Steve Blank Leaving Government for the Private Sector – Part 2

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 |