Pros
Unlimited PTO, several paid holidays. Ability to level up your skills really quickly due to wearing many hats. Team collaboration and the willingness to help each other grow in your own job function was great.The problem space at Tailwind is really interesting. Marketing can be fun and helping small businesses is an engaging mission. Tailwind has some very smart and talented people who want to do good work. They are consistently pushing for better products externally and better tools and processes internally.
Cons
I have spent my time in tech working for small startups that struggled with both internal politics and product market fit and Tailwind is no exception despite them marketing themselves to the contrary. In the 2 years I worked at Tailwind, I was on 4 different teams. I was never on a team for longer than a year, some stints were as short as 3 months each. Sometimes I was moved as retaliation, other times I was moved to silo my work from the toxic co-founder just so my team could try to get things done. People are treated like cogs to be moved around and are given little to zero recognition for their hard work, even when it shapes bigger initiatives later on. There is no room for a team to fail; teams that take on ‘riskier’ or exploratory work are given arbitrary deadlines and then disbanded when moving goal posts are not met. The founders do not understand the marketplace they are in and would repeatedly bully and move any employees who pointed out how out of touch they were, even when the words were coming from Tailwinds own users. User needs are dismissed or ignored if they do not suit the higher level vision – despite the market moving in the opposite direction from this vision. Tailwind is currently trying to market themselves as “remote first” and this was not true in my experience as an employee who transitioned from in-person to remote only. First, there is no remote work stipend, internet reimbursement, or home office support. The OKC and NYC office have started in-person events again with no offering for remote employees. I was getting immense pressure to return to the office and participate in these events. One high level employee started blaming the high rate of turnover on people being remote, and that they felt ‘disconnected’ while at the same time rewarding in-person employees with free lunches and parties. Pay is well under market rate, especially for remote first. By leaving I was able to almost triple my earnings. During the height of the great resignation, I had to demand a promotion, but was only given it after agreeing to take on outside duties, and that raise was still under market rate for that title. Even after I had been performing at that skill level for well over 6 months, I was only given the title change after a male coworker in my department left and got that title at a different company. I was then told I could not have the first title I was offered and given a lesser one – I later learned that title was offered to a male candidate. Managers and other higher level staff are improperly equipped to do their roles. A lot of individual contributors are given direct reports without training or support and no compensation bump. When I told my boss I was feeling burnt out and overworked, the solution was for me to block off my lunch hour so no one would schedule me. I received passive aggressive messages from my product leads over any time off I took and even not being on early enough (they were a timezone ahead of me). I personally spent about 8 months on a team led by a bully, yelling and degrading me and others for 1+ hr a day, even after upper management asked me to spy and report on his performance when I started on the team. When I flagged his behavior, he was not removed until 4 months later, and he was removed for yelling at a male higher up. He was not the only employee acting this way, in fact it was very common for product meetings to devolve into screaming matches. The cofounder himself yelled at me in an all hands meeting. Needless to say leadership never apologized to me for how I was treated during my time there even as I constantly flagged issues. There is also a huge diversity problem. I repeatedly saw female ICs pick up the tasks of their male manager/coworkers and receive zero recognition. The female head of product was forced out after only one year on the job. During a layoff, 14 members of the staff were let go, and 8 of them were POC. When called out on this, the CEO said “we were aware of the DEI implications, but they were not measuring up”. Measuring up to whose standards?? I know one of my coworkers was managed out directly by my boss and the head of product for speaking out about issues on the product team (issues like the cofounder and others yelling and screaming at people). Now our CEO is on a PR tour claiming to care about diversity and how hiring remote will help. Newsflash, you can’t harass your marginalized employees for speaking out about their negative experiences and then block them on LinkedIn and claim to be some pillar in the community. Also there’s no money. All the recent compensation increases came from the high turnover rate and layoffs. The company has been a leaky bucket for years, and social networks like TikTok are going to finish Tailwind off because of the cofounders insistence on Pinterest being the pinnacle of social media marketing.
