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Career Corner

Hill Happenings features career advice from DC professionals of all kinds.
Read their takes on choosing a career, job hunting, and success in the workplace.

Q&A with Brent Sullivan

Brent Sullivan is the founder of Time On The Hill, a successful platform focused on optimal congressional and professional job searches. A former congressional staffer himself, he works with job seekers to strengthen their search strategy, sharpen their applications, and prepare for the final interview. With the 2018 midterms almost upon us, staffers on both sides of the aisle are dusting off their resumes in anticipation. I sat down with Brent to get his thoughts on what people should be doing in preparation for their dream Hill job.


What kind of services does Time On The Hill provide and how can people benefit from them?

When you think about the full search, when it comes to landing a job on the Hill or a job off the Hill, there isn't really anything that we don't cover in terms of our strategy. You could say that it's about really being meticulous. You could say that we really roll up our sleeves and work on the mechanics of the search. Yes, we can have a conceptual conversation about your five-year vision, but at some point you need to kick it into gear.

When you're talking specifically about services, we cover new congressional resumes, custom cover letters, LinkedIn photographs, LinkedIn profile updates. The job search strategy is a long chain of events and every link in the chain is critical. Selecting Members, written deliverables, presenting yourself digitally, checking social media, coffee tips, interview preparation, navigating the offer negotiation—it’s a marathon from start to finish. We can take someone who's at the starting line and we can take them through the entire process until they accept an offer. There isn't really anything that we don't cover.

Is there some basic homework you think people should do before they sit down to meet with you or before they even start their congressional job hunt?

First, I would say it helps to cover the basics. Select a party. Pick members. Also consider the private sector as we focus on Congress. As someone who is very nonpartisan, I understand the conundrum of being forced to select a party, especially now. But we have fewer and fewer moderates, and it’s very difficult during the networking phase to solicit outreach to Republicans if you're currently networking with Democrats. Select a party and then we go from there.

Next, think about the issues you care about. Public service is about solving problems. So is it healthcare? Veterans’ affairs? Criminal justice reform? Judiciary? Energy? Transportation? Just about everybody under the age of thirty says foreign affairs. Issue selection helps you with the next very critical element, which is Member selection. 

So you want to select your Members based on your geographic ties as well as the committee assignments that cover those specific policies that you care about. So, for example, if you really love healthcare, you want to focus on the Members that sit on the Ways and Means and Energy and Commerce Committees. Those are the core committees that focus on healthcare policy. When I was searching for a job on Capitol Hill, I was told not to work for a freshman Member on the Agriculture Committee if I wanted to manage a healthcare portfolio. I badly wanted to work on the Hill so I thought that was crazy. But, looking back, that advice was incredibly sound because you’d never do any healthcare policy work. You would create proposals that relate to agriculture. If you really love agriculture policy, that would be the perfect Member. If you want to work on healthcare, that would be the totally wrong office.

But I so badly wanted to work on the Hill that I was willing to work for anyone—that was not a sound strategy, and I didn’t know that. And that's why it took me seventy-four coffees and interviews to get my first job on the Hill, because I didn’t understand the process. Pick a party, pick the policy areas you care about, put together a list where you have geographic coverage, and then start to reach out to legislative directors, chiefs of staff, and committee staff based on a strategic plan.

You don’t just help people get on the Hill, you also help current Hill staffers navigate their way towards promotions. So what's some advice you have for people looking to move upward once they’re on the Hill?

Number one is keep your head down and work. You don't be a job hopper. There are people who, as soon as they get the legislative correspondent job, they immediately want to become a legislative assistant. They become a legislative assistant and now, within minutes, they want to be a legislative director. Your mission in life is to work hard, position yourself for promotion, achieve the promotion, and then grow where you're planted. If you are exceptional, you will get promoted—it is a guarantee that you will get promoted.

The question is: are you focusing on getting to that next level or are you growing where you're planted? Are you constantly focusing on what you need to do in order to market and present yourself for the next opportunity? There are too many people who work very hard to get on the Hill and then, as soon as they get on the Hill, they stop networking. They stop updating their LinkedIn profile. They stop polishing their resume. I think that’s unfortunate. That's a big mistake. Getting on the Hill is unbelievable, but that is not your last job. There will be many positions and many jobs between retirement and today. And so it saddens me when you see someone who worked incredibly hard to get on the Hill and then, as soon as they get the congressional business card, they stop doing the things that got them there.

Let’s say that I'm someone who's looking to get on the Hill and it’s the day after the 2018 midterm elections. What should I start doing as soon as possible so I can start working in the 116th Congress?

The very first thing that you need to do is to look at all of the states where you have ties. Look at the election results and put together a list of all of those congressional delegations.

The next thing that you need to do is take a look at the committees that have jurisdiction over the policy areas that you care about and write down all of those names. So now you've got a list of geographic ties, you've got a list of committee members. Then we get into some of the mechanics: LinkedIn accounts, resumes, a cover letter, perhaps a writing sample.

The chiefs and legislative directors of all new offices are going to be extremely overwhelmed with candidates. Please keep in mind that campaign employees are now out of a job. And so many turn towards Capitol Hill because they're not thrilled with the thought of unemployment. So you're competing against tens of thousands of individuals who go from campaign mode, from a full on sprint to, “Oh my God. Job’s over. Money’s over. Unemployment.” So you're competing against that entire batch of applicants.

You need a strategic plan to focus on Members that make sense, and you need to focus on where the skills in your background bring the most value. If you happen to be someone who's been doing campaign work in Florida, you would want to start off with every single Member from the Florida delegation. If you love foreign affairs policy, you're going to want to have your list of Florida members and then, below that, is everyone who serves on the Foreign Affairs Committee. You also, within sixty days, are going to have committee assignments for every member. You can see who's been assigned to each committee of jurisdiction. Before you send a single email to senior staff—whether that’s chiefs of staff, campaign directors, campaign finance directors, or legislative directors—you need to have that list ready.

Then, before you send out anything, your materials must be perfect. There are tons of candidates who fire away, fire away, fire away. They’re amazing candidates ready to work, but the materials look terrible. They would be better off taking two or three days at most to really sharpen their materials, and then start reaching out to folks. If they don’t craft perfect materials, they don't get the results they want and they become frustrated. This has a spiral effect.

So step one is Member selection, committee selection, and policy selection. Then, after that, it’s about direct outreach. And if you go about your outreach the right way you will be massively successful with your networking.

After the midterms, how should you approach sending application materials to senior campaign staff of successful campaigns?

There will be at least sixty new members and several dozen new chiefs. The chiefs of staff will be looking for exceptional talent. They would love it if exceptional talent would come out of nowhere delivered on a silver platter. And you can absolutely deliver yourself on a silver platter if your resume is perfect and if your LinkedIn account is perfect.

Do keep in mind that, in most cases, hiring is done top down. So they don't want to hire legislative assistants and the staff assistant without the legislative director present. They want to make sure that they have a legislative director who’s heavily involved in building out the team because it will be a legislative director who manages and who handles oversight for this team. So when the chief comes in, they select a legislative director and someone as comms director to run the communications shop. After that, there is usually someone from the campaign who handles scheduling, and then they need to build out two legislative assistants, a legislative correspondent, and a staff assistant. 

So yes, contact new offices but don't send half-baked materials. Take your time. Quality is better than speed. If you have exceptional materials, you're highly likely to get a call back. If you're an amazing candidate who’s sending in junk, odds are you will not get the attention you deserve and that's how it goes. So many people fall victim of that.

Speaking of half-baked materials, what's the most common application mistake that you see among people applying for congressional jobs?

Education at the top of the resume. Career services offices really do a disservice to students. Education over experience makes absolutely no sense. Chiefs of staff are looking for experience. I have no idea why people put education at the top. It has no business being there.

Make sure that your resume lists a D.C. address. Use an address of a friend or family member if need be. It is so much easier to hire somebody who already has a plan for D.C. housing. If you can hop on a train from New York and get down here for an interview, put down a D.C. address.

Also, I think a lot of people submit resumes that don't articulate the skills for the job that they are applying to. So, for example, if you’re focusing on being a scheduler, make sure that there is material on your resume that indicates you've done scheduling work. For some reason, you have a lot of people who apply to scheduling jobs and they haven't listed a single bit of scheduling work. You either need to do a better job of creating your resume, or you need to do a better job of applying to positions that make sense for your background. It’s very difficult to consider someone for a scheduling position with zero scheduling experience.

Finally, a resume that is longer than one page is a major mistake. You have senior advisers who work for the Majority Leader, staffers who have been on Capitol Hill for a decade, and they have one-page resumes. If you're a 25-year-old with no Hill experience, you can get your material down to one page as well.

What's something unique about congressional interviews that people should know when they're preparing for them?

You need to focus on the goals of the office. Too many candidates focus on themselves and what they can get from the office. It’s not about you, it’s about the office. When you go to an interview, they're trying to learn as much as they can about you, and they're trying to determine whether or not you will work well with the chemistry of the office as a team player. The best way to be successful in the interview process is to focus on the goals of the office and the Member. Because it's not about what you want to do, it's about what they need. If you're focusing on what they need and you can determine what you're capable of achieving, you can bring an extraordinary of value to a congressional office. 

It's conventional wisdom that informational interviews with staffers, “grabbing coffee,” is essential to a Capitol Hill job hunt. What's a single piece of advice you’d give to someone who's going into these informational interviews?

Listen more and speak less. They don't need to learn a whole lot about you, you need to learn a whole lot about them. How did they get on Capitol Hill? What policy areas do they love? What do they see in the year ahead in terms of the political agenda? You're trying to learn as much as you possibly can during that coffee about that staffer. For some reason candidates feel that these meetings are big opportunities to do this huge download and gush. You should be focusing on learning as much as you can about the individual who works on the Hill.

In your experience, is there a certain type of person that is generally more successful when searching for a job on Capitol Hill?

The people who are incredibly successful view themselves and view their careers as a commodity. Say to yourself: “Am I a Honda Civic or am I a Rolls-Royce?” The people who treat their careers like it's a Rolls-Royce are the ones who are extraordinarily successful. They are the ones who are always being asked for interviews and the ones that are always being promoted. They don't spend 24/7 thinking about their careers, but they give it the attention it deserves and they're being very thoughtful with their decisions.

Is there a major success story that you have from somebody that you've worked with? Someone who made it to the Hill but had to work especially hard to overcome unique obstacles.

So my favorite example in the six years and more than 1,600 candidates I’ve worked with is a young man who was in the military and, at the time, he was in Hawaii. He was not sure how he was going to get from Hawaii to a job in Congress. I remember working with him and his materials were excellent. We started to go through the interviewing preparation process. He got his first Senate interview, and then a second Senate interview, and then his third and final interview with the Chief of Staff for the Senator. He landed the job and called me at 5:30 PM on a Friday. I was overwhelmed. It was like a drug. And he was a Veteran.

It feels amazing when someone sends you a text message and it says, “I got the job.” When it all comes together it’s euphoric. You know this is a guy, and you know his commitment to public service. You know that he will be a tremendous asset on Capitol Hill as a former Veteran. It’s the best feeling on the planet. The happiness is that great. Because you have someone who you know has already been committed to service for eight years in the military and now he's able to get from the islands of Hawaii to Washington, D.C. That to me was one of the most special placements that we've ever done.

When it comes to working on the Hill or searching for a job on the Hill, is there a piece of conventional wisdom that you take issue with?

I think my biggest concern is when a candidate believes they are somehow entitled to a job on the Hill. The smartest men and women from all over the United States want to work on very serious problems on Capitol Hill. You are entitled to nothing. Everyone deserves a shot, but you have to earn your spot in Congress. If you're willing to work extremely hard you can be massively successful, but it will take hard work to get a job and a whole lot more work when you have the job. 

I want to ask you a little bit about your own career, since it's been unconventional and fascinating in its own right. You've been a Hill staffer, you've been the healthcare lobbyist, you currently have your own firewood service business on the side, you invest in real estate, and you founded Time On The Hill. What do you think has been the greatest asset to your career?

My parent’s work ethic basically. As everyone can tell you, I am of extremely average intellect. A B+ student. There are people in Washington, D.C. with PhD’s from MIT and Stanford—we’re talking truly brilliant people. But the question is: how hard are you willing to work? Are you willing to try to support others and to work tirelessly? That has been my father's work ethic, that has been my mother's work ethic, and that has been my sister's work ethic.

I am not a political mind and I'm not very savvy with partisan politics. I don't study congressional district percentages with Charlie Cook. But when it comes to trying to help people, I think I've got a pretty solid work ethic. I think a lot of people would like to talk about how to get a job on the Hill and how to help others get a job on the Hill, but are they willing to roll up their sleeves and do the work? I don't see very many people who are actually willing to sit down with you and actually get into the work. I love doing the work.

If you could go back and change something about your career, what would it be?

My career is my career. In your twenties, you roll with opportunities and you try to learn as much as you can. At the moment, I’m exactly where I’m supposed to be. Looking back on the opportunities that I've had, I’ve been very lucky. I’ve worked in Manhattan, Richmond, Raleigh, Washington, and Houston. I’ve worked for nonprofits, the Congress, the campaign trail, and the corporate world. I’ve seen the big positives and serious negatives in all of it. But I wouldn’t be able to navigate careers with major success without those experiences. You can live, and work, and learn, and try again. But you can’t read about it. You have to do it.

Brent Sullivan