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From scaling engineering teams at Uber pre-IPO to building Jarvis for Healthcare—my talk with Anant Gupta, the SVP of Engineering and Data Science at Included Health, reveals timeless lessons about building impactful teams and the future of AI in healthcare.
Here are some of the key takeaways from our conversation.
1. The True Role of a Leader: Impact Over Team Size
Early in our discussion, Anant shared a story that stuck with me: when he took on a role at Uber, he started with just two engineers—a career low in terms of team size. Yet, he embraced this challenge because he believes that leadership is less about managing a large team and more about the impact a leader can create. As he put it, “You don’t have to look at the number of people you manage; it’s the impact that you can create.”
This insight is a reminder that, as leaders, we should focus on multiplying our influence and driving results rather than simply counting heads. Anant’s ability to scale that initial team from 2 to 70+ mobile engineers at Uber exemplifies how a leader with the right mindset can transform even the smallest of teams into a powerhouse.
2. Creating a ‘Get Things Done’ Culture
At Uber, Anant experienced a unique culture that focused on speed, execution, and, above all, getting things done. Uber’s obsession with metrics, a high level of autonomy, and the encouragement to push forward despite challenges created an environment where innovation thrived. Anant highlighted the value of “metric ownership” over “surface ownership.” Rather than owning a specific part of the product, engineers owned the results, like trip growth, which gave them the freedom to make changes across the user experience.
It’s a powerful concept: when your team has clear goals and the freedom to pursue them, they can innovate without being bogged down by silos. Anant emphasized that this culture came from the top down, where even Uber Co-Founder Travis Kalanick would roll up his sleeves to unblock obstacles, inspiring the entire team to adopt the same mindset.
3. Navigating the Hiring Challenge in Hyper-Growth
One of the biggest challenges Anant faced was hiring at scale, particularly during Uber’s explosive growth. Hiring 70 engineers is no small feat, and Anant’s approach offers valuable lessons. He underscored the importance of a clear vision when attracting top talent. Early in his tenure at Uber, Anant often found himself explaining why building the platform was technically complex and why engineers should join. He learned that a compelling vision can be the key to attracting the right people.
Anant’s experience with Uber’s “bar raiser” program highlighted the importance of maintaining a consistent hiring standard, especially in fast-growing organizations. Programs like these help build trust across teams and ensure that everyone shares a common commitment to excellence.
4. Balancing Risks in Hiring: False Positives vs. False Negatives
Anant also touched on a dilemma that many leaders face: when building a team, should you prioritize avoiding false positives (hiring someone who doesn’t work out) or false negatives (missing out on a great candidate)? He admitted that his stance on this shifts depending on recent experiences, but he stressed the importance of avoiding false positives when hiring for leadership roles. The wrong leader can have a significant negative impact, so taking the time to find the right fit is crucial.
For more junior roles, he’s willing to take calculated risks, betting on candidates who have potential but need development. This approach reflects a nuanced understanding of how different roles impact a team and the organization’s broader goals.
5. AI’s Role in Transforming Healthcare: A Vision for the Future
Anant’s perspective on AI was especially enlightening, as Included Health aims to transform how people access and experience healthcare. He sees AI as a tool that can create efficiencies in internal processes, such as automating code reviews or helping clinicians make better decisions through data insights. Yet, what excited me the most was his vision of AI as a partner to patients, guiding them through their healthcare journeys.
He shared the aspiration of building a “Jarvis for healthcare,” where AI can use patient data to deliver personalized recommendations, making complex health decisions more manageable. Anant’s vision is grounded in a belief that AI can both improve internal processes and deliver a more seamless, personalized experience to patients. It’s not about replacing human care but enhancing it—helping clinicians and care coordinators provide better support to patients when they need it most.
6. The Road Ahead: How AI Will Reshape Software Development
Anant’s thoughts on how AI is already reshaping software development were equally compelling. At Included Health, engineers use tools like GitHub Copilot and internal AI integrations to boost productivity. While the improvements are currently incremental—about 10-15%—he sees a future where AI becomes an integral part of a developer’s toolkit, much like IDEs today.
He envisions a world where AI agents assist engineers, accelerating tasks and freeing up time for creative problem-solving. This hybrid model, where AI augments human capability, is likely to redefine the way we think about software development in the coming years. Anant believes that as AI and humans learn to work together more seamlessly, the impact on productivity and creativity will be profound.
7. The Human Touch: AI’s Limitations and Opportunities
We also discussed the limitations of AI and the importance of human judgment. Anant made a great analogy comparing AI in healthcare to self-driving cars: while AI can navigate complex data and automate tasks, human intuition and empathy remain crucial in many interactions. Just as self-driving cars face challenges coexisting with human drivers, AI in healthcare needs to find the right balance between automation and the human touch.
This point is especially relevant as companies across industries rush to integrate AI into their workflows. It’s a reminder that while AI can be a powerful tool, it’s most effective when it enhances rather than replaces human capabilities.
Final Thoughts: Building Teams and Embracing AI’s Potential
My conversation with Anant was a masterclass in how to lead through hyper-growth, build high-impact teams, and embrace the transformative potential of AI. It’s clear that the lessons he learned at Uber and LinkedIn have deeply shaped his approach at Included Health. From focusing on impact over size, fostering a culture of innovation, to thoughtfully integrating AI into healthcare, Anant’s insights are invaluable for any leader navigating the complexities of scaling teams and leveraging new technologies.
As we continue to explore the intersection of technology, leadership, and human potential on the Tech Teams Today podcast, I’m grateful for conversations like this that push us to think bigger and challenge the status quo. If you’re interested in how to build stronger teams and embrace the future of AI, I highly recommend listening to this episode. Anant’s journey is a testament to the power of vision, resilience, and the endless possibilities that lie ahead.
Tune in to the full episode of Tech Teams Today for more insights from Anant Gupta and other leaders at the forefront of tech and engineering.
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