After years of tech community leadership, Kory Bailey is now UpSurge Baltimore’s CEO

After spending the better part of three years stewarding much of UpSurge Baltimore’s relationship-building work within the region’s tech and entrepreneurship ecosystem, Kory Bailey is now heading up the organization as its CEO.

UpSurge Baltimore on Tuesday formally announced that Bailey, a former professional football player who built a career in tech and entrepreneurship support over the last near-decade, is taking its top spot. Bailey confirmed in a phone interview with Technical.ly that his tenure in the role effectively began at the beginning of November. He is replacing founding CEO Jamie McDonald, who said in September that she was stepping down to focus on assisting her husband as he deals with a Parkinson’s diagnosis.

McDonald said in a written statement that Bailey “is a visionary leader and community builder who has played a key role in shaping UpSurge’s outsized impact over the past nearly three years.”

Bailey became the organization’s second employee around the time of its launch in spring 2021, moving from its director of relationship development role to the chief ecosystem and relationship officer one in July 2022. Throughout his tenure with UpSurge, Bailey was instrumental in shepherding the weekly Equitech Tuesday meetup, the Equitech Accelerator with Techstars, a pair of reports about the local tech sector and more of UpSurge’s projects. Through it all, Bailey has become a familiar face at regional tech events; he recently spoke at the B’More BOLD Conference, DC Startup Week and a vigil for late EcoMap Technologies CEO Pava LaPere. Technical.ly named him to the RealLIST Connectors list in 2022.

Bailey said he threw his hat into the CEO ring as UpSurge and members of its board searched for McDonald’s replacement. As UpSurge navigated the transition, he and COO Maddy Stokes (a 2023 RealLIST Connectors honoree) took on more team management and strategy execution work. Through this process, Bailey said, he maintained close communication with the organization’s transition committee — a group that included board members like Johns Hopkins Technology Ventures Executive Director Christy Wyskiel and Conscious Venture Partners Managing General Partner Jeff Cherry — on both UpSurge’s work and his candidacy.

“I’m just, by nature, a person that wants the best for the organization, whether or not they thought that it was my leadership or someone else’s,” Bailey told Technical.ly. “Ultimately, I think, we all agreed that it was mine, and so I’m happy with the outcome. But managing the process, I think, was fairly easy because of how well the transition committee communicated with me and vice versa.”

Bailey will relinquish his role as chief ecosystem and relationship officer, which he said the organization likely won’t try to fill. That said, he plans to continue much of the relationship-building and networking work that he was doing while also determining what capacity might help UpSurge continue its impact on the ecosystem. He also plans for UpSurge to focus more on how to unlock more capital to help local startups.

Jamie McDonald (left) speaks alongside Kory Bailey during UpSurge Baltimore’s first anniversary event, June 2022. (Courtesy UpSurge Baltimore/Brandon Towns)

Bailey’s tenure as CEO started soon after Baltimore was designated one of the Economic Development Administration’s (EDA) 31 Tech Hubs. UpSurge was part of the consortium that applied for the Tech Hubs designation under the Greater Baltimore Committee’s (GBC) primary leadership. Baley sees the opportunity as one of several “catalytic opportunities” for growth.

With EDA feedback on the consortium’s winning proposal expected this week, Bailey said UpSurge will continue working with the GBC and other stakeholders to further bolster the proposal before applying for Phase 2 of the federal program. All 31 Tech Hubs designees are eligible to apply for millions in funding to bolster their regional tech work.

As UpSurge strengthens its relationships within local and state government — Gov. Wes Moore notably spoke at this year’s Techstars Equitech Accelerator demo day — Bailey also plans to figure out how the Tech Hub bid might overlap with legislative advocacy to support tech in the region.

“[We’re] also having conversations with Maryland Tech Council and GBC to really help inform the conversation around: What do we advocate for in this legislative session?” he said. “Where are some foundational things that the state might be able to contribute to? Maybe even putting some foundation under or behind the Tech Hubs award if we’re fortunate enough to be designated as a Phase 2 winner as well.”

UpSurge is also moving forward with the Equitech Accelerator, which is currently accepting applications for its third cohort. The accelerator, like much of UpSurge’s work, revolves around “equitech” — the organization’s framework that sees tech scene vitality as inseparable from creating an equitable economy.

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Bailey began leading the organization while he was attending last week’s AfroTech conference in Austin. Over 60 members of the Maryland ecosystem attended, he said, and stayed connected through Coordle, a group communications and logistics platform created by Baltimore-based founder Jen Fry. UpSurge also sponsored a Maryland tech-focused portion of the popular Culture House networking event, which Bailey said was created by Baltimore native Rodney Williams.

“Anytime that you can build a uniquely cultural experience around innovation, it gets really exciting,” Bailey said. “And so, we hope to bring a lot of that energy and activity and focus here to Baltimore as well, because I think this is a city where culture and innovation coming together makes it really interesting.”

His career on the front lines of Baltimore’s evolving tech world also gave him insights into what he thinks will be particularly resilient tech and tech-adjacent careers in the city. He cited technical roles that can best use generative AI – part of the Tech Hub bid’s main foci — and non-technical professionals who can usher in a company’s vision.

“There is no shortage on need for good operators, people who can see the landscape, take a strategy into motion and then execute,” he said. “I think the more operators that we have in our ecosystem, to be honest, here in Baltimore, the better we’ll be for it.”