Pros
Free catered good, good facilities, some good people, this company at least tries to pay lip service to be too nice
Cons
Oh boy! where should I begin? This WAS a promising company ONCE Unfortunately management ineptitude has squandered it. Let's start one at a time: 1) Technology - Upwork is not a tech company. It needs to stop fooling people that it is. It has a platform that's over 2 decades old, which has seen integrations with competitors along the way. It's only holding together since it is duct-taped. Building anything on the platform, or getting analytics is like pulling teeth. Engineers - be aware. 2) Product - The product is laughable. It feels like a website from web 1.0 era with a long google form that gets you started. Hello - it is 2020! there are smarter ways of customer onboarding. Assuming you somehow manage to get on, then you try to either submit a bid or create a job. Both are flawed approaches. To think that a customer knows everything they want or a worker has enough context to bid just does not work in the process of hiring knowledge workers. Due to this flawed approach, the next step in the process i.e matching, suffers. Search and matching is a mess and I have rarely seen relevant results. Shocking that this is the state for a company that's been trying to perfect "matching" right for nearly 20 years. You would think they would have figured out the ontology behind the scenes, which could have served as a backbone of better search? The rest of the experience after that (check-out, follow up, communication between the worker and the employer which they force through another web 1.0 era program: dash) is as amateurish as the early part of the experience. Sprinkle this with silly features such as time tracking and taking screenshots of the worker's laptop to keep track of work, the platform really feels from another era (hello. it's 2020!). They also have other focus areas like Enterprise (still struggling with a sustainable business model or a truly enterprise ready product after years at it) and Trust & Safety (also feels duct-taped. Hello, we live in an AI first era!). Things get shipped here without proper data analysis (which, by the way, is another challenge altogether). Upwork likes to think it's data driven, but reality is far from that since it is impossible to get proper analytics for anything. 3) Marketing - Their digital marketing machinery is getting better in recent years, but still far behind what I have seen in other companies in technology. Marketing team has quite a few new people as most of the old guard quit in frustration with the culture / politics (more on that below). The new guard is focused on some aspects of brand, product marketing, events to help enterprise teams etc. It is still to be seen how this would play out, though I have serious doubts about Upwork's Enterprise efforts. 4) Legal - Legal *controls* everything at Upwork and loves to throw around its weight. While well intentioned, this has resulted in part of the product / go-to-market challenges as well as challenges with agility and conservative nature of the company. Unfortunately, this has been tolerated too long and is rooted deep in the culture. 5) Ops - The ops team has a lot of people, but it's not clear whether they're utilizing the team smartly. For one, the ops team is not in sync with the product efforts. Secondly, it does not feel they are using analytics or AI to their advantage (hello, 2020!). Hence it feels this team is constantly in the reactive mode, than being proactive. 5) Misc (HR, Finance, etc) - HR is knee-jerk and reactive and only there to CYA for the mis-management (more on that below). 6) Culture - Bureaucracy, Nepotism, Sexism, Favoritism -all are rampant here. It goes all the way to the top. The senior most leadership team has long tolerated incompetent managers, and hence it trickles down. Most of the leadership is incredibly long tenured in the company and has not seen what agility and "real world" is like. They feel threatened when someone shows them the light. Pockets of "touchy-feeley-ness" and unwillingness to open eyes to hard truth are rampant. Incredibly poor management, which is willing to back-stab you at a moments notice. Though Upwork is a relatively small company, it reeks of politics like a 100K+ sized organization. Finally, if you have an iota of willingness to have an impact, check that at the gate before you join Upwork. In fact, some well meaning senior management have told me "why do you bother about trying to make a difference? what's the worst that would happen if things don't change? Upwork will be just fine. Don't try to change the river". 7) Final thoughts - if you any doubts about the above, don't take my word. Instead, go check out the senior departures in the past 1.5 years. Almost every department has seen lot of departures. Go ask these people what they felt about Upwork culture and the current leadership there. I think you will have your answer.
