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Taking Up The Baton: Obama Alumni Making a Difference in State and Local Government

Stories

January 26, 2024
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 individual images of our five featured alumni. From left to right: Brady Chalmers, Craig Dorsett, Tess Hetzel, Anuj Gupta, and Paul Monteiro Jr.

Over the past fifteen years, hundreds of alumni from the Obama campaigns and White House have built on their commitment to public service. Some have become doctors, others educators, but a select few have reaffirmed their dedication to building strong and resilient communities through the power of state and local government. 

We recently connected with five alumni working in a range of state and local government positions about their current roles and the values they’ve carried from their time working as part of the 44 Alumni community. Learn more about them below.

Brady Chalmers

“One lesson I learned in D.C. was that all politics is local. If I wanted to make a real impact, I had to go do it for the people who needed me most.”

Brady Chalmers is in the center of the photo smiling at the camera. He has a medium skin tone with closely-shaven hair and black rectangular framed eyeglasses. He is wearing a black suit jacket, a light blue collared shirt, and a plaid tie with black, white and gray in its color scheme. Behind Brady are two standing flags. The flag on the left is the U.S. American flag and the flag on the right is the Cook County flag.

2012: Deputy State Director for Paid Field, Obama For America ‘12

Recent: Chief of Staff - 5th District, Cook County, IL Government 

Then

Brady Chalmers  entered into the world of politics as a volunteer. In 2007, he moved from his hometown of Chicago to the DC Metro Area to learn more about politics and government action in real time as a canvasser in Northern Virginia. Taking his knowledge and passion, Brady eventually became the paid field team lead for the St. Louis region on the Obama 2012 campaign. 

“Even back then, I spent my time communicating with voters in places like Ferguson, Missouri on how much President Obama needed their help…we went into areas of St.Louis that no one else wanted to work in because oftentimes, those people, my people – primarily black, working-class, and low-income – needed an administration that would fight for them.”

The Legacy  

After his work on the campaign, Brady pursued a career in public service, specifically looking towards opportunities to support his community through local government. In addition to his tenure in constituent services for a Chicago alderman, Brady formerly served as the Chief of Staff for Cook County, Illinois’ 5th District. 

In his position, Brady worked with direct service programs for low income students and on programs such as the Medical Debt Relief Initiative – which took a $12 Million investment from American Rescue Plan funds and worked with hospitals to forgive over $280 million in medical debt for Cook County residents. 

For Brady, the work that supports community members in his native hometown makes the harder days more bearable: “Programs like these, where I know we've made a direct impact on people, are the reason I love local government.”

Brady’s Advice for People Interested in Working in Government

“Go into government because you want to do the right thing. You can change lives every day. But not every day will be a good day and every victory comes after many defeats.”

Two men stand at the center of the image facing each other: one is President Barack Obama, the other is Anuj Gupta. President Obama is wearing a dark blue suit with a white collared shirt, and a light blue tie. He has an American flag pin fastened to the left lapel of his suit. He is in mid-conversation. Anuj is a brown-skinned man with short dark black hair. He is wearing a gray suit with a white collared shirt, and a purple tie. He has an Obama campaign pin fastened to the left lapel of his suit. Anuj is clutching his hands together and smiling at President Obama. In the image, the two men are located on Air Force One. On the plane are brown leather reclining chairs and a brown wooden desk. On one of the chairs are three newspapers – publication and copy indiscernible. The walls of the plane are beige. There are three plane windows, each of which are fully open.

Anuj Gupta

“The ultimate reward of working in government is the ability to shape and shift the levers that can truly impact people’s lives for the better.”

2008: Director of Special Projects & Press Aide, Obama for America ‘08

Now: Director of the Department of Transportation, City of Santa Monica, California 

Then

Galvanized by the words and leadership of President Obama, Anuj Gupta took a leave of absence from his position at a law firm in Los Angeles to volunteer for the 2008 California primary. Later, Anuj continued on to campaign staff roles in the Texas, Indiana, and South Dakota primaries, and then to Virginia for the general election. 

Following his time on the campaign trail, Anuj came to Washington and served in President Obama’s Administration, first on the nominations team in the Office of Legal Policy at the U.S. Department of Justice and then in the White House as Associate Staff Secretary. While working in the administration, Anuj got a first hand look at what it takes to develop policy and the incredible importance of diversity in political representation: 

“The community organizing model to achieve change – focusing on storytelling, the power of person-to-person engagement, and the guiding principles of Respect/Empower/Include – have shaped my commitment to inclusive and meaningful public engagement.”

The Legacy  

After leaving the White House, Anuj returned to California and began working in city government. In 2017, he assumed the role of Deputy City Manager for Santa Monica, spearheading policy initiatives on homelessness and mobility, and guiding the city's economic recovery during the COVID-19 pandemic Opens in a new tab . Today, he leads as Santa Monica’s Director of the Department of Transportation, overseeing a team charged with offering the Santa Monica community an array of mobility options that address climate change and reduce traffic congestion. These initiatives include the Big Blue Bus transit service – a project that installs zero-emission, fully electric fleet of buses – and a pedestrian and bike-friendly redesign of Santa Monica’s roadways. Opens in a new tab

I grew up as the youngest child of immigrants from India, and my entire immediate family -- both parents and both older sisters -- chose medicine as their profession. I saw each of them making a vital difference for the countless patients they served, and it made me consider how I too could make an impact on people’s lives in my own way. While I knew early on that I had different aspirations, through public service I have connected with my own ability to make change to improve the lives of the most vulnerable around the country and in my own community.” 

Anuj’s Advice for People Interested in Working in Government

“Be open to opportunity, and don’t get too attached to one fixed path or plan. I walked away from a stable, well-paying job at a prestigious law firm to take a chance on an initially unpaid campaign role in 2008, but not for a moment could I have imagined or planned that this decision would eventually lead to me working in the West Wing of the White House or traveling with President Obama. While you may not know what waits behind every door, if you let your values and passions guide you, and commit to causes and leaders you truly believe in, you will rarely make a wrong move.”

Paul Monteiro, Jr.

“Getting to see how your work improves people's lives is incredibly meaningful. It's especially true working in state government, where it feels more personal and closer to local communities.”

The image features two men standing at a podium. In the background of the image is a beige wall with crown molding and a standing Maryland State flag. The man at the center of the image is Paul Monteiro Jr. He is a brown-skinned man with closely cropped black hair. He is wearing a dark colored suit jacket, a white collared shirt, and a green tie. He is gesturing with his hands and talking into two microphones placed in front of him. Behind Paul Montiero Jr. is another man. This man is a brown-skinned man who is bald. He is wearing a dark blue suit, a white collared shirt, and a light blue patterned tie. On the left lapel of his suit is a flag pin. He is staring at Paul Montiero.

2008: Deputy Director of Religious Affairs, Obama for America ‘08

Now: Secretary, Maryland Department of Service & Civic Innovation

Then

Early in his career, Paul worked in then-Senator Obama's Capitol Hill office before transitioning to Chicago as Deputy Director of Religious Affairs for Obama for America in May 2007. In his role, Paul was tasked with engaging local and denominational faith/belief leaders around some of President Obama’s campaign issues. Following the campaign, Paul was asked to join the White House Office of Public Engagement, where he  worked with faith leaders, public service organizations, and others to support the White House’s My Brother’s Keeper Program.  

During President Obama’s second term, Paul was appointed Director of AmeriCorps VISTA at  the Corporation for National and Community Service (CNCS) in 2014 and then Acting Director of the Community Relations Service at the Department of Justice.

The Legacy  

Today, Paul works alongside a team of Maryland leaders – and 44 Alum Tess Hetzel – as the first-ever Secretary of Maryland’s Department of Service & Civic Innovation Opens in a new tab . The department, established through the (SERVE) Act of 2023 works to promote opportunities for young people in the space of service and volunteerism throughout Maryland.  

In his journey, Paul cites the values of the Obamas as guiding light for the work he continues to do: 

“They [the Obamas] exemplified excellence in public service and proved that kindness and civility doesn't have to be sacrificed in order to work at the highest levels of government. For someone like me who wasn't born into privilege, they also embodied the hope that we don't have to be limited by the circumstances we're born into and that the halls of power have a place for all of us.” 

Paul’s Advice for People Interested in Working in Government

“Maryland has a number of vacancies at all levels of government. There are amazing people that work here, opportunities to work on relevant challenges and leading edge solutions to improve our society. Those of us in the public sector should take every opportunity to remind those looking for purposeful work that government service is a preferred destination."

 In the image, five people are standing in the center of the Maryland State House floor podium. They are posing for this image. From left to right: The first person in the image is a brown-skinned woman with short dark black hair. She is wearing a black suit, an ID lanyard around her neck while smiling at the camera. The second person in the picture is a brown-skinned woman with dark curly hair, wearing eyeglasses. She is wearing a yellow blazer, a black shirt, dark pants, and has a large circle necklace on. She is smiling at the camera. The third person in the picture is Tess Hetzel. She is a pale-skinned woman with long blonde-red hair. She is wearing a light blue blazer and a white patterned shirt. She is smiling at the camera. The fourth person in the image is a pale-skinned woman with medium-length dark brown hair. She is wearing a black blazer and a blue dress. She is smiling at the camera. The fifth – and last person – in the picture is Paul Montiero Jr. He is a brown-skinned man with close cut black hair. He is wearing a gray suit, with a white collared shirt, and a mauve (pink) colored tie. He is smiling at the camera. The background behind the five people is a marble arch with two large columns, an awning with a roman numeral clock at the top, and two standing flags. The flag on the left is the U.S. American flag and the flag on the right is the Maryland State flag. In front of them is a larger desk/podium made of brown wood. On the desk is a small black monitor. To the right of the desk, is a dark brown podium with a microphone.

Tess Hetzel

“The best thing about working in government is getting the chance to see the impact of our work and the real difference we are making in the young people's lives.”

2008: North Carolina Field Organizer, Obama for America 2008 

Now: Chief of Staff for the Maryland Department of Service and Civic Innovation

Then

At 19 years old, Tess Hetzel dropped out of college to join the 2008 Obama presidential campaign. From that point on she knew her path lay in public service and community organizing. During her time on the campaign, she worked to organize western, rural areas of North Carolina, which helped bring about a decisive victory for the campaign.  

“Organizing in rural Western North Carolina was one of the hardest things I had ever done and the thing I am most proud of in my life. Despitemultiple vandalizations and threats of all kinds we persisted.” 

Following her time on the campaign, Tess went back to school, while still keeping a foot in politics. She went on to intern in the East Wing of the White House, and subsequently worked at the White House Visitors Office after graduating. Her time spent within the administration and on the campaign shaped her decision to work in government and provide support for millions of people. 

“Working with the Obamas and the incredible team showed me the power of public service and the responsibility we have to be civically involved. Over the years I've loved being able to shine a light and uplift the voices of people doing incredible work all over the US.” 

The Legacy  

Tess continued on her path of public service, working for AmeriCorps, promoting national service and volunteerism, through the end of President Obama’s second term. Now – in a reunion of two 44 Alumni – Tess recently began her position as Chief of Staff for the Maryland Department of Service and Civic Innovation, continuing her efforts to support young people as they pursue opportunities for workforce development and service in the state. “Secretary Monteiro and I worked together during the Obama Administration at the White House and AmeriCorps. It’s been an honor to continue that work, building a department from scratch, launching a first-in-the-nation Service Year Option program, that honors the values we upheld in the administration. We’ve done so much in the first couple of months and we’re just getting started!” 

Tess’ Advice for People Interested in Working in Government

“You can find some of the most passionate and inspiring folks working in public service. Find those people, figure out how to make the change and GO FOR IT.”

Craig Dorsett

“As President Obama encouraged us in his 2017 farewell address to staff, I saw an opportunity to make a difference locally, so I eventually picked up a clipboard, collected signatures, and ran for local office in 2021 to continue serving my community.”

The image is located in a room in the White House. In the background of the image is an open door, a dark brown desk with a computer and files on top of it, and a beige wall with a square picture and a gold frame. In the center of the image are six men standing in a circle and one man standing behind the desk. In the six man circle, President Obama stands in the center. He is wearing a dark colored suit and a light blue button-down shirt. On the lapel of his suit is an American flag pin. He is in mid conversation. Surrounding him are five men, four of the men are indistinguishable because their faces are turned away from the camera. One of the men whose profile is towards the camera is identified as current President Joe Biden. He is wearing a blue polka dotted tie and standing with his arms crossed against his chest. The man – outside of the circle, standing behind the desk – is Craig Dorsett. Craig is standing profile to the camera staring at the conversation between the circle of men. He has one hand on his hip and another on the desk. He is a pale man with short dark brown hair and a dark brown goatee. He is wearing a light gray button-down shirt, a dark color tie, dark pants, and a watch on his right arm. On his neck is a White House ID, hanging on a chain.

2009: Special Assistant to The White House Chief of Staff 

Now: Ridgefield NJ Council Member and Chief of Staff to Bergen County, NJ Executive Jim Tedesco

Then

Like Brady and Anuj, Craig’s tenure with the Obamas began as a 2008 volunteer. He quickly worked his way up, becoming an organizer in his native New Jersey for the general election. Following his time on the ‘08 campaign, Craig joined the White House Office of Presidential Correspondence, where he was part of the team of writers charged with drafting policy responses, presidential proclamations, and messages to constituents. He credits the experience with introducing him to several lifelong friends, and eventually making it possible for him to take a position serving as Special Assistant to two White House Chiefs of Staff, Bill Daley and Jack Lew. He later spent several years as an appointee in the Department of Interior. 

The Legacy  

After President Obama’s term ended, Craig moved back to New Jersey where he held multiple positions in New Jersey state government. In 2017, he joined the New Jersey Department of Environmental Protection, working with the state’s Natural and Historic Resources program, and eventually served as New Jersey’s first Administrator for Urban State Parks. Still this wasn’t enough for Craig. Motivated by the tireless work of his peers and inspired by the legacy of President Obama, Craig decided to run for local office in 2021, and won. 

“As a Councilman, I have found that what smaller governments may occasionally lack in scale or complexity of problems, it more than makes up for in the speed with which progress can be made and solutions explored…the opportunity to take action on behalf of and work to improve the lives of your neighbors, even in modest ways, has been extraordinarily rewarding.”

In addition to his work as a Council Member in Ridgefield, today Craig serves as Chief of Staff to the County Executive of Bergen County, Jim Tedesco.

Craig’s Advice for People Interested in Working in Government

“DO IT! It might not end up being for you, and that's okay, but you won't know if you don't give it a chance. I think the best case for our democratic republic writ large is made through effective government, which can be achieved by thoughtful and caring leaders serving at every level, doing their best on behalf of their neighbors and communities.”

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