Campaign Inc.: How Leadership and Organization Propelled Barack Obama to the White House

Campaign Inc.: How Leadership and Organization Propelled Barack Obama to the White House

by Henry F. De Sio., Jr.
Campaign Inc.: How Leadership and Organization Propelled Barack Obama to the White House

Campaign Inc.: How Leadership and Organization Propelled Barack Obama to the White House

by Henry F. De Sio., Jr.


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It takes more than an excellent candidate to win elections; it takes an outstanding campaign organization, too. Campaign Inc. is the story of how leadership and organization propelled Barack Obama to the White House. As the chief operating officer of Obama’s 2008 presidential campaign, Henry F. De Sio, Jr., was positioned to view this historic campaign as few others could. In this fascinating behind-the-scenes account, he whisks readers into Obama’s national election headquarters in Chicago to glimpse the decision-making processes and myriad details critical to running a successful and innovative presidential campaign. From the campaign’s early chaos to the jubilation and drama of winning the Iowa caucus, to the drawn-out Democratic nomination process, to Obama’s eventual election as president of the United States, De Sio guides readers through the challenges faced by the Obama for America campaign in its brief twenty-one-month lifespan.

De Sio shows readers that Obama himself was direct about his vision for the campaign when he instructed his staff to “run it like a business.” Thus, this is less the story of Barack Obama, candidate, and more the story of Barack Obama, CEO. Because campaigns are launched from scratch during every election cycle, they are the ultimate entrepreneurial experience. In the course of the election, the Obama campaign scaled up from a scrappy start-up to a nearly $1 billion operation, becoming a hothouse environment on which the glare of the media spotlight was permanently trained.

Campaign Inc. allows readers to peek behind the curtain at the underdog organization that brought down the Clinton campaign and later went on to defeat the Republican machine, while offering lessons in leadership and organization to innovators, executives, and entrepreneurs.

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Product Details

ISBN-13: 9781609382698
Publisher: University of Iowa Press
Publication date: 09/01/2014
Edition description: 1
Pages: 224
Product dimensions: 8.90(w) x 5.90(h) x 0.70(d)

About the Author

Henry F. De Sio, Jr., was the 2008 Chief Operating Officer (COO) at Obama for America and was appointed deputy assistant to President Barack Obama during his first term in office. De Sio currently promotes the principles of personal and organizational leadership through his writings and public speaking engagements. He has been a featured speaker at the Skoll World Forum in Oxford (UK), Ben & Jerry’s Social Entrepreneurship Summit 2013, and on C-SPAN’s “Road to the White House” series airing in October 2012. De Sio earned his BA in Political Science from University of California, Santa Barbara, and an MA in Public Administration from Harvard's Kennedy School. He lives in Alexandria, Virginia, with his wife, Sine, and two sons, Dante and Zane. Learn more at

Read an Excerpt

Campaign Inc.

How Leadership and Organization Propelled Barack Obama to the White House

By Henry F. De Sio Jr.

University of Iowa Press

Copyright © 2014 Henry F. De Sio, Jr.
All rights reserved.
ISBN: 978-1-60938-287-2


No Drama Obama

APRIL 5, 2007: The note from Campaign Manager David Plouffe flashed from my BlackBerry this morning. Subject line: Stop the Spending.


I dreaded my new campaign BlackBerry, yet habitually fumbled for it immediately upon waking each day. The device delivered the regular dose of SOS's that as the "organization guy" I could not avoid. I was the fireman. When people needed my help it was often an emergency, and at this early stage of the campaign, it seemed like every morning there was an appeal that was sure to consume the first couple hours of my day.

Some of the requests were to facilitate cooperation between certain staff or departments. At other times I was needed to sooth tensions that had grown from the confusion over roles and responsibilities. Then there were the frustrated leaders in Iowa who couldn't navigate Chicago for needed services because they didn't have reliable points of contact at a time when our staff and volunteers were constantly shuffling into new positions. On top of all this, there were the myriad problems associated with the physical move from the campaign's temporary quarters into our new national headquarters.

Mostly, though, I was on alert for messages from David Plouffe, our campaign manager, who stayed up late into the night working through the many unique challenges of a complex campaign start-up. On the morning of April 5, he was rightly worried about the spending appetite of this growing and ambitious organization.

At the time I'd received David's email appeal, I was still battling to get people and systems in place. Only about a hundred of us were on payroll at this point, though the number of volunteers buzzing around was an indicator of the many more wanting to be hired. And while most of our staff were located at headquarters, the four early primary states of Iowa, New Hampshire, Nevada, and South Carolina were also building up. The eleventh floor of the downtown Chicago high-rise, only days ago empty and silent, was now quickly being overtaken by complete chaos as people moved in from temporary office locations around the city.

We were still mostly strangers to each other. Phones and computers were being installed by Sam Falkoff, known by many of us as "Sam the Red Sox fan" since we all had yet to learn last names. He tried his best to fulfill his duties while taking care not to intrude on the staffers who feverishly worked to get their newly assigned seating areas put together.

As soon as folks had their workstations up and running, they were off, scurrying past each other and moving quickly between desks to get answers to pressing questions. There was motion to be sure; progress, on the other hand, was still difficult to discern. This is always a challenging time in a campaign. Like any good business, you would ideally like to have key systems and personnel in place before you launch. But our campaign was still very much unformed and struggling to catch up to the high volume of inquiries and demands that had been generated from our candidate's announcement that he would run for president just weeks earlier.

The crush of enthusiasm from outside increased the pressure on us inside. Our reception desk was overrun with phone calls. The small correspondence team was collecting a mountain of print mail to go with an incredible volume of incoming email. Our staff in the political department and others of us in the campaign attempted to manage the many requests coming our way from influential leaders and organizational representatives who wanted time with the candidate or a signal of support for their core objectives. And our fundraisers had the daunting challenge of competitively raising money behind a little-known Barack Obama brand in a clear mismatch against Clinton, who was quite literally the "Campbell's Soup" of politics, with the high name recognition and deep relationships that came with her two decades of national service.

Building the Airplane in Midflight

The weight bearing down on all of the other departments increased their reliance on those that I oversaw. Looking back on my work, even from the earliest days, I thought of myself as one part chief executive officer, one part chief people officer, and one part chief firefighter. If I properly tended to the first two, I had fewer fires to fight. At the outset, however, I mostly battled both brush fires and blazes.

The teams I managed struggled to get a handle on the flurry of demands coming our way. With only about a dozen staff around me at the beginning of April, managing the surge with so few people was a Herculean undertaking for all of us. The chief financial officer (CFO), Marianne Markowitz, had a small staff at the beginning and was still setting up the financial infrastructure. Marianne was going to be outstanding in her new role, but she had very little support back then. She diligently worked to establish budgets while pulling together spending and accounting processes. Not distant from her memory were her very first days of the campaign when she hastily opened bank accounts to accommodate the deluge of checks that were suddenly flooding in.

We also had a very capable chief technology officer (CTO) in Kevin Malover, our big catch from Orbitz. However, by the first week of April, he had only hired a handful of people. His team was racing to get servers up and the technology infrastructure built out, while also laboring to service newly issued personal computing equipment. Our Iowa HQ was often on the phone clamoring for urgently needed help with ordering phones, computers, and BlackBerry devices for their staff as well as equipment for the offices that were quickly beginning to dot that state.

Our personnel department had only three people at this point. It was ridiculously shorthanded at a time when every headquarters department and each of the four early state offices were desperate to hire. Director Jenn Clark and company had to do everything manually on spreadsheets, while managers with skeleton crews pressured her to expedite their priority hiring requests. Approaching paydays were particularly stressful as last-minute, unreported roster changes were handed to her by distracted department heads just as her team was preparing to process the payroll. This always caused a scramble to finalize the payee list against pressing deadlines to hit the "send" button so that money could be transmitted into employee bank accounts on the promised day.

The other departments that I oversaw within campaign management—including national field operations, legal, correspondence, the call center, headquarters management, and travel—were still mostly stacked with volunteers and also overwhelmed. With insufficient staff, limited technology, and undefined systems for hiring, spending, and contracting, we were building the airplane in midflight.

Impatience Erupts

The mounting challenges facing the staff in my departments were of little concern to others around us, who had their own fires to fight. Impatience quickly became epidemic in this pressure-filled environment, where systems were underdeveloped and communication was lacking. A get-it-done-at-any-cost attitude emerged, evident in the alarming instances of rogue spending and hiring that began to surface.

For example, occasional unknown hires that should have been preapproved and processed through personnel were only uncovered after our IT staff received random requests for computing and communications equipment. A trickle of unauthorized campaign purchases were discovered by the CFO only after she'd received questionable invoices or unexplained shipments. She also stumbled across some contracts that had been signed by individuals who didn't have the authority to do so. Lastly, we had intermittent reports that staff was occupying some field offices before the leases had been finalized. This particular piece of news caused me extra heartburn. Similarly, the organizers in the states who had properly followed the prescribed office-opening procedures became aggravated at the protracted negotiations and lease reviews by us in Chicago that kept them working out of local coffee shops.

These kinds of incidents were limited and mostly born from the confusion of the time. But they were indicative of the tensions resulting from competing demands within the campaign between those at HQ who had to be deliberative and the managers in our states who had time-sensitive matters that required speedy resolution. We were all working toward a common cause, but the unique pressures on every one of us had the potential to create unfortunate missteps that only increased frustration and further flared tempers.

The campaign's management, my units in particular, had to quickly finalize proper systems and processes so that we could close these gaps in our operation. Our early work in this regard was critical to producing the structural capacities, work flow efficiencies, and collaborative advantages required to compete at the highest level against the daunting Clinton machine. How gracefully the organization moved through this awkward phase would have a direct impact on its future development and ultimate performance.

But the enormity of that challenge cannot be fully comprehended without my first offering a tutorial on the peculiar forces at work within the environment of the campaign start-up that, for us, was primarily driven by its explosive early growth.


The migration to the campaign is a testament to the lure and reward of entrepreneurship. It is the uniquely American phenomenon of leaving everything behind to pursue the unimaginable. For many of us, the pilgrimage culminated at Obama for America (OFA) headquarters in Chicago, making it a gathering place for idealists, innovators, and risk takers. While it may be true that the campaign was a magnet for the young who had more to believe in and less to risk, we had folks walk through our doors who left behind high-paying employment at law firms, Wall Street companies, private businesses, and consulting practices. Personally witnessing the number of people streaming in without the promise of a job but who were instead motivated by a higher purpose was inspiring.

As is typical in campaigns, getting hired in the earliest days was mostly based on whom you knew. Friends, confidants, and trusted associates circled the candidate first. Next in were the reputable campaign and policy experts who were slotted into the top spots. They often recruited proven colleagues from their pasts to fill key positions under them. Finally, the self-selected arrived, eager to volunteer for anything with the hope that they would get noticed and quickly picked up. There was no time in this fast-moving environment for the conventional practice of interviewing candidates who'd responded to thoughtfully written job postings. When hiring in a pinch, managers tapped the high achievers they'd worked with previously or one of the impressive volunteers directly in front of them. It was a crude screening process, often referred to internally as "try and buy."

Everybody who got in the door had somebody open that door. This fostered strong loyalties around the directors, creating a tribal feature that is not uncommon in the campaign setting. Like any large or growing enterprise, a departmental identity is a natural development. In the campaign start-up, this characteristic is more sharply sculpted by the race against the others for expanded responsibilities and the competition for limited resources. The imperative for us in higher campaign management was to ensure that budding rivalries didn't take hold. If periodic outbreaks of infighting were to develop into serial disputes, entrenched camps could emerge threatening any possibility for enduring internal harmony. The ensuing drama would become crippling over time.

Managing in Silos

We were organized into predictable units for a political campaign. The communications team handled our public messaging and traditional media outreach, as well as monitoring campaign-related news in real time. New media was a flagship unit that wouldn't have existed independently in previous cycles. Giving it a unique and autonomous place in our structure signaled the innovative spirit of our campaign, while also recognizing digital communications as a maturing medium. This team had responsibility for our email communications, our innovative website, and our online organizing activities. The scheduling and advance department—we casually called it "Schedvance"—was essentially divided into two pieces. One part of that unit managed the candidate's appearances and, frankly, his time, while another section was focused on precisely organizing the activities around him in the communities he visited. As the campaign progressed, managing the surrogates—the VIP supporters who spoke on the candidate and campaign's behalf—became another major responsibility. Along with campaign operations I led, those were the larger shops.

Beyond that, we had smaller departments in headquarters that numbered about four or five staff in each. They included research, political, and national field, the latter with the mission of identifying and mobilizing local volunteers in the non-early-states and organizing our initial canvassing activities there. Lastly, we had a paid media department that was comprised of a very small team that coordinated our message activities and managed a universe of contracted firms for polling, producing TV and radio ads, and other related services.

We struggled from the outset with a type of tunnel vision and departmental isolation that quickly hardened into a series of individual silos inside headquarters. This was reinforced by our traditional organizational structure featuring clear lines of authority flowing through department heads to teams assembled around defined functional responsibilities. This system suited the management style of David Plouffe, who typically liked to work individually with the respective shop leaders to move projects forward.

His approach frustrated a few of the more collaborative-minded among us, who would have preferred that ideas be presented in our morning senior management meeting so that details and differences could have been hashed out together. These folks seemed to crave dialogue and, frankly, a more strategic role. That just wasn't David's way. But absent such a platform, communications between the departments and within the campaign generally were disjointed in the beginning, which made it feel at times like our right hand didn't know what our left hand was doing. New initiatives that had been launched by a given department just appeared suddenly on the headquarters floor, usually in the form of very last-minute requests for assistance that were then difficult for others to fulfill. These might take the form of door-to-door canvassing projects or fundraising house party blitzes, for example, requiring multidepartment involvement to be carried off effectively. At a time when we were still learning how to work and communicate together, the resulting pandemonium could lead to occasional and sometimes contentious skirmishes between staff.

Over time, our top management adapted to David's leadership style. We became better at talking offline together, and we shared information more immediately. This formed the basis for what would, in the long run, become unique, nimble, and proactive partnerships that ultimately served the organization well. Problems were solved informally and meetings occurred only as needed with just the necessary stakeholders attending. Work eventually got done more efficiently in this brand of management ecosystem.

Working without Boundaries

It was an electric time in the campaign: spirited, innovative, and hopeful. A highly driven, uninhibited group of people had been unleashed into this competitive environment. The mix of pace, purpose, and passion they brought with them was intoxicating, but in a workplace without boundaries it was a combination that had the potential to become toxic. We didn't have intrinsic parameters or organizational history to direct us.

Unlike the traditional business start-up where the assimilation of the work force can be modulated and the corporate culture systematically shaped, campaigns are hastily constructed and grow from these seeds of early turmoil and disarray. This causes a Wild West atmosphere in the beginning. What we were attempting was the organizational equivalent of creating a village from scratch, where a stream of people arrived all at once to a place that had no rules, no norms, and no structure. Chaos was the immediate consequence.

Everyone had their own personal tactics for getting what they wanted, and in an immature setting, even good people lost control of their "inner jerks." This resulted in failed first impressions and missteps that mortally wounded some very decent people early on. When reputations were on the line, blame could fly. Without systems or standards in place to help employees resolve their personal grievances, relationships risked being spoiled.


Excerpted from Campaign Inc. by Henry F. De Sio Jr.. Copyright © 2014 Henry F. De Sio, Jr.. Excerpted by permission of University of Iowa Press.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
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Table of Contents


1. No Drama Obama,
2. Stick to the Plan,
3. Rise to Big Moments,
4. Be Faster,
5. Yes We Can!,
6. Bend, Don't Break,
7. In Crisis, Stay on Offense,
8. Run It like a Business,
9. Lead from Within,
10. Contrast Thyself,
11. Know Where to Be to Effectively Lead,
12. Close the Deal,
After Words,

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