SALISBURY, Md. – For an up-and-coming architect, Jake Day was building an impeccable résumé. As an undergraduate at Maryland, he was elected national president of a top professional student organization. For grad school, he landed a spot in a prestigious program overseas at Oxford. He went on to join a well-known nonprofit on his native Eastern Shore.
But something was missing – something that made him think back to his childhood growing up in Salisbury, Maryland, when he would spend hours and hours in camouflage sweatpants playing pretend soldier. Even as a little boy, Jake Day felt called to service.
“I finally came to face the fact that I did not want to go any further in life without joining the military,” he said. “It’s one of those things I knew I was going to regret if I didn’t do it. Something said to me, I owe it to this nation to serve.”
With the blessing of his boss, and against his family’s wishes, Day went off to basic training. Now, a decade into his military career, he’s a Captain with the Maryland Army National Guard’s 110th Information Operations Battalion out of Annapolis.
But this isn’t a tale of another small-town guy who decided to join the military after college. What makes his story special is how Jake Day, 36, is now the mayor of Salisbury, where he’s applying the Army’s leadership lessons to City Hall, and is guiding his hardscrabble hometown into a community that’s ready to flap its wings and start soaring.
Day was a 19-year-old college student when terrorists attacked the United States in September 2001. Then and there, he felt inspired to enlist – “I remember it vividly, I didn’t not want to be a part of responding to that,” he recalled – but on his parents’ recommendation, he stayed put in College Park.
The future councilman and mayor got his first taste of the campaign process when running for national president of the American Institute of Architecture Students. That term rolled over into a student representative spot on the elite American Institute of Architecture board of directors. Day said he marveled at the chance to be a part of a body that even the nation’s best architects wait their entire career to join.
And, unsurprisingly, local leaders noticed Day stepping up. Civic leaders who couldn't stand to be in the same room with each other all seemed to agree that Day had a bright political future if he wanted it. Salisbury’s mayor at the time needled him to make a run for an open City Council seat in the 2013 election.
“I thought, well, maybe they’re right. Maybe I should be involved,” he said. “If it could appear to them that I could be not just neutral but potentially a uniting influence, then maybe other people would think so too. I thought, maybe there’s hope for something better.”
Hope was in short supply. These intervening years were more than just a rough patch for the once-proud city of Salisbury. The economic recession continued to take a devastating toll on the former manufacturing hub. Jobs dried up. Crime was on the rise. Many young people, Day said, were concerned for the city’s future.
At age 30, Day ran for City Council. His opponent attacked him for his youth, inexperience, and pie-in-the-sky promises for a better tomorrow – for his hope.
Day was a 19-year-old college student when terrorists attacked the United States in September 2001. Then and there, he felt inspired to enlist – “I remember it vividly, I didn’t not want to be a part of responding to that,” he recalled – but on his parents’ recommendation, he stayed put in College Park.
The future councilman and mayor got his first taste of the campaign process when running for national president of the American Institute of Architecture Students. That term rolled over into a student representative spot on the elite American Institute of Architecture board of directors. Day said he marveled at the chance to be a part of a body that even the nation’s best architects wait their entire career to join.
Another AIA board member at the time was Jeremy Harris, the mayor of Honolulu, Hawaii. The duo struck up a friendship over months of travel and meetings as Day began to ponder his own future in public service.
“I would always pick his brain about getting involved,” Day said. “He would always tell me: ‘go back to your hometown. Don’t go to D.C., don’t go to New York. Go back to your hometown.’”
After pursuing graduate degrees at both Carnegie Mellon and Oxford University, Day moved back home to Maryland, where he accepted a position with the nonprofit Eastern Shore Land Conservancy. Six months later, however, he came to a decision point.
He couldn’t shake the feeling any more. It was time to enlist.
“I sat down with my boss in a coffee shop and I said, ‘I want to join the Army,’ fully prepared for her to fire me. Instead, she said, ‘that would be awesome training for you, to be a great small-unit leader for us. Go.’” Day signed his recruitment paperwork, and was shipped off to basic training at Fort Benning, Georgia – at age 26, his nickname was “grandpa,” he said with a laugh – followed by a 16-months of Officer Candidate School.
His OCS experience forged in him such an appreciation for the responsibilities of the officer corps that he decided to work there, serving four years at Aberdeen Proving Ground as an OCS senior tactical officer.
“I learned to articulate more about leadership there than I did anywhere else,” Day said. “Whether it’s a learned quality or a gifted trait, I believe it is a skill set that’s got to be practiced in order to be refined. You’ve got to be actively engaged in those experiences to continue to be an effective leader.”
Taking the advice of his friend Mayor Harris of Hawaii, Day indeed went back to his hometown, armed with “a burning and rising passion,” he said, to be an agent of change for Salisbury. He started taking on roles with municipal groups and civic organizations. He also made a decision to forgo additional Army education that would keep him away from home.
“I thought, well, maybe they’re right. Maybe I should be involved,” he said. “If it could appear to them that I could be not just neutral but potentially a uniting influence, then maybe other people would think so too. I thought, maybe there’s hope for something better.”
Hope was in short supply. These intervening years were more than just a rough patch for the once-proud city of Salisbury. The economic recession continued to take a devastating toll on the former manufacturing hub. Jobs dried up. Crime was on the rise. Many young people, Day said, were concerned for the city’s future.
At age 30, Day ran for City Council. His opponent attacked him for his youth, inexperience, and pie-in-the-sky promises for a better tomorrow – for his hope.
Not only did he win his district with 71 percent of the vote, but his fellow council members also unanimously picked him to be Council President. He was compelled to execute the plan he created as a candidate to lead the legislative branch.
“I had the bully pulpit, and influence, and a voice,” he said. “But I really felt the major difference that could be made was in the mayor’s office.
“So I decided to run for mayor.”
Day ran unopposed for Mayor of Salisbury in 2015 with abundant community support. When he took the job, he said he found an organization that had “suffered a vacancy of leadership, for a long time.”
“Part of my military background, knowing how to make an organization feel like a team, and oriented on a clear set of goals was something I felt comfortable with,” he said. We did a lot of things differently. This is management in furtherance of leadership.”
“I had the bully pulpit, and influence, and a voice,” he said. “But I really felt the major difference that could be made was in the mayor’s office.
“So I decided to run for mayor.”
Day ran unopposed for Mayor of Salisbury in 2015 with abundant community support. When he took the job, he said he found an organization that had “suffered a vacancy of leadership, for a long time.”
“Part of my military background, knowing how to make an organization feel like a team, and oriented on a clear set of goals was something I felt comfortable with,” he said. We did a lot of things differently. This is management in furtherance of leadership.”
It wasn’t a wholesale revamp of how City Hall worked, but it came close. Mayor Day met with every team, every department, trying to understand their concerns and frustrations. Day instituted regular all-staff meetings and Q&A sessions. He oversaw dozens of organizational changes to streamline government operations and services.
Operationally, he instituted a new system of measurable metrics, called Result SBY, that ties directly into budgets and performance evaluation. Day calls it “a high-functioning battle rhythm.”
“Every week we’re looking back at the big measures of what progress our city is making on the things we agreed were important,” he said. “It exposes our strengths and our weaknesses, then zero in on that issue and refine it. We never lose sight of those big metrics – are we turning this tanker in the right direction?”
Transparency was the new buzzword, too, under the Day administration: New social media accounts where none before existed. A unfiltered live online broadcast of public safety meetings from the police department. They even created a smartphone app for residents to ping City Hall to fix broken streetlights, unsightly rubbish, potholes, and more; it geo-locates the exact location where the problem lies so crews can get right to the spot.
As a result of all this, Day’s leadership led to an improved level of accountability and, more importantly, a growing sense of ownership among city staffers.
“We’re trying to push that sense of responsibility to the lowest levels possible,” he said. “Everybody’s got to re-think the way we think about public service.”
Three years into Mayor Day’s term, Salisbury is now in the middle of a remarkable turnaround.
Its median age has dropped to 27.2. The city has more college-educated residents than ever. Wages and property values are going up. The business community is reinvesting in the town, and jobs have outpaced population growth. Crime has reached record lows. Public officials from around the state have taken notice.
Operationally, he instituted a new system of measurable metrics, called Result SBY, that ties directly into budgets and performance evaluation. Day calls it “a high-functioning battle rhythm.”
“Every week we’re looking back at the big measures of what progress our city is making on the things we agreed were important,” he said. “It exposes our strengths and our weaknesses, then zero in on that issue and refine it. We never lose sight of those big metrics – are we turning this tanker in the right direction?”
Transparency was the new buzzword, too, under the Day administration: New social media accounts where none before existed. A unfiltered live online broadcast of public safety meetings from the police department. They even created a smartphone app for residents to ping City Hall to fix broken streetlights, unsightly rubbish, potholes, and more; it geo-locates the exact location where the problem lies so crews can get right to the spot.
As a result of all this, Day’s leadership led to an improved level of accountability and, more importantly, a growing sense of ownership among city staffers.
“We’re trying to push that sense of responsibility to the lowest levels possible,” he said. “Everybody’s got to re-think the way we think about public service.”
Its median age has dropped to 27.2. The city has more college-educated residents than ever. Wages and property values are going up. The business community is reinvesting in the town, and jobs have outpaced population growth. Crime has reached record lows. Public officials from around the state have taken notice.
Just like he would as a military officer, Mayor Day claims a responsibility to give his staff the vision, guidance, and motivation to get the job done.
“You have to inspire them to feel like they’re part of something special,” he said. “I think mayors are the best public example of visionary leaders because they have to be able to see a better future for their city.
“I’m going to continue to try to be the best mayor of Salisbury I can be,” he added, “and to make Salisbury the best city it can be. One day I’ll get to look at my city and say, wow, we did so much in such little time, and we changed this place for the better.’ I want the people of Salisbury to feel that way about their town.”
This profile appeared in the April 2019 edition of At Ease magazine. Photos by Todd Dudek.
“You have to inspire them to feel like they’re part of something special,” he said. “I think mayors are the best public example of visionary leaders because they have to be able to see a better future for their city.
“I’m going to continue to try to be the best mayor of Salisbury I can be,” he added, “and to make Salisbury the best city it can be. One day I’ll get to look at my city and say, wow, we did so much in such little time, and we changed this place for the better.’ I want the people of Salisbury to feel that way about their town.”
This profile appeared in the April 2019 edition of At Ease magazine. Photos by Todd Dudek.
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