Shopify

• Relaxed and friendly work environment
• Good food
• Opportunities for personal development (internal ted-style talks, after-work programs and classes)
• Quarterly hackathons

• Ideologically inbred

Shopify insists that it is very different from a traditional company, but as far as I can tell, they have no concept of the workings of a traditional company. They don't seem to know what works well in a normal company, or why things that don't work, don't work. As a result, they don't know how to do normal things effectively (having meetings, organizing work, etc.).

• Management is not involved or aware

Managers didn't really know what was going on with our projects and didn't ask, which is good if you're screwing around all day, but bad if you're trying to actually get something done and need their help. The vacuum left by management is filled by informal structures: cliques and popularity contests.

• Feels like high school

Having friends and being popular is extremely important. Your boss won't know if you're doing a good job, but they will know if somebody doesn't like you, or if you're not getting along.

• Lacks diversity

As with most tech companies, most of the people working on the tech side of things are of the same race, gender, and age group. While not as bad as other places I've worked, brogrammer culture is very strong. Women and minorities are at a disadvantage.

• Opportunities for advancement are largely illusionary

The company will tout the rich field of opportunities that are available to you, but the management defers to the workers for indications of who should be promoted, which goes back to what I said about the popularity contest. Creativity and innovation are stifled by entrenched workers.

I'm certain that none of the middle management will do anything to address the points I've made in the Cons section. They appear to be focused on maintaining the facade that the CEO expects to see: all singing, all dancing, and good vibes all around.

I don't blame them, because that's the best way to get by when the sun is shining on your company. Instead, I'll address Toby, the CEO who I feel genuinely cares about the workplace he's created:

You need help.

The company needs more leaders. You can't be the only one people look to for all of their cues, or pretty soon, employees will be interpreting your AMA comments like the Dead Sea Scrolls.

You need executives and leads who are real leaders: people that make decisions and take responsibility. To get that, you'll need to set expectations for them and be present to their work.

Focus on the work of your managers, and ask your managers to focus on the work of their employees (whereas right now, everyone is focused on you). Let all the other games fall to the side.

Stronger, more diverse teams are built by overcoming adversity together than by having a beer on Fridays. Ask your people to focus on the work, and as they succeed in their mandates, you'll see more genuine bonds between workers and the blossoming of a more gratifying work environment.