Applying lessons from government to the chief of staff role at a tech company

Throughout the cities that Technical.ly covers, we’ve seen the chief of staff role pop up at more tech companies over the last couple of years. In Baltimore, SmartLogic was among those introducing the position: Michael Castagnola started as the software development firm’s first chief of staff in May. Since the role can look a bit different from organization to organization, we caught up with Castagnola to learn about how SmartLogic is applying it.

Castagnola, who moved to Baltimore five years ago, brings experience in government and politics. He held that same title working with 1st District City Councilman Zeke Cohen, and went on to D.C. in 2019 to connect the work of Congress to Baltimore on the staff of the U.S. House of Representatives Committee on Oversight and Reform, which was chaired by the late Congressman Elijah Cummings.

At SmartLogic, the greater civic good remains in focus. Part of the chief of staff role involves leading on the company’s externally facing initiatives. This includes the work it is doing with organizations for Baltimore such as a microgrant program for Black-led organizations in June and the recently-launched youth design thinking challenge COVID Slam.

“We’re trying to figure out how to be in greater partnership with other tech companies locally, supporting youth and actively engaging in diversity, equity and inclusion work,” he said.

With the community-facing work, it’s important to center it with the organization’s values and priorities. So it’s important to understand the company’s internal work, as well.

“They hired me with the intent to do a lot of externally facing work,” he said. “I started towards the beginning of the U.S. and global pandemic shutdown and my feeling was before thinking heavily about the external work. [But] I should know the foundation I’m standing on to be able to go externally and know what’s up.”

After digging in, he also took the lead on projects internally that cross different functions of the firm. This included an effort to streamline the hiring process as the team grew to 19 people, and putting policy around pair programming, where two developers use one workstation. With these two sides of the role he’s supporting business development, as well.

Castagnola said there’s a lot to apply from government to working in the chief of staff role at a tech company. He is finding the “relational” side of politics applies, as engaging with people and managing in all different directions becomes important. There’s also the effort to stay help the “principal” — in this case, not an elected official but company president Yair Flicker — move forward, whether it’s generating ideas that fit the organization’s priorities or “blocking and tackling” for them.

“A business owner has so many things to do and there’s only so much one person can do,” Castagnola said. So a chief of staff can help to “create priorities, identify issues, prioritize them and then resolve them.”

For an organizational leader who might seek to introduce the role in the future, Castagnola said it’s important to think through not just this person’s responsibilities, but what they want for the role and how it can help the organization.

“They should really have an idea of what gaps they want that person to plug, and what degree of autonomy they want that individual to have,” he said.