Switching companies to get the title

I was hired at Fastly as a Principal Engineer. So, to be honest, for me, the biggest factor was changing companies. The type of work I was doing didn’t dramatically change, but changing companies was the thing that ultimately enabled me to get the title. ‐ Keavy McMinn

My father was a professor of economics. After he completed his Ph.D. in his late twenties, he started teaching at one university, got tenure at that university, and walked out forty‐some years later into retirement. Working in technology, that sounds like a fairytale.

There are very few software companies with a forty‐year track record, and even fewer folks whose forty‐year career consisted of one em‐ ployer. There used to be a meme that many engineers spent either one or four years at each company to maximize their equity grants and then bounced on to the next. If that ever happened, it certainly isn’t common behavior for folks who aspire towards or reach Staff‐plus roles.

Instead, generally, those folks stay and are rewarded for staying at a given company as long as the circumstances support their success. If those circumstances change, they tend to either leave shortly there‐ after or spend a while burning out and then leave after exhausting their emotional reservoir.

It takes years to build the visibility and social credibility to get pro‐ moted from a Senior Engineer role to a Staff‐plus role, which makes it very difficult to walk away if you feel like you’re just one hump away from the promotion. Leaving, it can feel like, means starting over from scratch.

Then again, as described by Keavy McMinn, it’s common for folks to attain their first Staff‐plus title by joining a new company. Even with all your internal credibility, sometimes leaving is the most effective path forward.

What’s the right decision for you?

Before going further, I want to recognize two very different job‐ switching experiences: one of privileged flexibility and another of rigid constraints. Your residency might depend on a work‐sponsored visa. You might be supporting an extended family. You might be constrained to a geographical area with few employers. This advice focuses on the former circumstances, which are more common circumstances for someone who’s deep enough into a technology career to pursue a Staff role. You should absolutely discount it to the extent this doesn’t reflect your circumstances.

Why leaving works

The company that knows your strengths the best is your current com‐ pany, and they are the company most likely to give you a Staff‐plus role. However, actually awarding the role depends on so many circumstan‐ tial concerns that this isn’t how it works out in practice.

If your current team is very senior, it may be hard to justify your im‐ pact at the Staff engineer level because it’s being attributed to your peers. Your manager might have a limited budget that doesn’t have room for another Staff engineer. You might lack an internal sponsor. There simply might not be the need for an additional Staff engineer at your company. Any of these can mean that while you ought to be promoted, your current company won’t.

Conversely, when you interview for new roles, you can keep interview‐ ing until you find a company that’s able to grant the title. You can also deliberately choose to interview at earlier stage companies who are likely to value your experience more highly. The interview process also brings an automatic sponsor with it–the hiring manager–whose incentives will never be more aligned with yours than in the interview process.

The technical interviews are an inconsistent and unreliable predictor of success, which is bad for the industry and bad for companies, but works in your favor if you’re set on attaining a Staff‐plus role and are willing to conduct a broad search. Interviewing creates the opportu‐ nity to play “bias arbitrage,” finding a company that values your par‐ ticular brand of bullshit disproportionately. That might be a company that values folks with conference speaking visibility, your experience designing APIs, or your Ph.D. thesis on compilers.

Similarly, sometimes you’ll get into a rut at a company where your rep‐ utation is preventing forward progress. Perhaps you’ve tagged “diffi‐ cult” after flagging inclusion issues. Maybe you embarrassed an influ‐ ential Director at lunch, and they’re blocking your promotion. A new company lets you leave that baggage behind.

Yeah, of course, it’s always an open question whether you can really leave anything behind you in the tech industry. It can feel a bit cliquey at times. If you’ve worked in tech hubs, at larger companies, and for more than ten years, then you almost certainly have mutual connec‐ tions with the folks interviewing you.

If you have a bad run at a company, maybe your manager was a bully, or maybe you were going through a challenging period in your own life, it can feel like a cloud poisoning your future prospects. That said, much like the interview process in general, references and backchan‐ nel reference checks are deeply random. If you need any further ev‐ idence of that, look to the serial harassers who continue to get hired job after job at prominent companies.

Things to try before leaving

If you’re planning to leave due to a lack of interest, excitement, sup‐ port, or opportunity, it’s worthwhile to at least explore the internal wa‐ ters first. This lets you carry your internal network with you while still getting many of the advantages of switching companies. Depending on your company’s size and growth rate, this might not be an option for you, but there are some folks who switch roles every two‐to‐three years within the same parent company and find that an effective way to remain engaged and learning.

On the other hand, if you’re considering leaving due to burnout or ex‐ haustion, it’s sometimes possible to negotiate a paid or unpaid sabbat‐ ical where you can take a few months recharging yourself, often in conjunction with switching internal roles. This is more common at larger companies. (In case you were wondering, no, your coworkers taking parental leave is not “on sabbatical” or “on vacation.”)

Leaving without a job

Speaking of burnout, if you’re particularly burned out, it’s worth con‐ sidering leaving your job without another job lined up. There’s a fairly simple checklist to determine if this is a good option for you:

• Does your visa support this?

• Are you financially secure for at least a year without working?

• Do you work in a high‐density job market remotely, or are you flexible on where your next job is?

• Do you interview well?

• Could you articulate a coherent narrative to someone asking you why you left without a job lined up?

• Are there folks at your previous company who can provide posi‐ tive references?

If all of those are true, I don’t know anyone who regrets taking a sab‐ batical. However, bear in mind that it’s only the folks who took six‐ month‐plus sabbaticals who felt reborn by the experience. Folks tak‐ ing shorter stints have appreciated them but often come back only par‐ tially restored. If you do take a sabbatical, I highly recommend flush‐ ing out your experiences into writing. Even if you don’t share what you’ve written, it’ll help process the experiences.

Taking the plunge

If you’re almost at the Staff promotion in your current company, there is absolutely another company out there that will give you the Staff title. Whether or not you’ll enjoy working there or be supported after getting there, that’s a lot harder to predetermine. If your internal reputation is damaged or if you’ve been repeatedly on the cusp of promotion but a victim to a moving criteria line, then you should seriously consider switching roles if the title is important to you. At some point, you have to hear what your current company is telling you.

Conversely, if you’re happy in your current role outside of the title, con‐ sider if you can be more intentional about pursuing your promotion rather than leaving. Many folks hit a rut in their promotion path to Staff‐plus, and using techniques like the promotion packet can help you get unstuck. If you’ve used all the approaches, taken your self‐ development seriously, and still can’t get there–it’s probably time to change.

That said, it’s easy to overthink these things. Few folks tell their decade‐past story of staying at or leaving some job.

Finding the right company

There are only a few magic spells to attain a Staff‐plus role: negotiate for the title while switching roles or find a supportive environment to “bake in place” while building your internal credibility with an empow‐ ered sponsor who’ll advocate for you. The most important reagent in both spells is picking the right company to perform them at.

The good news is you’re applying to a new company is that while you might invest weeks of energy into determining if you can get a Staff role there, you won’t need to invest years. On the other hand, if you’re looking for a company to join and grow within, you’re embarking on a years‐long journey into an unknown organization. This is a daunting decision to make, and picking the right company for you will have a considerable impact on whether you attain a Staff‐plus role.

Disproportionately values you

If career velocity is your aim, then join a company that, for whatever reason, disproportionately values what you’re good at. For example, Fastly valued Keavy’s API design experience, and Stripe valued Dmitry’s work on compilers. If there’s a gap matching your particular shape that’s limiting their success, your impact on the company will be uniquely high.

Well, run organizations value you for what you’re good at. Less well run companies value you for your identity. For example, a culture that views aggression as leadership would indeed promote and center the most aggressive folks, but to their culture’s and team’s detriment. Sometimes you’ll find a company that net values you appropriately be‐ cause it values your incidentals without valuing the contributions that you consider to be valuable; that seems like it’ll work out, but generally speaking, it’s a recipe for frustration.

Meritocrats and Proceduralists

When you’re trying to identify your company to make the Staff transition to, there are a number of company values to consider in your decision. One that’s particularly important is understanding if the company’s leadership fundamentally subscribes to an exception‐ heavy “meritocratic” view of the world or a consistency‐heavy “proceduralist” view. Few companies exist exclusively at one end of this continuum, but most slant heavily in one direction.

Of course, folks won’t describe themselves in these terms. The first style would have called themselves a meritocracy a few years ago. Now that the term has fallen out of favor, they’d avoid it, but their core be‐ liefs remain intact. This style is particularly common in Silicon Valley, is heavily exception driven, and consolidates its efforts feting a small cadre of treasured individuals. Generally, in these companies, you’re going to be very successful if you pattern match with whatever they believe high potential looks like. You’re likely in for a rough ride if you don’t.

Another style of company you’ll find out there believes that consis‐ tency drives fairness. They’re the sort that work the policy rather than the exceptions: they design the clock, set it in motion, watch it tick, and make occasional repairs. These companies tend to be more structure‐driven and less intuition‐driven, which can create wider access to opportunity for more folks, but they can also be rigid bureaucracies who look smugly on while their machinery grinds an individual down.

Inevitably, both meritocrats and proceduralists view their world‐view as a moral position and depending on who you are and who the com‐ pany’s leadership is, you’ll have a radically different experience.

Some ways to explore during your interview process to help distin‐ guish these mindsets:

• Companies with rigid compensation bands and who actually stick to them tend to be run by Proceduralists. Those that willingly eschew their bands are Meritocrats.

• Companies that create one‐off roles for individuals to get them on board tend to be run by Meritocrats. Those that hire to their planned roles are Proceduralists.

• Companies with ad‐hoc or unstructured interview processes looking to get your “feel,” particularly for senior roles, tend to be run by Meritocrats. More structure means Proceduralists.

• Companies that perform ad‐hoc conjurations of new, rubric‐less interviews tend to be run by Meritocrats. Those that evaluate you rigidly, even if it doesn’t let you shine, tend to be Proceduralists.

Neither meritocratic nor proceduralist companies have inherently better odds of propelling you into a Staff‐plus role. Rather it’ll depend on your identity and the identities of folks in a company’s leadership roles. Depending on how those pieces align, you can estimate the level of support and friction you’ll encounter pursuing a Staff‐plus role.

Archetypes

Most companies only hire one or two of the Staff archetypes, even though they all use the same titles to describe the role they’re hiring for. If you’re trying to figure out a given company’s preferences, it’s most effective to reach out to some of their existing Staff‐plus engi‐ neers and get a sense of the work they do. Most companies don’t delib‐ erately think about the sort of Staff engineers they support, so asking directly rarely works as well as it should.

Sufficiently large companies end up with at least some folks operating in each of the archetypes, but it takes a long time until that’s the case, usually after their engineering organization has scaled to thousands of engineers.

Growth

If you’ve exclusively worked at fast‐growing, successful startups, then it might not cross your mind that there can be a lack of room for additional folks operating in Staff‐plus engineering roles, but it’s sur‐ prisingly common for slower‐growing companies to simply not have the work or the budget for more folks in leadership roles. This is also a common constraint for companies that haven’t reached product‐ market fit–there are limited leadership slots when a company needs to remain highly aligned while frequently changing–with potential exceptions for those that happen to be selling a developer‐centric or technical infrastructure product of some sort.

If you join a fast‐growing company, new Staff opportunities will organ‐ ically open up. In slower‐growing companies, you may need to wait for someone to vacate their current role before another becomes avail‐ able. That’s not to say that you should necessarily join a fast‐growing company if you don’t want to–they’re often stressful and run on per‐ petually out‐of‐date processes–just another factor to consider.

Sponsorship

Getting a Staff‐plus offer at a new company requires someone inside that company who believes in you and is willing to push through a fair amount of organizational friction to get you the title. Getting pro‐ moted to Staff‐plus requires a manager and management chain who believe in you and their willingness to push through even more friction to get you the title. Without an empowered leader within a company who’s willing to invest their organizational capital in you, you can’t get a leadership role.

When looking for a company to pursue a Staff‐plus role at, a big part of the equation is identifying a company where you’ll have an effective sponsor. Interviewing outside of your current company is often effec‐ tive at finding you a sponsor: your would‐be hiring manager tends to have well‐aligned incentives to extend you a Staff offer. Equally im‐ portant, your time investment is high but still relatively low compared to working at a company for two years to realize you’re never going to reach your goal.

The easiest sponsors to find are folks who you’ve worked with before. The flying wedge pattern of one senior leader joining a company and then bringing on their previous coworkers is a well‐known and justifiably‐despised pattern that relies on this built‐in referrer‐as‐ sponsor, but it doesn’t have to be toxic if done sparingly.

This is also where having an external presence and network can greatly aid your search. Folks who’ve seen your presentations, read your blog posts, or nodded in agreement at your tweets are more likely to become your proactive sponsor in the interview process and later during promotion discussions.

Durability

Particularly if you’re earlier in your career and pursuing a promotion into a Staff role, it’s important to consider the company’s durability: will the company even exist five years from now when you’re hoping your work will culminate in a Staff‐plus promotion?

Somewhat more subtly, you also have to consider the longevity of your would‐be Staff sponsor. There are some wonderful engineering lead‐ ers creating pockets of equitable access to Staff‐plus roles, but all too often, these turn into a Values Oasis that can’t sustain itself once the sponsoring leader departs the company or changes roles.

Derisk durability by ensuring you join companies with business mod‐ els that actually work and work for leaders who are values‐aligned with their organization’s senior‐most leadership (that way, even if they leave, you’re still aligned with potential sponsors).

Pace

Throughout a forty‐year career, there are times when you’re rested and looking for a challenging, enveloping role. There are going to be other times when you’re drained and worn out. You will harm yourself by accepting a role that demands more pace from you than you’re able to presently sustain. When taking on a technical leadership role, it’s particularly important to make sure that the company’s pace expecta‐ tions align with what you’re able to provide because you’ll be evaluated in part on being a role model for the company’s pace.

And everything else, too

Job searches for leadership roles are much slower than the typical soft‐ ware search, taking months rather than weeks, and it’s trying to rush it rarely works out. As you evaluate whether a company might be an effective place to reach a Staff‐plus role, you also have to assess it on everything else that you’d look into in a typical process.

Dig into your whisper network for toxic issues and individuals. Make sure the mission is something you can stay supportive of and engaged with for years. Search for the folks you’ll be able to learn from during your work. If you find that these Staff criteria are pulling you towards a company that you otherwise have concerns about, the good money is that you’ll regret that decision.

Interviewing for Staff-plus roles

When you decide to interview for a Senior engineer role, you roughly know what to expect. You’ll refresh your resume, work through Crack‐ ing the Coding Interview, and do some research on the company to pre‐ pare questions. When you go into the interview, you know it’s go‐ ing to be five‐ish interviews composed of a few programming exer‐ cises, something about technical architecture, and some cultural, be‐ havioral, or career questions.

It would be amazing if you could start a Staff‐plus interview process with similarly clear expectations, but most companies struggle with their Staff‐plus interview loops. It might be the same exact interview you’d get for a Senior engineer role. It might be an engineering man‐ ager loop with a programming question added. It might be something else entirely.

Getting comfortable navigating ambiguity is a core part of the Staff‐ plus role, so a particularly optimistic person might view the state of Staff‐plus interviewing as a good opportunity to demonstrate your skills. If you’re less optimistic, you might find it a bit frustrating, but a bit of preparation can go a long way in making these interviews more predictable.

Draw your lines

The engineering leadership phase of your career may last twenty years, but if you think of that in terms of roles, how you spend that time will likely come down to four or five pivotal decisions. Each of those decisions is a scarce resource, and you should allocate them deliberately. Before jumping into an interview process, spend some time refining your criteria for the kinds of processes you’re willing to participate in, as well as reflecting on the right company for you.

There are certain signals you’ll get during an interview loop that the company doesn’t quite know how to interview Staff‐plus engineers. Because most companies have mediocre Staff‐plus interview pro‐ cesses, you shouldn’t automatically opt‐out of poorly run processes, but you should consider which of those signals represent a line you’re unwilling to cross.

One line that many folks in Staff‐plus roles draw is they’re unwilling to practice interview programming. This often means they are slower or make more mistakes in the sort of algorithmic questions that many companies use to evaluate early career candidates. Folks who don’t practice take that stance because they’ve decided that a company who cares about fast programming is likely to misuse its Staff‐plus engineer. Is that a line _you _want to draw? Maybe, decide for yourself.

Debug the process

After you’ve drawn your lines, next, you’ll need to figure out the actual interview process used at the company you’re interviewing with. It might feel like asking these questions could push the company to re‐ consider your candidacy, but it’s always reasonable to ask the recruit‐ ing team and hiring manager for more details about your interview process. At the Staff‐plus level, it’s almost a point of concern if you don’t ask for more details. Companies want you to exceed, and under‐ standing the process is an essential part of preparation.

The three most important things to understand before you start inter‐ viewing are:

1. What are the interview formats, including what are they evaluat‐ ing for?

2. Do any of the interviews require specific preparation?

3. Who are the interviewers?

Once you’ve answered those, then it’s just a matter of preparation. Take notes about how you want to approach the different kinds of questions. Prepare materials for any presentations interviews. Briefly research the interviewers to tailor questions to their background.

This is also a moment to debug if you’re in the right process. If your interview panel is composed primarily of early‐career and mid‐level engineers, it will rarely generate a Staff‐plus offer; the panel will be ill‐equipped to evaluate your strengths, and folks are often resistant to offers more senior than their own. If there are no deep‐dives into your previous accomplishments and no presentation opportunities, it’s sim‐ ilarly hard to demonstrate the expertise to support a Staff‐plus offer.

If it’s the wrong loop, but you’re exceptionally good at whatever the loop does measure, then you’ll potentially get a Staff‐plus offer anyway. However, if you’re less confident in those incidental measures, then raise your concerns politely and constructive, perhaps point them at resources around designing Staff‐plus interview loops. Don’t allow momentum to pull you into a process that doesn’t support your goals.

It’s particularly valuable to understand is when leveling happens within the company’s progress. Some companies advertise roles with level‐specific titles, which lets you apply directly to the level you think is appropriate. If you’re hoping for a Senior Engineer role, then apply for the Staff Engineer job posting. However, many companies use those as provisional titles and finalize them later; other companies are quite rigid. The only way to know is to ask.

It may feel very unnatural to take more control over your interview process, and in theory, you might miss out on some opportunities this way, but that’s a good outcome: your goal is to find the best available leadership opportunity, not the first available opportunity.

Finish well

Even if you skate through the interview process, always negotiate the details, and remember to finish well. Brief your references on the role’s details. Send follow‐up emails to interviewers. Accept the of‐ fered sell chats and bring thoughtful questions into them. In this case, the last mile is the easiest as long as you take the time to walk it.

Negotiating your offer

Back in 2012, Patrick McKenzie wrote Salary Negotiation which has since become the defacto guide to negotiating salaries for software engineers. It’s a great piece and a good primer on how you’d negoti‐ ate any offer, including a Staff‐plus offer: if you haven’t thought about this topic much before, start there.

For much of your career, the offer you get is generated in a relatively formulaic way. Maybe they have a compensation calculator, or maybe they base it off your previous compensation, but it’s the company’s sys‐ tem driving the numbers. However, there is a threshold where offer negotiations shift, and companies are willing to engage in a bespoke offer rather than a system‐driven offer, but you’re expected to some‐ how intuit that you’ve crossed the threshold–no one will ever tell you.

This sort of bespoke offer starts with more flexibility around compen‐ sation, and in particular more flexibility around the equity component of your offer. That said, it’s more than just the raw compensation. It’s also about other aspects of the offer that the company doesn’t gener‐ ally have flexibility around but is willing to make private exceptions around for senior leaders.

For example:

• Their standard contract might give them three months to exer‐ cise vested equity after leaving, but they might be willing to ex‐ tend a Distinguished Engineer’s exercise window to five years.

• They might not operationally be prepared to support early exer‐ cise for everyone but might be willing to make an exception to close a Sr Staff Engineer offer.

• They might be willing to offer a deferred compensation plan to support a tax‐advantaged payout schedule (this is mostly a thing at public companies).

• Additional vacation days if they’re using metered, as opposed to unlimited, vacation.

• Flexibility around work‐from‐home, working hours, or incorpo‐ rating in a state or country they don’t currently support employ‐ ing folks in.

It can be hard to know if a given role at a given company is over the threshold, and it’s hard to ask the other Staff‐plus folks already at the company because it’s likely they didn’t negotiate these aspects (per‐ haps because they were promoted from within and never given the opportunity). As a rule of thumb, if a company has more than twenty and fewer than five hundred employees, it’s pretty unlikely they are go‐ ing to do much custom work for you unless you’re coming into a quasi‐ executive role–they simply don’t have the operational ability to do so. However, if a company has thousands of folks but only a dozen at your level, it’s fairly likely they’re open to negotiating bespoke terms.

It’s important to be strategic about what you negotiate for. If you hold firm on First Class flights for all your business travel, you might get it, but it’ll probably also send a message about your priorities that the company doesn’t like.

Whatever you attempt to negotiate, take the time to frame your request in a narrative of why it’s important for you. For example, I worked with one senior candidate who framed their request for an extended exercise window in the context of having just bought a house and re‐ cently exercising their previous company’s equity after leaving. That’s a lot more palatable than just asking for more cash compensation. The right narrative gets the negotiation done and does it without generat‐ ing a negative signal about your motivations.