Inside the Ecosystem: Spotlight Series · Innovation Works

She Sees Every Small Business Owner in Pittsburgh as the City’s Client. Here’s What She’s Doing About It.

Mary McKinney Flaherty came to city government with a lawyer’s eye for broken systems and a Pittsburgh native’s belief in what this city can be. As Deputy Director of Economic Development, she’s focused on the small businesses who bring vibrancy to our neighborhoods and making government work better for them.

As Pittsburgh’s new Deputy Director of Economic Development under Mayor Corey O’Connor, Mary’s focus is specifically on small businesses and neighborhood business districts, a part of the economy that carries risk for individual owners and can be difficult to navigate. She came to the role not through a traditional urban planning or policy career, but through a legal and then M&A practice shaped by a recurring question: what do systems actually cost the people navigating them?

We sat down with Mary for the latest installment of Inside the Ecosystem, Innovation Works’ spotlight series on the founders, builders, and connectors shaping Pittsburgh’s innovation community. What follows is her take on what it really takes to open and grow a business in this city, what’s broken, and what the city is doing about it.

“I work to expand opportunity and vibrancy across Pittsburgh — by strengthening our neighborhoods, championing our arts and culture, and making it easier for small businesses to thrive. It all supports the larger work of attracting, retaining, and growing business here, and making Pittsburgh every family’s first choice.”

— Mary McKinney Flaherty

The City’s Client

Mary’s framing of her role is unusually direct for a city official. Shaped by her background as a partner in a professional services firm, she sees every current or future small business owner in Pittsburgh as the city’s client. That’s the lens, and it shapes everything that follows.

For the first time under Mayor O’Connor, the city has separated real estate development and economic development into two distinct leadership tracks. Steve Wray leads the broader economic growth agenda. Mary’s day-to-day is meeting people where they are: the restaurant owner stuck in permitting, the retail shop trying to figure out what approvals it needs, the child care center burning through its loan waiting for a certificate of occupancy.

These are not hypothetical examples. They’re the clients she serves.

Why Permitting Was the First Executive Order

When Mayor O’Connor took office, his first executive order targeted permitting reform. To anyone outside the city government, that might sound like a procedural priority. The stakes, she says, are higher than the language suggests.

The problem isn’t just that permitting is slow. It’s that the cost of slowness falls hardest on the people with the fewest resources. A large corporation with a legal team and a balance sheet can absorb months of delays. A small business owner who has already signed a lease, paid contractors, and taken out a loan cannot. Every week in permitting limbo is rent on an unopened space, interest accruing on a pre-revenue business, and mounting professional fees from repeated plan revisions that could have been avoided with clearer requirements from the start.

The city’s response targets three things: increasing efficiency, clarifying requirements upfront so owners know exactly what’s expected before they begin, and reducing the overall cost of the process. The goal isn’t just faster permitting. It’s a fundamentally more navigable experience for the people who have the most at stake and the least margin for error.

“Unlike large businesses that have architects and engineers on staff or retainer, small business owners disproportionately bear the cost of confusing systems, multiple plan revisions and the burden of professional fees.”

— Mary McKinney Flaherty

The Misconception That Costs People

The biggest misconception about opening a small business, Mary says, is that it’s primarily about having a good idea and being willing to work hard.

It’s both of those things, as well as financing, legal entity formation, assembling a team, securing a physical space, and navigating compliance requirements at the city, county, Commonwealth, and federal levels simultaneously. For a first-time owner without professional support, that web of requirements can be paralyzing. And sometimes the business never opens.

What makes this harder than it needs to be, she says, is that the support often already exists. It just isn’t visible enough. Innovation Works supports technology-focused companies. The Urban Redevelopment Authority offers free technical assistance, expanded loan opportunities, and grant programs, including a current facade improvement project as part of Mayor O’Connor’s Main & Main initiative that provides up to $25,000 for storefront enhancements. Both the University of Pittsburgh and Duquesne University operate Small Business Development Centers offering free help with business plans and growth strategies.

A meaningful part of Mary’s job is simply closing the information gap between what exists and who knows about it.

“This is everything from many child care businesses we interact with to small restaurants to hair salons to um office space. I mean, it really is everything. It is the biggest impact, the biggest change on people who have the least resources. That’s really the gap that we need to fill and the place in which increasing the efficiency so speeding up the process reducing the cost of the process which then also reduces and and clarifying and simplifying the process to reduce all of the secondary costs that aren’t necessarily captured when you look at it initially from a governmental perspective. That’s the benefit that it delivers to every small business in every small business district.”

— Mary McKinney Flaherty

Pittsburgh, Then and Now

Mary grew up in Pittsburgh. She left, built her career, and came back. Ask what she sees now that she didn’t see growing up, and the answer is more personal than political.

The Pittsburgh of the 1980s and 1990s, she reflects, was still looking backward. The steel industry was gone, and the identity hadn’t caught up. Today, it’s a city of possibility: an active innovation ecosystem, a thriving arts and culture scene, and a more diverse and global population. She names things she took for granted growing up, the topography, the parks, the neighborhoods, as genuine assets she now sees clearly.

The work, she says, is making sure what Pittsburgh is becoming reaches everyone who lives here. Growth that doesn’t bring people along isn’t the kind worth pursuing.

“Pittsburgh today is a place filled with possibility. We have an active innovation ecosystem, incredible arts and culture, and a city that’s proud of what it’s becoming, not just what it was.”

— Mary McKinney Flaherty

Where the Opportunity Is

Mary sees Pittsburgh’s biggest growth opportunity at the intersection of innovation and place. The existing foundation in robotics, AI, life sciences, and autonomy is something most cities would spend decades building. But realizing that potential requires more than supporting companies. It requires investing in the neighborhoods, public art, and cultural infrastructure that make Pittsburgh a place people actually want to live and build in.

Inclusive growth isn’t just a value, she says. It’s a strategy. A city that only works for some of its residents eventually stops working for any of them.

A Career Shaped by Human Cost

Mary is an attorney by training. Her legal career was shaped early by a question that never left her: what does the system actually cost the people inside it?

That question took concrete form through pro bono work with clients who had almost no institutional resources. Watching people struggle with systems not designed for them became a through-line that runs from her legal work directly into the city government. Her experience across small and large businesses, arts organizations, social services, and
Leadership Pittsburgh gave her a cross-sector view of Pittsburgh that shapes how she approaches a role most people would define more narrowly.

In her current job, she describes her role as a connector: ensuring that the resources available across the city are effectively matched with the people doing the work.

What Success Looks Like

Mary’s definition of success is concrete. More open storefronts. Fewer vacancies. A measurable decrease in permitting time. Those are trackable, and she intends to track them.

But she’s equally focused on what can’t be captured in a spreadsheet: positive feedback from business owners about their experience with city government, and a visible increase in neighborhood life. More services. Public art. Streets that feel active.

The data tells you what’s happening. The experience tells you whether it means anything.

“Success means more open storefronts, fewer vacancies, and shorter permitting times. But it also means business owners who feel genuinely supported when they interact with the city, and neighborhoods that feel vibrantly alive.”

— Mary McKinney Flaherty

Mary McKinney Flaherty came to this job because she believes Pittsburgh is a city of possibility, and because she’s spent enough time in broken systems to know that possibility alone isn’t enough. Someone has to do the work of making the systems match the ambition.

That’s what she’s here for.

Follow Mary on LinkedIn and learn more about Pittsburgh’s economic development programs at pittsburghpa.gov.