👋 Hi, this is Gergely with a free issue of the Pragmatic Engineer Newsletter. In every issue, I cover challenges at Big Tech and startups through the lens of engineering managers and senior engineers. If you’ve been forwarded this email, you can subscribe here. Getting an Engineering Executive JobAn overview of successful, tried-and-true routes into CTO, VPE, and Head of Engineering jobs, from the new book, ‘The Engineering Executive’s Primer’ by Will Larson.
So, just how do you win that first, coveted CTO, VP of Engineering, Head of Engineering, or Director of Engineering role? I know several professionals who have achieved such promotions internally, and a couple who were successful external candidates for their first CTO role. These jobs are usually classed as executive roles, and author and CTO, Will Larson, has just published a handy book about these upper echelons. Before this latest title, he wrote a book on engineering management (An Elegant Puzzle,) and one on staff+ engineering (Staff Engineer). Side note; we almost overlapped at Uber, with him departing the San Francisco office just as I joined the company in Amsterdam. We met in-person last year when I was in SF. I picked up this new book, The Engineering Executive’s Primer, and can report that I’m thoroughly impressed. It’s honest in how it covers topics like navigating tricky power dynamics with CEOs, surviving “peer panic,” dealing with competition within leadership teams, and in its overall breadth and depth. There’s the usual topics: onboarding, hiring, engineering processes, performance processes, compensation, etc, and the book also goes deep into how to navigate mergers and acquisitions, cultural surveys, and how to onboard peer executives.
I reached out to Will to ask if he’d be open to publishing a chapter from the new book in this newsletter, and he generously agreed. In today’s issue, we cover two topics:
As usual with all my recommendations, I am not paid to recommend this book, and none of the links are affiliate ones. See my ethics statement for more detail. 1. The book’s and Will’s backgroundsBefore we jump into the chapter, Will answered a few questions: How did you get your first engineering executive job? ‘In late 2019, I was getting close to four years at Stripe, and understood the problems I was working on a bit too well. I started thinking about how to get my hands on a new set of problems. In particular, I was interested in finding ones to bring me back into product engineering, rather than continuing along the infrastructure engineering path, which I got on to somewhat accidentally at Uber. ‘Most inbound interest I received was for roles similar to the one I was in. So I asked some recently-hired executives how they’d found their jobs. Most mentioned working with executive recruiters, and I asked for referrals. This led me to Sam, the executive recruiter who helped find my CTO role at Calm, which I accepted following deep discussions with 3-4 other companies.’ What made you decide to write this book on executive roles, and can you discuss your choice to be so candid about the behind-the-scenes reality? ‘This is my third book, and I learned a lot from writing ‘An Elegant Puzzle’ and ‘Staff Engineer.’ There’s a curse in authorship, where I see so many things I could have done better in writing those books! Still, writing two intentionally different books helped me understand what I want to accomplish with my writing. ‘My goal when writing is to create something both useful and unique. Being useful is the only good reason to write a professional book, while being unique is the only way to create something durable that resonates with readers over time, and doesn’t fade away after a year or two. ‘When I first became an executive, I learned a lot by making mistakes. I wanted to scrutinize those errors, figure out frameworks that would’ve helped me avoid them, and collate these insights in a book to help others entering that role. Helping others avoid my mistakes is my best tool for advancing the technology industry, which is the professional goal I’m trying to channel my energy toward.’ How did you write the book, and how long did it take? I guess you started taking notes a long time ago, with so many observations across 24 chapters and more than 300 pages. ‘I have two concurrent writing processes:
‘Writing this book took about 14 months. I started working on the outline in late 2022, and iterated on it three or four times, before it stabilized roughly into these chapters. I wrote about two-thirds of chapters before I started talking with the publisher, O’Reilly, about whether they’d be interested in it. ‘After signing the contract, I reworked the topics a bit with my editor, Virginia Wilson, completed the remaining chapters, and revised individual chapters several times based on feedback from her and reviewers. Writing books really does get easier the more you do it, and this book was relatively peaceful compared to my first two.’ You’ve been a software engineer, and are now a CTO. What are the biggest differences between these roles? ‘A friend recently emailed me asking if it’s possible to have friends at work as an executive, because he was finding that harder and harder, the more senior he’d gotten. In general, I’ve found it’s complex to have work friends as an executive, and that it only works when both individuals take the long view on outcomes. I miss my earlier roles where these things were less fraught. ‘Conversely, I’m really motivated by being able to engage with problems blocking forward progress, and being in an effective executive team is a job characterized by exclusively dealing with that kind of problem. For me, engaging with problems is the most energizing part of being an executive. At the same time, in my earlier work as an engineer I often found myself stymied by organizational constraints. To be fair, I was also a lot less effective at navigating organizational constraints back then.’ What’s your advice for software engineers ambitious to be a Head of Engineering, VP of Engineering, or CTO? ‘Spend more time understanding why people’s perspectives are “right,” rather than why they’re “wrong.” I think of this as extracting the core of what people say. ‘Being able to learn from those who don’t communicate clearly is a super power. Many who are theoretically good communicators – maybe the executives you work with – are too busy to always communicate clearly, and getting good at understanding them despite messy formatting is invaluable. ‘Spend less time on pursuits you don’t find energizing. For example, I’ve seen so many people try to become “content creators” to further their career, despite having no interest in creating content. The vast majority of successful executives don’t write stuff online and don’t speak at conferences. Do so if it’s energizing for you, but if it isn’t, find something that is!’ Thanks Will for sharing your thoughts! With that, we dive into Chapter 1 of the book. 2. Getting an Engineering Executive JobThe below excerpt is from The Engineering Executive's Primer, by Will Larson. Copyright © 2024 Will Larson. Published by O'Reilly Media, Inc. Used with permission. At Digg, I ended up running Engineering, but I certainly wasn’t hired to do so. It wasn’t until a decade later, when I joined Calm, that a company deliberately hired me into my first executive role. If you start researching executive career paths, you’ll find folks who nominally became Engineering executives at 21 when they found a company, and others who were more than 30 years into their career before 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 folks assuming executive roles, the more they start to sound pretty similar. I’ve condensed the many stories I’ve heard, along with my own experiences, into a repeatable process that prospective candidates typically follow. This chapter will cover:
If you’re kicking off the search for your first executive role, reading through this chapter will provide a clear roadmap through the process. 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). There’s no right answer, but here are some examples from real people:
The rationale doesn’t need to be particularly compelling, just something positive that expresses your excitement and qualification for the role. Don’t get discouraged if your statement isn’t profound—there are very few profound ways to say that it’s the next logical step in your career. 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. (If you don’t have peers or mentors in executive roles, do some cold outreach to executives at companies you’ve worked at with your rationale and see if they’ll weigh in.) 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, jealousy, excessive status-orientation, and ambivalence. One of OneLimited-release luxury items like 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 20 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 processes for executive roles are well-structured, but more often they 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, stories, and 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. It’s not just the hiring process that is not standardized; the Engineering executive roles themselves vary greatly as well. Sometimes they’ll include managing Product Management, and sometimes they’ll exclude managing some parts of Engineering. Working with technology-oriented founders, you may provide more organizational support than technical guidance, whereas working in an older business may mean there are few other executives with a technology background. “One of one” means that anything is possible, in both the best and worst possible sense. Finding Internal Executive RolesRelatively few folks find their first executive job through an internal promotion. These are rare for a couple 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 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 who may feel slighted by not getting the role themselves. This makes their new job even more challenging, and can lead to departures that hollow 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. Because of that, even if an internal transition into an executive role goes poorly for you, don’t assume that means you wouldn’t do well as a newly hired executive at another company. Finding External Executive RolesMost 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:
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—ideally one that peers have worked with before—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. It’s important to note that the most desirable roles, and roles being hired by a well-networked and well-respected CEO, will never reach an executive recruiting firm. If you try to enter your search without an established network and rely solely on executive recruiters to find roles, you are almost certain to be selecting from second-tier opportunities. This is, by the way, absolutely not a recommendation against using executive recruiters. Executive recruiting firms can be fantastic. A good executive recruiter will coach you through the process much more diligently than the typical company or investor’s in-house recruiter. I found my first executive role through an executive recruiter, as did the majority of my peers. (Note that the executive recruiters of tomorrow are your internal recruiting colleagues of today, so learning to partner effectively with Recruiting will pay dividends in both your current hiring and your long-term career options.) 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, and respond politely to recruiters who do reach out. Both have a surprising way of creating job search serendipity, and ensuring 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 for making 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). Most companies with strong principles like to talk about them a lot, and you should be able to find public evidence to support their posting coming from a principled belief. If you can’t, then it’s likely desperation. 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 (more on this in Chapter 12), work in a role where you get exposure to the company’s investors, create more visibility of your work (more on this in Chapter 12 and Chapter 15) to make it more likely for founders to reach out to you, or get more relevant experience growing and operating an Engineering organization. Interview ProcessThe 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 second, the interviewer usually has never worked in the role. There are, inevitably, exceptions! Sometimes your interviewer was an Engineering executive at an earlier point in their career, but that usually isn’t the case. A relatively common scenario in startups 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 and 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 for executive roles is as follows:
Here are a few tips that I’ve found effective for these interviews:
If this sounds surprisingly vague and a bit random, then you’ve read it correctly. Gone are the days of cramming in all the right answers. Now, it’s a matter of reading each individual effectively and pairing the right response to their perspective. If that feels arbitrary, keep in mind that navigating various perspectives will be a significant part of your role as an executive going forward! Negotiating the ContractOnce 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 important to remember that these are one of one jobs. Compensation consultants and investors will have recommended pay ranges, but each company only hires one Engineering executive at a time, and every company is unique. Fair pay 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 14A 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: Equity Equity is issued in many formats: stock options, Restricted Stock Units, and so on. Equity is 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; or negotiate an extended post-departure exercise window, even if that isn’t an option more widely; or 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 Equity acceleration is another negotiation point around equity. This is 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 knowledgeable about the topic rather than it being a particularly nuanced aspect of the discussion. Severance packages 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 have 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). Bonus 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 with other companies that employ bespoke, per-executive goals instead. Parental leave 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 that this is often negotiable in less senior roles, as well.) Start date 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 Support to perform your role successfully is another point that can be negotiated. 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, negotiating for an executive assistant can free up hours every week for focus work, and negotiating a 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 JobOnce 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, and that will bias you toward 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, and 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 take before finalizing your decision:
As you work through these steps, ask yourself: Are you still excited? Have you explained your thinking about the role to at least two friends (who didn’t raise any concerns)? If the answer to these questions is yes, then take the job! Not Getting the JobYou can’t talk about running an Engineering executive search without talking about not getting the job. Who doesn’t have a story of getting contacted 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. They 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 knew we wouldn’t be a good fit to work together. I’ve discussed roles where both I and the CEO wanted to move forward, but where I lacked a specific skill they felt was required to succeed (for example, deep experience in machine learning). Although rejection isn’t fun, the perspective that I find helpful is: The goal of your search is not to find an executive job, but rather to find 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. Gergely again. I hope you have enjoyed this in-depth look into how to get a coveted engineering executive role, via The Engineering Executive’s Primer. Many things Will discusses above are open secrets among engineering leaders; like that each executive role and hiring process is unique, and CTO roles at different companies often have vastly different processes, expectations, and compensation ranges! Nearer the heights, compensation also becomes more negotiable; not only equity and salary, but also equity acceleration. That’s why, when negotiating a compensation package in a new country, it’s sensible to invest in tax advice about the equity component from a local accountant or equity expert. I recently spoke with an engineering director in San Francisco who was offered a CTO role with generous equity in Germany; but equity taxation is quite different there and they were researching it, first. The rest of this book keeps up the quality, with lots of behind-the-scenes insights. If you’ve gotten something from this excerpt, you’ll likely get even more from the rest. So, if you’re an engineering executive, or want to become one, I reckon The Engineering Executive’s Primer is a very useful volume, as the author hoped for. This week, there won’t be a new issue of The Pulse on Thursday, as I’m on spring break. As of next Tuesday onward, things are back to the usual schedule. Thanks for your support! You’re on the free list for The Pragmatic Engineer. For the full experience, become a paying subscriber. Many readers expense this newsletter within their company’s training/learning/development budget. This post is public, so feel free to share and forward it. If you enjoyed this post, you might enjoy my book, The Software Engineer's Guidebook. Here is what Tanya Reilly, senior principal engineer and author of The Staff Engineer's Path said about it:
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Getting an Engineering Executive Job
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