Pros
- The company has created a work communication category, which is now catching the attention of larger players. No small feat. - The company is growing and the product is loved by many customers. Most startups, including many who have recently reached "unicorn" status, have not and will not ever have this happen. It matters a lot and can carry companies through upswings and downswings. - Loom's compensation is in the 85th+ percentile for given roles in tech by region, and they have pay parity across the US. This is very progressive and employee-friendly. - Loom has the most employee-friendly option pool structure I've ever even heard of having started a company, worked at other startups, and invested in some. The founders and the investors put themselves at a significant disadvantage in the short term to help employees own a meaningful portion of the company. - Loom actually understands what it means to be remote-first and is ahead of its time in remote/async ways of working due to the nature of the product. My work-life balance was never been better despite working hard for this reason. - The ICs at Loom are some of the most competent and fun people I've ever worked with. Video is a hard technical problem. Category creation is hard. Scaling a company and culture during a pandemic is hard. They made it a lot easier and more joyful. - The founders care a lot about the employees and customers of the company and the mission. They are actively trying to improve in every way they can. - The tool is free for educators forever. That is no small thing. It costs the company a lot of money. - There are teams in Loom that I think are quite literally the best at what they do. The phrase "world-class" is overused and cliche, but it's sometimes hard to imagine what "better" looks like in some of these orgs, especially customer support and customer success.
Cons
Context: The founders are doing this for the first time. Loom scaled from 1M -> 13M users in <18 months, growing from 40 to 200 people in the same period with massive revenue growth. It's a rocket ship piloted by first-time pilots. Everyone's learning. Challenges: - The remote culture at scale has been difficult because it's hard to build trust between teams and ensure that the individuals doing the best work are being recognized and rewarded. I don't think the next 2 years will look like the last two years. Remote-first is very different from prohibited collocation/COVID restrictions. This will continue to be a big challenge, but I think the leadership team is up for it. - Although it's the exception and not the rule, a few managers and execs are "junior" in their skills as managers and seem to lack the self-awareness to improve. In some cases, they are purely managers and not leaders. Most are excellent. On a relative scale, Loom's management team is more impressive and capable than most companies at its stage in terms of experience and skillset, but individual experiences may vary. - The video space is getting very competitive. Loom still has the best and cheapest product, and it is making strides towards becoming a true video and work platform, but as always with startups, it's a tale of David vs. Goliath.
