10 learnings through becoming a leader in software engineering.

A natural born leader who thrived as an Eagle Scout, Willy Xiao originally intended on being a lawyer because he saw them as the major decision makers in the United States. Going to Harvard from Johns Creek, Georgia, he aimed to use words and leadership to exhibit more influence in his career than his parents did.

Unexpectedly, he found a natural knack for computer science that was energizing. Seeing that Harvard clubs were eager for tech talent, he realized how useful the field is in today’s society. 

Ultimately beginning his career in software engineering at Facebook instead of consulting at McKinsey, he embraced his career calling with a sense of wisdom, purpose and leadership.

Below are 10 key learnings he picked up on his journey so far.

Boy Scouts of America, one of the largest youth organizations
National Executive Board Member and 24th World Scout Jamboree Executive Committee
Remote
2012 – present

Lesson 1: Scouting allows for learning opportunities one step ahead of your actual career.

“Scouting is constantly a spot where there’s a lot of work to be done. That’s where opportunity is – to try something new that’s one step ahead of your career. When you’re in 7th grade and go on a camp-out, you teach other kids to set up their tent or lead a small patrol. In high school, you do an Eagle Scout project – fundraise, plan your project, get it approved, think about the resources you need. 

In my 20s, I did a lot of small team leadership like planning the Jamboree, which is a 50,000 person event over 12 days with a $60 million budget. I was on the Executive Committee.

It allowed me to learn the next stage of my career. I’ve had those experiences early and learned the engineering stuff later. For a lot of engineers, it’s the flip side where you learn this technical skill set, but you’re not used to thinking about outcomes of things as much as doing a task.” 

Harvard University, oldest university in the US
Student
Cambridge, MA
2012 – 2016

Lesson 2: Harvard teaches students to think critically about complex topics.

“Harvard grads are high intention people, being able to think about topics broadly. In the engineering world, you see a lot of people who are very focused on the function of engineering, can do the tasks, can cross a lot of things off of a list. But when you start peeling back the layers of abstraction and having to think deeper, not just about the engineering task, but the business outcome, Harvard people have had a lot of exposure to different topics and ways of thinking.”

Lesson 3: Leading startups, some people might not even learn that much.

“I had seen some of the people who I respected the absolute most throughout college go off into startups, and after one year come out and just be beat up. A lot of people talk about how it’s hard to make money, but you at least learn a lot. I had friends who were coming to me like ‘you don’t even learn that much.’” 

Facebook, technologies that help people connect, find communities, and grow business
Tech Lead, Data Science, Software Engineer
New York, NY | London, United Kingdom
2015 – 2021

Lesson 4: Big companies require a depth of thinking that makes small company problems seem easier in comparison.

“I learned how to operate at scale and think about problems legitimately, both in terms of large deployment of software and business processes – how to move those, optimize those where it’s not low hanging fruit. Every problem that you face at that level of maturity, you have to study. And then when you try to unravel it or fix one problem, it unravels another. So you have to think much deeper about these problems and align multiple people. 

It gave me confidence. The depth of thinking is such that I could solve a lot of problems at other places. When I went to a startup, any ‘hard problem’ was really simple because it’s only one or two layers deep. It’s a different level of maturity.”

OfficeTogether (acquired by Envoy), workforce collaboration platform for the hybrid office
Head of Engineering
New York, NY
2021 – 2022

Lesson 5: Startups remind you of first principles.

“At a company that small, you’re learning everything from first principles. It’s just you and base business. Being forced to focus ultimately on an outcome and not think of your job as a function. It really makes you understand the end to end of why there are certain structures around your job. When you go somewhere bigger, you know what the core building blocks you need for a business to work.”

Lesson 6: There’s so much competition out there.

“You’re constantly trying to find product market fit. You’re iterating on the product. You’re talking to customers a lot. And you’re trying to hobble together people from various places, convincing people.

Our product was pretty reasonable in terms of how it worked, but I don’t think we were differentiated enough. There were 3 or 4 companies in the YC batch right afterwards and maybe 40 competitors the next year. The main competitor in this space was Envoy and when they launched, very quickly they got to $10 million ARR because they had a big customer base already.

We had 40 customers, signed contracts, multi-year deals but it didn’t grow enough for us to be able to scale out in a way that we thought was going to be exciting business.”

Lesson 7: For software engineers, the opportunity cost is huge, but that cost helps with VC funding.

“A startup is such a big opportunity cost, but it only works for people who could otherwise get a much higher paying job. Part of what makes it attractive to fund software engineers is as long as I am putting my time into the company, it’s as if I’ve given up hundreds of thousands of dollars. So it makes it much easier to raise money and build trust with investors because they know you have some skin in the game. 

Every single day, there was a joke I had with other ex-Meta people. We should wake up and put on a sticky note the amount of money we were not making every single day. To be like yes, that’s what we’re aiming for. From a financial perspective, we better be doing something big. That can be motivating. 

Lesson 8: It’s easy to align people at startups because there’s only vision, no money (yet).

“When you’re at a big company like Facebook, let’s say you crush it, you’re the best engineer and moved Facebook’s top line revenue by 0.1%. That’s a ton of money, but it doesn’t matter for your stock. Some group of humans now need to decide qualitatively whether or not to confer a lot of money from this big bucket of wealth onto you and do performance reviews. 

At an early stage startup, it’s very easy to align everyone because it doesn’t matter. There’s nothing else the CEO can give me, it’s just, ‘does this company work or not.’ People are really bought into the vision because that’s the only thing that we have.”

Envoy, workplace platform 
Engineering Manager
New York, NY
2022 – 2024

Lesson 9: Hiring is a sales job with repeated failure and should instead be approached as a puzzle.

“In many ways, for engineering managers, hiring is the first time they’re doing a sales job. For engineers, you’re used to having a high success rate of anything you do. If you code something, you have to go through many interactions, but at the end of the day, it’s going to work out. 

For hiring and any sales job, it’s a repeated failure, and it doesn’t feel that you’re building towards something. It’s really draining, so I had to reconceptualize what I was doing in hiring, thinking of it as a puzzle. 

Instead of trying to sell the role, I thought about it as: this candidate has some long-term dreams and goals, I need to figure out what that is. I have some things that are set, and some things that can move. Depending on who it is, I could change a lot of stuff to make it an attractive role for them.”   

Rippling, workforce management system
Engineering Manager
New York, NY
2024 – present

Lesson 10: In today’s tech climate, good hiring alone is not enough for managers.

“When I was at Facebook, the main job of any manager during the Silicon Valley crazy growth moment, was to hire, hire, hire. That was how you affect the technical product. 

Now, growth is much more stable, so you need managers to exhibit direct technical influence and impact. Everyone that I work with is really confident and really smart. Leaders on the engineering side at Rippling are held to a really high technical bar. 

It’s amazing because your management chain deeply understands what you’re doing, so you feel good about decision making.”

All photos courtesy of Willy Xiao.