Real People, Real Jobs — Sierra Lai
A Marketing Manager at the website you visit most
Early on in your career, it’s easy to place a large focus on job titles — driven by social pressures or our own ambitions, we seek roles at companies everyone knows. The ones we think will elicit reactions of praise and approval when we’re faced with the inevitable (and sometimes dreaded) question, “So what do you do?”
But if there is one thing I’ve learned in my six years in the workforce, it’s this: jobs are often not what they seem. Your colleague with the shiniest title and highest salary dreams of leaving everything and working at an organic feta cheese factory in Greece. Your college classmate who seems to have struck gold as a viral creator has fantasies of throwing his selfie stick into the LA River. And your friend who can barely make it awake past 8pm because she is so overworked and underpaid as a teacher is actually the most satisfied of you all.
At Business Casual, one of my goals is to offer an unfiltered, honest look at what it’s like to work in different jobs. In Real People, Real Jobs, I’ll talk with people about their work, from under-appreciated roles to those at high-profile, well-known companies. In both cases, instead of sharing only the polished LinkedIn version of the job, we’ll peel back the curtain and show you what that role is really like, and offer insider tips on how to get there.
Today, we launch Real People, Real Jobs with one of my friends from college, Sierra.
Sierra Lai is a Marketing Manager at YouTube, where she oversees go-to-market strategy for NFL Sunday Ticket. YouTube has been Sierra’s first and only job since graduating college six years ago, making her somewhat of an anomaly among our generation. On the side, she’s the Co-Founder of that dinner thing, a dinner party in New York City. She lives in Brooklyn and is a proud mother to her Australian shepherd, Sunday. Here’s the inside scoop on what it’s really like to have her job.
90% of my time [at work is spent] on something not listed in job descriptions: talking to people. I often find that job descriptions in my field rely heavily on competencies that I spend about 10% of my time doing.
On a workday in her life: Tuesday, February 11, 2025
My first alarm goes off at 7:30am, but my dog, Sunny, is already up at 7am and usually snuggling up next to me because she wants breakfast. We get up and I feed her while I do a very regimented and multi-step skincare routine. I make a matcha every morning, usually Rocky’s, and take it with me when I’m in a rush (which I am today), as I walk Sunny around my neighborhood. When I get back, I eat a yogurt bowl with jam, granola and dried mulberries (new obsession) as I start looking through emails, which I try to do as soon as I can so I can catch up from the work left behind from my coworkers on the west coast and can have the rest of the morning to do deeper work as they start their days. I am a morning person and my brain does its best executive functioning before noon so I try to power through as much work as I can during this time. I slowly make my way to the office around 10 or 10:30am. This is the time I use to read a book or listen to a podcast, which is usually related to food & beverage because it’s my personal interest, but also because it helps me think about that dinner thing, even when I’m not working on it. I’m reading Unreasonable Hospitality by Will Guidara and listening to an episode of Front and Center featuring Gander, a design agency in Brooklyn that specializes on a lot of food products and spaces.
When I get to the office, I say hi to my coworkers and immediately grab water from our kitchen and settle into any remaining tasks. Today, I’m working on a creative brief for our biggest campaign for NFL Sunday Ticket: Kickoff for the 2025-2026 NFL season! Which yes, isn’t until September, but planning starts much earlier. This creative brief is what will set off all of our work ahead of the actual campaign and drive what the creative ends up looking like.
My job is very meeting heavy, and so are a lot of marketing jobs, so in the afternoon I’m usually jumping from conference room to conference room and stopping to have lunch in one of our very many office cafés. We are very lucky to get free lunch. My meetings are a combination of presentations to executives to get approvals on the campaign work, collaborating with other teams, and meeting with creatives to give feedback. I leave the office around 5pm.
When I get home, I have a few things to continue to work on and do that while making myself an adult snack plate of crackers and cheese. I force myself to stop work around 6pm so I can feed and take Sunny out for her evening walk while talking to my mom on the phone.
After work, I meet up with my that dinner thing co-founder, Ryn, at our neighborhood Irish pub for a Guinness to celebrate the success of our first pop-up, which we hosted to raise money for Los Angeles wildfire relief (we raised $6K!). It was the first time we held an event that wasn’t a sit-down dinner, and we wanted to celebrate and also talk about what’s next. We had two rounds and some popcorn with lots of truffle and cheese on it. I typically go out for dinner or drinks 3-4 times a week…it really feels like a professional sport in New York. I walk home, do another regimented and multi-step skincare routine, drink a bunch of water, and am in bed, scrolling until around 11:30pm, then fall asleep.
On a misconception people often hold about her job:
That you need to know a lot or have done the job before to be successful. I have been on four different teams in my six years at YouTube and so much of working in marketing is leaning on your common sense for the who/what/when/where and why and learning how on the job. Yes, there are definitely principles and terms, like the “marketing funnel” and “ROI,” that I reference every day but for the most part, I picked up everything I know by just doing the work.
On something about her role that you wouldn’t know from the job description:
90% of my time is on something not listed in job descriptions: talking to people. Marketing is a very collaborative and human-centric job and when you work at a global company like YouTube, your colleagues are all over the world and you’re often calling them all day. Obviously, there is some work outside of meetings, but I often find that job descriptions in my field rely heavily on competencies that I spend about 10% of my time doing.
On what someone who wants her job can do right now to get there:
Talk to people and have opinions on marketing, whether it’s on a large corporation’s marketing or a small business on social media. While there are so many free certifications and educational resources you can tap into to “learn” marketing skills, I think the best experience for the marketing industry is out in the world. When you interview, the thing that will make you stand out is not the number of skills you have listed, but whether you can talk about your perspectives, story tell, and connect that back to whatever company or product or business or person you’re trying to work for.
On her favorite part of her job:
Meeting YouTube creators. In my early career at YouTube, I was meeting creators while organizing Creator Summits, producing video shoots for brand moments, and attending VidCon. And even my current role working on NFL Sunday Ticket has allowed for some pretty out-of-the box activations bringing together creators, athletes, and athletes-turned-creators. Every single time I meet and get to talk to the real people who use our platform (from creators to their most engaged fans) I’m reminded why I work here: YouTube helps people find their passions, share their stories, and find each other. I’m really starting to sound like a spokesperson for YouTube, but I really mean it. If you’ve never gotten to sit down with someone who has a YouTube channel (big or small), I highly recommend it.
On the most challenging part of her job:
The only thing constant is change. The tech industry is one of the fastest moving industries there is and when your tech product is also at the forefront of culture, it tends to move even quicker. The priorities we have are always shifting and the teams and roles and people working on those shift alongside it. Learning to go with the flow has been essential to my career, and while it never really gets easier, contending with change all the time has made me more nimble, dynamic, and creative…all important things to be when you’re in marketing.
On having only one job since graduating college:
It’s not for everyone. I’ve been lucky to move teams and roles in the 6 years I’ve been at YouTube and not every company can offer that breadth of work. I think if I wasn’t able to switch teams (I went from Events & Partnerships, to Learning, to Brand, to now NFL Sunday Ticket on the YouTube TV team), I may not have stayed for as long as I have. It’s impossible to know that for sure, but I do believe early on in your career is the best time to jump around and I got to do that, all while staying at YouTube.
One thing (tool, skill, secret, etc.) anyone who wants her job must know:
When to use AI.
One person or publication you must follow if you want her job:
Cool Shiny Culture which happens to be written by two women I have worked with at YouTube (shameless plug).
Her work-life balance on a scale of 1 to 10 (1 = works all the time, including weekends, and doesn’t have any personal free time; 10 = standard 9-5 job with manageable demands):
3 during high demand or campaign periods, but the 3s get balanced out with 7.5s most of the time outside of those periods.
Thank you for reading! Let me know what you liked/didn’t like, or any questions you’d like me to ask my next interviewees. And if you want to refer yourself (or a friend!) for a future edition of Real People, Real Jobs, reply to this email or DM me through Substack.
Aww, appreciate the shoutout from our girl Sierra! 🥰 🫶🏻
This is a great concept and, as someone who's formerly from the tech world (and trying to make sense of that departure in my Substack), validating to hear the perspectives from a younger generation. Following your work!