Every ambitious person has a mental model of how careers are supposed to work. Pick a lane. Get good at it. Climb. The model is tidy, reassuring, and according to three engineering leaders at Two Sigma, largely fictional.
Angela Wang, Cecilia Ye, and Mae Santos have experience in civil engineering, technical sales, telecom, insurance, publishing, fintech startups, and quantitative finance. They’ve managed teams across time zones and continents.
Here are five commonly accepted career rules these leaders broke—and what they learned by doing so.
Myth 1: The fastest route is a straight line
Cecilia studied civil engineering and worked at it for two years before attending grad school for operations research, stumbled into a fintech startup, and has now been at Two Sigma for 11 years building optimizer engines that make real-time trading decisions.
“I didn’t set out to become a software engineer,” she said. “That was the job I found. And it turns out I really, really did enjoy it.”
Mae’s route is even more winding. Born and raised in the Philippines, she worked there for two years, consulted in Italy, and then moved to the U.S. where she ping-ponged through telecom (what’s now Verizon), insurance, and Citigroup. Then, she became the first Chief Enterprise Architect at John Wiley & Sons, the publisher. However, finance eventually found her: Two Sigma recruited her for three years before she finally said yes.
The standard advice says lateral moves are distractions. These careers suggest lateral moves are where the compounding effects happen.
Myth 2: You’ll know a detour when you’re on one
Angela started her career as a software engineer at Amazon Web Services. But she was curious about how the things she built actually impacted users, so she pivoted to a customer-facing role in solutions architecture. By pure software engineering metrics, she’d gone off track.
“Now I look back, and that experience really helps me a lot in my current role,” Angela said. She now leads the feature engineering team at Two Sigma, where she sets product direction and has to deeply understand her users’ needs. The “detour” into technical sales gave her precisely the skills she relies on today: product sense, user empathy, and the ability to speak the language of the people she’s building for.
“I think you want to keep an open mind about the opportunities that are available,” she said, “and learn as much as you can in that opportunity. You find surprising ways that those experiences combine in the future.”
You can’t always identify detours in real time. The experience that looks like a digression at twenty-eight might be the thing that makes you uniquely qualified at thirty-five, but you won’t know until you get there.
Myth 3: Set your goals early and work backwards
“I didn’t even think I would ever leave my country,” Mae said. Today, she’s leading reliability engineering, including global support. “You don’t really know what to dream about, because you don’t know what will present itself to you.”
The “visualize your future and reverse-engineer it” approach to career planning assumes you have enough information to set the right goals. If you grew up where certain paths weren’t visible, or if the field you’ll end up in doesn’t even exist yet, that assumption falls apart. What all three leaders described instead was a different kind of intentionality centered around building trust and executing.
“When you do that and you do a good job, people notice,” Mae said.
Cecilia made a related point about staying current: “The hot topics from 10 or 15 years ago — public cloud, distributed systems — those were emerging technologies then, and now they’re table stakes. What’s emerging now has a chance to become foundational later.”
You don’t actually need a master plan. But you do need to keep learning, because the landscape is moving whether you are or not.
Myth 4: The most experienced person in the room knows the most
Imposter syndrome comes up a lot in career conversations, usually as a feeling you’re supposed to manage and overcome. Cecilia offered something more useful: the idea that everyone knows more than you is often inaccurate.
“Don’t assume everyone knows more than you do, even when you’re new,” she said. “It’s easy to think, ‘that person has five more years of experience, they must know everything.’ But if you’re the one who’s been deep-diving into a problem or a system, chances are you’re the expert in the room.”
Expertise is a function of proximity, not necessarily tenure. The person closest to the problem usually understands it best, and that person is often the one who’s least confident about speaking up.
Angela described a version of this from earlier in her career, when coding interviews— different from classroom or day-to-day engineering work— made her question whether she belonged in the process. “Eventually with focused practice, I passed interviews at many companies. It was a good reminder that most new skills feel hard in the beginning, but get easier with repetition. The first time something feels uncomfortable doesn’t mean you won’t get good at it.”
The discomfort of being new is simply proof that you’re learning.
Myth 5: Technical skills are what matter most
All three leaders are deeply technical. Angela’s team builds tools that transform raw data into input features for models. Cecilia’s team develops optimizer engines that make real-time trading decisions using mathematical optimization and quantitative portfolio construction. Mae’s team runs production systems and provides global support. And yet, when asked what advice they’d offer to earlier-career engineers, none of them led with technical skills.
Angela emphasized initiative. When she joined Two Sigma, she didn’t just complete her assigned projects; she leveraged her AWS expertise to improve her team’s operational standards. That proactive approach, she said, “really helped me build trust with my team, which led to a lot of the leadership opportunities that came along in the future.”
Mae emphasized relationships. “Peer mentors are so valuable because they will tell you from a perspective of knowing, because they live it too,” she said. She also pointed to something subtler: the value of how people talk about you when you’re not in the room. “It’s one thing for people to talk about you when you’re in the room,” she said. “When people talk about you when you’re not in the room, that means you’ve made an impact—and they will actually stand up for you.”
Every job change in Mae’s career, across multiple industries and countries, came from a referral. Someone who’d worked with her recommended her to someone else. Technical skills got her in the door, but relationships opened the next one.
The takeaway
These leaders didn’t follow a strict plan so much as they accumulated experiences, stayed open to what came next, and trusted that the pieces would connect, often in ways they couldn’t have predicted.
“Think of your career as a marathon, not a sprint,” Angela said. “Anything you do will only add to the bag of skills you bring to the table.”
Cecilia: “Stay curious, and have confidence in your growing skills and expertise.”
And Mae, who spent decades crossing industries and continents before landing at Two Sigma: “The world will always surprise you. Be ready for that surprise, because it might be good.”
This piece is adapted from a panel discussion at the 2025 Grace Hopper Celebration.
