Leaving Government for the Private Sector – Part 2

Posted on October 23, 2023 by steve blank

Laura Thomas is a former CIA operations officer. Reading how she moved in 2021 from CIA ops to a quantum technology company offered insightful career transition advice for those leaving her agency. Most of her lessons were applicable to any government employee venturing out to the private sector.

Below is the second of her three-part series. Read part one here.

Before leaving government service one of my biggest challenges was to understand how my skill as a Case Officer would translate into a job in the commercial world. I had to spend a lot of time learning a new language and new job descriptions. Here’s what I learned.

What would you like to do/can do? Some commercial company roles:

Business Development or “BD” roles: Case Officers are well suited for business development (BD) roles as its akin to first half of the CIA recruitment cycle. In a business development role you’re out shaping the perception of your company in the market (networking), determining leads, and contacting leads. The larger the company, the more they’ll separate out business development and sales, with business development focused primarily on lead generation and sales focused on sealing the actual sale of the product or service.

Sales roles: The sales cycle is similar to the recruitment cycle of a source. At a small company, you have the ability to do the whole sales cycle, which integrates strategy, business development, sales, and customer success: figure out what you should sell, who you should sell it to, how to get in touch with them, actually get in touch with them, sell it, keep selling to them and make sure they’re happy (customer success), and at some point, decide whether to move on to better sales targets, or convince your company they need to be selling something different. At a large company, sales usually means someone else has done the broad shaping for a potential customer. You just have to go in and work through the mechanics of selling them on your product or service.

Customer Success roles: This is akin to handling a source. You make sure the customer is happy and keeps buying, preferably more.

Security roles: Some ex-Agency people gravitate to roles in security. I discovered that while I know a lot about tradecraft-related security and how to stay alive for the first minutes of an ambush, I know little about building security and computer systems security. Some companies will see your CIA background and confuse it with roles that are more akin to FBI or law enforcement. If you worked in an actual cybersecurity or security role, you can learn it and integrate well into those teams.

Trust and Safety roles, Threat and Business Intelligence roles: If you’ve been a targeter and/or an analyst these might be good fits. The role broadly is to protect a company and its people/users (or multiple companies) by tracking bad actors and threats. In large companies these roles report to a security division (however there are entire companies  just providing Threat and Business Intelligence).

Government Affairs/Legislative Affairs roles: Large companies pay to have people represent them on Capitol Hill and advocate for their interests. If you have significant experience engaging with and briefing the Hill, this is a possibility, however you’ll be competing against staffers rotating off committees who are actually much better equipped than you as far as networking and know-how. You may be able to join a larger company’s government affairs team at a more junior to mid-level, and you’ll probably find your skills most relevant to a company that works on national security-related issues.

At first many start-ups hire a lobbying firm. You may be able to step in once they want to transition into an in-house role for this, but keep in mind that they’re looking for the Capitol Hill contacts you already have, as well as your ability to work the legislative process, not just your briefing or networking skills.

Strategy and Operations roles: These roles help make sure vision, resources (budgets and people), and the market opportunity are aligned. Working closely with the CEO or CFO, they help figure out what to do to make things go right, and what to do when things go wrong. The smaller the company, the bigger your chance at a role like this.

A Chief of Staff role, for example, is largely a strategy role, but is heavily dependent on the needs of the CEO/company. In my case, at Infleqtion I’m the person who tells our CEO what he needs to hear, not necessarily what he wants to hear. I also serve as an executive advisor – from product strategy to setting business milestones to working with investors. I also work closely with all members of the executive team, the Board of Directors, and Advisory Board. I think this role is ideal for a former Case Officer, but I’m obviously biased.

Larger companies hiring a Chief of Staff often look for someone who has an MBA, experience with one of the big consulting firms, or experience doing the job already.

Entrepreneur: A successful CIA case officer must be able to operate amid ambiguity and make judgment calls that require strong second- and third-order thinking. Achievement-focused and good storytellers, they know how to figure things out, “read the room,” and assess and mitigate risk. Most people believe case officers and entrepreneurs are big risk takers, when, in fact, they’re risk mitigators.

If you find an A-player CIA officer jumping into a founder role mid-way in their career (or decide to start something yourself,) they’ll probably go on to do great things. They have enough confidence in themselves to leave without the safety net of a future pension as well as the energy, ambition, and know-how to navigate uncertainty. The same Emotional Quotient and approach that attracts investors will also attract excellent employees.

Venture Capitalist: An early-stage VC requires some of the same skills as a Case Officer – spotting, assessing, developing, recruiting, and handling founders building a company amid an uncertain operating environment that will bring a heavy return on investment. (However, many VCs have also accrued years/decades as domain experts in the technologies/and or industries they invest in.) Being a successful VC and successful case officer both involve some levels of luck and timing misattributed to skill. The biggest difference is in the VC world, nobody is going to die.

If you’re a Retiree leaving with a full pension – you have different choices than a “job.” You can:

  • consult
  • sit on a company Advisory Board or Board of Directors
  • serve as a senior executive at a small company (you’ll be expected to actually work, not pontificate and delegate) or mid- to senior level at a larger company (you might just be a face)
  • get hired by Wall Street/Private Equity/VC firms assuming you’re senior enough and have enough New York or Silicon Valley connections

For 2-4, you’re generally being hired for your name and the introductions you can make assuming you’re within the top 15 of leadership.

Boards: The term “board” can mean two very different things in the commercial world – an Advisory Board versus a Board of Directors. An Advisory Board provides advice. It has no legal role in the company. Often companies will put you on their advisory board just to use your name and image (and not really want your advice). Every company can organize and compensate its advisory board any way it likes. Some Advisory Boards meet once a quarter, others once a year. Advisory Board members may field weekly to monthly emails and calls from the company executive team to provide feedback on strategy and positioning and make introductions. Advisory Board members are often paid in a balance of equity (stock options) and cash (“cash” is the industry term for money wired to your bank account).

A Board of Directors has a formal and legal role. It provides governance and financial oversight to the company. They can vote to hire and fire the CEO. CEOs seek their advice (and often must seek their formal approval) for major strategic decisions such as acquisitions, major budget changes, hiring of C-level executives, etc.) Formal Board positions are harder to come by. If you’re an A-player from the senior-most ranks, consider joining a private company board if you’re aligned with their mission and team. They need you.

For me, personally: People in the senior ranks at startups usually call themselves operators. Obviously, that’s a different definition of the term. I knew I wanted to stay/go into an operator role because that’s where the business learning I sought would happen. I didn’t want to have to sell back into the intelligence community, because I didn’t want to leverage my contacts so tactically, but plenty of people do it (and we need good people to do it. We all know how badly the government needs commercial technology solutions). From the start, my job was closest to a business development role. Because it was a small company and I was going from top-down with the CEO rather than responding to a job advertisement, I was able to craft my function and initial title as, “Senior Director of National Security Solutions.” I began writing unsolicited strategy docs for the CEO. This ultimately led me into a strategy role, which led me into a strategy and fundraising role. I also took an advisory role with another startup working on national security technology, QuSecure.

Where should you go? Big company or small?  Choose big for stability and higher salaries. Choose small for learning, growth, and impact. In large companies, they usually want you in a narrow and specific role. However, you will have more roles you could move into if the first one isn’t a great fit. If you join a big company, assuming it’s public, you’ll get stock which immediately can translate into financial gains assuming the company performs well. The salaries are almost always higher. You can get rich in a big company (at least by our humble government standards), but rarely wealthy based on returns from that company alone.

At small companies, you wear many hats at once. I wanted to understand the daily challenges a company faced at the senior levels in trying to push a new technology in government markets and commercial markets, and how capital flows impacted all of this. However, a bigger company is more defined in terms of a 9-to-5. I work just as much now as I did in the field. And though I work from an office most days, I also work from home, which affords a lot of flexibility because I’m not chained to a SCIF.

You can get wealthy with the right startup, but many startups fail, so it’s a long shot. Of course, “wealth” is subjective. More than money, most of us crave impact. Both are possible on the outside.

How should you think about and mitigate risk if joining a startup? Know your appetite for risk. If you’re really bold, join an early-stage company (seed stage, Series A), but have conviction about the team. You may need to cover some portion of your own salary for a year. If you need to make a salary equivalent to what you make in government, target startups that have closed a Series B round within the last few months. If you’ve received a formal offer from a startup, ask how much runway (months of cash left) they have. If they won’t discuss any aspects of runway or value of the equity package they’re offering, look elsewhere.

Look before you leap. Talk with multiple employees at the company. Try to talk with an investor in the company. Research their Board of Directors and Advisory Board members and contact some of them. Look for people on LinkedIn who used to work at the company, reach out to them and ask why they left.

Being part of a “failed” startup is not a badge of dishonor. Most startups fail, especially those in the early stages. So long as you and the company weren’t operating unethically and illegally, it’s not a red flag on your resume. In fact, this sort of experience matters far more to the next prospective tech startup employer than the decade+ that you put in at the Agency.

Action:

A) If you’re an A-player, stay in government.
B) If you’re an A-player and leave, do great things on the outside and return to government service at some point.

Coming up next:

  • Part III – title, compensation (salary + equity + bonuses) and resources you can use.

Read the rest of Laura’s blogs at https://www.lauraethomas.com/

Filed under: Corporate/Gov't Innovation | Leave a comment »

Leaving Government for the Private Sector – Part 1

Posted on October 10, 2023 by steve blank

Laura Thomas is a former CIA operations officer. Reading how she moved in 2021 from CIA ops into a quantum technology company offered insightful career transition advice for those leaving her agency. Most of her lessons were applicable to any government employee venturing out to the private sector.
Below is the first of her three-part series.

—-

At least a few times a month, people looking to jump ask about my transition, which has led to me consolidating my answers 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.

Is it really a big jump to the private sector? It wasn’t a big jump. At the Agency, 85% of my time was spent navigating bureaucracy and equities, arguing for resources and 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 now have. 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.

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 Communist Party 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.

Today, 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.

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 current role as a Chief of Staff is in many ways like a DCOS (deputy chief of station) or a traditional Chief of Staff in government. I work behind the scenes, and sometimes out front, to shape our company 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. 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 I 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. Knowing how to navigate various stakeholders and interests, avoid landmines, and bring people together is an extremely useful skill in industry. If you’ve been a “doer” who knows how to communicate, work, and gain buy-in across an enterprise that is 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.

Did you make any resume missteps? Most often your resume is not what will get you a job, and submitting one to a recruiter or resume bank is not the right move. Odds are your resume is 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.

Having a resume that says you served in country X and wrote reports that went to policymakers, and “the President,” might get you a curiosity interview, but won’t get you a job. Unless you can translate how your skills provide commercial value, you won’t get hired.

For starters, first figure out which industry you want to work in, narrow it down, and work hard to get intros at the senior levels to a handful of companies (Board of Directors member, Advisory Board member, member of the C-suite (CEO, CTO, CFO, etc), and/or investor.) You have to do a lot of networking to create your list and build your network. Find a way to meet and captivate them with a story of what you did, and how your skills can transfer this to industry and add value to their company.

An early learning point for me came as I was speaking with a prospective VC about a job. He flat-out told me he didn’t understand my value to the company. He asked point blank, “How much money did you net the U.S. Government over your career, what exactly did you do in order to get those results, and how would you bring me those same returns?”

You will 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 my 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. I’ll turn my salary 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.”

How did you get your current job? 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 the agency who would vouch for me.

For my current company Infleqtion, I was introduced to a former senior Intelligence Community official who previously served on a board with the CEO, who made an introduction. When we met I asked the CEO his challenges and outlined how I might be able to help. 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.

Meanwhile, three years before I left the Agency I had done a cold outreach on LinkedIn to the person I suspected was the hiring manager for a job advertisement for a company that I liked. 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 including 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.

Action: A) If you’re an A-player, stay in government. B) If you’re an A-player and leave, do great things on the outside and return to government service at some point.

Coming up next:

•  Part II – what are the 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  – title, compensation (salary + equity + bonuses) and resources you can use.

Read the rest of Laura’s blogs at https://www.lauraethomas.com/

Filed under: Family/Career/Culture, National Security | Leave a comment »