The First Day

Launching the #TechDiaries series

This is the first post in a new series called #TechDiaries that are more memoir/narrative style about different moments of my tech career. Would definitely be interested in y’alls feedback on this format!

On my first day at P,  I got lost on the subway three times. Turns out, Google Maps does a terrible job of telling you which direction of the train to take. Or maybe I was just bad at following directions. The train car was packed like sardines, and every time I tried to grab a seat, someone else took my spot. I blasted my Bad Bitch playlist on Spotify, Megan the Stallion’s powerful raps calming the growing nausea in my stomach. I opened the camera app on my phone, and removed the remaining lipstick smudge from my face, a poor last minute decision to improve my confidence. But the lipstick made me look at best, trying too hard, and at worst, a clown. 

NYC subways: love to hate ‘em

When I arrived at the office, I texted my manager, who took me upstairs into the office. I had forgotten he was tall, so tall that I had to crane my neck just to maintain eye contact. Or maybe I was just really short. The office was an open floor space, with six desks in each row. There were two phone booths in the back, and a wall of post it notes in the front. Large, open windows let in light, though the sky was cloudy. He showed me to my desk, which was covered with boxes of new supplies: monitor, laptop, and notebook. There were three autographs scribbled in the book. So stoked to have you and jam together. Signed by the head of design. Of course. Welcome Vinamrata! Signed by my boss, the COO of the company. A man of few words? Welcome to P. We can’t wait to see what impact you have on the company. Signed by the CEO. The real reason I was here. 

I had wanted to work for the CEO ever since one of my college professors had introduced me to him. Post graduation, we had a brief correspondence over email and Twitter, though he didn’t always have the bandwidth to respond. After all, I was just some random recent grad, and he was an entrepreneur saving poor people. During my interview, he assessed me on “values alignment” by probing on my failures (and what I took from them). It felt uncomfortable to admit that I had failed in front of him, but I also knew that not admitting to failure would be a red flag. I wanted him to like me, to promote me, because he had done the impossible: use technology to create real impact in the world while scaling a for-profit business. I wanted to be his protege.

“Let’s get coffee,” my new manager, who happened to sit right next to me, said. I grabbed my coat, tripping over my seat mate’s furniture in the process. I got a black tea while my boss opted for a black espresso. We sat in a cozy corner of the coffee shop near the entrance, which was also the coldest part. I wanted to say something about moving further inside, but I didn’t want to be an inconvenience. 

Five minutes later, when we had run out of small talk, he launched into all the things I needed to do: take over partner integration calls, run sprint planning, launch the MVP, analyze the results from prior pilots, and propose the next iteration of the product roadmap. What’s the timeframe for all these tasks? I wanted to ask, but I didn’t want to seem like I was complaining.  I’ll figure it out. After all, I came here because I wanted to work so hard. 

Lunch was catered at the office, and I sat with a random group of coworkers. In an effort to fit in, I made a joke about Staten Island as the pit of New York, only to find out that one of my coworkers had family living there. I recovered by claiming I hadn’t been to Staten Island yet, and would ask her for recommendations. She switched topics, and I excused myself to go to the bathroom. 

I locked the stall door and took some deep breaths. Fat tears rolled down my face. I was dumb to think I could handle this challenge. Maybe I should have stayed at my cushy, big tech job and left the startup world to people who were meant for this. But I’m not a quitter. I stepped outside of the stall and plastered a smile on my face. “Dry eyes,” I told the other woman in the bathroom. Thankfully, I was smart enough to cry silently. 

My day ended with a final 1:1 with the CEO. My heart fluttered as I entered the conference room. The CEO wore a dark sleeved shirt and jeans. I felt like an odd duck in my bright blue sweater. Note to self: buy more muted colors. He had distinct dark circles and floppy, straight hair. He fired off Slack messages on his phone. I stared awkwardly around the conference room, taking in the broken projector and whiteboard filled with engineering diagrams. 

We engaged in precisely three minutes of small talk. Then, he asked me what I had shipped today.  “It’s very important that we move fast. Especially as a new hire and leader at the company, you need to keep up the pace.” 

“I have a document about my first impressions of the app.” I offered. 

He looked unimpressed. “Maybe you can launch a survey in our CRM to gather some customer learning. It will help you better understand what we’re doing here.” 

I didn’t know what a CRM meant (or how to build a survey) but I nodded. I wanted to show him that I could be scrappy, which I had heard was a flag during my interview process. I didn’t want him to regret hiring me. 

I pivoted the conversation to ask some questions about the business that I had prepared in the afternoon. I wanted to learn more about why we decided to build this new product, the one that I would be working on, and how it fit into the company vision. The founder sighed, and then dropped a massive history lesson: how he came up with the idea for the first product, struggled to fundraise, and finally cracked product market fit and eventual scale with the first product, despite almost shutting down multiple times. But there’s more we could do to help our customers, which is why they decided to build this new thing, and it helped that these were bigger markets. But isn’t the existing product already growing? Why do we need to enter a new market? And do our customers even want this? I had so many more questions, but the founder seemed so confident that this new product was it, and all I needed to do was keep making it better. 

“I know this is early, but do you have any early thoughts on the product roadmap?” he asked in the last minute of our 1:1. 

I was honored he cared what I thought, but my brain came up empty. The five hours of sleep was finally hitting me.

“I’m not sure yet.” I replied.

“I see.” Was he disappointed in my answer? I opened my mouth to apologize, but he had to leave for his next meeting. I wondered if his question was secretly a test, a test that I had failed. I needed to do better. I furiously scribbled another item on my never ending to-do list: come up with smarter thoughts on the roadmap.

Thing of Note

Recap: This section is my way of bringing attention to a thing, person, or idea that’s meaningful/related to the mission of this newsletter. This week, I want to highlight a workshop that I’m running. 

This narrative essay has been such a throwback to my startup life, and the true challenge of the transition. It was tough y’all, especially coming from a big company. It felt like constantly drinking from the firehouse, feeling overwhelmed without any real structures for support. Many days, it felt like a victory to just make it through another day. 

Therefore, I’m offering a small (virtual) workshop for product folks making the transition from big company to startups. This is applicable for anyone in the middle of a transition or considering the transition. It has everything I wish I had when I first started at a startup- mental models on understanding the startup world, tips to leverage your value from your big co background, an action plan for success, and a cool community of other people making a similar transition. 

If this sounds like something that could be beneficial for you, please feel free to sign up (only four slots left!) Otherwise, feel free to pass it onto someone that could benefit. If there are any questions, feel free to reach out to me directly :)

Thanks for Reading! 

I’m on a journey to create a blended career across the creative arts, tech, and business. This newsletter is my way of sharing my reflections, thoughts, and advice along the way. Here are some ways to support or further collaborate together! 

• I would love feedback on this post. 

  • If you want to see more content like this, heart the post. 

  • Hearing from readers also gives me a ton of energy. Drop a comment if you: 

    • Have feedback on the narrative structure? (Did it work for you? Any boring/slow parts? Any engaging parts?) 

    • Felt connected with any parts of this experience? 

    • Have thoughts on what else you want to hear more about?

• If you’re figuring out your own career transition or looking for more support in your product career, consider working with me as a coach. Here’s my calendly if you want to get the ball rolling.