How My Political Career Prepared Me for My Job in Fintech

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My decision to leave a rewarding career in Washington, D.C. to take a job in business development for a fintech startup in New York City left many of my friends and colleagues a bit mystified.

"Are you really sure you want to do that?" one friend said. "There's not really a chance of success, is there? I know someone at [a large bank]. You should talk to them."

"Why not lobbying or something? There's great money there," another one later chimed in.

"Do you think you know enough to make it there? It seems so different from your current job.  Can you actually close deals?"

And my personal favorite: "I'm just concerned about this career move. What about trying to do guest spots on TV?"

These unguarded responses were well-intentioned, but not exactly the supportive reactions you'd want when embarking on a new and exciting life chapter. Don't worry, I received plenty of positive responses, too. But this experience caused me to reflect on our attitudes – overblown fears, really about straying too far off the path and about the transferability of skills in a nontraditional career switch.  

To appreciate how these reactions could be well-meaning, you must first understand the mindset of the D.C. crowd. Most who live and work in D.C. circulate between jobs on Capitol Hill, at federal agencies, law firms, political consulting and lobbying shops, public relations agencies, government affairs positions at large corporations, and the occasional interruption of time spent on a political campaign. These are all great opportunities for the right person at the right stage in their career. But none of them is much of a bold step away from the tried-and-true path that generations of politicos and policy wonks have followed. The desire to try something different, as in my case, is often met with blank stares or misguided interventions.  

Even before I branched out to join the bustling but still mostly unknown world of Fintech, I knew that there wasn't a lot of career creativity in Washington. Most political junkies who find themselves working in D.C. spend their school years with a single-minded focus on earning a political job that offers access to the most challenging policy issues, exciting political campaigns, and powerful public figures. Their reward is generally an entry-level position that can be very different from their initial expectations.

Few envision the countless hours spent responding to constituent letters, stuffing and licking envelopes, handling bizarre inbound telephone calls, scheduling meetings, taking meeting or call notes, holding purses and coats, picking up food for others and cleaning up after others have eaten, leading tour groups, fetching documents – the list goes on and on. It's a far cry from the lionized staff roles depicted in The West Wing or House of Cards, where every staffer is either working for a noble purpose or facilitating high crimes and misdemeanors. Burnout is, unsurprisingly, very high.  

But here's the deal: if things go well, over time these staffers absorb the unwritten knowledge of how Washington works, and gradually can earn the confidence of their bosses that enable them to progress to senior staff positions and gain more influence. They can develop people and project management skills, fine-tune political and communications strategic thinking, build coalitions around policy issues, become stone-cold negotiators, gain expertise of the federal regulatory infrastructure, and offer great insights into how policy and markets intersect. What's more, they learn to operate within the often extreme environment of the pressure cooker that exists in the nation's capital. Every company, regardless of industry, can benefit from an employee with this combination of skills.  

Just as I did for myself, I encourage others considering a career change to break down their current job into its most basic parts to understand how what they do on a daily basis can appeal to a hiring manager at a company they want to join. I had the benefit of coming to Washington after spending a few years working in finance in the private sector. So I knew that even though I was working at the fairly opaque Treasury Department and that my product was the abstract and intangible concept of policymaking, I could translate my duties into functions and skills that companies could recognize.

For instance, my job required me to be entrepreneurial in the policy issues I chose to explore and bring to the attention of more senior officials. I had to identify new issues of concern, research them thoroughly and develop a workable thesis on how to proceed. Then, I needed to build a written and verbal case for how the agency should or should not act, assess which government and private sector players were stakeholders and collaborate with these players on final actions (even if they had different points of view). Lastly, I had to sell my ideas to these internal and external officials at every stage along the way.  

These functions were remarkably similar to those of a business development role, which requires identifying commercial opportunities, building a marketing plan, relentlessly pursuing potential targets, developing partnerships, and executing the deal. If I could provide some specific examples and paint this picture along the way to hiring managers, I knew I could convince them that hiring me was a good investment.  

So, why jump to a Fintech startup? I'd already had the large corporate, political campaign, and government agency experience, and I was interested in transitioning back into the private sector. I also wanted to have a more direct impact on the bottom line, and learn more about technology and new ways that companies are interacting with their customers. From where I sat, I observed that CommonBond was a Fintech company addressing the huge problem of student debt in this country – plus, they were doing so with an honorable social mission. That marriage of corporate ambition with good intentions appealed to me in a way that no company had before then.  

Since joining the CommonBond team in April this year, I've been able to contribute across several company functions, well beyond what's listed in my job description. Both my colleagues and our external business partners have leaned on my intimate understanding of the policy and political world to help them evaluate strategic decisions.  

Looking back, perhaps I wasn't overly discouraged when I was challenged on my decision to move into Fintech because it reminded of a time when I switched careers once before.  I left my first job in commodities trading in 2008 to join the presidential campaign of a young and unproven first-term U.S. senator with an exotic name and a long-shot chance to win the biggest political prize on the planet. On my last day in my commodities job before leaving for the campaign, there was the now-familiar mix of disdain, wry humor, and indifference to the strange decision to leave the comforts of the known in favor of the uncertainty of the unknown.  

Then again, you should have seen my inbox the night he won.

Kevin Bailey is Director of Business Development at CommonBond.

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