The truth about tech, from an insider who got out

Animal House

After landing a lucrative job at a tech start-up, I embraced the office culture wholesale: the lingo, ping-pong tables, beer carts, tropical retreats, stock options and virtuous mission statements. Then I realized I had made a terrible mistake

By Mark Pupo| Illustrations by Kagan McLeod
| December 10, 2018

Four years ago, I made what I hoped was an inspired leap. Since grad school, I’d worked as a journalist, food critic and editor, mostly at this magazine. Then Vision Critical, a tech start-up, came calling, and I saw a way to apply my skills to a growing industry. I’d recently turned 40 and was finally getting around to planning a family—if I was going to change careers, it was now or never. Vision Critical is what’s known in the tech world as a B2B company—a business selling to other businesses (as opposed to a B2C, which sells to consumers). Its software helps market researchers at Fortune 500 companies easily collect and analyze feedback from thousands of their customers, replacing older and slower research methods such as mailed surveys and in-person interviews. Vision Critical counted ESPN, Toyota, Hyundai, DeWalt, Adobe and LinkedIn as clients. In Canada, it had Maple Leaf Foods and Canadian Tire. But outside of those offices, it wasn’t a well-known company.

It had become trendy for tech companies to hire media refugees like me to serve as “brand storytellers” instead of spending millions on conventional advertising. Vision Critical had invented a position for me on the marketing team—senior director, content. I knew next to nothing about promoting software to market researchers, yet I would be overseeing an in-house propaganda machine of writers, videographers, graphic designers and social media managers. My salary would be double that of the average magazine editor. I signed the contract.

My new employer occupied two floors in a tower at Yonge and Bloor. On my first day, the office manager ordered me, the newbie, to push the afternoon beer cart. My co-workers lived for beer-o’clock. You probably assume, like I did, that tech start-ups are staffed exclusively with antisocial computer nerds. The reality is that the software developers (called “devs”) are usually outnumbered by sales, and the sales team was a testosterone-charged, protein shake–fuelled, almost all-male team. For all the aspirational talk of gender equality in tech, men far outnumber women, and most of the women on staff worked in “customer success”—account managers who in effect served as our clients’ personal assistants and whose ultimate responsibility was to ensure those valuable clients never “churned” (i.e., cancelled their contracts).

The sales bros remade the office into their frat house, hanging alma mater pennants over their desks, playing pranks, tossing mini-footballs and bringing bulk bags of Doritos to meetings. Sometimes they wore suits to impress clients, but mostly they worked the phones in Jays jerseys. They’d clang a cowbell every time a big deal got signed. Many were just a few years out of university and already making six-figure commissions.

Two weeks into my new job, I boarded a plane with 200 colleagues bound for the Hard Rock Hotel in Cancun. In case you’ve never been, here’s a snapshot: the lobby is a museum of pop star cast-offs, with vitrines of a lime green James Brown suit, a sequined Cher jumpsuit (is there any other kind?), and a pair of Britney Spears’s boots; the mini-fridges in the rooms contain full-size bottles of tequila, rum, vodka and whisky; and the DJ beside the main pool doesn’t take requests. Our sales, marketing and customer success teams had assembled there for SKO—the company’s annual sales kickoff, a combination training session, town hall and week-long party. The executives got their own rooms, and everyone else doubled up. I shared a room featuring a two-person hot tub with Bruce, another recent hire—he was known on the marketing team for calling long meetings to review intricately colour-coded Gantt charts. I’d been to many off-sites in my previous jobs, usually in nearby, windowless hotel conference spaces. Never had my employer flown me to a tropical resort. There was some work to do: we spent hours watching presentations on sales techniques, product updates and competitor analyses. At one point, for reasons unexplained, two of the sales directors hustled onstage a resort employee dressed in a Barney costume and did a little dance.


Staff would compete for the “sombrero of shame,” worn by the person who’d partied the hardest the previous night


The company had grown fast, and many of the SKO attendees were recent hires like Bruce and me. Yet I seemed to be the only person even mildly surprised when Andrew Reid, the company’s 30-something founder and a legendary partier, arrived at the first night’s party in Burt Reynolds aviators, a disco pantsuit and a flaming-red mohawk wig. He passed around tequila shots.

The presentations about sales targets and so on were really just a prelude to something more important. Our Cancun week was about building company culture. Culture is an obsession at start-ups. They talk about it nearly as much as they talk about sales targets. Our company culture, we were assured, was what set us apart from our competitors. Other companies might claim to be disruptors, but we were the true revolutionaries and world-changers. Old-school companies like the one I’d left were dismissively referred to as legacy industries—slow, pitiful and ready for retirement.

One afternoon, we split into teams and, equipped only with our cellphone cameras and our wits, competed to create the best promo video about our company culture. Competitiveness, I was discovering, was a core value. That week, we competed at beach volleyball, we competed at rounds of golf and we competed at knocking back margaritas. At the start of each Cancun morning, we’d all stumble into a conference room and Andrew Reid would summon to the stage the employee who’d partied the hardest the previous night. We’d cheer and whoop. It was an SKO tradition for that person to wear the “sombrero of shame” for the rest of the day.

I didn’t get to wear the sombrero, but I was having more fun than I’d ever expected to on a work trip. And, after the third or fourth night of tequila rounds, I was starting to feel like less of an outsider. My co-workers seemed genuinely interested in me and what I would be contributing to Vision Critical. This wasn’t a job in any sense I was familiar with—when the executives told us that we were all winners, everyone nodded in agreement instead of rolling their eyes. It felt good to be among people who looked to the future with so much irony-free optimism. Maybe I was also a super-competitive high-performer. Maybe we really were disruptors, revolutionaries and world-changers.

The last day, we boarded coaches for an outdoor supper club on the beach. It was formal night—dresses and heels, chinos and jackets. A mariachi band started up as we sat down to eat. There were more speeches about the great things we’d accomplish in the year ahead. If all went according to plan, the company was headed for an IPO—the start-up holy grail. We clinked glasses and hollered a little more.

Then, behind my seat, a bubble of commotion, a dropped beer bottle, laughter. I turned around to see three of the sales bros stripping off their clothes and running naked, full tilt, into the pitch-black surf.

If it seems like everyone you know is leaving their outmoded legacy job for a start-up, that’s because they are. The late-’90s dot-com boom and bust—when companies like burned through millions in venture capital funding and flamed out months after an IPO—largely passed over Toronto. It was a Silicon Valley phenomenon. Today’s boom is wised-up, diversified, global, and Toronto is one of its most active hubs. AngelList, a service that connects investors with tech entrepreneurs, counts more than 5,000 start-ups in the city. And some 400,000 people are working in tech in the Toronto, Peel and York regions—a number that’s growing by the thousands every year.

When I confessed to my media colleagues that I was abandoning them for tech, the reaction was surprise followed by jealousy. Tech was glamorous. I had a security pass to Silicon Valley North, and they didn’t. They’d seen stories about new start-up offices with meditation rooms, in-house baristas, free lunches, powered standing desks and beanbags as far as the eye could see. They wanted that. They wanted to leave the legacy industry death march. How could they get their own passcards?

Tech is where all the money is going. The mystical aura around start-ups—of fast wealth, fun and rooms full of brainiacs—is why the prime minister is always touting “superclusters.” That aura is also what seduces investors into betting millions on every tech founder with a half-decent PowerPoint pitch. The funding announcements from Toronto start-ups come so frequently that we’ve become blasé about the volume of money pumping into the industry. Ten years ago, tech entrepreneurs complained that Toronto would never take off because of a shortage of venture capital. Today, they’re fighting off interested investors. Wealthsimple, the online consumer investment service, has raised more than $167 million, the vast majority of it from Power Corp’s Paul Desmarais III. Wattpad, a company whose apps let self-publishers share stories (mostly teen girls writing fan fiction), has raised $101 million over six rounds of funding, including $38 million at the beginning of this year from China-based Tencent Holdings. Then there are the comparatively lesser piles of money raised by companies like the health benefits service League ($85 million), the marketing software company Uberflip ($44 million) and the “brand advocate” mobilization company Influitive ($41 million).

Vision Critical’s early funding came from Andrew Reid’s wealthy father, Angus Reid, who’d sold his market research company to Ipsos for $100 million. In total, Vision Critical raised $41.8 million from blue-chip investors. An especially large chunk came from OMERS Ventures, the tech speculation arm of the Ontario municipal workers’ pension fund. In the start-up world, your chances of success have as much to do with the impact of your tech as with the smarts and reputation of your investors. It doesn’t get much better than investment from OMERS Ventures, which supported three of Canada’s most recognized tech companies: the social media management software company Hootsuite, the learning management system D2L and, most famous of all, the e-commerce company Shopify, whose stock value has ballooned by 500 per cent since its 2015 IPO. Vision Critical was next. Get ready, our leaders said, to ride a rocket ship.

More proof of Vision Critical’s promise: Derek Smyth, the managing director at OMERS Ventures who led the investment in Vision Critical, left OMERS in 2014 to become our COO. Smyth was legendary in the Canadian tech world. He sat on a dozen boards and had a reputation as the Zen master of accelerated growth. He was imposing: as tall and broad as a bear, with a shiny bald dome and dad glasses. We rarely saw him; he was always on flights to the company’s satellite offices or to elite conferences, only replying to emails in the dead of night.

The truth about tech, from an insider who got out


Some mornings, I had to reassure myself I hadn’t joined a cult. We were teammates, not co-workers, and our meetings would end with a rousing “Go team!”


Back when I was being vetted for the job, Smyth invited me for a lunch meeting. His assistant ordered us boxed salads and seated us in a boardroom. Smyth said he didn’t need to ask why I wanted to leave my magazine job—the answer was apparently self-evident. What he wanted to know was, what did I think of Vision Critical’s name? I paused, weighing whether it was a bad move to dump on the brand before I had even been hired. I opted for brutal honesty and said it sounded like a company from the early 2000s, possibly the name of a contact lens manufacturer. He nodded, hands forming a triangle under his chin. Great, he said—let’s change it.

Tens of millions in venture capital induces nausea. And panic. The bigger the investment, the more intense the pressure from your board and investors to deliver extremely fast growth and position for an IPO. Start-up founders all seem to believe in the principle of “10X” from the 2011 business book The 10X Rule, which argues that the only scale of growth worth pursuing is a target 10 times greater than your current size. Anything less is a waste of time. The objective is not to compete with other companies; it’s to obliterate them.

There are, broadly speaking, two categories of tech founders. The most common is the engineer who, slaving for hours in the proverbial garage, programs his (or, infrequently, her) way to glory and gets showered with millions by venture capitalists. He is the tech cliché—nerdy and socially awkward. He wears T-shirts and hoodies, no matter the occasion, and probably bought four dozen of the same T-shirt so he doesn’t need to waste time thinking about what to wear. He’s startled when his company scales fast and he suddenly needs to hire hundreds of staff and learn how to keep them happy. His approach to any decision about his software or his staff is that of an engineer: look at the data.

The other founder type is the rich or well-connected man (or, infrequently, woman) who, like Vision Critical’s Andrew Reid, has a clever idea for an app or a software service and enlists engineers to help him build and improve it. This type of founder styles himself as a visionary. He yearns for speaking invitations to elite tech summits. He wants to see his name in “40 under 40” lists, to be quoted regularly in Forbes, Fast Company and Bloomberg Businessweek. He closely follows the trajectories of his peers and burns with envy when they get more attention. Says The 10X Rule: the biggest problem in business is obscurity.

Andrew Reid had gone to film school in Vancouver, picked up HTML and Photoshop, and got into tech. He founded Vision Critical in 2000. By the time I was hired, he was in his late 30s, but his standard uniform, even when he took meetings with investors or clients, was that of a perpetual teen: scuffed Converse high-tops, shredded skinny jeans and hair sculpted into Bart Simpson spikes. His office was cluttered with vintage Macs and photos of himself snowboarding. In 2012, Vision Critical’s investors and board installed a confident CEO named Scott Miller, who had an impressive track record building global brands. The company moved Andrew into a different role—leading a non-revenue-generating division exploring new product ideas. He was also responsible for company culture, which included making sure the company party had a good DJ.


Our lingo was dense with acronyms. It took me a day of overhearing my teammates discuss tofu before I realized they were referring to TOFU, the top of the funnel


I was initially mystified by how a company that’s been around since 2000 could still call itself a start-up. It turns out it’s not unusual for software companies to hold on to the start-up classification long after the point when businesses in other industries would be considered established. Software companies are forever “pivoting”—changing their business plans, chasing emerging markets, pushing their platform in new directions. The day I joined, Vision Critical had some 700 staff and two main offices: most of the execs, the sales team and I were housed in Toronto, high above Yonge and Bloor, while Andrew Reid and the majority of the devs were in Vancouver, where they’d taken over part of a tower that used to house the Vancouver Sun newsroom. The company also had sales offices in the U.S., Europe, Asia and Australia. It was established, but it was also very much a start-up, and had only recently pivoted the business to cloud-based market research software.

Start-ups are all about change and believing it’ll pay off. Change is better than certainty, agility better than stability. Or, as one senior vice-president put it in a stump motivational speech, “We need to fix the plane and fly it at the same time.”

Some mornings, I had to reassure myself I hadn’t joined a cult. We certainly showed cult-like tics. We were teammates, not co-workers. We’d assemble for “standups”—team meetings in which, while standing in a circle, we’d report on the progress of the current “sprint” (project), identify “blockers” (self-explanatory) and end with a “Go team!”

Our cult’s lingo was dense with acronyms, which I figured was because speaking in complete words is too slow for such a fast-paced industry. On beanbags, at the pop fridge, and at the foosball table, we discussed KPIs (key performance indicators), CAC (customer acquisition cost), ROI (return on investment) and asked our BDRs (business development reps—junior salespeople) to update us on the latest developments in the CRM (customer relationship management software). It took me a day of overhearing my teammates discuss tofu before I realized they were referring to TOFU, the top of the funnel—marketing jargon for the degree to which a customer was aware of our products.

Six months in, I started to see through the acronyms and the carefully maintained optimism of my teammates. For all the talk of agility and disruption and 10X, there was a deep fear of fucking up. A bad decision about a product, a marketing campaign or a sales tactic could cost the business millions. When there was no data to back up a decision, we suffered paralysis.

Derek Smyth had given his blessing to look into a name change for the company. None of the executives, aside from perhaps Andrew Reid, was fond of the existing one. So we quietly hired an outside consultant to conduct a study of the brand and make a recommendation for a new name. The consultant spent months interviewing people throughout the company as well as its customers, studying the market, and leading a subset of employees through word-association exercises to pinpoint our core identity. In the end, he presented us with a handful of alternatives, all vaguely tech-sounding, none memorable. Worse: we had no compelling data to convince us that a new name would improve sales. The report got buried. We kept the company name.

The truth about tech, from an insider who got out


Even the most junior marketing specialist was expected to be always on-call, day or night. Anything less was inconceivable


Just like Google’s “Don’t be evil” or Facebook’s “Bring the world closer together,” Vision Critical had a motto: “People matter.” It was supposed to encapsulate the value that clients got from the company’s software—reliable feedback directly from real people. It appeared on the “about us” page of the company’s website and on the T-shirts we wore to work. It was part of our sales pitch and was repeated, like a call to arms, at our company town halls. It struck me as hollow. Who, after all, believes that people don’t matter? We ignored the small irony that our clients had to use our software, a digital intermediary, to collect information about their customers—the people who mattered. What our software “disrupted” was the unpleasant tedium of a market researcher interviewing customers in person.

Despite the motto, the execs cared first and foremost about our work ethic and maximizing productivity. People I met at other start-ups said the same thing. The reason the company entrusted you with a laptop and a brand new iPhone (with unlimited data!) wasn’t because the company was cool—it was so you could take your work home with you, so you could always be reached and always be accountable. Even the beer cart was a ploy to own your time instead of letting you leave the office for a pub. If another team member “pinged” you in the middle of the night about the status of a project, you’d better respond or be labelled “not a team player.” It was a full-time job just keeping up with team communications: we exchanged messages over iMessage and Google Talk, over several dozen team channels on the team productivity apps Slack and Basecamp, over the chat function on our Salesforce database and, of course, by email. I’d had jobs where I had to be available after hours, but here even the most junior marketing specialist was expected to be always on-call, day or night. Anything less wouldn’t get us to 10X.

Here was the biggest surprise about working in tech: even though everyone wears their team T-shirts and hoodies, rah-rah chants at the monthly all-staff meetings and competes for the sombrero of shame at the tropical off-site, no one loves the start-up they work for. No one feels secure. No one is loyal. There’s no certainty your start-up will exist in a year—or next week.

I’d held on as long as possible to the fantasy, sold to me by Sesame Street, that the people in your neighbourhood—the newsstand operator, the dentist, the shop owner, the taxi driver, the teacher, and the grouch in the trash can—have jobs for life. That they’re fixed objects. If you need a newspaper, the newsstand operator will always be there. They’re the people you meet each day.

A job for life also meant that your job was your life. You went into teaching or sports reporting or proctology because it was a calling—it was who you were meant to be. But it’s been a long time since anyone has been able to count on a job for life. The tech industry led the way: our shift to precarious employment was hastened by more efficient algorithms, apps and Amazon. No legacy industry was safe from disruption. The 2008 financial reckoning forced companies—or gave them the excuse—to replace staff positions with cost-efficient contract workers and orchestrate attrition by a thousand humiliating cuts. Company pensions and RRSP matching now seem like quaint throwbacks to an innocent time. Our cubicles were replaced by Dickensian open-concept rows of computer terminals.


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Precarious employment is the new normal. The Canadian Centre for Policy Alternatives found that 22 per cent of Canadian professionals lack stable jobs or don’t feel secure in their full-time jobs, and that women are disproportionately affected. In the U.S., a study conducted by two leading economics professors found that “alternative work arrangements,” which include contract work and gig-economy income from companies like Uber and TaskRabbit, accounted for as much as 94 per cent of the net growth in jobs from 2005 to 2015. Peter Fleming, a professor of business and society at the University of London, writes in The Death of Homo Economicus, not without hints of disbelief and anger, that we live in a state of “wreckage capitalism.” Tech companies, he says, have cynically taken advantage of a generation of workers by packaging temporary “sharing economy” work as self-determination and delicious freedom. The same phenomenon drives the growth of co-working property managers like WeWork, which, capitalizing on the new reality of so many free agent workers without offices to call home, will rent you a temporary desk. The company plans to open a total of 20 shared workspace locations in downtown Toronto by 2020.

Pining for a long-term job was incredibly old-fashioned of me. A month didn’t go by without a hiring, a departure or a shift in the direction of the company. My marketing colleagues were forever burnishing their personal brands by @-mentioning influential marketers on Twitter and fluffing their profiles and skill sets on LinkedIn. They would often disappear to take calls with prospective employers. For the first time in my life, as soon as I updated my LinkedIn profile to “content marketer,” headhunters and recruiters contacted me, wanting to convince me of a great new opportunity. My teammates spoke of “Vision Critical years” as if they were dog years. So much happened every day—we juggled so many initiatives and worked so many nights and weekends—that a month felt like a year, and a year like an eternity.

Our work approach was lifted from The Challenger Sale: Taking Control of the Customer Conversation, another business book with a dedicated following at software companies. Every project my marketing teammates pursued was evaluated on whether it was “challenger enough.” The book’s thesis, in effect, is that the best marketing and salespeople are demonic Tony Robbinses who manipulate prospective clients with an onslaught of terrifying facts about why their seemingly stable world is about to crumble beneath them. The authors call this process “rational drowning.” Inspired by this approach, I’d poke at our prospective customers’ insecurities with blog posts, video testimonials and white papers addressing all the forces changing their industry, then hit them with even more bad news, pushing them deeper and deeper into the muddy waters of misery. If I did my job right, they would independently come to the realization that our software promised salvation.


The biggest surprise about working in tech: even though everyone rah-rah chants at the monthly all-staff meetings, no one loves the start-up they work for


In the media world, my goal was to get the story right and be worthy of the readers’ trust. In marketing, I was using my storytelling skills to manipulate our audience, to make them believe they had deep problems and ultimately point them to a salesperson who stood to make a huge commission.

After a year of preying on customers’ anxieties, I began attending a meetup of fellow Toronto tech marketers. There were representatives from big companies like Influitive and Wealthsimple and smaller start-ups like Pressly, Collage and Crowdriff. The agenda was to trade marketing tips, but each meeting inevitably became a group therapy session. We’d commiserate about our bosses, team tensions and the challenge of hiring from Toronto’s small talent pool for specialized roles. We’d also gossip about the companies that had just raised another round of funding, the ones that were rumoured to be burning through cash too fast and the ones that had badly missed their targets. We speculated about what start-up was positioning itself for an IPO or to be acquired. We all dreamed of getting in on the ground floor of a unicorn—a company that grows incredibly fast and hits a billion-dollar valuation.

In the office and at meetups, I ran into a breed of serial start-up employee: opportunists who would strategically jump from company to company, looking for the biggest payout. They’d usually stick with a company for one year—never more than four—then split. Their LinkedIn profiles read like Yellow Pages for Canadian tech. Someone eventually explained this phenomenon to me: most start-ups, including Vision Critical, offer employees stock options, but you can only buy them in stages. A quarter of your options vest on the first anniversary of your employment, and the remaining get released over subsequent years. Like office perks, stock options are a tactic to encourage you to feel personal investment in your work—if you perform at 110 per cent, and the company succeeds, then your options are worth more. These serial employees didn’t fall for it. Once they got their options, they moved on to another firm to acquire more. If one of those companies IPO’d, they’d walk away rich and retire before 40.

I wished I was smart enough to be a serial start-up employee. I liked my teammates and enjoyed the parts of my job that were most like my life back in media, but there was far more manipulation and tedium. My what-the-hell-am-I-doing moment came during a surreal debate I had with Andrew while helping him script a presentation for a high-stakes company conference. He wanted to make a point about how badly some companies (that is, companies that weren’t smart enough to use our software) treat their customers, and envisioned a slide emblazoned with the statement, “Don’t treat me like a piece of shit.” I tried to dissuade him on the grounds that the conference’s audience of prim market researchers wouldn’t appreciate profanity. I’d think I had him convinced, only to fall back into the debate. This went on for what felt like hours. Instead, he wondered if we could show the smiling poop emoji. He’d worn me down. Anyhow, it was his company—there was no stopping him. On the day of the presentation, the audience loved it. A month later, at the end of 2016, I received an offer from another tech company. I quit.

It was time for round two. I’d been recruited by Top Hat, then a seven-year-old Toronto tech start-up. The company’s software was used by professors, mostly at public colleges in the U.S., to quiz students in large lecture halls via their smartphones. The timing of my move felt right: Vision Critical was suddenly under a lot of scrutiny from business journalists and its investors because of a protracted fight between some board members and Andrew’s dad Angus, who remained a major stakeholder. Angus was displeased by the executives’ plan to sell off the company’s market research services division (close to his heart) and focus on its cloud-based subscription software. The executives, especially Derek Smyth, believed a software focus would better position the company for an IPO, but all the fighting raised doubts about whether the company was ever going to pull one off.

Part of Top Hat’s appeal to me was its size: just a couple of hundred employees in an office at Yonge and Carlton. I was “getting in on the ground floor,” with potentially more valuable stock options. The company was also swimming in venture capital—it had just raised a Series C round of $17 million. That buys a lot of beanbags. It also meant investors expected incredibly fast growth from tiny Top Hat. The newest rounds of investment were predicated on Top Hat going one giant, 10X-style step further: becoming an inescapable teaching platform with a lucrative digital textbook service. If we were successful, we’d displace legacy textbook publishers. Said the execs: we are disruptors, revolutionaries and world-changers.

Top Hat had genuine IPO momentum. The founders, Mike Silagadze and Mohsen Shahini, almost never left the office. They met while studying engineering at the University of Waterloo. Mike served as CEO. (There are three prominent start-up CEOs in Toronto named Mike—League’s Mike Serbinis, Wealthsimple’s Mike Katchen and Top Hat’s Mike Silagadze—and they’re known as “the Mikes.”) He was the type of engineer who solves problems by examining the data. He wore a Top Hat T-shirt or a Top Hat hoodie (or both) every day, without fail. He had a hands-on management style—he stood at a standing desk in the same open-concept room as everyone else, personally interviewed all new recruits and, even though he was always overcommitting to meetings, refused to hire an executive assistant. I really liked him: he was smart and accomplished but humble and always transparent—he didn’t play games.

Mike was analytical and data-driven but, like Andrew Reid, given to whims. One week, he was convinced we should buy all the billboards along the Gardiner so we could lure more high-performing sales team members. Another week, he wanted to do the same thing but throughout the subway. Neither came to pass.

To reach our revenue goals for 2017, the company had to nearly double the size of its sales team. Over the year, the marketing team would grow even faster: from five to 25. Soon we were too big for our office, and half of the staff relocated. The plan was for everyone to reunite in a new, three-storey Bloor-Yorkville headquarters with the usual start-up frills (foosball tables, beanbags, yoga sessions). We all joined a dedicated Instagram account with photo updates of the renovation.


I don’t miss the rowing competitions, the beanbag meetings, wearing the team T-shirts or pushing the beer cart


As we were planning to move into the new space, Mike decided he wanted an awesome sculpture in the lobby. (“Awesome” is a favourite superlative of tech founders.) As the guy in charge of our content marketing program and PR, I was somehow also responsible for the sculpture. Mike’s idea: a tree of knowledge. When I pointed out that Wattpad had a tree sculpture in its office, he backtracked. I proposed an open-call for artist submissions and ran through the costs of a competition and a guesstimate to manufacture the winning sculpture. After we’d moved in, the lobby became home to ping-pong and foosball tables. There was no more talk of a sculpture.

It didn’t take long to see that the culture at Top Hat wasn’t all that different from Vision Critical. The pressure to deliver was extreme and the hours long. The sales bros tossed mini-footballs and clanged a gong (instead of a cowbell) when they closed a big deal. At our monthly all-team town hall, while we drank beer and ate pizza, Mike would run through the names of the new hires, asking them to stand. It often seemed like a third of the people in the room were new. Was that really possible?

Staff morale was a constant preoccupation. Our weekly internal e-newsletter was mostly read for the upcoming week’s lunch menu and the list of “shout-outs” congratulating Top Hatters who lived and breathed company values. Our values: “Aggressive growth,” “Treat professors like heroes,” “Good in the woods” and “There is no I in Top Hat.” The first two are self-explanatory, the third a fanciful way of encouraging us to be resourceful under any circumstances, and the Kumbaya-ish “No I” value seemed in direct conflict with the general mood in every start-up of cutthroat one-upmanship. In a typical e-newsletter, team members would be congratulated for “being a savage BDR,” “being a true warrior” and “killing your quota.” Sales fought to be at the top of the leaderboard, the customer success team to complete the most calls in one day, and the marketing team for a weekly “marketing ninja” trophy. For a team bonding afternoon, we raced one another at an indoor rowing gym.

Once a month, the “people team” (i.e, the human resources and recruiting staff) asked everyone to fill out a Net Promoter Score, a simple survey that asked if we’d recommend Top Hat as a place to work. Companies usually rely on NPS surveys to quickly assess if their products and services are making their customers happy—not as blunt instruments to measure internal morale. And if the score was low—as it often was, month after month, for the marketing team—the executives frowned and asked, without hiding their exasperation, what was wrong. Were the lunches not good enough? Did people want more flavours of pop? Should we book more rowing competitions?

We were told that the NPS was anonymous, but I had my doubts. At the start of last year, I became a net detractor—I wouldn’t recommend the company. I was burnt out, bored by the narrow scope of our marketing campaigns and irritated by the extra responsibilities I was told to gamely take on despite having little expertise or interest. I was also depressed by the constant churn of team members leaving for other jobs or, in one case, for a year of travel to places far away from BDRs, CRM, CAC and TOFU. At our weekly one-on-one meetings (what we booked in our calendars as “1::1”), my supervisor would probe, more pointedly than usual, about my mood. After months of this, at another uncomfortable 1::1, we agreed that I wasn’t a good fit. Two weeks later, I was free.

I don’t miss the acronym conversations, the rowing competitions, the beanbag meetings, pushing the beer cart or wearing the team T-shirts. If I ever go back to Cancun, I’ll skip the Hard Rock. In my Instagram feed, I’ll sometimes see photos of Top Hat and Vision Critical staff cheering each other on at ping-pong and group-hugging for the camera, and I can hardly believe that was my daily life. I meet regularly for drinks with two fellow ex–Vision Critical marketers—we’re stuck with one another for life, like survivors of a hostage-taking. In the year after I left Vision Critical, Andrew Reid resigned from his executive position to run a new start-up he called VC Labs. The company parties must be a lot less fun without him.

After leaving Top Hat, I met with recruiters and execs at a dozen start-ups about another marketing position. There was always something being revolutionized: meal delivery, small-business investment, retail-supply forecasting, mattresses, even corporate charitable giving. I’d talk about the challenger-style campaigns I’d produced, they’d brag about their team culture and perks, and I’d walk out feeling queasy and certain I’d never accept an offer.

Today, I’m back working in magazines—I’ve recently become an editor at Chatelaine. There’s no certainty the publication will exist in a year, or even next month. The same is true of every media company these days. But I fit on this team, and I’m happy.

Only after turning in my Top Hat laptop and security pass did I admit to myself that I was never a true disruptor. Tech companies always equate efficiency and speed with virtue and perfection. Top Hat’s software could very well make higher education more efficient but possibly less rewarding and meaningful for the student. The legacy textbook publishers the company wants to disrupt aren’t perfect, sure, but that doesn’t mean they need to be destroyed. Those publishers do many things very well, and they do them slowly, with great care, for a reason. We should resist change for change’s sake.

I’m being naïve, aren’t I?

This story originally appeared in the January 2019 issue of Toronto Life magazine. To subscribe, for just $29.95 a year, click here.

January 17, 2019

An earlier version of this story mistakenly reported that Andrew Reid owned a chalet in the Rockies and wore Air Jordans. Toronto Life regrets the errors.

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