Greg Gershman wants government to be easier to use

Greg Gershman went to the Wright Brothers National Memorial and noticed the bird. It was perched on the sculpture of the first flight, a small, living spectator on a monument to human ingenuity. He thought it was a gray catbird. An engineer might have confined his attention to the machinery. Gershman found room for the creature on the wing.

The visit became a 2020 essay about birds, bicycles, and government. He had been listening to David McCullough’s The Wright Brothers, and the connections pleased him: bicycle makers learning about control, inventors watching birds, public information helping them choose a place to experiment. He was interested in the conditions that let useful ideas become working things.

That is a revealing preoccupation for the co-founder, CEO, and Board Chair of Ad Hoc. Gershman’s working life has moved from blog search to federal search to building a company around public services. Across those changes, he has kept returning to a rather reasonable expectation: people ought to be able to use the things built for them.

A bird on the wing

His Wright Brothers essay ends with an appreciation of government’s ability to support invention. For Gershman, a museum visit could accommodate both birdwatching and a consideration of procurement. Few holiday itineraries promise so much range. He even photographed a copy of the brothers’ original government contract.

The pleasure is in how the pieces connect. He described the Wrights’ bicycle experience as a way into understanding a pilot’s control. He lingered over observation and testing. Reading his account, you get a sense of someone interested in the practical steps between an appealing idea and an object that behaves as intended.

There is also a disarming absence of professional tidiness. Birds, bikes, a book, a public agency, a contract: all make the cut. The essay allows curiosity to wander without requiring each stop to present a business case. A catbird is entitled to appear simply because someone looked up.

First, make it findable

Gershman grew up in Gaithersburg, Maryland, outside Washington. He earned a master’s degree in computer science at Johns Hopkins. His early entrepreneurial work included Blogdigger, a search engine for blogs, launched in 2003. It belonged to a period when finding an interesting independent voice online was itself an absorbing engineering problem.

In 2008, Odeo acquired Blogdigger and brought him aboard to lead search and engineering. A contemporary post by fellow entrepreneur Pete Caputa remembered years of trading ideas and feedback with him, and admired his persistence in turning a small project into a business. Search software had supplied an education in staying with a problem.

By 2010, Gershman was working on federal search at the General Services Administration. USASearch applied his experience to a different collection of information: government content that people needed to find. His work there also brought agile development and lean startup methods into the federal setting, connecting technical practice with the way a team organized its day.

In 2012, he joined the inaugural class of Presidential Innovation Fellows. He worked on MyUSA, a platform intended to make government digital services more centered on the people using them. The move placed him among technologists trying to bring different habits into an institution with very established ones.

The work behind the website

Gershman co-founded Ad Hoc with fellow software engineer Paul Smith in 2014. Their experience working together on a federal website recovery effort had exposed an opening for teams with practical development skills. The company gave them a way to keep applying that experience, rather than treating the assignment as an exceptional episode.

Software engineering was the starting point. The work soon demanded more. Ad Hoc added people skilled in human-centered design, user research, product management, DevOps, and cybersecurity. A service had to make sense to its users, and the people building it needed several kinds of expertise in the same conversation.

By 2023, Gershman was making the broader organizational argument in a customer-experience discussion with federal leaders. Better service required attention to the institution behind the interface: onboarding, policy, accessibility, security, and the understanding employees brought to their work. A screen could carry only so much of that responsibility.

“A total organizational change is required.”

Greg Gershman, on improving customer experience, 2023

The example is useful because it resists a convenient answer. Hiring a specialist or commissioning a website produces something easy to announce. Changing how decisions get made, and how staff help the public, is harder to fit into an unveiling. Gershman’s interests had expanded to include the machinery behind the machinery.

A useful measure of progress

In 2021, Gershman and Smith set out proposals for improving unemployment systems. They began with goals and measurement. Spending money on modernization would reveal little if the government could not tell whether people were receiving a better service. The intention needed to be clear before the technology shopping began.

Their recommendations were concrete: more usable forms, clearer claim tracking, digital document uploads, and tools that supported the employees administering programs. They argued for reusable components and for involving government workers in design. An applicant’s experience and an administrator’s working day belonged in the same account of improvement.

It is a helpful window into his thinking. Progress becomes visible in a completed task, a clearer next step, or work a member of staff no longer has to repeat. The ambition is substantial; the evidence can be wonderfully ordinary. A form that accepts the information it asks for has already improved someone’s afternoon.

Small teams, larger responsibilities

Ad Hoc’s acquisition of Cascades Technologies in June 2022 showed how Gershman intended to widen the company’s reach. Cascades brought experience in data analytics, compliance, help desk support, mobile development, and bilingual user experience. It also brought relationships with additional federal agencies. Growth meant taking on different sorts of work.

In announcing the deal, Gershman described the capabilities Ad Hoc had added since its engineering beginnings. He emphasized small teams with people from different disciplines. The larger organization would supply the range of expertise; the working team still needed enough closeness for its members to improve one another’s decisions.

His own responsibilities had widened, too. At Ad Hoc, he leads strategy and operations, oversees the executive team, works with customers and partners, and participates in business development. For a software developer, that is a considerable increase in the number of problems that decline to be solved by writing code.

Professional practice areas offered one way to sustain technical standards. Engineers, designers, product managers, and data specialists could seek advice from colleagues beyond their immediate assignments. Gershman’s emphasis on support and learning gave the company’s size a practical purpose: a person facing a difficult problem should have someone to ask.

Ad Hoc was built around remote work from the start. That made culture a matter of deliberate arrangements, rather than an office everyone happened to enter. In 2024, it received USA Today Top Workplaces recognition based on employee survey feedback. Gershman connected that recognition to giving people room to try things, make mistakes, and learn.

The recognition followed a Washington Post Top Workplace award in 2023. That year, Gershman and Smith were also named Mid-Atlantic finalists in EY’s Entrepreneur Of The Year awards. The distinction was a finalist place, and the story behind it was shared work: people choosing to bring technical skills into public service.

A partnership with a purpose

In October 2023, Gershman announced Peregrine Digital Services, a joint venture between Ad Hoc and IronArch Technology. It combined Ad Hoc’s digital-service experience with capabilities in cloud and platform work. The partnership also carried a personal connection through IronArch CEO Joe Punaro’s fellow Marine, Alexander Wetherbee, who was killed in Iraq in 2004.

Peregrine was founded partly to honor Wetherbee, an Outward Bound instructor. Its commitment included donating a percentage of profits to a memorial scholarship fund helping surviving family members of service members attend Outward Bound courses. The joint venture tied a business arrangement to a particular person’s memory and a particular form of opportunity.

In October 2024, Peregrine earned a prime position on the Department of Veterans Affairs’ SPRUCE contract vehicle. It created a route for the partnership to compete for further work. Gershman’s company-building had progressed from assembling a team to assembling relationships between organizations, with each combination bringing its own responsibilities.

The long view, preferably outdoors

Outside that work, the Chesapeake Bay holds his attention. Gershman has supported efforts to establish a national recreation area around it. His interest includes conserving the landscape and telling a fuller account of the communities whose lives have been shaped by the bay. The outdoors and public institutions meet again.

He also sings live-band karaoke. It is an agreeable detail to preserve beside the degrees and executive responsibilities. There are settings in which a microphone exists for reasons other than explaining a delivery model. Even a government technology founder may occasionally be allowed a chorus.

When Ad Hoc turned ten in 2024, Gershman reflected on the challenge and fulfillment of building it. The anniversary invited reflection, but the company’s subsequent work has kept moving. In March 2026, Ad Hoc released Activate Framework to help teams guide AI coding tools with explicit, reusable working practices.

On October 20, 2026, it followed with an AI Coding Agent Skills Guidebook, announced by Mark Headd. The guide asks teams to capture knowledge, involve subject experts, and evaluate whether instructions improve the resulting code. It is company work with an old concern running through it: useful tools need context, judgment, and people who know the problem.

Back at the memorial, the bird had supplied a small reminder that a familiar object could reward another look. Gershman’s career has made room for that habit: look closely, notice who needs help, and work out what would make the thing useful. There is plenty left to build. There are also birds.