The most recent chapter of the innovation struggle within City Hall might sound familiar to lots of civic technologists: old guard meets new in a clash over workplace culture.

Technical.ly broke the news earlier this month: Two years into his tenure, Chief Innovation Officer Charlie Brennan, the head of the city’s Office of Innovation and Technology, had been fired.

Per mayoral spokesman Mike Dunn, the city felt “a change in leadership was appropriate at this time.”

The move left Philly’s tech community puzzled, but not surprised. Now an Inquirer report published Thursday sheds light on the last straw that drove Brennan’s ouster: sexist comments and an ongoing rift between Brennan and Chief Administrative Officer Christine Derenick-Lopez, according to reporters Holly Otterbein and Claudia Vargas.

“At a staff meeting, someone asked a question about the difference between men and women in tech,” the paper reported. “Brennan, according to the two sources, answered with what he thought was a joke: The women have more shoes. A female employee then allegedly complained that Brennan’s comment was sexist.”

Per the report, Derenick-Lopez asked Brennan to attend sensitivity training, setting off a spat between the two. That, plus differences in management choices, led to Brennan being shown the door.

Sources tell Technical.ly it’s not the first time Brennan’s “old-school” behavior has caused trouble.

One former OIT staffer said she recalled Brennan, while leading an all-staff meeting, telling a joke in a similar, sexist vein.

“Honestly, I’ve blocked some of those things because they were traumatic,” the ex-staffer told Technical.ly. “The women at the table looked at each other as if asking themselves, Did that just happen?”

When reached at a phone number associated with his company, Carolus Consulting, Brennan hung up on us. Twice. He did not respond to emailed questions.

To understand the bigger picture, though, it’s important to look at the issues that marred the former cop’s tenure at OIT — almost from Day 1.

Culture clash

Brennan was appointed in 2016 as the replacement for Adel Ebeid. Ebeid had spent much of the Nutter administration ushering in a wave of young, civic-minded coders who were looking to change the way Philadelphia provided services to its citizens. Under new Mayor Jim Kenney, Brennan had a different set of priorities. Legacy systems were the focus.

Those first few months saw Civic Tech Director Aaron Ogle forced out and Chief Data Officer Tim Wisniewski’s team moved under the purview of then–Chief Administrative Officer Rebecca Rhynhart. Other key staffers left as well.

Perhaps telling of the central tension here, Brennan delivered that infamous “nap room” line at a City Council budget hearing. Brennan credited the lack of office perks with OIT’s struggle to retain talent and fill key staffing positions.

“One city business, they have a nap room,” Brennan said in April 2016. “A nap room wouldn’t go over well here in the city. They have very flexible hours, they work from home. … They offer things like free food, massages, things like that. We just can’t compete with that.”

The line, which at the time elicited swift response from the civic-tech community, echoes another quote in the Inquirer article, in which Brennan reportedly told a roomful of people at an OIT event to enjoy the food that “we probably can’t afford.”

“Disdain” is a word the former OIT staffer might use to describe Brennan’s view of the new guard that he found himself overseeing.

“Arguably, it was fear of change,” she said.

The rift in culture contributed to the departure of Gabriel Farrell (who now goes by the name Sean Fern). The “rigidity of working for the city” and things like a “byzantine work-from-home policy,” he told Technical.ly in early 2016, made the engineer step away from public service for a role at adtech firm Vistar Media.

The clues were there, and Ogle himself shared more of them in a 15-page report published by MIT’s Open Leadership Camp this month. The timing, within days of Brennan’s firing, was apt.

1/ I'm pleased to finally share this case study I coauthored with @daeaves about how @PhiladelphiaGov built an amazing digital transformation team, and the ramifications of changes in leadership. https://t.co/0uakXe9NDV pic.twitter.com/CRxC5KlnqL

— Aaron Ogle (@atogle) January 17, 2018

“The differences between Brennan and Ebeid were apparent,” the report, co-authored by David Eaves, reads. “The opportunity to run the innovation program was what brought Ebeid to Philadelphia in the first place. Brennan, on the other hand, was more concerned with backoffice systems, and saw City departments as his primary customer.”

It also mentions the departures of Ogle and Fern:

“The Alpha team felt unvalued, whiplashed, and that their talents were being wasted on tasks that they felt bolstered the ego of department heads rather than benefited the public. Morale plummeted, and by March 2016 both Director of Civic Technology Aaron Ogle and Civic Technology Engineer Gabriel Farrell had resigned. Many others were on the verge.”

The environment described by Ogle is one that, per another former staffer, caused a division between teams that, by nature, need to be able to work together.

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Editor-in-chief Zack Seward contributed reporting.