Accomplishment: An Interview with Jen O’Malley Dillon

“I think if I could recommend one job that anyone should have in their life, it would be a field organizer.”

Jen O’Malley Dillon, founding partner at Precision Strategies, considers herself an organizer by trade. An extremely hard worker with high standards, Jen is one of the most productive leaders I know. Jen (and the teams she builds) is always able to accomplish amazing feats that don’t seem possible—and now she does so while raising twin girls. All of this success she credits to her foundation in organizing.

Jen officially became an organizer fresh out of college on a Massachusetts governor’s race, but she was born into a political family and raised learning the values and tactics every organizer needs to be successful. The daughter of two public school teachers, Jen remembers a very serious conversation her dad initiated with her when she was 10. Worried it would be something mortifying like a discussion of the bird and the bees, Jen was relieved (though a little confused) when he instead told her that if she ever left the Democratic Party, she would be leaving her people. He really hoped she could find a way to fight for her people when she got older.

Though it would take a few years for Jen to truly understand what her father meant, she has truly never let him down, dedicating over 15 years of her life to electing and supporting Democratic candidates and causes.

Traveling all over the country, working on every type of race in every type of field and leadership position, Jen has played a pivotal role in many important Democratic campaigns and groundbreaking developments. As the 2008 Obama campaign’s battleground states director, Jen managed the largest grassroots organization in presidential history and built the first ever in-house analytics team focused on targeted voter contact, resource allocation, and program efficiency. She then served as President Obama’s first executive director of the Democratic National Committee, building the largest DNC operation in history until she joined the 2012 Obama campaign as a deputy campaign manager.

Now at Precision Strategies—the data, digital, and communications strategy firm Jen founded with two of her Obama colleagues, Stephanie Cutter and Teddy Goff—Jen and her cofounders lead a firm of 50 people working with non-profits, corporations, and domestic and international political campaigns and organizations.

It’s hard to believe Jen’s extremely impressive and impactful career started just like most organizers’ stories. Supportive of a Democratic candidate, interested in campaign work, and frustrated with her current job, Jen began to volunteer regularly on a governor’s race in Massachusetts. An immediate superstar, she was noticed by campaign staff and was quickly hired to answer the office’s 27 phone lines. After handling this busy job exceedingly well,

her hard work was rewarded again as she became the college volunteer coordinator.

“That was the moment I became an organizer.”

Longtime friend and protégé of Jen, Mitch Stewart, remembers the first time he met Jen in Chamberlain, South Dakota. At an introductory staff training for the 2002 Tim Johnson for Senate race—a race their team would go on to win by a mere 524 votes — Mitch was equal parts terrified of and in awe of Jen, the campaign’s field director and his boss. Too scared to ask what Jen meant when she said the acronym GOTV, Mitch just nodded and smirked like all of his colleagues. Even now, as Mitch leads the grassroots consulting firm 270 Strategies, he constantly thinks, “How would Jen do this?” when thinking through how to solve a difficult problem.

Throughout each step in Jen’s career, she has remained an organizer through and through. Always an excellent and effective leader, Jen has never grown used to the perks that her leadership positions come with. She is not at all like those who jump at every opportunity to schmooze with the bigwigs; she much prefers to lead from behind the scenes. One particularly embarrassing story for Jen to remember happened when she worked for Senator John Edwards in the 2004 Iowa Caucus. Shortly after meeting him for the first time at his first Iowa event in 2003, Edwards called Jen to tell her the event went well. All she could think to say (to the candidate the event was built for) was, “Thanks for coming.”

Occasional gaffes with elected officials aside, Jen has found amazing success through her investment in organizing. Jen has never worried about titles or perceived importance as she continues to accomplish more and more following each new challenge she takes on. She’s always much more focused on how important the work itself is, how big of an impact it will have, what she can learn, and the people she will work with and learn from.

Along the way, she has mentored, taught and supported many individuals who are now doing amazing things on their own. One of them, Mitch, says, “[Jen was] a great first campaign boss. I wouldn’t be where I am without her.” With Jen’s far- reaching leadership and influence, we know Mitch is not alone in that feeling.

*********************************************************************

AM: Do you remember when you began to fall in love with organizing?

JOD: On the first race I did [a Massachusetts governor’s race], the whole thing clicked for me in terms of this was the kind of environment and experience that I really enjoyed, that suited me, and that was very team-oriented. I played sports my whole life and in college, and I felt like being on a campaign was similar to being on a sports team. I was able to see that young people had a lot of responsibility. Also, I think you always hear that politics is about who you know, but when I was working hard as a volunteer, people on the campaign saw that I worked hard so then they hired me to answer the phones. When I did a good job answering the phones, they moved me to working with volunteers. I felt like it was really merit-based.

That first experience, I really caught the bug because I thought it suited me personally, but also that the experience was incredibly rewarding. The opportunity to do hard work and have hard work rewarded was really thrilling. I actually felt like I was having an impact. And I felt like I had an impact even though we lost that race.

AM: Yes! I think people are known for the races they have won so we forget that everyone in organizing has lost before.

JOD: My first race that I worked on full time was a loss. We lost by a couple points and it was totally heartbreaking.  I went through all the stages of grief. My biggest loss—I’ve lost a lot and I mean a lot—was when I worked for Al Gore [in the 2000 presidential race]. That was the second campaign I did. I started in New Hampshire in 1999; I was a volunteer coordinator there and then moved to five or six different states and I ended up at the recount at the end. I went through this entire experience that was a crazy experience in the history of the country, but I also worked so hard, gave up so much, sacrificed so much, learned so much… and then we lost.

Those experiences really help me see that I can have impact and actually make a difference, even if the final outcome isn’t what I wanted. It also taught me how to handle loss, dust myself off, get up again and finally figure out how awesome it is to actually win—what a big deal it is.

AM: Yeah, how important it is to win. Besides learning how to move on from a political loss and keep fighting, how else did your early organizing days give you a foundation for the future?

JOD: I believe that being an organizer is the best training ground for any job that you could want in the future. The reason I say that is because I feel like the role of field organizer allows you to do every aspect of the campaign and see it up close: managing volunteers, maybe managing staff, being able to go and speak at events. I remember when I was on the Gore campaign, I was speaking on panels and at big events with members of Congress and a senator. I was like, “What in the f*@k am I doing?” I was terrified, but I had to talk about field so I just had to figure it out. I had to meet with elected officials and community leaders. I had to meet with activists. I had to do event planning. I had to work on messaging and writing and talking points and all of that stuff.

As I’ve gotten further and further along in my life, I feel like organizing gave me the opportunity, at a very young age, to try on lots of different roles because I did so much in a campaign. I was able to not only figure out what I like to do—which I think is really important—but also what I was good at. I was able to ground my future and the path I wanted to take by having a pretty good sense of what was possible on a campaign because I’d seen it; but I also learned what I liked to do and what I was good at. I think there’s very few other jobs that allow for that kind of perspective and hands-on training.

AM: While you were doing so much as an organizer, what were some key skills you developed that have contributed to your success?

JOD: There are two really big ones that I’ve really carried through my life; not even just in my professional life, but in my personal life too.

I can remember sitting at a desk in Manchester, New Hampshire with so much work and so much to do and it was 11:00 at night. I honestly thought my head was going to explode or I was going to have a panic attack. I didn’t even know how I was going to get through it and I didn’t see any way to get help. I’ve come back to that moment and that feeling over time because I still have times where I have a lot of stuff going on.

All I could do was three things in that moment:

  • The first was I needed to take some really deep breaths. That was number one.
  • Number two was I had to think about what was most important to do first and then put together a plan to do that. What are the things that had to be done? How can I focus minutely on that goal and try to just take everything else away? That focus was really important and I still use it now. If I don’t prioritize, I tend to do a little bit here and there. Thinking about what is most important first always brings me back to what I have to do.
  • The third thing was that I needed help. I had to ask for help. First, I had to figure out how to communicate what I needed. I had to find somebody to support me and we had to work as a team. And that took me a little bit of time because I was like, “I’ll just do it. I can get it all done, I can do it the way I want to do it.” Figuring out how to delegate, how to find help, and how to build plans to get more people to support me was critical and I use that to this day.

The other big skill I learned was that in order to plan events or to figure out how we get from A to B, I really had to go through the exercise in my mind, or on paper, or in a brainstorm; list of all the steps that had to take place and how we were going to accomplish these steps to be best prepared. I learned this the hard way by having some massive failures of some gigantic canvasses.

I was working in Missouri for the coordinated campaign, I ran the St. Louis area in 2000. This was the year that Mel Carnahan was running for office and passed away on a flight during that campaign, so there’s all this crazy stuff going on. I had this big canvass and I remember Karenna Gore was coming to this canvass and we had hundreds of people coming and all these stations and all these local elected officials. And because I hadn’t thought through all the steps and I was so exhausted and it was just me doing everything, I ended up sending out Karenna Gore with the wrong lit with a candidate who was knocking on doors without his own lit.

I got in trouble to the most extensive degree, but it was because I hadn’t gone through all of those steps needed for success ahead of time.

Once I started taking the time—even in the craziness—to say, “Okay, we have this huge canvass, how do we work back from that? What do we need by when? How do we get to success?” I was able to do bigger events and even smaller events more successfully. Even now when I organize my kids to get on a plane, I do the same thing. It’s just become the way that I think and it helps me come prepared to every thing. I didn’t realize this at first, but intentional planning helps me to have more of a calm going into any important or stressful situation because I know I’ve already thought through all of the pieces.

The time an organizer spends for 30 minutes by themselves at a coffee shop working through a strategic plan in their minds is more valuable than any time spent doing something else that feels more urgent.

AM: Did you do anything else when you were an organizer that wasn’t directly required of you (like strategic planning) that made you a better organizer?

JOD: I think that it’s actually only now that I am much better at taking care of myself as a person. I think that I always sort of sucked at that until I got much older. So I wouldn’t necessarily say that I did this when I was starting out, but to have that time where you’re just getting away for 30 minutes is so crucial. I had a friend who was a really great athlete and she traveled with me on several campaigns. We were just up to our eyeballs with work when she came to me one day and said, “The only way I’m going to survive this is if I can get 45 minutes to myself to go run in the morning.” So I told her that was fine and once she started that, that was how she found sanity.

I tried to make sure I had some routine and that I had friends. When I was on the Gore campaign very early on, every Sunday night, we started a tradition of going to the restaurant Jillian’s. All the field organizers that could come in would come in, and there would be a place just for us. We would commiserate, spend some time together and drink some beers. It gave me the ability to kind of lean into the next week and do what I needed to do. Finding that time was really important for me.

There was one other thing I did. Just by the nature of the work that we do, we’re around incredibly smart and talented people who come from different experiences and have different skillsets. A lot of my friends were on other teams in the campaign. I not only built friendships with those folks, but I also tried to learn from them. I tried to make sure that if there was something that I didn’t understand, I asked; I saw there was value in understanding their work better. Sometimes that was just chatting over beer at the end of a long day and sometimes that was trying to make sure I got their perspective for something we were planning.

There is a big opportunity for organizers today because of the folks that they’re around. Of course organizers don’t have time to just go and have days’ long discussions about the best tactics for communicating, but they do have the opportunity to bring in other voices into a field program that might not always be there and to make a priority of these other perspectives. I think by doing that, you learn, you gain a wider view and it also just makes you better and better able to support the work that you do.

AM: Thinking back to productivity, what practices can an organizer borrow from you that you do now that will help them do their job better?

JOD: To be honest, I’ve tried tons of organizational tactics over the years— color-coded pens, tabs, etc. I now do my to-do list on one page with a red tab and I try to keep it with a checkbox so I can check it off. I also feel like it’s really common to take notes and then never go back and look at them. So if I’m taking notes, I always try to re-read my notes and then when I have an action item, I always put a star and a circle. Even when I’m just flipping through my notes, I can recognize something I need to do.

But I think at the end of the day none of my organizational tactics are groundbreaking. It’s most important that I force myself to take the time to think about what I really have to do and to look forward. Using some opportunity to think about what’s coming up before you is important.

On campaigns, I would always try to use the weekend because even though I had canvasses and stuff, the calls would be less and I just felt like I could have some breathing time where I would think about what is it that we have to do coming up. That gave me a perspective so even when I was exhausted, I’d already thought through some of the things that I knew I had to deal with. It just helped me propel the action forward.

When I was a field director, I would always do weekly newsletters or weekly bulletins; they were ridiculous and I gave people rewards and it was like clip art gone mad. But it forced me to put the organization—not just myself but the full field team — in a forward-focused perspective.

I think there’s an anecdotal narrative that I often find can get lost when it comes to organizing, because you’re just looking at numbers. But it’s still really important to think about where you’re going, why you’re doing what you’re doing, and the direction you need to be on. Giving that compass to your staff and your volunteers can make all the difference, especially when they’re struggling.

AM: Any parting words for organizers?

JOD: If I could recommend one job that anyone should have in their life, it would be a field organizer. If I could recommend one job for someone thinking about political work and not sure about their path, it would be an organizer. Not only is the experience so enriching, but also the importance of that work is so dramatic for the races that organizers work on. The older I get, the more jobs I see, the more industries I work with, I still can’t see any other role that has a greater impact at a younger age and gives you the ability to see so many different aspects of work and potential jobs than being an organizer.

Be an organizer! You’re doing great.
***************************************************************************************************************