Career roadmap: Head of engineering

The head of engineering presides over an organization’s front- and back-end development teams, driving the design, strategy, and implementation of integrated systems, according to Cleverism, a career services site.

This individual leads development teams and collaborates with other business departments in sales, marketing, and finance, in the effort to roll out new applications and implement ongoing process improvements to existing systems.

Among this role’s key requirements are keeping up with new technologies and industry best practices and identifying correct schema for the sites and software in development, Cleverism says. “This leader has a strong vision for the department and promotes the best organizational patterns and practices.” A head of engineering should be prepared to tackle high-level challenges and balance quality software development with speed.

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Necessary skills include considerable experience in software engineering, application development, working with industry business models, deployment of APIs, and agile development practices. A head of engineering also must possess an in-depth understanding of data modeling and SQL for scalability and performance, as well as a background working with various RDBMSs, web development, and MVC framework technologies. This role requires strong communication and interpersonal skills.

To find out what’s involved in becoming a head of engineering, we spoke with Uday Sreekanth, head of engineering at TerraTrue, provider of a data privacy platform.

Early education and employment

Sreekanth received an undergraduate degree in mechanical engineering from the Indian Institute of Technology, Madras. After graduating, he went to Georgia Institute of Technology to work on a PhD in industrial and systems engineering. It was during his time at Georgia Tech that he got heavily involved in computer simulation work.

A professor in the computer science department was a pioneer in the area of parallel discrete event simulation, and Sreekanth took courses in computer science to learn more about this area. “Consequently, I got more intrigued by the computing aspects than the domain modeling aspects in systems engineering,” he says. It was then that he decided to pursue a PhD in computer science.

A year later, he took on an internship with Silicon Graphics, “and loved the work and felt it was more exciting than a PhD,” he says. “So I took a longer leave of absence and [ultimately] never returned to school. I wound up with master’s degrees in both industrial and systems engineering and computer science.”

That Sreekanth ended up in a STEM-related field was not surprising, he says, given that his father was a professor of aerospace engineering, his mother taught physics in high school, and his older brother worked in computer science.

“I was also influenced by my roommate while I was in grad school,” Sreekanth says. “He was a senior from college and a gifted PhD student in computer science, and was able to articulate the enormous potential in the field at that time. He nudged me to focus on computer science as a discipline itself, with all its depth, rather than a tool used to solve engineering problems.”

Becoming a head of engineering

Silicon Graphics (SGI) “was the company to be at in the mid 1990s, and I worked on a fascinating project that built an interactive television system through a partnership with Time Warner, AT&T, and NTT in Japan,” Sreekanth says. “I got involved in the data storage aspects and developed an interest in databases.”

SGI struggled with the massive costs of building its own hardware, facing intense competition from the rapidly growing personal computer industry, Sreekanth says. “I perhaps sensed the end of the fun earlier than others and moved on to work at an object database company called Versant to build a native Java language binding to the database,” he says.

This was the early days of Java and extremely satisfying, Sreekanth says. “We generated bytecode to achieve automatic refreshes of stale data,” he says. “After a tenure in development, I moved on to be a technical consultant for sales for the company, and enjoyed working with prospects and a large number of customers to help engineer and build their solutions.”

From Versant, Sreekanth went to work for a small startup called Covia, where he handled workflows related to company data before the company became a victim of the dot-com meltdown. He moved on to be the lead architect at Yodlee, another startup doing financial account aggregation.

That’s where he became familiar with the role of security engineer. “Security engineering was still a nascent area at the time, and I first learned about the way to build secure systems from the small yet brilliant team at Yodlee,” Sreekanth says.

Following that stint he briefly worked at a startup that attempted biometrics-based payments, started his own venture with a friend, and then moved from the Bay Area to Omaha, Nebraska, when his wife decided to go to school for a fellowship in medicine. He worked for the CTO at InfoUSA, a large consumer data company. That, in turn, led him down a path of working for the 2008 Hillary Clinton presidential campaign as a data architect.

When Clinton conceded, the Barack Obama campaign hired him as its chief data architect. “It was a thrilling experience to be at the ground level in the widescale use of technology powering all aspects of campaign management,” Sreekanth says.

In 2009, Sreekanth went to work for the Graham Holdings Company, owner of the Washington Post. “Graham Holdings had this intriguing structure of fully owned startups, and I worked for two of them and had a wonderful ride for eight years,” he says. In this job he worked on data services for the newspaper’s online news innovation lab—personalized news for mobile apps and digital marketing—attaining the title of principal architect.

Following brief stints at other organizations, Sreekanth in 2021 joined TerraTrue as head of engineering. Given his experiences of being in the middle of data across industries and realizing the still-nascent landscape of privacy engineering, he jumped at the opportunity. “The mission resonated beyond just the technology,” he says.

A day in the life of a head of engineering

A typical workday in a startup “constantly evolves,” says Sreekanth. “Flexibility is the key.” Currently, he manages the company’s two-week sprint cycles in engineering, along with the technology leads. He works to understand the complexity of the various parallel development efforts, chipping in where he can add value, tracking support tickets raised by customers, and reviewing product specifications produced by a team of project managers and privacy lawyers. “Every two weeks, I coordinate the deployment at the end of the sprint,” he says.

The majority of Sreekanth’s time is spent in meetings, most of them being one-on-one with colleagues. He is also constantly interviewing candidates to join the engineering team. “Orchestration and continuous improvements in engineering our vision—that sums up my role,” he says.

“My medium-term focus is on how to scale our engineering efforts while we still retain the creativity, freedom, uniqueness, and camaraderie that is invariably present when a team is very small,” Sreekanth says.

Certifications and further training

In 2018, Sreekanth pursued a self-driving car nanodegree—a certified online educational program to develop specialized skills in areas related to computer science—through educational services provider Udacity. He pursued the training even though it was unrelated to his startup work at the time.

“The curriculum and the reviews of the program showed it to be cutting edge and timely,” he says. “The experience far exceeded my expectations. It was a whirlwind, hands-on exposure to a lot of machine learning and AI [artificial intelligence] applied to challenges of a self-driving car. I spent an average of eight to 10 hours every weekend over almost a year. I wish I had more hours in the day to continue to acquire cutting-edge peripheral knowledge like this.”

Career inspirations and advice received

“I am inspired by Reinhold Messner, the incomparable mountain climber,” Sreekanth says. “Messner was the first climber to scale all the 14 eight-thousanders, and did so without assistance from sherpas nor relying on the use of supplemental oxygen—defying what everyone thought was humanly possible.” Eight-thousanders are mountains that are more than 8,000 meters in height above sea level.

“Messner was invited to write on the 50th anniversary of the ascent of Mount Everest,” Sreekanth says. “Talking about how he approached his career and his mountaineering philosophy, Messner concluded with his belief that failing is way more important than having success. That the most successful mountain climber ever focuses on what he learned from failures, rather than basking in the insurmountable heights that he singularly conquered, was inspiring. It is a perfect reminder for the need to always stay humble and that every step is an opportunity to learn.”

Asked about advice that guides his career, Sreekanth cites Indian philosophy: “Single-minded focus on the responsibility and every incremental step of your journey.” With that, he says, “the result automatically sorts itself out.”

A leader’s perspective on the field

“Digital computing as a field and the depth of its impact in our everyday lives is just about getting warmed up,” Sreekanth says. “A natural consequence of this journey is the handling of data through every stage, where the expectation is that data is handled securely, and inferences drawn from it are both transparent and respectful.”

Shaping a technology-focused career with this as backdrop “is a way for you to architect the checks and balances you would expect and demand with the use of your own data,” he says. “The importance of this area with its fundamental goal of doing good for the consumer [or] customer cannot be understated.”