Transition to the Private Sector, Part I

It’s Not That Different

Action: A) If you’re an A-player, stay. B) If you’re an A-player and leave, do great things on the outside and return to government service at some point. C) Send me your transition questions and let me know if you’re interested in a seminar on the below topics.

At least a few times a month, people looking to jump ask about my transition, which has led to me consolidating my comments below. To be up front, some of what I write will be controversial and all of it is biased. Due to length, I’ve broken it up into a three-part series that will be published over the next few weeks.

•  Part I addresses the basics of how & where there are differences between the Agency and the private sector, an assumption of what aspects of government you’ll miss based on my own nostalgia, as well as how to characterize old skills to new roles, job hunting advice, and resume missteps.

•  Part II will address criteria for choosing your next role, the most common types of business roles that formers go into, and how to think about big vs small company risks and current markets.

•  Part III will be about title and compensation (salary + equity + bonuses) and resources you can use.

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PART I

1. It must be a really big jump to the private sector, huh?

To begin, many people on the outside use the term “industry” not “the private sector.” It wasn’t a big jump. At the Agency, 85% of my time was spent navigating bureaucracy & equities, arguing for resources & permission for operations, and dealing with the bottom rung of employees, all while making decisions with little data or data overload. Only 15% of my time was doing the more exciting operations. Though that 15% - along with the camaraderie of some of my colleagues - made the work deeply meaningful.

Industry is similar. Human nature is human nature, and I deal with many of the same challenges and pull many of the same levers of satisfaction. The difference is my decisions now aren’t life or death.

Another large difference is the greater level of autonomy I have nowadays. Making decisions on the fly in operations is an extreme example of autonomy, of course, but there is always a back-end overhead. Depending on company culture, decision-making can be driven dramatically down with less overhead. As an example, I can make direct recommendations to Congress with no oversight, no internal reporting requirements, and with the trust of the CEO and Board.

2. Do you miss it?

Yes. Nothing beats the rush of bumping a target who agrees to meet with you again or landing in a foreign country for the first time. I no longer know the stories behind the headlines, and I’m not the person making those stories happen. Aside from close friends, I am now treated as an “outsider” by former colleagues.

Fortunately, I still work with smart people solving hard problems every day. And there is still meaning in what I do. Raising tens of millions of dollars from investors to advance a technology faster than the Chinese CCP is fulfilling and uses the same skillset. Learning how M&A deals are structured gives me the same thrill as first learning the mechanics of a surveillance detection route. It’s the excitement of being a beginner again, but one with deep and profound experiences, which blunts the downs and enhances the ups that you will face post-Agency.

I get to move our national security mission in emerging technologies farther and faster in ways that I could not in government. And while there is some level of self-justification in these statements, there is nonlinearity in industry. You can move at exponential speed. At the Agency, I felt like I would have had to wait another 10 years for positions of significant responsibility & authority despite proving early value, only to face even greater levels of risk aversion as I moved upwards. 

3. How do you transfer your old skills to your current role?

Driving decisions, organizational change, and operations in a deep tech company presents many of the same challenges and opportunities as my time in government. Leading and managing people amid uncertainty, high degrees of change, and making decisions remain my day-to-day functions. My role as a Chief of Staff is in many ways like a DCOS or traditional Chief of Staff in government. I work behind the scenes, and sometimes out front, to shape vision, strategy and then execute, measure, and refine. Rather than giving away bags of cash in my old job, I now ask for money from investors. Relationship dynamics are the same, minus the burden of extreme secrecy. Painting a vision for those in the company and those wanting to put their money in the company is vitally important, but so is being authentic, genuine, and a truth-teller. All the things that most of the outside world doesn’t understand as being critical to a handler-asset relationship are just as critical to relationships in industry. Judgment remains paramount.

In the Agency, as I got to more senior levels, I spent most of my days writing precisely worded emails to advocate for resources and challenge risk aversion. At times, it was an exhausting and never-ending match of written and verbal jujitsu, yet exhilarating when we got everyone on the same page and did the thing that needed to be done. I also dealt with a few difficult personalities focused on empire-building and metrics rather than running sound operations. You likely will still deal with this in industry, though there are far fewer layers and entrenched interests to deal with. Even in larger companies, people’s motives are usually quite obvious. Whereas in the Agency, there is a larger concentration of people forged under the flames of constantly “working angles,” some whose coups aren’t known until carried out.

Knowing how to navigate various stakeholders & interests, avoid landmines, and bring people together is an extremely useful skill in industry. If you’ve worked in a big bureaucracy and been a “doer” who knows how to communicate, work, and gain buy-in across an enterprise that may also be geographically dispersed, as well as with and against external third parties who are frenemies (or outright hostile), this will serve you well in industry. Talk about it when you’re seeking jobs and interviewing.

4. How did you get your job? Did you make any resume missteps?

I networked nonstop and ran a full targeting campaign for multiple companies to get to their CEOs. I didn’t have a resume when I was looking for jobs. I had to find senior people who had left who would vouch for me.

For Infleqtion (then named ColdQuanta), I was introduced to a former senior IC official who previously served on a separate board with the then-CEO of ColdQuanta, who made an introduction to this CEO. We met and I asked the CEO his challenges and outlined how I might be able to help, and indicated that I was having a lot of different conversations to determine my next steps. Five months later, the CEO called and said he may have a job for me and invited me to visit and speak with others in the company for their input. I received an offer shortly thereafter.

In another case, I did a cold outreach on LinkedIn to the person I suspected was the hiring manager for a job advertisement for a company that I liked. This was approximately three years before I left the Agency. The person told me they wanted someone with more business experience for the role, but then came calling three years later when another role opened that they thought would be a good fit. Ultimately, I met each layer up in that company, to include with the CEO. This all came in handy when negotiating salary, title, and function. From the many, many hours of networking hustle, I received two job offers, which happened in parallel, and I negotiated around the same title and compensation levels. Throughout the entire process, I forwarded them relevant articles and commentary on opportunities to demonstrate my value. Ultimately, I chose Infleqtion because of its mission, its people, and its reputation amid US Government circles.

Typically, if you’re going for a senior level role straight out of the Agency, your resume is not what will get you the job, and submitting one to a resume bank is not the right move. Even if you have a resume, it’s almost certainly written in government-speak, and probably more terrible than you realize. It likely talks about all the jobs you held (to the degree you can share) and the dates and maybe the general locations but says nothing about what you actually accomplished or how it specifically relates to industry. You probably won’t even get beyond the AI filter. Serving in a country and writing intelligence reports that go to policymakers, and “the President,” does not cut it. While it might make you a curiosity to them, industry rarely gets how it makes you useful. Some may want to meet you based on curiosity, and unless you can translate how it provides value, you’ll get stuck. Even still, they may fall back on what they know and choose someone with a lengthier business resume. Some will automatically discount anyone with government service, even the Agency, because they assume bureaucrat. Unless you’re trying to join a think tank or a company packed with formers, you’re unlikely to get very far with your basic resume and even in-person, you must describe your value proposition.

First, figure out which industry you want to work in, narrow it down to a handful of companies, and work hard to get intros at the senior levels of those companies. You have to go out and do a lot of networking to create your list and build your network. The highest leverage way to get hired is to find a way to meet a Board of Directors member, Advisory Board member, member of the C-suite (CEO, CTO, CFO, etc), and/or investor in the company and captivate them with a story of what you did, how you want to transfer this to industry, and ask them lots of questions about their personal experiences at that company and others. I had to do this virtually because of COVID, which made it more efficient, but in-person is always better for forming a stronger bond and making a good impression.

You’ll fail along the way. A learning point for me came early in my transition as I was speaking with a prospective VC about a job. My contact flat-out told me he didn’t understand my value proposition, even after I had tried to explain it in-person. He asked point blank, “How much money did you net the US Government over your career, what exactly did you do in order to get those results, and how would you bring me those same returns?” While the book The Billion Dollar Spy loomed in my head, I fumbled through the question. I most certainly did not recruit “a billion dollar spy” nor did anything that turned the tides of war. Yet, I had learned to craft and pull levers of power & influence usually only afforded to people with decades more experience & prominence in the private sector, and more so than my interlocutor. I fumbled the response. I don’t even recall what I said, but he didn’t reach out again (though now we’re friendly as we run in similar circles and were able to laugh about this recently).

If you get asked a question like this, my suggestion is to say something along these lines: It’s exponentially harder to be hired by the Agency than it is to get into Harvard, and not only was I hired based on an assessment of strong judgment and the ability to operate in ambiguous situations, I then was trained to do just that, and then did it for years. I was entrusted to create and carry out some of the most sensitive and most important missions that the U.S. Government conducts, often with little direction. Not only did I have to plan and do them, I had to do so in secret, with lives on the line, which is hard to put a price tag on. You can give me your toughest problem, and I will figure out how to solve it in record time with buy-in from those whom you rarely get buy-in, and position you for multiple shots on goal for future opportunities because I will have your company and sector wired. I can do for you what I did for our country: evaluate opportunity, mitigate risk, and make quick and smart decisions that attack problems differently than a typical insider would. Give me a couple hundred thousand of combined salary and operating budget, and I’ll turn it into millions of dollars in returns or investments within two years - not singlehandedly - but in a cooperative way that leverages many parts of the company. We’ll row in unison and we’ll row in the right direction. And I’ll do it all from a supporting role, with you at the helm and you as the ultimate decision-maker.

I know this sounds boastful, especially to you, humble public servant, but this is industry speak. Your experience is valuable and allows you to think differently. You know how to navigate situations that are highly relevant to the business world. You simply have to find the right target and find the right way to convey it.

I’m considering doing a live seminar for formers that goes into more specifics and contemplates various scenarios. If you have interest in this, please subscribe and let me know.

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