Pros
Remote work. Autonomy. Pay. Benefits.
Cons
The company is effectively dead. Just look around: AI is fueling massive shifts across the industry. New companies are emerging, old ones are reinventing themselves, and innovation is everywhere. And then there’s Nylas. Stagnant. Out of touch. Laughably behind. It’s almost comical how disconnected we are from where the market is going. We had a head start and a war chest, and we squandered both. Watching the rest of the tech world evolve while we spin in circles isn’t just frustrating....it’s embarrassing.
The company raised $120 million back in June 2021, a massive sum that should have secured several years of runway and positioned us for real market leadership. Instead, every cent has been squandered. There’s no other way to put it. The executive team, former and current VPs, SVPs, Chiefs, each had a hand in setting fire to that money. Bad bets, bloated teams, zero accountability, and an inability to build or sell anything of substance. It's not just poor execution. It’s willful incompetence masked as leadership.
Now, our former CTO and the original founder (Christine Spang), has appointed herself CEO. She was elevated from interim to permanent despite being completely lost. She has no strategy, no clarity, no credibility. In fact, she might be worse than Gleb. And that’s saying something. But instead of owning up to the failures, she doubled down. She promoted the SVP of Engineering to CTO and the SVP of Product to President. Why? Not because of performance. Not because of outcomes. But because they’re her inner circle. Promotions that padded executive resumes with inflated titles, bigger paychecks, and more equity, while the rest of us have been watching the ship sink. it has sank and now we are waiting to be rescued.
There’s zero career growth for anyone outside that bubble. No development. Some recognition. And a whole lot of failures. Just the same people at the top failing upward while everyone else is stuck doing damage control. The April AI launch, our so-called “big moment”, was an outright disaster. The product barely functions. Customers consistently say the same thing: “It’s a cool idea, but everything is still buggy.” They’re not wrong. Months later, none of the core issues have been addressed. Stability is nonexistent. Reliability is laughable. And Engineering? No one knows what they’re doing, because whatever they built is fundamentally broken. Worse, when the topic gets tiptoed around during all-hands meetings, leadership responds like political spin artists; gaslighting the entire company. “It’s not buggy. It’s stable. That was fixed three quarters ago.” Spoiler: Nothing was fixed. The product is still broken, the complaints are still coming in, and the trust is gone.
Churn is out of control. Revenue is declining. There's nothing left to raise, and no story worth investing in. The market has moved on. We burned our chance, and now the desperation is palpable. Morale is at rock bottom. Almost everyone is quietly or not so quietly looking for a new job.
This is not just a company struggling. This is a company actively collapsing under the weight of ego, denial, and bad leadership.
About Fundraising: When you’re struggling and desperate for cash, you don’t negotiate — you take what you’re given. And what we’ve been given are brutal, investor-friendly terms that do nothing for employees.
Down round: The valuation in August 2024 was almost certainly lower than the prior round, wiping out past gains and pushing the 409A down even further. This directly devalues every employee’s equity.
Liquidation preferences: New investors likely secured 2x or 3x liquidation preferences — meaning they get double or triple their money back before employees see anything in an exit.
Participating preferred stock: These investors don’t just get their investment back — they also get a cut of any remaining proceeds, leaving even less for employees.
Anti-dilution protection: If future rounds happen at an even lower valuation, new investors are protected from dilution. Employees? Not at all.
Bottom line: Every time we raise more money, the cap table gets worse for you — not better. Equity is being diluted, devalued, and deprioritized. And it’s happening quietly, behind the scenes, while leadership pretends it's business as usual.