Oscar Health CTO Alan Warren on Taking Your Engineering Team from Start-up to Scale-up

Captured by Denali Tietjen

At General Catalyst, we aspire to back the world’s most ambitious and transformative companies. The most successful companies we’ve seen have scaled quickly and brought on hundreds and eventually thousands of employees to join in their missions.

In periods of growth, leadership teams can become hyper-focused on product and sales. But there’s one huge and often unforeseen challenge that comes with rapid growth: building a strong organizational infrastructure.

While early-stage startups embrace fluid structures and even rely on employees having flexible roles, this organizational model is typically unsustainable at scale. As companies grow, structured management and clearly-defined responsibilities become essential.

At what point does this dynamic shift? How do you develop infrastructure in tandem with sales and product growth? How do you instate a management structure that both fosters innovation and provides clarity?

To tackle these questions, we hosted Alan Warren, Chief Technology Officer of GC-backed Oscar Health and former VP of Engineering at Google, and engineering managers from high-growth startups across New York City like ZocDoc, ClassPass, RentTheRunway, and Giphy, for a conversation on how to build scalable engineering teams.

Warren has experienced the challenges of high-velocity organizational development firsthand. As cofounder of Juice Software, a computer software company started back in 2000, Warren helped grow the team from 2 to 60 people in a year a half. When Warren joined Google as New York’s engineering director in 2004, the office staffed 45 engineers. Under Warren’s purview, Google NYC grew to nearly 3,000 engineers and 6000 employees, making it Google’s second largest office. Today, it’s become an engineering powerhouse driving Google’s Ads, Search, Apps, and Maps operations. Earlier this year, Warren returned to his roots in healthcare joining today’s leading industry disruptor, Oscar Health, as its first-ever CTO. At Oscar, he is focused on building a full stack healthcare system and product experiences designed to put people’s needs first and assembling the next generation of technical talent that will pave the way for the future of healthcare.

Here are some of Warren’s key perspectives on building and managing high-growth engineering teams:

1) Promote based on capability, not convenience.

Lightening your own workload should never be the motivation for promoting someone else, Warren warns. Promotions should be based on capability, not convenience.

Demonstrating his commitment to this idea, Warren points out that he had a surprising 75 direct reports at Google, saying, “I wasn’t going to say ‘ok, now this person’s a manager’ just because I wanted to get responsibility off my plate.”

2) Cultivating strong leaders requires time

Developing strong leaders requires significant time investment from upper-level management. At Google, Warren struggled to recruit senior engineering talent that met his high standards. So instead, he hired junior engineers and developed them into senior roles. How long did that take? At times, ten years.

Warren acknowledged that Google is a sticky environment with long employee tenure and that not all companies can justify pouring significant resources into internal development. Still, Warren stresses the importance of mentoring and growing junior talent.

3) Tenure doesn’t equal talent

Dispel the notion within your culture that tenure deserves titles, Warren says. Promotions should come on the basis of performance, not tenure.

Career progression is not one-size fits all. Move away from the idea that promotions are earned every two-years, four-years, six years. At Google, it’s respectable to retire as a level two software engineer, reflecting Warren’s position.

Millennial redefinition of “tenure” poses a significant challenge to this philosophy. Three years is now considered a long time to be at a company, so millennials expect promotions much earlier. Making young employees feel valued without diluting your management structure is a balancing act.

The definition of “tenure” depends on the stage of a company. Creating a strong management structure at a mid-size startup is in many ways harder than at a larger one, Warren explained.

A 24-year-old engineer at a Series B startup, for example, may feel they are worthy of a promotion, having been at the company since its inception.That engineer, however, still only has two years’ experience and may not have demonstrated requisite competency to merit promotion.

4) The best leaders are reluctant leaders

An engineering manager should always be as strong as the best engineers in the room. They want to code, but realize that they could have a stronger impact on the company as a leader.

This selfless leadership philosophy is actually reflected in Google’s compensation structure. At Google, in some cases, managers make less than individual contributors at the same level. “That gets your priorities straight,” Alan recalled. “We reward doing, including especially, strong individual contributors.”

5) Encourage leadership, not management

Warren encourages a management model of “engineering leaders” rather than “engineering managers.” While leads have some management responsibility, management contribution is a dial that slides and never hits 100%. Rather than simply delegating tasks, the lead should be immersed in the product and team.

6) Create a bottom-up mentorship structure

Rather than spending one-on-one time with each direct report, Warren suggests holding weekly office hours. This open-platform model encourages employees to be proactive by enabling

them to steer the conversation.

This model is particularly effective at early-stage startups, where time is a limited resource.

7) First hire is the hardest

Don’t compromise on your first management hire. While the hiring process can be challenging and exhausting, the first hire is is the hardest. After that, referrals kick in. Your organization is your best advertisement and your leaders become role models both internally and externally.

8) Embrace an engineering-centric culture

“If you hire at the right level, you don’t supervise engineers, you hang on to the ropes and run with them while they’re taking off,” Warren said. By allowing engineers to drive a product’s direction and innovation, they develop more genuine products. Engineering leads should serve as a sounding board for engineers, rather than simply assigning tasks.

In an engineering-driven culture, product managers should operate as partners to tech leads, Warren says. The role of of the product manager includes helping coordinate projects by gathering information from relevant stakeholders and such, but ideation is shared with the engineers on their team. This is different from most companies where product managers have a stronger directional and creative role.

9) Grow responsibility rather than handing it off

Rather than handing off responsibility to a new leader (or even individual contributor) all at once, increase her responsibility as she proves capable.

Warren encourages a scope and responsibilities model of three concentric circles: the internal bubble, the external bubble, and the ring in between. The internal bubble represents tasks and decisions clearly within the individual’s scope. Tasks that fall within this bubble don’t require approval and she should feel complete ownership and responsibility. The external bubble is comprised of tasks that are outside of that person’s scope. Tasks that fall in this arena should involve a higher-up. Lastly, the middle ring represents tasks that fall somewhere in between. Consider this the “fyi” or “please-confirm” realm. As a mentor, you should focus on developing the skills to help a manager or individual expand this internal ring, so their “owned” internal circle continues to expand.

Make sure these circles are well-defined to ensure transparent expectations and responsibility.