barcelona to Dallas with a one-year-old and a not-yet-three-year-old by accepting beforehand that it would be horrible — and why pre-accepting the struggle removes the frustration when it arrives.
• The two tools she uses when doubt sets in: reminding herself of hard things she has already done, and surrounding herself with people who will do the same reminding when she can't.

About Katherine: CEO of Sigma Software Group Americas, Katherine rose from junior software developer to CEO in 16 years. She leads the Americas expansion for a global software company originally founded in Eastern Europe, including building the company's Brazilian office from the ground up. She is also a Half Ironman finisher and a Portuguese speaker.

Her first year in corporate. She noticed her male peer was getting more technical work than her. She raised it with her supervisor — not loudly, not aggressively, just directly. Instead of addressing it with her, the supervisor took it to a broader forum and told others there was "a trouble candidate in the team." The message filtered back to her. She had asked for fair treatment and had been labeled a problem for it.

What happened next is what makes the story worth hearing. A senior leader stepped in, routed someone to talk to her properly, understood what she actually needed, and gave her a product certification project. She suspected it was a test. She treated it like an opportunity. She delivered. That quarter, she won a company excellence award.

Aditi is Managing Director at Accenture's Cloud First Data and AI Group, where she leads digital transformation for large clients. She has been called outspoken — a label she has never apologized for — and decisive, a word she noticed women rarely claim for themselves.

In this episode she gets specific about what it actually looks like to speak up when you're new, when the reception is hostile, and when the outcome is uncertain.

You'll hear:

• Why being labeled "trouble" for asking a fair question was the moment that taught her the most about how organizations actually work — and why she considers the outcome a net positive even though it was uncomfortable to live through.
• What she did when a senior client contact told her directly "I don't think you even know this stuff." She didn't react. She absorbed it, reported it proactively to her leadership before it could reach them filtered through someone else, and stayed focused on delivery. What she learned about the difference between reacting and responding.
• Why outspokenness without data is just noise — and why outspokenness backed by facts, research, and conviction is one of the most useful things a leader can bring to a team.
• How she creates conditions for her own team members to speak up — and why, when she opens a conversation by sharing her own honest view first, she consistently finds that people who had something to say but were waiting for permission start talking.
• What "decisive" actually means in practice when you're managing a team with competing voices, a client with high expectations, and no time to wait for perfect information.

About Aditi: Managing Director, Accenture Cloud First Data and AI Group. Digital transformation leader.

She Stopped Leading With Her Title and Started Saying "I'm a Technology and Business Diplomat." People Immediately Wanted to Know More. Equifax SVP D'Lovely on Networking, Personal Boards, and Career Infrastructure

She was laid off twice. Both times, by the time the hiring manager called her, three or four people at the company had already been talking about her. Not because she got lucky. Because she had spent months having breakfasts, following up on cold contacts, asking questions instead of pitching, and making it easy for people to pass her name along. One of those contacts had been on a month-long holiday — not ignoring her. She kept following up. They finally had lunch. That person said: "You're the real deal." She talked to people. The hiring manager called within a month.

D'Lovely is SVP of Product, Data and Analytics, and Technology Planning and Execution at Equifax, a finalist for Woman of the Year in Engineering by the Women in Technology organization, and the person who calls herself a "Technology and Business Diplomat" — a title that took years to develop and immediately makes people want to know more.

In this episode, she breaks down how networking actually works as a career infrastructure system, not a social obligation.

You'll learn:

• Why being laid off the first time forced her to admit her network wasn't working — she was going to events and talking to people, but she wasn't being methodical. What changed after that realization and how she got both subsequent roles entirely through network relationships.
• The five-week story: how she targeted a specific company, got stonewalled on LinkedIn, shifted to building relationships across the organization, finally got a lunch, listened more than she talked, and had the hiring manager call her a month later saying people had been talking about her.
• Why "I need a job" is the wrong thing to be broadcasting in your network — and what to ask for instead. Almost nobody has a job in their pocket, but everybody can give you their story, their honest read on a company's culture, and an introduction to someone who needs to know you exist.
• The three-tier model for a personal board of directors: close inner circle, mid-range colleagues in similar roles and at similar levels, and the periphery of executive mentors and coaches. Who belongs in each tier, how often you should connect with each, and why having everyone at the same level above you actually limits what your board can do for you.
• Why you should never introduce yourself by listing what you do — and how to develop a power statement that makes the other person immediately want to know more. The difference between "I manage software projects" and "I turn engineering chaos into customer results."
• The exact tactics for staying top of mind without being annoying: leaving voicemails during your commute, following up twice without apology, sending a draft message someone can forward on your behalf so they have to do almost nothing to help you. Make it easy, close the deal, don't wait to be remembered.
• Why the most important networking conversations never mention work at all — and how those are often the ones that lead to the most powerful long-term relationships.

About D'Lovely: SVP of Product, Data and Analytics, and Technology Planning and Execution at Equifax. Finalist, Woman of the Year in Engineering, Women in Technology. Self-described Technology and Business Diplomat. Based in Atlanta.