Written by Florence Robson
Photography by Pearl Metin

Kate Matthews

“It’s the purest form of empathy. To have a good software engineering solution you need to put yourself in someone’s else’s shoes”


Kate Matthews is squeezed into a small meeting room in the New York offices of Chegg, a connected learning platform, where she works as the Senior Software Engineer. 

Initially unsure if she will have anything meaningful to say, it quickly becomes obvious that this won’t be a problem, and her hesitancy gives way to deep thinking and verbal fluency on a number of complex topics. 

Kate studied Mathematics at Bard College, which she credits with helping her develop the critical thinking skills that helped with programming, “particularly wrestling with abstract concepts and complicated logic.” 

“Computer science began as a branch of mathematics, so many coding concepts, such as functions, variables, boolean logic and recursion are originally mathematical concepts,” she says, adding that understanding the vocabulary and mindset of mathematics would later set her up for success with learning to code.

Growing up in Staten Island, New York, her family were “pretty tech friendly,” she says. 

“I grew up spending a lot of time on the internet in the 90s AOL heyday. My older brother was very interested in programming so I picked up some of the basic concepts by osmosis.”

But Kate and code didn’t immediately hit it off. Years later, during her time at Bard, when considering a Computer Science degree, she took an ‘Intro to Programming’ class that put her off the discipline for some years.

“While it helped me translate my vague osmotic understanding of code into a set of very basic skills, I decided I couldn’t hack it,” she says. She wouldn’t learn to code until a decade later, in late 2018, when she was 33 and had decided on completing a bootcamp.

During a Fullstack-focused prep course, another participant recommended to her the Codesmith Hard Parts lecture. “I hadn’t heard of Codesmith before, but after doing that session I decided I liked the vibes and committed to joining,” she says.

She joined Codesmith in the April 2019 cohort in New York, “there was no remote Codesmith back then”, and enjoyed it so much that she would stay on to work for the academy herself for nine months, first working as a teaching assistant before being promoted to Lead Technical Mentor. 

While at Codesmith, Kate built SeeQL, an open-source application to democratize access to relational data using both React and Node.js. 

Kate explains that SeeQL “was designed to put everything I learned into practice and the goal was to provide a tool to let you interact with and visually understand the relationship between SQL databases.”

The product is powered by Electron, a “technology that makes it easy to use the tools of web development to create apps that can be run on a desktop or laptop computer, but not in a browser,” Kate says. 

The nerdier part of my brain likes understanding how back-end services and databases are structured, as that’s where the core of the product business logic exists

Codesmith to Chegg

In May 2020, one month after concluding her teaching at Codesmith, Kate was offered a job at Chegg, a California-based education technology company created to improve education by helping students learn more in less time at a lower cost.

It does this through providing its users, which now number over 8.2 million students, with learning services such as digital and physical textbook rentals, online tutoring and help with homework.

“It was actually the first company that I got to a final round interview with. I started as a Software Engineer I, was promoted to Software Engineer II after about 18 months and then promoted to Senior Software Engineer after another 18 months,” she says.

She was drawn to Chegg because ed-tech interested her and had a lot more appeal “than finance or social media,” as her work “would directly be helping students.” 

Most importantly, she says she liked the people interviewing her. “It felt like an environment that would be both supportive and challenging in terms of both soft and technical skills, both of which ended up being true,” she says.

At Chegg, Kate focuses on front-end work, building tools that help students with common academic tasks like adding citations and grammatical and plagiarism checks. 

“I started by working on Chegg’s writing services, helping build out features relating to personalized writing feedback, various product experimentation and building a revamped UI for those acquired writing services.”

Her personal preferences, though, lean towards full-stack.

“Working on the front-end means you are directly impacting what the user sees,” she says. “But the nerdier part of my brain likes understanding how back-end services and databases are structured, as that’s where the core of the product business logic exists. Luckily I’ve had the chance to get that diversity of experience.”

Focusing on the front-end also makes it easier for Matthews to integrate some of her personal values into her work. Drawn to making a difference, she is always searching for ways to marry the business’ interests with her passion for social justice.

“I was instilled with a strong sense of fairness and intellectual curiosity, which in my experience makes it hard to not take issue with how society is structured"

Integrating Empathy Into Engineering

At Chegg, integrating empathy manifests most commonly as developing thoughtful user experiences (UX).

“Most developers work on new machines with fast internet connections that allow everything to load really quickly, without really thinking about users in developing countries who have low-powered mobile devices and slower connections,” she says. 

“There are business benefits to engaging with that group of people but it’s also an area where I feel like I can actually make a difference and cater to the diversity of users out there.”

Matthews has also undergone training to learn how to create UX that works for people with different access needs, such as color blindness and autism. “It’s the purest form of empathy. To have a good software engineering solution you need to put yourself in someone’s else’s shoes,” she says.

She attributes her interest in social justice and empathy to being raised as a “good New York progressive,” and her own experience as a transwoman.

“I was instilled with a strong sense of fairness and intellectual curiosity, which in my experience makes it hard to not take issue with how society is structured, and growing up with a marginalized gender helped me develop better empathy for others.”

Although she describes her own coming out as trans back in 2006 as a historical footnote, Kate has also made efforts to integrate empathy into her work by participating in Chegg’s employee resource groups.

“I’m a member of the women’s group CheggHer and the LGBTQ+ group Chegg Pride,” she says, where employees are “encouraged to congregate around shared identities and discuss cultural considerations at the company.”

This mainly involves conversations and social events, however more recently she had the opportunity to use her own experience to support others more directly.

“A colleague of mine recently came out as trans at work and I am trying to be there for her as she navigates her career. I’m grateful Chegg leaves space for people to assert their own identity.

“I’ve not experienced any discrimination from the teams I work within from a gender or queer perspective. It’s a liberal progressive company and everyone is very supportive. But, being trans, I do feel it’s important to be active in those groups,” she says. 

Kate also supports other minority employee groups as a “passive member”, including one Black and Latinx peoples, and another for invisible disabilities.

Other ways empathy can show itself in engineering is through communicating with, and building code for those with perhaps a different skill set or needs. 

In this regard, Kate is a big fan of TypeScript, a Type Safe “programming language that makes web programming less of a wild west free-for-all, and forces you to write your code more thoughtfully,” which she writes on “pretty exclusively.”

“ Software engineering tends to attract more introverted types with a level of obsessiveness and a proclivity for abstract thinking, which might make them more prone to existential crises ”
"Software engineering is a way to make things easier for people, to allow them to do things they couldn’t do before."

Kate’s Future in Tech

Although it may appear a natural extension of her studies in Mathematics, software engineering wasn’t always a given for Kate, and the lack of inevitability has always left her questioning her future in the industry.

“Do I really see myself working in this way for the next twenty years? How can I get through the day, the month, the year in a way that’s interesting and challenging but also meaningful?” She says.

“I find my work interesting but—and I think this is a common experience—over time it can start to get a bit monotonous.”

On the other hand, she reflects, this propensity towards existentialism may be a sign that she is doing exactly the right job.

“Software engineering tends to attract more introverted types with a level of obsessiveness and a proclivity for abstract thinking, which might make them more prone to existential crises.”

Like the kind of programmer that “loves computers but also dreams of quitting tech, moving to a cabin in the woods and becoming a mushroom forager,” she laughs.

“I definitely have fantasies of moving to a commune in a remote area. I’m not sure it will ever happen but the nature of this career can inspire that thinking. There’s a duality in focusing specifically on the anti-humanness of a computer that can cause you to swing in the extreme other direction.”

Rather than heading into the woods, Kate is getting into the proverbial weeds of her career. She has undertaken professional experiments to understand what nourishes her as a person.

One was taking on additional management responsibilities to push herself out of her, admittedly fairly restricted, comfort zone. She discovered managerial duties weren’t right for her, but says that this knowledge has helped her refine her understanding of what she wants from the software engineering industry, which in turn gave her a sense of ownership over her career.

“It confirmed that, at least for now, the nitty-gritty individual contributor stuff is what works for my brain. That has helped me to move forward, even if I’m still not sure of the bigger picture.”

Kate’s concerns about the future are compounded by the way software engineering, and technology more broadly, is dominating headlines and increasing its role in society’s future.

Her response to this is to ally herself with Chegg’s value proposition to protect its market share in the face of disruptive technologies. Chegg risked being one of the first businesses to become completely outflanked by AI platforms which could render it obsolete.

Instead,the company leaned into the issue and adopted a strategy of acting as an intermediary between AI platforms and its users, through the development of CheggMate with OpenAI.

The CheggMate feature, yet to be released, is a virtual tutor that leverages the power of AI to pair students with the vetted content and help construct personalized study plans.

“ The world ten years from now is going to look very different, and lines of code will be directly what makes that happen ”

Software Engineering As A Human Pursuit

For Kate, it was important to bring her software skills to a company like Chegg, one with a vision of improving people’s lives.

“In an ideal world, software engineering is a way to make things easier for people, to allow them to do things they couldn’t do before. There shouldn’t be an inherent contradiction,” she says.

“Software engineering is a human pursuit and all human pursuits should have empathy as their guiding principle.”

The notion of empathy driving software engineering is important to Kate. She explains that for her, the original technology landscape was populated by people who made empathy central to technology, before the industry became commodified and profitable.

“There is a tradition of geeks and nerds, who are by virtue of their nature on the margins of society, having an appreciation for inclusion, diversity and existing outside the norm, seeking out those narratives through SciFi and adopting utopian ideals.”

Those people were also inherent to the rise of modern technology, bringing those ideas into the industry they built. But she points to the gradual fading out of Google’s ‘Don’t Be Evil’ tagline from the early 2000s as an indication of how big tech has moved away from those early ideals.

“That ‘good versus evil’ narrative is a strong thread throughout the history of computer science but was most dominant in the 1980s and 90s, when technology was dominated by passion, intellectual curiosity and a focus on ideals,” she says. “Capitalism means that the dominant forces aren’t incentivised to care about those things any more.”

However, Kate acknowledges that her concerns are shared by many others in the technology industry. While concerns about inequality in technology, from hiring practices to biased datasets, aren’t new, the recent explosion of AI has brought the topics out of Silicon Valley and into everyday vernacular.

“There are large subsets of the technology community having these conversations and trying to make a difference.”

She references Timnit Gebru, the ex-leader of Google’s ethical AI team, who was pushed out of the company after co-authoring a paper on the ways in which commonly-used AI-enabled platforms are exacerbating inequality.

“The world 10 years from now is going to look very different and lines of code will be directly what makes that happen,” she says.

Despite the potential pitfalls associated with this, Kate feels uplifted by conversations about how software can be a force for good when empathy is central to an engineer’s worldview.

“I find it inspiring talking about how software is foundational to society and the complex issues we’re grappling with right now. Even though I don’t feel empowered to fix all of those problems tomorrow, I do feel privileged that I am in a better position than many people to contribute to building a brighter world. I feel some degree of theoretical ownership over the future.”

One of the ways she does feel she can influence a future guided by empathic engineering is through her mentorship of beginner engineers. She explains that her concern is not so much about “moving up the ladder” as it is about holding it steady for others to climb.

“Being able to provide a mentorship role is something that appeals to me as a microcosm of how to resolve these tensions between personal and professional priorities,” she says.

She does this both at Chegg, and occasionally when joining in at Codesmith alumni events and women’s panels.

“Software engineering can be a mindset and approach as much as any particular technical knowledge. The main thing I try to encourage is a belief that the bootcamp path is a real, viable one that does work, as incredible as it might seem.”

Side Projects

With programming being a mentally demanding job day-to-day, it’s unsurprising Kate’s life outside of work steers clear of code.

“Once I'm done with work at the end of the day, I'm really not interested in spending any more brain power on coding,” she says, and describes herself as a musician first and a coder second.

“I played guitar in a band for a few years after college and I try to keep up with playing and recording music on my own in my apartment.”

As all strong engineers do, Kate is continuing her development through constant learning and is about to start college courses in music composition and audio engineering to “stimulate the musical and creative side” of her brain.

“Aside from the struggles of the single dating life, I've also started playing in a—very casual—women's basketball league, which has been a fun little world to get into, as well as kickboxing classes and random adventures like walking the entire length of Manhattan.”

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