Getting a job as an engineering executive.

I started my first executive job search when I was 25. Eventually, I got an offer to lead engineering at a startup with four engineers, which I turned down to join Uber. It wasn’t until a decade later that I joined Calm and started my first executive role. If you start researching executive career paths, you’ll find folks who nominally become engineering executives at 21 when they found a company, and others that are 30+ years into their career without taking an engineering executive role.

As these anecdotes suggest, there is no “one way” to get an engineering executive job. However, the more stories you hear about finding executive roles, the more they start to sound pretty similar. If you’re looking to find an executive role, I’ve condensed the many stories I’ve heard, along with my own experiences, into the repeatable process that prospective candidates typically follow.

To be explicit, I am defining “engineering executive” here as “the functional leadership role responsible for all of engineering at a given company.” This is title independent because companies use titles in inconsistent ways. Sometimes companies will extend titles like CTO, VP of Engineering, or Head of Engineering to someone managing a fraction of engineering. Other times you’ll find a VP of Engineering reporting to a CTO, but where the VP is performing all functional leadership duties. You will also find companies that describe all 200 of their Engineering Directors as executives. That’s fine, just not how the term is being used here!

This is an unedited chapter from O’Reilly’s The Engineering Executive’s Primer.

Why pursue an executive role?

If you’re spinning up your first executive role search, you should have a clear answer to a question you’ll get a number of times, “Why are you looking for an executive role?” It’s important to answer this for yourself, as it will be a valuable guide throughout your search. If you’re not sure what the answer is, spend time thinking this through until you have a clear answer (maybe in the context of a career checkup.

Once you’ve written your rationale down, review it with a few peers or mentors who have already been in executive roles. Incorporate their feedback, and you’re done.

The other side of this is that interviewers are also very curious about your reason for pursuing an executive role, but not necessarily for the reason you’d expect. Rather than looking for your unique story (although, yes, they’ll certainly love a memorable, unique story), they’re trying to filter out candidates with red flags: ego, jealously, excessive status-orientation, and ambivalence.

1 of 1

Limited release luxury items (e.g. fancy cars) sometimes label each item with their specific production number along with the size of the overall run. For example, you might get the fifth car in a run of twenty cars overall. The most exclusive possible production run is “one of one.” That item is truly bespoke, custom, and one of a kind.

All executive roles and processes are “one of one.”

For non-executive roles, good interviewing processes are systematized, consistent, and structured. Sometimes the interview process for executive roles are well-structured, but they often aren’t. If you approach these bespoke processes like your previous experiences interviewing, your instincts may mislead you through the process.

The most important thing to remember when searching for an executive role is that while there are guidelines, there are stories, there are even statistics, there are no rules when it comes to finding executive jobs. There is a selection bias in executive hiring for confidence, which makes it relatively easy to find an executive who will tell you with complete confidence how things work, but be a bit wary. “One of one” means that anything is possible, in both the best and worst possible sense.

Finding internal executive roles

Relatively few folks find their first executive job through an internal promotion. These are rare for a few reasons, the first is that each company only has one engineering executive, and that role is usually already filled. The second is that companies seeking a new engineering executive generally need someone with a significantly different set of skills than the team they already have in place.

Even in cases where folks do take on an executive role at their current company, they often struggle to succeed. Their challenges mirror those of taking on tech-lead manager roles, where they are stuck both learning how to do their new job in addition to performing their previous role. They are often also dealing with other internal candidates who were previously their peers and may feel slighted by not getting the role themselves. This makes their new job even more challenging, and can also lead to departures hollowing out the organization’s key leaders at a particularly challenging time.

That’s not to say that you should avoid or decline an internal promotion into an executive engineering role, just that you should go into it with your eyes open. In many ways, it’s harder to transition internally than externally. Even if you have a rough experience, you may well be wholly qualified to join another company externally.

Finding external executive roles

Most executive roles are never posted on the company’s jobs page. So before discussing how you should approach your executive job search, let’s dig into how companies usually find candidates for their executive roles. Let’s imagine that my defunct company, Monocle Studios, had been a wild success and we wanted to hire our first CTO.

How would we find candidates? Something along the lines of:

1. Consider any internal candidates for the role
2. Reach out to the best folks in my existing network, seeing if any are interested in interviewing for the role
3. Ask our internal executive recruiter to source candidates; I’d skip this step if we didn’t have any executive recruiters internally, as generally there’s a different network and approach to running an executive search than a non-executive search
4. Reach out to our existing investors for their help, relying on both their networks and their firms’ recruiting teams
5. Hire an executive recruiting firm to take over the search

Certainly not every company does every job search this way, but it does seem to be the consistent norm. This structure exposes why it’s difficult to answer the question, “How do I find my first executive role?” The quick answer is to connect with an executive recruiter, but that approach comes with some implications on the sort of roles you’ll get exposed to. Typically these will be roles that have been challenging to fill for some reason. The most desirable roles, and roles being hired by a well-networked and well-respected CEO, will never reach an executive recruiting firm.

This is, by the way, absolutely not a recommendation against using executive recruiters. Executive recruiting firms are fantastic. A good executive recruiter will coach you through the process much more diligently than the typical company or VC in-house recruiter. I found my first executive role through an executive recruiter, as did the majority of my peers, simply a perspective to keep in mind. Similarly, it’s not true that all founder-led searches are for desirable jobs–almost all executive roles start as founder-led searches before working their way through the pipeline.

Looking at the pipeline, there are many ways to increase your odds of getting executive opportunities at each step. The basics still matter: maintain an updated LinkedIn profile, respond politely to recruiters who do reach out. Both have a surprising way of creating job search serendipity, and make sure your network is aware that you’re looking. If you don’t personally know many recruiters at investors or executive recruiters, your network can be particularly helpful at those introductions.

There are also a small number of companies that do post executive roles publicly, and there’s certainly no harm in looking through those as well. The one challenge is that you’ll have to figure out whether it’s posted publicly because the company is very principled about searching for talent outside their personal networks (often a good sign), or if the role has already passed unsuccessfully through the entire funnel described above (often not a good sign).

Finally, if you’re laying the groundwork for an executive search a few years down the road, there’s quite a bit you can do to prepare. You can join a large or high-growth company to expand your network, work in a role where you get exposure to the company’s investors, create more visibility of your work to make it more likely for founders to reach out to you, or get more relevant experience growing and operating an engineering organization.

Interview process

The interview process for executive roles is always a bit chaotic. The most surprising thing for most candidates is that the process often feels less focused or effective than their other recent interviews. This is because your hiring manager as a Director of Engineering is usually an experienced engineering leader, but your hiring manager as an engineering executive is usually someone with no engineering experience at all. In the first case, you’re being interviewed by someone who understands your job quite well, and in the latter the interviewer usually has never worked in the role.

There are, inevitably, exceptions! Sometimes your interviewer was an engineering executive themselves at an earlier point in their career, but that usually isn’t the case. The most common scenario is when a technical founder interviews you for the role, potentially with them staying as the CTO and you taking on the VPE title, but even then it’s worth noting that the title is a bit of a smokescreen, and they likely have limited experience as an engineering executive.

Consequently, engineering executive interviews depend more heavily on perceived fit, prestige, the size of the teams you’ve previously managed, being personable, and navigating the specific, concrete concerns of would-be direct reports and peers. This makes the “little things” particularly important in executive interviews: send quick, polite follow-ups, use something like the STAR method to keep your answers concise and organized, prepare questions that show you’re strengthening your mental model of how the company works, and generally show energy and excitement.

The general interview process that I’ve seen is along the lines of:

• Call with a recruiter to validate you meet the minimum requirements, are a decent communicator, and won’t embarrass them if you talk to the CEO. Also a good opportunity for you to understand whether there are obvious issues that might make this a bad role for you (wrong job location, wrong travel expectations, etc)

• Call with the CEO or another executive to assess interest in the role, and very high-level potential fit for the role. You’ll be evaluated primarily on your background, your preparation for the discussion, the quality of your communication, and perceived excitement for the company.

  Coming to this interview having researched the opportunity, and showing excitement for the company, is your biggest leverage point to influence the hiring process

• Series of CEO or founder discussions where you dig into the business, and their priorities for the role. This will be a mix of you learning from them, them learning about you, and getting a sense of whether you’ll work together well. The exact structure will vary depending on the CEO, and give you an understanding of what kind of person they are to work with

• One-on-one discussions with a wide smattering of peer executives and members of the team that you would manage. These vary widely across companies, and it is surprisingly common for the interviews to be poorly coordinated, having e.g. the same topics come up multiple times across different interviewers.

  This is somewhat frustrating. Generally it means the company is missing someone with the right position, experience and energy to invest into designing the loop, so it ends up being rather chaotic. I’ve had these interviews turn into general chats, programming screens, architecture interviews, and anything else you can imagine. All I can say is: roll with it to the best of your ability

• Presentation interview to executive team, your directors, or a mix of both. Usually you’ll be asked to run a sixty minute presentation describing your background, a point of view on what’s important for the business moving forward, your understanding of what you would focus on in the new role if hired, and your plan for your first ninety days.

  A few tips that I’ve found effective for these interviews: ask for feedback on your presentation before the session, make sure to follow the prompt directly, prioritize where you want to spend time in the presentation on the highest impact topics, and make sure to leave time for questions (while also having enough bonus content to fill the time if there aren’t many)

If this sounds surprisingly vague and a bit random, then yes, you’ve read it correctly. Gone are the days of cramming all the right answers. Now it’s a matter of reading each individual effectively, and pairing the right response to their perspective.

Negotiating the contract

Once a company decides to make you an offer, you enter into the negotiation phase. While the general rules of negotiation still apply–particularly don’t start negotiating until the company knows it wants to hire you–this is a moment when it’s particularly important that these are 1 of 1 jobs. Compensation consultants and investors will have recommended compensation ranges, but each company only hires one engineering executive at a time, and every company is unique.

Fair compensation will vary greatly depending on the company, the size of its business, your location, and your own background. Your best bet will be reaching out to peers in similar roles to understand their compensation. I’ve found folks to be surprisingly willing to share compensation details. It’s also helpful to read DEF 14 filings for public companies, which explain their top executives’ base, bonus and equity compensation (for example, here is Splunk’s DEF 14A from 2022).

There are a few aspects of this negotiation that are sufficiently different from earlier compensation negotiations that they’re worth mentioning:

• Equity is issued in many formats: stock options, Restricted Stock Units, and so on. They are also issued with many conditions: vesting periods (often 4 years), vesting cliffs before vesting accrues (often 1 year), and the duration of the period after you depart when you’re able to exercise options before they expire (often 90 days).

  Most of these terms are negotiable in an executive offer, but it all comes down to the particular company you’re speaking with. You may be able to negotiate away your vesting cliff, and immediately start vesting monthly rather than waiting a year. You may be able to negotiate an extended post-departure exercise window, even if that isn’t an option more widely. You may be able to have the company issue you a loan to cover your exercise costs, which combined with early exercise might allow you to exercise for “free” except for the very real tax consequences.

  To determine your negotiation strategy, I highly recommend consulting with a tax advisor, as the “best” option will depend on your particular circumstances

• Equity acceleration is another negotiation point around equity, that’s worth calling out as it’s common in executive offers, and extremely uncommon in other cases. Acceleration allows you to vest equity immediately if certain conditions are met. Many consider this a standard condition for a startup contract, although there are many executives who don’t have an acceleration clause.

  One topic that gets perhaps undue attention is the distinction between single and double trigger acceleration. “Single trigger” acceleration has only one condition to be met (for example, your company is acquired), whereas “double trigger” acceleration will specify two conditions (for example, your company is acquired and you lose your job). My sense is that people like to talk about single and double triggers because it makes them sound knowledgable about the topic rather than it being a particularly nuanced aspect of the discussion.

• Severance packages can be negotiated, guaranteeing compensation after you exit the role. There is little consistency on this topic. Agreements range from executives at very small companies that’ve pre-negotiated a few months salary as a severance package, to executives leaving highly compensated roles that require their new company to make them whole on the compensation they’re leaving behind. There are also many executive contracts that don’t pre-negotiate severance at all, leaving the negotiation until the departure (when you admittedly have limited leverage to work with)

• Bonus size and calculation can be negotiated. On average, bonus tends to be a larger component of roles outside of engineering, such as a sales executive, but like everything, this is company and size specific. A CTO at a public company might have their bonus be equal in size to their salary. A CTO at a Series C company might have a 20% bonus. A CTO at a 50 person company might have no bonus at all.

  In addition to the size of your bonus, you may be able to negotiate the conditions for earning it. This won’t matter with companies that rely on a shared bonus goal for all executives (sometimes excluding sales), but may matter a great deal at others that employ bespoke, per-executive goals instead

• Parental leave can be negotiated. For example, some companies might only offer paid parental leave after a year of service, but you can absolutely negotiate to include that after a shorter amount of service. (It’s worth noting, this is often negotiable in less senior roles as well.)

• Start date is generally quite easy to negotiate in less senior roles, but can be unexpectedly messy for executive roles. The reason it gets messy is that the hiring company often has an urgent need for the role to be filled, while also wanting to see a great deal of excitement from the candidate about joining.

  The quiet part is that many recruiters and companies have seen executive candidates accept but later not join due to an opposing offer being sweetened, which makes them uncomfortable delaying, particularly for candidates who have been negotiating with other companies, including their current one

• Support to perform your role successfully. The typical example of vain requests for support are guaranteed business or first-class seats on business travel, but there are other dimensions of support that will genuinely impact your ability to perform your role. For example, an executive assistant can free up hours every week for focus work, and sufficient budget to staff your team can easily be the difference between a great and terrible first year.

  The negotiation phase is the right time to ask for whatever you’ll need to succeed in the role. You’ll never have an easier time to ensure you and your organization can succeed

Negotiate knowing that anything is possible, but remember that you have to work with the people you’re negotiating with after the negotiation ends. If you push too many times, you won’t be the first candidate to have their offer pulled because the offering company has lost confidence that you really want to be there.

Deciding to take the job

Once you get an offer for an executive position, it can be remarkably hard to say no. The recruiters you’re working with will push you to accept. The company you’re speaking with will push you to accept. You’ll have invested a great deal of work into the process as well, and that will bias you towards wanting to accept as well.

It’s also challenging to evaluate an executive offer, because ultimately you’re doing two very difficult things. First, you’re trying to predict the company’s future trajectory, which is hard even for venture capitalists who do it a lot (and they’re solving for an easier problem as they get to make many concurrent investments, you can only have one job at a time). Second, you’re trying to make a decision that balances all of your needs, which a surprising number of folks get wrong (including taking prestigious or high-paying jobs that they know they’re going to hate, but just can’t say no to).

I can’t really tell you whether to accept your offer, but there are a few steps that I would push you to conduct before finalizing your decision:

• Spend enough time with the CEO to be sure you’ll enjoy working with them, and trust them to lead the company. While it changes a bit as companies scale, and particularly as they go public, the CEO is the person who will be deciding company direction, determining the members of the executive team, and responsible to resolve the trickiest decisions

• Speak to at least one member of their board. Admittedly, board members won’t directly tell you anything too spicy, but their willingness to meet with you is an important signal, and it’s the best opportunity to start building your relationship with the board

• Make sure you’ve spoken with every member of the executive team that you’d work with regularly. Sometimes you’ll miss someone in your process due to scheduling issues, and it’s important to chat with everyone and make sure they’re folks you can build an effective working relationship with

• Have someone on the finance team to walk you through the company’s most recent profit and loss statement. You will need to sign a Non Disclosure Agreement, but it would be a very odd sign if a company was unwilling to share this information with you

• Make sure they’ve actually answered your questions. I once interviewed to be a company’s head of engineering, where they refused to share their current valuation with me! I pushed a few times, but ultimately they told me it was unreasonable to ask, and I decided I couldn’t move forward with a company that wouldn’t even share their valuation with an executive candidate.

  Don’t assume they’ll tell you after you join if they won’t tell you when trying to convince you to accept their offer. You will never have more leverage to get questions answered than in the hiring process: if it’s important and they won’t answer, be willing to walk away

• If the company has recently had executives depart, see if you can get an understanding for why. This could be mutual friends with the departed executive, or even chatting with them directly

As you work through those steps and are you still excited? Have you explained your thinking about the role to at least two friends, and they didn’t raise any serious concerns? Then, generally speaking, take the job!

Not getting the job

Finally, you can’t talk about running an engineering executive search without talking about not getting the job. Who doesn’t have a story of getting reached out to by a recruiter, who then ghosts them after an initial screen? A public company recently invited a friend of mine to interview in their CTO search, got my friend very excited, and then notified them the next week that they had already tentatively filled the role. I’ve had first discussions with CEOs where we both immediately know we won’t be a good fit to work together.

Although rejection isn’t fun, the perspective that I find helpful is that your search’s goal is not finding an executive job, but rather finding an executive job where you will thrive. It’s much better to realize a job isn’t the right fit for you before taking it, and each opportunity that doesn’t move forward is for the best.

As an aside, I find Phyl Terry’s Never Search Alone a helpful book when thinking about executive job searches.