What does Homer’s Odyssey have to do with AI advisory agents? Quite a bit, says Matt Greenwood, Two Sigma’s Chief Innovation Officer, whose 20-year tenure at Two Sigma has some epic qualities of its own.
Over the course of a wide-ranging discussion on the Dev Interrupted podcast, Greenwood connected the dots between classical wisdom and cutting-edge technology, sharing insights on how to navigate the constantly shifting landscape of AI and how to foster a thriving engineering culture when change is the only constant.
The Innovation S-curve
Innovating intentionally isn’t about always chasing the shiniest new tech, but strategically navigating the “S-curve” of technological advancement—the initial slow growth, followed by rapid acceleration, and eventual plateau as a technology matures.
Anticipating the next curve is crucial for sustained innovation. Greenwood advocates an approach he calls “epsilon and omega” that’s become a cultural touchstone at Two Sigma and entails small, iterative steps (epsilons) contributing to a larger, long-term vision (omega).
Sustained innovation also means acknowledging past decisions, learning from them, and when necessary “forgiving ourselves,” as Greenwood puts it, recognizing that what seemed optimal at one time may not be suitable for future challenges. But the rewards of a curious and adaptive mindset can be great: “Once you’ve built a platform, you can stand on it and you can see further than you did, and you can see problems that you never had before.” At that point, he says, the cycle begins again.
A Framework for Using LLMs and Other AI Approaches in the Investment Process
Applying machine learning in the investment process presents both exciting possibilities and very complex challenges, says Greenwood–though Two Sigma is certainly no stranger to either. “Happily, we’ve been doing this for a long time. We’ve been doing machine learning…for literally decades.” Taking a curious, adaptive, and long-term approach has helped the company progress through multiple AI S-curves over the years.
Still, the pace of AI innovation is so rapid that it can be difficult for leaders to decide where to focus time, resources, and attention. He suggests a framework he’s been using for thinking about AI’s role in the systematic investment process, categorizing its key uses as:
- Advisory: Providing insights and suggestions.
- Oracle: Validating outcomes and ensuring accuracy.
- Operational: Automating routine tasks and workflows.
- Agentic: Coordinating multiple AI functions to perform complex tasks at scale.
Matt believes this framework allows teams to harness AI’s power strategically, freeing up human talent from repetitive tasks. Greenwood believes this shift enables a focus on higher-level thinking and innovation—”ultimately retaining human creativity and control, not ceding it to machines.” The question for leaders, then, is not whether to adopt AI, but rather how the technology can be best incorporated to empower human ingenuity and drive meaningful progress.
Cultivating a Thriving Engineering Culture: The Human Element
Over the course of his career, Greenwood has learned that building a successful engineering organization requires more than just cutting-edge technology; it requires cultivating a supportive and stimulating environment. He stresses the importance of empathy, recognizing that “everyone brings their whole self to work”–not just their technical skills. The more of an employee’s “whole self” is engaged, the more likely they are to stay and be excited about their work.
To help foster this depth of engagement, Two Sigma created a “hacker lab“—a “gym for the mind,” as Greenwood calls it, where employees from all backgrounds can learn, share knowledge, and create things ranging from robots to racing simulators. This holistic approach, he argues, makes employees more likely to stay engaged and excited about their work, recognizing that a thriving work environment nourishes not just an individual’s technical abilities, but their overall well-being and intellectual curiosity.
This focus on development allows individuals and teams to adapt, evolve, and thrive in the face of constant change–and ultimately contribute their unique talents to the collective success of the company and its clients.
Continue the Journey: Listen and Learn More
Listen to the full conversation on the Dev Interrupted Podcast to dive deeper into Matt’s insights on AI, innovation, and engineering culture.
And don’t forget to explore our open roles and discover how you can contribute to the future of finance at https://www.twosigma.com/careers/.
