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.

She credits three people with transforming her career trajectory at AWS and beyond. Tatiana got her into AWS. Wayne sponsored her advancement within it. Dan helped her break into venture capital as a partner at Felicis Ventures. She did not stumble into these relationships. She built them intentionally, maintained them with discipline, and gave back at every stage — even when what she could give seemed small compared to what she was receiving.

Nancy was Director and General Manager at AWS Data Protection when this episode was recorded. She has since been promoted to CTO. She is also the founder of Advancing Women in Tech (AWIT), a venture partner at Felicis Ventures, and served on the board of UPenn's School of Engineering Online. She gave the commencement speech at the University of Pennsylvania. The central idea of that speech: build your personal board of directors.

In this episode, she breaks down the full framework.

You'll learn:

• Why she calls her personal board of directors the most important career strategy she has used, and what it gave her that mentors, managers, and luck could not.
• The three specific people on her board, what each one did for her, and how those relationships were built over time rather than asked for upfront.
• The right way to ask for raw, unfiltered feedback from someone who outranks you significantly — including why the first or second meeting is almost never the right time, and what you need to establish first.
• Why follow-through is a bigger differentiator than IQ, communication skills, or credentials. "They need to want it more than you want it for them" — the advice from her own board member that she now uses with every mentee she works with.
• How compound interest applies to professional relationships: why small, consistent gestures build more than a single impressive one, and what she does quarterly to keep her board relationships healthy without it feeling transactional.
• She was preparing to meet a Fortune 500 CEO to ask him to join her board. His dog had just had surgery. She planned to bring dog treats. The reminder: every successful person is still just a human being, and treating them that way is both the right approach and the most effective one.
• The Lululemon wardrobe mistake: her first Silicon Valley job, she bought a whole new wardrobe to fit in with the casual culture. Hated it. Didn't feel herself. What she learned about knowing who you are and using that as a career filter rather than a liability.
• Why at her leadership level she says no far more often than yes, why she uses Amazon's "have backbone, disagree and commit" principle to push back when the room disagrees with her, and what she tells her mentees about having the courage to hold the unpopular opinion.

About Nancy: At the time of this recording, Nancy was Director and General Manager, AWS Data Protection at Amazon Web Services. She has since been promoted to CTO. She is also the founder of Advancing Women in Tech (AWIT), a venture partner at Felicis Ventures, and has served on the board of directors of the UPenn School of Engineering Online. AWIT's Coursera curriculum has reached tens of thousands of learners globally.

Advancing Women in Tech: https://www.advancingwomenintech.org/

She came to the United States from Cameroon almost 30 years ago with a master's degree in education, almost no exposure to computers, and a goal to pursue a doctorate. Her two sisters, both already in IT careers, redirected her. She thought she could never succeed in the field. She became an IT help desk worker. Then a network administrator. Then an IT manager. Then a director. Then a CIO. Then a COO in Spain. Then a Chief Technology and Innovation Officer. Then a Vice President and CIO at a California State University. Her PhD — the original goal from 1995 — she completed in 2019. Twenty-four years later than planned.

Dr. Monique is Vice President for Information Technology and CIO at California State University, Chico, and a multiple CIO award winner. In this episode, she shares the specific moments — some planned, some forced on her — that defined how she uses her voice to steer her career.

You'll learn:

• Dr. Monique was the only person of color in senior leadership at an elite STEM university. She organized the conversation her organization wasn't having: a roundtable on race and social justice with her IT team. She went first, dropped her own protective mask, and shared her own experiences with racism — which is what unlocked everyone else. The sessions grew into a six-cohort DEI program across the entire university, co-developed under her executive vice president.
• A junior male employee publicly questioned in a group meeting whether she was being overpaid. Her two white male predecessors' salaries had never been questioned by that same group. She stood up calmly and said: "I did not come to this meeting to discuss my salary. But if I must, I believe I am appropriately compensated for the work that I do." The room went silent.
• How she trained herself to respond to the angry Black woman stereotype: when emotions rise, her voice drops lower instead of higher. She slows down. She puts her hands on her thighs. She stands with her feet flat on the ground. She stated her intention to her team before a difficult conversation: "I am standing up not to be overpowering, but because having my feet on the ground helps me control my emotions." Days later, people were still reaching out saying it changed how they see her.
• At a conference in Chicago, a vendor friend insisted she skip the Super Bowl to meet someone he knew. She agreed. The stranger asked her about her career. She "unabashedly spoke up" about her achievements. He told her they were building a role to lead technological innovation. She applied. She got the job as Chief Technology and Innovation Officer.
• She applied for Deputy CIO at the Colorado School of Mines with none of the required higher education experience. Got interviewed. Got the job. Eight months later: interim CIO. Three months after that: full CIO. She directly asked her executive vice president there to sponsor her — sharing her goals specifically and asking for stretch assignments. That EVP let her serve as deputy COO while still serving as CIO.
• The framework she and Ivna coin in this episode: "confident humility." Women often embrace the humility and delete the confidence. The combination of both — taking no apologies for what she has accomplished while doing so with poise and grace — is what she credits for attracting sponsors throughout her career.
• Why she asks directly for sponsorship by naming specific career goals and specific asks, and why she audits her sponsor network regularly — including thinking about what would happen to her if her strongest advocate left the organization tomorrow.

About Dr. Monique: Vice President for Information Technology and Chief Information Officer at California State University, Chico. Multiple CIO award winner. Immigrant from Cameroon. Former CIO at Colorado School of Mines, Chief Technology and Innovation Officer, and Chief Operating Officer in Spain. PhD in Education and Organizational Leadership. Started her IT career at the help desk.

Her Peer Kept Misattributing Statements to Her Team. She Let It Slide Once. The Second Time She Confronted Her Directly.

She had a verbal offer within four days. They were eager. Before she accepted, she called HR and said: "Before I accept, I want to speak with my manager's manager." That request could have cost her the role entirely. She had already weighed it: if they say no, that tells me everything I need to know about this culture. If they say yes, I make a more informed decision. Within 24 hours, the executive cleared his calendar during a conference lunch and took a 30-minute call. He opened with: "What questions do you have for me?" She asked everything. She took the job.

Saadia is Global Chief Information and Technology Officer at Coverys, a medical liability company, with 20 years of IT experience across multiple Fortune 100 companies. In this episode, she walks through the specific moments in her career where courage was required — and exactly how she built it.

You'll learn:

• Her peer kept misattributing statements to her and her team in leadership meetings. She let the first incident slide. The second time, she requested a direct conversation: "This is what I heard. You were named as having stated this. Can you explain why?" The peer was speechless. Saadia set a clear expectation for next time — and never had the problem again.
• How she built a two-year disagreement relationship with a boss who actually respected being challenged: listen first before responding, don't feel obligated to disagree on the spot, return with facts, and always explain your thought process rather than just your conclusion.
• The career pivot her mentor pushed her into: leave IT entirely — her entire professional identity — and take a business strategy role with a Chief Marketing Officer. She lost her direct reports and became an individual contributor. Her biggest fear: disrupt her tech trajectory and never get back. Her mentor's answer: "Try it. If you don't like it, come back." She did it for two years, returned to IT as an executive, and credits that pivot for how she now thinks about strategy, stakeholders, and technology implementation.
• Why she stopped procrastinating in meetings after watching male peers say her exact ideas out loud and get the credit. The mindset that unlocked it: "I am in this room for a reason, and so is everyone else. Equal footing." Think you're the smartest: you stop listening. Think you're the worst: you stop speaking. Find the middle.
• Her direct advice on bias: keep an eye on how your ideas and voice are treated from day one. You will know quickly whether biases exist. Your manager and your peers are the most critical variables. If your manager has bias toward you, it will not work. Find a leader who respects what you bring, not just who you are.
• Why she proves herself to herself rather than to others — and why she has watched other women leaders make flawed decisions every time they shifted into "proving to others" mode.
• The skip-level coffee chat practice she has run for four years: meets individual contributors without their managers, no script, asks what challenges they are facing, never names names when sharing themes upward. The trust it builds has changed how her organization speaks up.

About Saadia: Global Chief Information and Technology Officer at Coverys, a medical liability company. Saadia has 20 years of IT leadership experience across multiple Fortune 100 companies and is a recognized voice on courage, leadership, and building speak-up cultures in technology organizations.

She Won a 40 Under 40 Award and Kept It Private. It Took Her 12 Years to Say Out Loud She Wanted to Be an Executive. People2.0 VP Erika on Self-Advocacy for People Pleasers

She received the SIA 40 Under 40 award. It was a big deal. And she kept it almost entirely to herself. She didn't know how to celebrate it externally without coming across as cocky. She treated it like a private accomplishment. Then she called her former leaders Kip Wright and Sunny Ackerman for advice on how to own it and talk about it. Their response changed how she thinks about her entire career: "Erika, if you don't tell the people around you — your internal sponsors, your mentors, everyone outside — we don't know how to help you get there."

That conversation also came with another realization. It had taken her over 12 years to say out loud, to anyone, that she wanted to become a company executive. Not because she didn't want it. Because the impostor syndrome was that loud.

Erika is VP of Strategic Account Management at People2.0, a SIA 40 Under 40 honoree, and by her own description a recovering people pleaser. She spent most of her early career waiting for leaders to notice her, navigate for her, and tap her for opportunities. It worked — until it stopped working. When she hit a plateau at Manpower, she realized: "If I didn't take those steps on my own, I would have stayed where I was at and probably gone stagnant."

In this episode, she breaks down what changed and how.

You'll learn:

• Why she kept her 40 Under 40 recognition private, what it felt like to not know how to celebrate her own win, and the mentor conversation that finally unlocked her ability to speak about her accomplishments.
• What it means to hit a career plateau as a people pleaser, and the moment she understood that waiting for others to drive her career was a strategy with an expiration date.
• Why she reached out to former leaders Kip Wright and Sunny Ackerman when she was ready to make a move, and why outside perspectives from people who know your results but are no longer your direct managers are some of the most valuable career input you can get.
• The 3 criteria she uses to choose mentors and sponsors who will actually move the needle for you.
• How she negotiated for work-life balance after years of traveling up to 90% of the time as a mother of two, and why the interview stage is the highest-leverage moment to ask for what you need.
• Why data-driven conversations change everything in salary and promotion negotiations: "For the past 24 months, I hit my targets at X amount" is a different conversation than "I think I deserve a raise."
• How to talk about your accomplishments in a way that reads as confident and grateful rather than arrogant, including what to do if you don't have formal SMART goals to point to.

About Erika: Vice President of Strategic Account Management at People2.0, SIA 40 Under 40 honoree, recovering people pleaser, and vocal advocate for women owning their career narrative. She has built her career across Manpower and People2.0 in strategic accounts and sales leadership.