My Abusive Relationship with a Tech Startup
Before I was a full-time writer, my job looked pretty different—and pretty bad. Welcome to the corporate hell story.
From the first interview, this job seemed too good to be true.
A six-figure salary, fully-remote Director of Marketing role for a software startup in the fintech space. In terms of my title, it was a lateral move; as far as everything else, I was entering the big leagues. Bigger budget, bigger team, bigger goals. Coming from the small salaries and smaller resources of the nonprofit tech world, I was ready to join the software upper echelon, and this seemed like the perfect entry point. My boss, the president of the company, was as charismatic as he was driven, rallying the team leads on daily calls and wrapping each week with sit rep sessions that celebrated personal and professional wins. Unlike my last role, this job would be collaborative, pushing me to grow in ways that former jobs didn’t afford me the opportunity to consider.
But like any opportunity, it came with a handful of downfalls.
The first was the volume of work: it would be much more demanding than my last job, where I probably logged a thirty-hour week on average. I’d been devoting the extra time to scaling my writing career, but if I took this offer, that would be sidelined for a bit. I didn’t want to set aside the novel I’d just started outlining…but that salary. I was willing to make the sacrifice.
But the sacrifices didn’t stop there. The offer letter (see: informal offer email) stated that I’d be hired on as a contractor, not a full-time employee, since the company was still in the process of obtaining licensure to hire in my state. The president assured me this was only a temporary solution that would be resolved with a W2 within the next quarter. As for the complete lack of health benefits, vision, dental, and 401(k)...he swore they were coming. It was a young company, just seven years old. I had to understand.
I added up the weight of what was missing and compared it to the salary, the life it could usher in for me. The president promised me the missing pieces were coming. I liked him, I trusted him, and I believed him. So I took the offer, although it never came with any proper paperwork to sign.
Two weeks into the role, we had a company off-site, gathering all the team leads in one Orlando Airbnb to lay the groundwork for the upcoming quarter. I caught a too-early flight, trying desperately to ignore the Disney-bound toddlers and the stressed parents steering them through the plane. I smoked joints with my boss on our breaks and expensed late-night meals to my hotel. We spent a long week envisioning a future for our product that was larger and more innovative than anything we’d seen in the industry before. I was hungry to learn, and luckily, I had a buffet before me. We left our off-site with a new business plan, lofty goals, and benchmarks on how to achieve them, all of which we’d pitch to the co-founders for approval.
Enter the man who would be a shadow looming over my career for the next nine months. Adam*, one of the co-founders, was far from a stranger to me. He played an integral role in my interview process, conducting the final interview in which he tested my marketing know-how in a rapid-fire pop quiz that he scored at the end of the call (I got a B+). I remember our conversation (if you can call it that) well. He was gruff and frowny and said some concerning things about COVID that I wasn’t particularly keen on, but he had made it clear that we wouldn’t be working together much. “An advisor to the president,” he called himself. I pictured Jafar, the sultan’s royal vizier. He’d be around, but not in charge of me, so I didn’t pay him much mind.
Until I had to. Because he fired the president.
With barely a month of work under my belt, Adam would be my new boss, and he would be changing some things. For starters, the business plan we had worked on in Orlando. It was trash, he said. Unattainable. Unrealistic. On top of that, we’d be ditching our daily meetings for once-a-week full staff meetings, which soon became quarterly meetings, which soon became quarterly videos from Adam, talking at the camera for 30 minutes. We were expected to watch them in full—a better use of our time than virtually gathering with our peers, of course.
After a month under new governance, the rest of my yellow flags turned bright red. When I asked Adam about the goal of getting me a W2 that quarter, he said it wasn’t in the cards. When I asked him about getting me a proper contract, he said I had a verbal contract, and that was enough. I was expected to be constantly available, even in the late hours of the night, because that’s what lined up best with Adam’s schedule. Messages were regularly met with ‘k’ or just a thumbs-up emoji. Compliments were nonexistent, only a new set of direction every week as to how we were going to make more money, take over our market, dominate over the competitors who were springing up like whack-a-moles. It was a startup, right? This was normal, right? I logged into Slack every morning before I even got out of bed, replying to messages while I brushed my teeth, wondering how my coworkers were doing. I didn’t talk to them anymore. It was just me and the ever-increasing goals and a stringent set of guidelines as to how I would achieve them. Did prior data suggest that these goals were attainable? No. In fact, it pointed directly toward the very real, very scary truth: the parameters given to me would set me and the company up for failure. But mentioning this to Adam earned me nothing but a ‘well, you better figure it out.’
Six months in, I put my foot down and demanded a contract, and Adam complied. On the morning it appeared in my inbox, he advised me to ‘use my own time’ to review and sign it. I should be ‘focusing on work during work hours.’ I told him that, as a contractor without a contract, this was technically my own time. He didn’t like that, but I didn’t like him.
The parameters given to me would set me and the company up for failure. But mentioning this to Adam earned me nothing but a ‘well, you better figure it out.’
I asked for a pay increase since I wasn’t going to get a W2. He said no. I asked for more PTO. He said that, as a contractor, I didn’t get PTO. I read over the contract, noting the demand for two months’ notice before terminating the agreement, meaning I’d get two months’ notice before being let go in exchange for the promise of two months’ notice for quitting, an outrageous request for a full-time job. I asked for it be shortened to one month, satisfied with a month of padding if they fired me.
And God did I secretly wish they would, because while the job didn’t come with benefits, it sure came with symptoms. I stopped sleeping through the night. I’d be up at 4 a.m. checking Slack. I cried in the bathroom for a full hour when the president made a rape joke on a call where all the participants were men, plus me. Any minor mistake on my part, Adam labeled it a CRISIS, all caps. Any major mistake on Adam’s part, he reminded me he had a lot on his plate. Not to mention how often he told me about his hatred for managing, which was fitting because I hated having him as a manager. I wondered if I could increase my antidepressant dosage. I wondered if there were brighter lights somewhere else.
I cried in the bathroom for a full hour when the president made a rape joke on a call where the participants were all men, plus me.
And then, the writing appeared on the wall. When I was tasked with hiring an employee to work beneath me, a winning candidate asked for five grand over our offer, and Adam gave me his professional advice: we’d bring him on and let him set everything up, then we’d fire him and hire someone in India to do it for a fourth of the price. My stomach churned. I knew I’d be the next to be replaced with someone cheaper they could abuse.
They finally let me go on the Monday after Thanksgiving, and I was already well into my second round of interviews for new jobs. I sipped my coffee, listening to Adam go on and on about how it wasn’t that I wasn’t doing a great job, it was that they were eliminating the role, putting my salary into sales roles instead of marketing. I nodded, unaffected. Happy, if anything. Sure, it felt shitty to be laid off, but knowing I’d have a full month of pay without having to face him again was a stronger high than any joint I smoked with my first boss back in Orlando. I gave Adam a few notes on how he might work to retain his existing staff and logged off. I was free.
We’d bring him on and let him set everything up, then we’d fire him and hire someone in India to do it for a fourth of the price. My stomach churned. I knew I’d be the next to be replaced with someone cheaper they could abuse.
It took a few weeks of sleeping till noon to recover from the months of lost rest, but it only took a few days for me to pick up the old novel outline I’d set aside nine months prior, re-familiarizing myself with the characters I had only begun to breathe life into. I sat down at my laptop (gifted to me by my former employer, thank God they let me keep it), and less than an hour later, I’d outlined the whole thing. The words spilled out of me like running water in a way I forgot they could. This job had rusted over any joy, hope, or creativity I had, but it all came right back. My spark was back. My life was back.
I was let go on a Monday at 9 am. By Friday at 5, I had a job offer from another company, working in an industry I’d been dying to get into. Another startup, even younger too. Only two years old, but with a full set of benefits, unlimited time off, and excellent health insurance. They made no excuses. The salary was less, although only by the slightest margin when you considered the self-employment taxes I was paying before. I told them I couldn’t start for another month while I was still under my prior contract, and they agreed. Then I broke the news to the other eight companies trying to hire me, wondering why I bothered sticking around as long as I did in this job market. I knew the reason. It was the money. But what good is it to gain six figures and lose your soul?
As I entered the onboarding process for my next role, a four-week process that guaranteed a strong foundation to set me up for true success, I was struck by a single sentence in the onboarding documents. Nestled in the section about sick days and personal time off, eight little words formed a simple sentiment from my new employer: your health is more important than your work. I wish they would’ve told me sooner.