my 12 weeks in a tech startup

Kristen Shi
TribalScale
Published in
12 min readDec 8, 2017

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and all the tech buzzwords I learned along the way

tech-y stock image

In August, I started working at a tech startup.

I didn’t plan to, nor was I even sure I was ready to. Prior to that, I had minor experience in tech, if you could even call it that — but it was in a corporate environment. My technical expertise included knowing what a computer language was, and interacting with a Google Home once or twice.

this thing.

Corporate environments are safe and familiar, and no matter where you go across the world, the culture tends to remain the same. You dress a certain way to go to work, you write overly long and wordy emails, you use strange business vernacular (‘hop onto a Skype call’, ‘the meat and potatoes of a problem’, ‘can we pivot on this’), and you make obligatory and painful small talk with the VP of your department in the elevator. Easy.

I was ready to return to the corporate world, but in a way was also ready to try something drastically different. When I was lucky enough to end up getting two offers for the fall — one at a large and reputable tech company, and one at the startup — I decided to take the leap.

On my first day to work, I wore tight formal flats, while everyone else wore runners or sandals. People sat at their desks with chip bags and granola bars scattered around their workspaces, with everyone working on different projects in close proximity. Within just one section of the office, I saw people doing everything from sales pitches over the phone, to Illustrator designs and wireframes, to coding, to blockchain research, to Amazon Echo tests — their monitors just feet apart from one another.

The difference between this and the corporate world was huge. At my first internship, my on-boarding lasted a full-day, and took place at a massive conference centre downtown. We were fed desserts, iced water and coffee throughout the day, given massive swag bags, and showered with attention by the campus recruiters. The CEO, CTO, and EVPs of my department all came to glow about how talented us interns must have been to have been hired, and how fortunate the company was to have us. The office tour was 2 hours long, showing off beautiful floor-to-ceiling windows, open concept spaces, plush couches, massive auditoriums, and marbled white bathrooms.

We’re all wearing blue, yay!

At the startup, my onboarding lasted 45 minutes, consisting of a quick Powerpoint that was given to another full-time hire at the same time, one walk around the one-floor office (my previous office has 31 floors), and a quick mention of how I was allowed to take foosball and ping pong breaks. The office had makeshift dividers between teams, standard windows, and a brown carpeted rug.

I was given a Macbook and told to just ‘start’ (I had never used a Mac prior.) The CEO never came up to me to tell me I was a gift to the company. In fact, in my first face-to-face interaction with the CEO, we were in a meeting where I was to take minutes; after a string of stressful sales updates, he stood and yelled, not hesitating to throw in profanity here and there.

(I left the swearing out of the meeting minutes.)

From the beginning, it felt like I was drowning.

In my previous internship, where I worked in a heavily business-focused segment of tech, I could get away with knowing only business and communication skills, minor knowledge of Excel, being soft-spoken, and only asking my manager questions. My projects were small and minor, essentially meaning my fuckups were also small and minor, and could be overlooked.

I could get away with having minimal skills, because I was easily forgiven for being young and just an intern. I was heavily praised for simple tasks, like building a slide deck in a week, and forgiven for failures quickly, like arriving to work 40 minutes late. And maybe because I was constantly being told how awesome I was just for being hired, and just for showing up, I started to believe it.

give me praise dammit

The world wasn’t the same in a startup.

I signed an NDA my first day and told to study the startup’s previous clients, only to be given a master list including well over 100 clients and well over 100 unique deals involving everything from mobile development to voice work to website redesigns. The goal was for me — as an intern who reported equally to the sales and marketing teams — to become familiar with the company’s work history and our full suite of offerings — all in one week.

There were some great perks. I could walk and sit where I pleased. I could wear jeans and a t-shirt to work, eat snacks at my desk, and take a lunch mostly when I felt like it. Breakfast was served every morning, the ping pong breaks were hilarious and a great way to destress, and at demos at the end of the week I had a great opportunity to see our projects grow from inception to fully-fledged apps and digital experiences.

But the tradeoff was the work, the speed, the demand, and the deadlines. I read over the massive list of collateral, feeling like the tech terms, pricing, and emails were flying over my head. In my new internship, by Monday of my second week, I was told to write a proposal in InDesign (do I remember how to use InDesign?) including technical language on an API (what’s an API again?), and to ask Josh or Ardy if I had any questions. I was told my manager was Rachel but that Imtiaz was my de facto superior for this project. (Who are all these people?) And that could I please get it in by EOD, thanks.

The guidance was minimal and the quantity of work huge. There was never anyone who told me how fortunate they were to have me — no one ever had time for it. My deadlines were two hours instead of a week, and being 40 minutes late had a far more massive impact here than it did before. Most of all, I couldn’t get away with being clueless. As part of the sales team, the work I did had a measurable impact on our revenue — and when mistakes were made, there was nowhere to hide.

In the corporate world, such a role would never be given to the intern. Something so high-level would not be owned by someone so junior; if that is the case, at least 30 people will check over your work before anyone external ever sees it.

The corporate world also doesn’t necessarily demand that you learn unfamiliar or new skills as quickly. There will always be a subject matter expert somewhere else who can fill in the gaps, so sticking to your own skills is good enough. I worked in tech before — but I never had to learn what language iOS apps were coded in, what the difference between front-end and back-end web development was, or what VUI stood for.

In the startup, I, as an intern, who had barely any knowledge of mobile, web or voice work development, was now being told to work on a crucial part of the sales process. A mistake that I made might be caught, but only if my superiors, already swamped with other work, didn’t catch it as they quickly skimmed it. I had to supervise myself, and on topics and work that I didn’t know well to begin with.

It wasn’t just okay for me to be passable at InDesign, and have a rough understanding of how sales worked. The ask now was that I was not only capable of using Adobe and Excel, but that I knew what Hubspot was, and Trello, alongside Slack and email — that I actively communicated with everyone ranging from co-op to senior leadership level — that I understood product development, engineering, QA, and design well enough that I could phrase it into a sales pitch — and moreover, that I could juggle multiple of these asks, on moving deadlines, and complete them quickly with minimal errors.

It struck me that the I work I did had incredible weight, and as such, that my mistakes had consequences. So my first month was just that — endless mistakes.

literally me for like, 5 weeks

It felt a little bit like walking around with your head cut off. Sometimes it felt unbearably helpless, having 4 or 5 assignments due by the end of the day, not knowing how to complete something, and not knowing who to ask for help. The startup world seemed so casual and carefree in the media, but I spent so much of my first few weeks chained to my desk, terrified of new assignments coming in, constantly unsure of what to do next, and always aware of who I was disappointing.

I sent cautious Slack messages to teammates, never certain if I was taking the right next step. I made the horrible communication mistake many women also commit — sending overly wordy and softened emails (just wanted to check in to see how progress is coming along!) rather than getting to the point (Where is the document?), not realizing that my attempt at being non-intrusive impacted efficiency. It was a harsh wake up call, realizing that no one would reward you just for showing up, and that the expectation was you would start acting like a full-time from the minute you showed up.

It hurt. At school, I was exemplary. I was president of a successful club. I won case competitions. It felt like things would come easy to me. People told me every day I was fucking awesome. I always felt like I had so much to offer — but here it felt like I was always falling short.

Sometime in my second week, after sending a 7th or 8th try of a proposal out to Sales for approval, I was told that I really needed to get it together — something I’d never been told before by anyone. I could sense the frustration and disappointment from everyone. It’d come after a day of a lot of disappointments and small mistakes, over and over. I felt tears prick at the back of my eyes — I’d never thought of myself as a disappointment to anyone.

Like most things, though, it became better with time. Over the weeks, the gaps in my knowledge began to fill.

I never learned how to code, but I’m familiar with what languages are for which platforms, plus understanding of different types of development and projects. I have a better understanding of Adobe than I ever did before — even though it wasn’t a job requirement. I learned what product management was, and how sales from a tech perspective work. I learned how to talk to senior leaders like people, and to see myself as a colleague worthy of respect, rather than as a child looking up to a parent or teacher.

Communication became easier too. Eventually it struck me that it was more important to finish things rather than to be polite all the time — so I started to call people out when work wasn’t getting done, or my messages were getting ignored. My projects got finished faster, and eventually, cleaner and with fewer errors.

I learned who Josh and Ardy and Rachel and Imtiaz were. I learned who a lot of people in the company were. And more importantly, I began to see them as people, rather than as their titles. In the corporate world, interactions outside of your immediate team are brief, so you start thinking of people based on their positions or rank or department, and their subsequent networking value to you, rather than as people.

Working in a startup feels a bit like working in the trenches — you are all working non-stop, working on everything all at once, and you have no choice but to get to know people well, on their good and bad days. You will begin to realize that people, whether at an intern or senior level, have strengths and weaknesses, personalities, senses of humours, and faults of their own, and you will appreciate them more as coworkers for it. I stopped seeing rank as I did before. This person is my manager — but they are also my collaborator for a project. This person is my CEO — but he can also be my friend, and someone I have a drink with after work. This person is outside of my department — but he can also be my lunch buddy and someone I share memes over Slack with.

The thing that surprised me most was that I started to care, a lot, about the company, and the people in it. Things I loved about my old job were some of the friends I made, and a great salary and a comfy office. But things I loved in my new job were the feelings of success when a deal went through, and how it felt like a win we all somehow shared. I felt excitement when I saw swag being created for the company — even though I knew that swag wouldn’t be available until long after I was gone.

If anything, I started to feel a sense of ownership — even though this was not my company and that my time here was most definitely impermanent. I felt like I had become a part of the company, in some small way, through the long hours, the overtime, the stressful calls, and the endless confusion and running around to complete projects.

The work I had done here had been important, even if it hadn’t been perfect — and the knowledge that what I had done would live on after I left, rather than rotting in a folder titled ‘Intern’ at some other larger companies, is something I wouldn’t trade for anything.

yay for sappy!

It’s a little bittersweet. I’m leaving here with a couple of really great skills. Technically, I’m much better than I was before in many aspects, and have been fortunate enough to sit in on enough design and engineering meetings that I can participate in discussions on tech meaningfully.

I’m more aware of the tech space in general, having worked in a sales and marketing role, and have a better understanding of how companies are modernizing for the next decade. It’s fascinating to see how companies in different verticals all approach tech differently — how they ask for it, how they respond to it, how they prepare for it, and how they invest in it — and I’m sure that knowledge won’t go to waste.

More than anything, I think I’ve learned to own what I do. In school, you feel like you are fulfilling a checklist till graduation, and recruitment is just a checklist to employment. In the corporate world, you are protected by low rank and by sheer numbers — no one will notice you in the crowd.

But this startup has taught me that what I do is important, and what I make is valuable. That caring about your work is equally as important as doing it. That coworkers can also be resources, friends, and mentors (some of my coworkers already feel like de facto family).

In the future, I still don’t know what I’ll do, since I’m still learning about myself, and learning about what my priorities are in the workplace. But I’m grateful for this time in this growing startup, already on its way to taking over Canada, and pretty soon the rest of North America. Even after I leave I’ll still be its biggest cheerleader.

hunting lessons, apparently

Kristen is the current Business Development Intern at TribalScale, working between the Sales and Marketing teams to help win deals. She loves writing, taking photos, especially of aesthetic food arrangements, and learning about tech and its impact on the world.

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Kristen Shi
TribalScale

tech enthusiast + storyteller | stuckintheairport p2