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Tech Careers

Tech Works: How to Build a Career Like a Pragmatic Engineer

Learn from The Pragmatic Engineer’s Gergely Orosz how to navigate senior engineering roles and how to make the big decisions — like if Big Tech’s big money is worth it.
Jan 26th, 2024 9:04am by
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Image by Diana Gonçalves Osterfeld.
Tech Works is a monthly column by longtime New Stack contributor Jennifer Riggins that explores workplace conditions, management ideas, career development and the tech job market as it affects the people who build and run the software the world relies on. We welcome your feedback and ideas for future columns. 

“During my first few years as a developer, I received little to no professional guidance. But I didn’t mind, as I assumed hard work would eventually lead to progress. However, this changed a few years into my career when I was passed over for a promotion to a senior engineer role which I thought I was ready for.

Not only that but when I asked my manager how I could get to that next level, they didn’t have any specific feedback.”

This is how Gergely Orosz prefaces his new book, “The Software Engineer’s Guidebook.” He promised himself that, when he became a manager, he would do it differently. He committed his career as first an engineer and then a manager, and then much of The Pragmatic Engineer Newsletter and this new book to offering that guidance.

Both Orosz’s interview with The New Stack and his book covers the breadth of engineering careers. Today we zero in on his guidance about how engineers decide where to work, what to work on and what’s really worth it.

There’s No Single Path to an Engineering Career

Orosz’s guidebook, he told us, is about growing as an engineer, “as a professional in the industry at either a large tech company or at a medium-sized tech company, going from the entry-level software engineer to senior engineer, tech lead and staff engineer.”

He draws on his own experience as a software engineer, as an engineering manager and mentor, and then as a skip-level manager. Especially during his four years at Uber, he jotted down the advice he wanted to give indirect reports, but felt he may be overstepping.

This book, four years in the making, is meant to be used as a reference, you check in with it at various stages of your career. The first section, “Developer Career Fundamentals,” is applicable to all, including a deep-dive into subjects that Orosz finds are usually under-discussed — performance reviews, promotions and compensation — while the rest will be useful at different times.

Just remember, he warned, there’s no such thing as universal advice. Everything in the tech industry — from your career to the technology you’re working on — is contextual. But the book helps you reflect within your context.

Specialist or Generalist?

This is the question Orosz is asked in his continued conversations with developers: Should they dive deep into one technology or go broad? In last month’s issue of Tech Works, Kelsey Hightower argued you have to go deep to then be able to back up and take in the big picture.

“It depends on the context of your company,” Orosz said.

He offered an example: “If you’re, let’s say, a native mobile engineer, and everyone around you is a native mobile engineer, and there’s no opportunities to do web development, then probably the right thing is to go deep into that technology.”

After all, you will have expert native mobile engineers around you to help you become an expert, too.

At another point in your career, you may find yourself at a larger company that has many opportunities to learn from different teammates, tools and contexts. Take advantage.

“As a software engineer, you don’t need any book, if you’re in the right environment — you have your peers, your colleagues, your mentors, your managers,” Orosz said. “And, if you’re in a good environment, they’ll help you grow with them.”

Of course this is the ideal, he acknowledged, and “unfortunately, not all places are like this, and you might have had manager changes or not a very good manager or a small company.”

That’s where external resources like books, courses and talking to people outside your company becomes essential. But the book can’t replace the help you can get from your colleagues, he said.

“I wrote the book, but it will not be a substitute,” he said. “The best thing you can do is go and work at a place where you work with inspiring people who give you that time that you need.”

That makes where you work one of the most important decisions of your career in engineering.

What Is a Good Engineering Salary?

Most of us struggle to figure out how to negotiate the tech salary we deserve. Part of that comes down to the awkwardness around talking about what you make — which is proven to hurt those farther they are from the white, male majority.

Add to this, U.S. tech companies pay far and beyond the rest of the world.

At least in Europe, Orosz observed, there is no average or standard salary for a software engineer. Instead, these averages occur across three distinct categories of companies. This trimodal categorization of engineer compensation — salary + cash bonus + equity or stock = compensation — that he’s developed is a combination of the company’s market presence and number of positions:

  • Tier 1 tech companies. These smaller companies benchmark compensation against local companies competing for talent. There tend to be a lot of these positions and they tend to have more work-life balance. He gave us the example of the U.K. government.
  • Tier 2 tech companies. Tier 2 companies benchmark their compensation against all local companies. There tend to be about half as many of these positions. He gave the example of the neobank Monzo, which offers competitive compensation by U.K. standards but isn’t yet trying to compete with FAANG salaries.
  • Tier 3 tech companies. This is a multinational company that is competing for top tech talent against all regional or global companies. Their compensation packages reflect Silicon Valley rates. There are far less of these positions but they can pay triple the first tier.

The earlier you’ve been at these companies, the more your salary is likely to multiply. There’s also an ability for technical career paths beyond individual contributors, like distinguished engineers or fellow roles.

Tier 3 is where Orosz has found public compensation data, on sites like Glassdoor, basically non-existent. These are the companies synonymous with Big Tech, like Alphabet, Apple and Meta, where the recruitment process, salary and performance expectations are all the highest.

“Most engineers making outsized compensation in Europe have done so by taking a moderate risk on a high-growth, road-to-public company, joining before the IPO, and negotiating for equity,” Orosz wrote.

Because there’s still a taboo around salary transparency causing a lack of overall data, he’s found that most companies tend to assume they are a tier higher than they actually are — which has the Silicon Valley companies still attracting the top talent.

When it comes down to it, what you get paid is entirely contextual, but it’s clear that the Big Tech companies pay more for technical roles.

Do You Need to Work in Big Tech?

There’s no doubt that having at least one of maybe 20 or 30 Big Tech companies on your résumé gives you an advantage across your entire career. But working at these giants doesn’t come without risk or sacrifice.

Back in 2016, Orosz made that jump from a principal engineer at Skyscanner — what he would call a Tier 2 company — to Uber — a definite Tier 3 — where stock options gave the appearance of doubling his compensation.

“So I didn’t make any more money day to day, but I was given all this stock, which, back in 2016, it was unclear if they would go public,” Orosz said. “But, if they would go public, that would just basically double — like every year [of work] would count for two years.”

And then, when Uber did go public almost three years later, his compensation indeed doubled; staying for four years, he said, he ended up with roughly eight years’ worth of compensation.

But that was still just a well-placed bet. If Uber hadn’t gone public, he would have just taken on a higher-stress job for no increase in compensation. However, in this case, he got lucky.

At these high-growth companies, however, you have what Ben Horowitz, of venture capital firm Andreessen-Horowitz,  has dubbed “wartime leadership.” During peace times, it’s business as usual. But, when a company starts running out of money or there are other external financial or board pressures, it becomes very do-or-die.

Think back to October 2022 when, right after Elon Musk took over Twitter, whole teams were found sleeping on the office floor to meet a sudden deluge of requirements.

Perhaps not quite as extreme, Orosz experienced this sense of urgency back in 2016 when Uber engineers paused all business as usual and spent three months rewriting the whole app and its million-plus lines of code.

“Unless we get these things done, layoffs will come, because the business is in such dire shape,” is how he describes the messaging during such urgent times, which finds C-levels becoming much more direct.

“We saw this a lot [in 2023]. Some CTOs sending emails saying, ‘OK, this is what the business is. This is where I need you focus on. Otherwise, we need to cut costs.’ Which means layoffs.”

Orosz compared working at the FAANG companies, where your compensation truly is doubled by the value of stock options, to working in investment banking. Both are hard to get into and are easy to get fired from.

“I think everything’s a trade-off,” he reflected. “I wouldn’t say if you want to retire early, you need to work at one of these companies because I think tech is still a very lucrative field, but it comes down to your personal finances.”

Still, there’s no doubt these companies add invaluable résumé clout — whether based on experience or just perception.

“If someone says they’ve worked at Google for 10 years, [versus] they worked at a lesser-known company for 10 years, most people would bias like ‘Oh that Google person must be smarter, better,’” Orosz said. “I don’t think that’s true, by the way, but there’s this perception.”

Balancing Work and Life

The last couple of years of endemic developer burnout have shown us that, once your basic needs are covered, there’s more to a career in tech than just compensation. You need to consider what success means for you.

Everyone, Orosz said, must continuously ask themselves, “How does this job affect your health and well-being?”

He elaborated: “I have a friend who was so burnt out from working at one of the Big Techs — that I don’t want to name because I don’t think it’s specific to that Big Tech —[that] they had to take a one-year break. They worked there for two years and then take a whole year break, completely wrecked mentally.”

Especially at those Tier 1 companies, he points to a common mental health trade-off. For that big salary and long-term bragging rights, you often find yourself unable to disconnect from work because you feel like you’re on call 24/7 — or you may actually be!

“When I was at Uber, I didn’t mind that much, but when I quit, I just realized that I started to sleep better because my pager or my phone was not next to me all the time,” Orosz reflected.

He only remembers getting 2 a.m. wake-ups as a manager maybe twice a year. Still, those mid-REM cycle interruptions were stressful, as he jumped out of bed wondering, “What’s going on? Are we losing a lot of money?”

There are more things to consider when deciding where to work (or stay), such as if you even like your colleagues.

“I think the reality is, we’re software engineers,” Orosz said. “We love measuring things. Compensation is easy to measure and compare — or relatively easy in the startup ecosystem — but people can say ‘I made this much’ and then you can compare. But how do you compare?”

Such compensation packages need to be measured against your personal needs, he suggested: “The fact that you can sign out at 5 or 5:30 p.m. and you can always get your kids if you have kids. Or that on weekends you’ve never thought about work and you actually just kind of can let go.”

Early in his career, he didn’t make that much money at smaller companies but had few complaints. “I often felt that: Hey, I will do this job for less because I just like what I’m doing. I love the people. I feel so lucky.”

So many of these things remain subjective, but Orosz has open sourced 12 questions on engineering culture that help you better know what you’re getting into.

Good luck on your journey!

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