From chaos to impact: Sandy Diao’s guide to career growth

When I was at UC Berkeley, I kept asking myself how I could grow as a person. I wanted to build social skills and practical abilities throughout school that I knew would matter in the workforce. So I took on a challenge: I signed up for five internships every semester while handling a full course load at a demanding university. I worked as a research assistant for a retired sociology professor, a corporate finance intern, an audit intern at a Big Four firm, an investment banking analyst, and a digital marketing apprentice. It was a broad mix. I wasn’t chasing money or status. I wanted to test my limits, absorb everything I could, and see how far I could push myself.

That experience convinced me there’s real power in being a generalist, and it’s shaped my whole career in growth. I call myself a full-stack growth operator because I understand how marketing drives top-of-funnel engagement, how onboarding helps users find value, and how the product keeps them coming back. My internships covered accounting, corporate finance, auditing, investment banking, user research, digital marketing, even helping that professor with his garden and writing. That mix of data, creativity, and finance skills let me stop stressing about picking one specialty. When graduation neared, I found Pinterest and reached out, offering ideas to improve their onboarding. They let me in, and that’s how I started there. At one point, I worried I wasn’t sleeping enough and might be hurting my grades, so I cut back to two or three internships to see if it helped my focus. It didn’t. My performance dropped across the board. I can’t fully explain why, but I think it’s because university exposes you to arts, math, creative topics, and more, training you to soak up context as a generalist. Doing internships alongside that made it all feel real and applicable. I retained more, especially in tough subjects like accounting. Finance textbooks with hypothetical financial statements were hard for me, but my corporate finance work at Dolby Laboratories brought it to life with real numbers, and it just clicked. I believe the more variety you tackle, the stronger you become overall. Pushing myself that hard taught me to prioritize and make smart trade-offs.

My first week at Pinterest, I jumped into support, handling about 500 tickets a week. That gave me a flood of customer data and intuition about the product. I spotted bugs in signup flows and onboarding gaps, so I wrote the first business onboarding emails Pinterest sent out, based on what I’d learned. It opened up tons of ways to improve things. We hit hyper-growth during my time there, climbing to over 150 million monthly active users. I was packing up my desk every week to switch desks because we kept hiring and running out of space. New engineering teams, new buildings, back to the original site after expanding. It gave me this sense that if I could see that kind of growth at Pinterest, I could do it anywhere, though maybe that was a bit optimistic.

I treasure that time. I met incredible mentors like Casey Winters, a growth expert I overlapped with, and learned so much watching him work. I still stay connected with many of those colleagues. Taking the Pinterest job was a shift for me. I’d planned on something stable and cushy after school, what my first-generation immigrant family hoped for, but I saw so much potential there and went for it. It was hands-on from day one, just as they promised.

Before Pinterest, I was set on finance. It promised smart teammates and big problems to solve. I interviewed at Goldman Sachs’ tech division and thought I would love the environment. But then I found Pinterest and chose that instead. Deciding between more investment banking interviews and Pinterest was clear to me. I felt 99% sure it was right. Without all those earlier experiences, I wouldn’t have had the gut sense to pick, unsure what mattered to me. Looking back, I see it as the right call, giving me a leg up on decisions. The nonstop pace at Pinterest, with office moves and constant hiring, forced me to move fast. I’d test ideas, tweak emails based on ticket insights, and sort out what worked without waiting for instructions. That pressure, plus my early doubts, shaped how I tackled everything.

After Pinterest, I stumbled into an opportunity that turned my world upside down. An entrepreneur from China visited our offices. Fast-growth companies always attract CEOs like that. I volunteered to give a tour. We sat down, and he shared his idea for a smart piano: a digital piano with light-up keys that sync to an iOS app. You plug in your iPad or iPhone, pull up sheet music, and the keys light up to guide you as you play. That hit home for me. Growing up, I was passionate about arts and creativity. In middle school, I taught myself piano using VHS tapes, library books, and later some YouTube videos. I’ve always wanted more people to play music, and I believe anyone excited about it should be able to, without needing private lessons or instructors. During our chat, he asked what I thought about marketing channels, product setup, and building it. Then he invited me to join his team and create it from scratch. Leaving Pinterest wasn’t easy, but the challenge felt familiar: a big problem, some resources to start, and a shot at something huge. I couldn’t resist. So I joined The One Smart Piano team, aiming to build the first digitally connected piano that teaches you how to play. It was quite a ride.

A piano is a physical hardware product, and that made it so different from anything I’d done before. Up to then, I’d been a knowledge worker, everything through a computer. Now I had to figure out how to find the best contract manufacturers and supplies, ensure quality control so customers wouldn’t face issues, manage shipping timelines, meet requirements for different markets and regions, and set up a customer service team to handle problems remotely since we couldn’t touch their devices. My confidence took a hit with those challenges. I ended up hiring and managing people 20 or 30 years my senior, and the pressure to deliver was intense.

I developed a habit, you might notice it when we talk, of keeping a poker face. It’s still with me, and it started as my way to push through imposter syndrome. Early on, instead of showing panic or nerves, which I definitely felt inside, I forced away smiles or confusion. I cut out filler words and told myself to act like I had it under control, like I knew what I was doing and was confident in my choices. In a small team, with employee retention and market success on the line, I couldn’t let on that I felt clueless and inexperienced in almost everything. That poker face carried me through negotiating with buyers at Target and Best Buy, huge retail chains in the US.

We teamed up with incredible music influencers, like Lang Lang, one of the world’s top classical pianists, who became an ambassador, and I met Stevie Wonder at a trade show. I even played piano on live TV for a major US news stream, despite having no real music background. Viewers probably wondered who I was. I held that poker face steady. Over time, it stopped being just a tactic and became a true reflection of my confidence to execute and solve problems. We launched, hit mainstream distribution, and I learned a ton about online to offline, offline to online, the showrooming effect. For physical products people need to try, a real-world presence is key to spark online purchases.

After the smart piano, I found myself spending a lot of time consulting other hardware founders on launching their products. I built a fascinating community of consumer hardware founders, and it made sense. Hardware is tough. Selling it, building it, you need the right connections and advice on avoiding mistakes. Nobody wants to order a huge batch of products costing thousands, only to find out they’re not compliant or up to standard. I found that there is a stronger sense of comraderie among hardware folks than in software, and I loved being part of that. Then, unexpectedly, the founder of Indiegogo, a massive crowdfunding platform, reached out. He wanted me to share a perspective with their product and engineering teams on how hardware founders approach success and give feedback on their platform’s experience. So many hardware products, like Oculus, Snapchat Spectacles, the Nest camera, launch on crowdfunding sites like Indiegogo and Kickstarter. I went in, offered some thoughts, using a similar approach to how I started at Pinterest and with the smart piano team. After a fireside chat, the CEO came up and said he’d love for me to work there. At first, I resisted. The smart piano was my baby, something I’d built from nothing, and I didn’t think I could leave it behind.

I thought it over, and one thing stood out: the smart piano’s scaling plan for e-commerce and physical stores, its global expansion, was pretty straightforward. We had a solid distributor playbook for global markets, and piano markets are stable and mature. No big guesswork on who’d use it. I figured I could hire someone to handle distribution, sales, and marketing specifics, freeing me to take on a new challenge and make a broader impact. That’s what I did, aiming to help more hardware founders succeed through Indiegogo’s platform. My deep dive into the smart piano, figuring out manufacturing, shipping, QA, all the gritty details, gave me an edge. I could tell Indiegogo’s team exactly what hardware founders need. How they think about timelines, customer feedback, launch risks, because I’d been there myself. Plus, the community I’d grown, those ties with founders, let me connect software and hardware worlds effortlessly. It wasn’t just a job change. It felt like stepping up to boost an entire ecosystem, and that’s why it worked so well.

AI is changing everything, and I see it everywhere. In growth marketing, it’s breaking workflows into pieces. One tool promises to create the most viral TikTok or YouTube short, another claims it can deliver the best campaign data, and a third offers agents to pinpoint outbound opportunities. As a single person, I’m managing over 2,000 tools like these. The catch is they’re not modular or connected, and they don’t share data. So I’m the one linking them, training models by explaining what one tool’s output means and how to act on it since they can’t figure it out themselves. Someday, we might toss everything into one platform that sorts signal from noise, but I doubt that’s coming soon.

These tools are built as walled gardens, with everyone aiming to grow their own slice, not unify. I don’t think bundling will happen, and I’m not sure a bundled solution is the long-term win. I don’t have the perfect fix or technical answer, but I believe the industry needs a shared reason to exchange data. Take influencer marketing. It’s still in its early stages compared to other tools. Every platform is a fortress, hoarding data, tracking, and monetization setups, with no push to join a bigger ecosystem because they’re all chasing profit for themselves.

In performance marketing, models like Google’s Performance Max or Meta’s optimized systems decide who sees my ads and who buys. They hand me vague stats, like 60% of users are men aged 35 to 45, and I’m left wondering who those people are. It’s hiding customer details behind a black box, pushing toward a future where models make all the calls. My key skill as an operator is executing on context, deciding where it fits without bogging down the system or wasting effort.

My main tip, one I use myself and tell students, is that everyone should become an AI generalist, no matter who they are. I start with applying AI in my personal life before even touching AI in work. If I’m a spouse planning recipes or trips with my partner, I think of myself as an AI generalist, using AI to improve my productivity with personal tasks. Students also adopt AI fast. Their goal is saving time and money, and they’ll use it for anything, even drafting notes to their parents. Once I grasp its power and get efficient, I naturally bring it to work and embrace it.

When I’m AI-native in my personal life and then at work, I turn into an orchestrator. It doesn’t matter which part of the workflow I handle. Coding, automating, or other pieces, what counts is I’m coordinating it all, shifting AI uses from personal to professional. I might see this in a bubble, but I’ve got plenty of examples, like students cutting corners with it. It gets me excited about what’s ahead without worrying too much about my identity changing. I get why people feel an existential crisis over their roles, but as an AI generalist, I focus on efficiency instead. Community helps too.

I’m a board member at Decode, a nonprofit supporting students in tech careers across the US and beyond, especially at UC Berkeley and Stanford. Being in that group connects me with diverse tech backgrounds and experience levels, widening my view for better decisions. It sharpens my sense of where AI fits, balancing human emotion and involvement with tools and automation. So my advice is simple: use AI personally, tap into the community, and you’ll stay ahead.

Being exceptional isn’t about a degree or being the brightest. It’s about an inner drive that keeps me moving. During my career, we did a team exercise with the Strengths Finder survey from Gallup, and my top strength came up as competitiveness. At first, I thought it was the worst strength possible, useless and a bit negative. But as I matched it to what I was doing, I realized I’m competitive with myself, not just outside standards, though those matter too. When I face a problem I can’t solve, I get almost upset, and that fires me up to tackle it, feeling like I can do anything to crack it. That’s what lets me build the quickest, workable version of a solution. I’m not an engineer, but if the product breaks, I can’t fix the code. Still, I can dig into the user experience that led to the issue, measure drop-off points across stages, pinpoint the exact moment it went wrong, and tell an engineer my guesses on why it broke, letting experts handle the rest. That competitiveness and curiosity push me to solve problems fast, getting 80% of the way there. I don’t aim to outshine data scientists or engineers. My goal is understanding what they do, so I can be a general manager who’s useful and impactful on the team. I see it as a T-shaped career. The top is my generalist skills, built in college and early on, touching a bit of everything. Over time, I grow offshoots, but experience deepens one big stem, like a superpower, from specific roles or challenges I’ve taken on.

I teach at UC Berkeley, and I push students to look past the textbook. One tactic I share is the reverse interview. If I spot something I want to do, I don’t wait for a job posting. I reach out to the people who care about the problem and share how I’d solve it. That’s how I landed at Pinterest and later Indiegogo and Descript. It’s about jumping in with a pitch. I tell students to test fast, try small changes, and see what sticks, because confidence isn’t innate, it’s earned through action. Early in my career, I had to fake it. At 25, managing hardware veterans with decades more experience, I’d use a poker face to mask my nerves. People found me intimidating at first, but one-on-one, they’d see I wasn’t so scary. That poker face wasn’t permanent pretending. It was acting until I owned it. I encourage students to do the same, picking up skills not to beat the experts but to gain enough context to lead. I’m not an engineer, but I can troubleshoot a user flow, track drop-offs, and hand tech folks a solid hypothesis. That’s how to stand out: act, learn, adjust, and keep moving forward.