We Pivoted Four Times in Six Months and I Pivoted Right Out the Door

Okay so buckle in because this one has plot twists, literally, the company kept plotting different twists into its own business model like a soap opera writer who forgot the last three episodes.

I joined this edtech startup as employee number fourteen, fresh out of uni, absolutely buzzing about the mission, which at the time of my interview was "democratizing access to STEM tutoring for underserved students." Beautiful. Noble. I would have worked for exposure alone at that point, don't tell my younger self that though, she deserved better boundaries.

Month one: we're building a tutoring marketplace. Month two: actually we're building an AI tutor because "marketplaces don't scale" (direct quote from an all-hands, said with the confidence of someone who watched one YouTube video about SaaS). Month three: the AI tutor demo crashes live in front of an investor and the founder, without missing a beat, says "this is actually a feature, it teaches resilience." I wrote that down. I still have the notebook. I show people at parties.

Month four we pivoted to "gamified corporate upskilling," which had nothing to do with our original mission, our original team's skill set, or honestly any coherent plan, but there was a LinkedIn post about how upskilling was "the next trillion dollar category" and that was apparently sufficient market research. We renamed the Slack channels. We got a new logo. The old logo cost us, a company of fourteen people, actual real money from an actual real designer, and it lived for eleven weeks.

Standups became a genre of theater. Every single day someone would say "no blockers, just heads down" while the entire product roadmap silently vaporized behind them. Our OKRs changed so often we started a private joke doc just tracking how many times "10x" appeared in slide decks. Final count before I left: 61. Sixty-one instances of the word 10x in six months, for a company that, as far as I could tell, had 3x'd nothing.

Compensation for all this uncertainty was, and I cannot stress this enough, a fridge stocked with kombucha and a ping pong table nobody had time to use because we were always "heads down." My salary was below market for someone with my role, justified every time with the word "equity," equity in a company that had, by my count, no actual product that had shipped to a real paying customer in the time I was there. Zero. Not one.

There was also a specific incident involving our "curriculum team," which was, at that point, one overworked woman named Trang and a spreadsheet, that I think about a lot. She'd built out a genuinely solid middle school math curriculum over three months, tested with actual teachers, actual feedback loops, the whole real deal. The week it was ready to launch, the founder saw a competitor's flashy demo video and decided our curriculum needed to be "reimagined as an interactive story format" instead, scrapping essentially all of it two days before launch. Trang requested feedback on what exactly was wrong with the math. The answer, verbatim from a Slack message I screenshotted and still have saved, was "it's not fun enough, think Duolingo but more fun." Duolingo, a company with hundreds of engineers and years of iteration, was our fun benchmark, to be hit by one woman and a spreadsheet in 48 hours.

We also had a rotating cast of "growth hacks" that were really just the founder reading a different Twitter thread every week. One week it was referral loops. Next week it was "community-led growth," which in practice meant asking our fourteen employees to post about the product on our personal social media, unpaid, uncompensated, framed as a fun optional team bonding activity that everyone understood was neither optional nor fun. I posted exactly once, got nine likes, four of which were coworkers, and quietly never did it again, a small act of rebellion nobody noticed because nobody was tracking anything consistently enough to notice.

The breaking point was genuinely funny in retrospect, though it did not feel funny at 11pm on a Tuesday. We had an emergency all-hands because the founder saw a competitor raise a big round, and the entire strategy meeting was him reading their landing page out loud and asking "should we just do this instead." A woman on the product team, bless her, said "instead of what, we don't have a this yet" and got quietly moved off the strategy channel the next day.

I left after my sixth month, right as we were apparently pivoting a fifth time into "AI-powered career coaching for Gen Z," a phrase I heard in a meeting that also included the words "TikTok but for resumes," which, respectfully, no. My exit interview, for what it's worth, was rescheduled three times and then just never happened, which felt like the most fitting possible ending for a company that couldn't commit to a single meeting, let alone a single business model.

Would not recommend. Great story material though, genuinely, I dine out on this stuff at parties and it always kills. Just don't expect stability, direction, or a product that exists past next quarter, or possibly next Tuesday. If someone tells you their startup has "pivoted a couple times," ask for the exact number, and if they hesitate before answering, that's your answer.