From Steel City to Smart City: What Pittsburgh’s AI Moment Means for Every Organization Building for the Future

What does a Rust Belt city’s reinvention have to do with your organization’s digital transformation? More than you might think.

At Innovation Summit 2026, a candid conversation between two leaders—one running the company that’s putting self-driving trucks on Pittsburgh’s highways, the other running the city itself—surfaced a set of principles that any organization navigating technological change can apply immediately. The session covered permit reform as a proxy for process modernization, the power of public-private partnerships built around specific outcomes, the importance of meeting people (and companies) where they are, and why the boldest leaders right now are the ones willing to pick up the phone.

These aren’t abstract civic talking points. They’re the same levers HIKE2 pulls when we help clients in financial services, the public sector, insurance, and high-tech build future-ready operations. Read on for the key takeaways—and watch the full session linked at the end.

About the Session

The conversation featured Gerardo Interiano, Senior Vice President of Government Affairs at Aurora—an autonomous vehicle technology company with nearly a thousand employees in Pittsburgh—and Corey O’Connor, the newly inaugurated Mayor of Pittsburgh. Interiano, a transplant who moved to Pittsburgh from Texas nearly seven years ago, moderated with the perspective of someone who has watched the city’s tech ecosystem evolve up close. Mayor O’Connor, 41, brought the unfiltered energy of an administration that has hit the ground running, offering a remarkably operational view of what it takes to modernize a city government while simultaneously selling Pittsburgh to the world.

Streamlining the System: Process Modernization Isn’t Just a Government Problem

One of the session’s most recurring themes was permitting—specifically, how a broken process signals a broken organization, and how fixing it sends a message far beyond the bureaucratic transaction itself.

Mayor O’Connor made the point directly: if a business owner in New York City can get a permit in four and a half weeks, why should the same process take eight months in Pittsburgh? His administration moved quickly to assign dedicated staff to walk applicants through the process—removing ambiguity, reducing unnecessary back-and-forth, and giving small entrepreneurs a fighting chance against the overhead costs of delay.

The lesson here extends well beyond city hall. In any enterprise—a law firm onboarding a new client, an insurer processing a claim, a SaaS company provisioning a new account—complexity that exists because “that’s how it’s always been done” is a hidden tax on growth. The question O’Connor is asking about permits is the same question every operations and technology leader should be asking about their own workflows: who is losing time, money, and confidence because our system wasn’t designed for them?

“It’s not for big developers. Look, they have four or five lawyers that can figure out the system. It’s for a small startup. It’s for a coffee shop. It’s for a yoga studio—that’s a young entrepreneur who’s trying their best and can’t funnel through our system and they’re losing overhead.” — Mayor Corey O’Connor, City of Pittsburgh

For organizations undergoing digital transformation, this is a critical frame. Technology implementations that only serve sophisticated, well-resourced internal users replicate the same inequity. Human-centered design means building for the full range of people who interact with a process—not just the power users. When HIKE2 works with clients on workflow automation, AI-assisted operations, or data platform modernization, the first question we ask is: who gets left behind by the current system, and how do we design so they don’t get left behind by the new one?

Proactive Outreach: The Organizations Winning Right Now Are Making the Calls

Perhaps the most striking moment in the conversation was Mayor O’Connor’s description of his personal outreach strategy: 10 to 20 calls per week to CEOs, small business owners, alumni who have left Pittsburgh, and companies that could be persuaded to open a satellite office in the city. He’s not waiting for inbound interest. He’s calling.

This posture—proactive, specific, relationship-first—is exactly what separates organizations that successfully adopt new technology and partnerships from those that wait for the right moment (which never comes). Gerardo Interiano echoed the point from the private sector perspective, noting that in the tech industry, companies that engage with government proactively fare far better than those who wait for government to come to them.

“You want to engage with government before they engage with you. The last thing you want is to have a government agency or an elected official come to your office and say, ‘Hey, what’s going on?’ You want to proactively go and reach out and build that relationship.” — Gerardo Interiano, SVP of Government Affairs, Aurora

The same principle applies across every sector HIKE2 serves. Organizations that wait for their workforce to demand AI training, or for a competitor to force their hand on cloud migration, are already behind. Leaders who are proactively mapping where their teams are, what capabilities they’re missing, and what partnerships could accelerate their journey—those are the ones building advantage, not just catching up.

Mayor O’Connor’s call cadence also revealed something about organizational intelligence: by talking directly to founders who’ve left Pittsburgh and asking “why did you leave?”—he’s gathering qualitative signal that no dashboard can surface. The lesson for data and AI leaders is a reminder that the most important intelligence is often conversational. Building feedback loops with employees, customers, and partners—not just dashboards—is a core advisory principle at HIKE2.

Outcome-Specific Partnerships: The Shift from Asking for Money to Solving Problems

One of the most practically useful frameworks in the session was O’Connor’s description of how his administration has fundamentally changed how it asks for private sector support. The old model: go to a foundation or corporation with a funding gap and ask them to fill it. The new model: identify a specific, mission-aligned outcome and make a targeted ask.

The results have been concrete. PNC Bank directed $2 million specifically to plow trucks, which turned into 35 new vehicles that serve the city. UPMC contributed $10 million designated for ambulances, directly aligned with their healthcare mission. Heinz Endowments funded a comprehensive neighborhood planning initiative rather than being asked to plug a budget hole. Each partnership worked because the ask was specific enough to pass a board vote—it was tied to an outcome the partner could defend to their own stakeholders.

This is a model that translates directly into how organizations should structure technology partnerships, vendor relationships, and internal AI initiatives. Vague mandates to “be more data-driven” or “embrace AI” rarely generate funding, talent, or organizational commitment. Specific, outcome-tied initiatives—reduce claims processing time by 30%, reduce manual review hours per loan application, reduce time-to-insight for compliance teams—generate alignment. They’re also easier to measure, iterate on, and celebrate.

For HIKE2’s clients, this framing is foundational to how we structure advisory engagements. We don’t ask organizations to commit to digital transformation in the abstract. We help them define the specific outcomes they’re trying to achieve—for their customers, their workforce, and their bottom line—and then build the data, AI, and cloud capabilities that serve those outcomes directly.

Talent, Narrative, and the Work of Selling the Future

A throughline in the entire conversation was the challenge of narrative: Pittsburgh has world-class assets—Carnegie Mellon, Pitt, Aurora, a growing AI ecosystem, extraordinary livability—but it’s still being sold through an outdated story. The steel mills are gone, but the imagery persists. O’Connor made clear that changing the narrative is as much a part of his job as fixing potholes.

For organizations leading digital transformation, the parallel is direct. Many companies have made significant investments in AI and data infrastructure that their own employees, customers, and partners don’t know about or understand. The technology is there; the story hasn’t caught up. Building future-ready companies requires not just building the capabilities, but communicating them in a way that attracts talent, builds confidence, and generates the momentum needed to sustain change.

This is especially true for workforce transformation. O’Connor’s vision for Pittsburgh includes filling rec centers with technology demonstrations for kids who might never have seen a robot, bringing universities into neighborhoods, and creating proximity between the communities that need opportunity and the institutions that generate it. That’s a human-centered approach to workforce development—meeting people where they are, not expecting them to find their way to the opportunity.

For HIKE2 clients undergoing AI adoption, the same principle holds. Training programs that assume a high baseline of digital fluency, change management efforts that communicate only from the top down, and AI tools that were designed without input from the people who will use them daily—these fail not because the technology is wrong, but because the human dimension wasn’t centered. The organizations getting this right are the ones investing in narrative, access, and design alongside their technical infrastructure.

Watch the Full Session

The full conversation between Gerardo Interiano and Mayor Corey O’Connor covers much more ground—including the story behind the $80 million investment that transformed Hazelwood Green from an abandoned steel mill site into a billion-dollar development, the unique role Pittsburgh’s geography plays in its economic competitiveness, and what the city’s preparation for the NFL Draft says about its emerging capacity to host a global stage.

Is Your Organization Building for What’s Next?

The leaders in this conversation—whether running a city or a global autonomous vehicle company—share something in common: they’re not waiting for conditions to be perfect before they act. They’re making calls, fixing processes, building specific partnerships, and investing in the people and places that others have overlooked.

At HIKE2, that’s the work we do every day with clients across industries. We help organizations build the data foundations, AI capabilities, and digital workforces they need to compete—not someday, but now.

If you’re thinking about what your next chapter looks like, we’d love to be part of that conversation.

Contact HIKE2 to start the conversation →