Pros
Working at RedRoute has a number of solid pros. ---------------------------------------------------------------------------------------------------- Learning a broad range of technologies: You’ll get exposure to a wide array of technologies that power systems at companies of every size. In my short time there I had the opportunity to learn the following: - Asynchronous programming and the pros and cons of building single-threaded vs. multi-threaded applications - Various db technologies (row based, columnar, document based, and warehousing) - Popular industry devops tools (AWS, Data dog, ansible etc.) - BI/BA tools (Power BI, Looker, etc.) - ETL tooling In the language department this is less broad as the entire tech stack is written in Python. The team is small and doesn’t always have a strong expertise in these areas so you will need to learn on your own to fulfill critical functions at the company. This is both exciting and challenging. Not only that, but I think this independence is probably the most important skill you can develop. In this vein you will have an “outsized” role. However much experience you have the expectation will be for you to perform as if it were double. This is great for certain types of people – you have the opportunity to rise to the occasion and take on a lot of responsibility. The pressure can get intense, but once you grow into the company’s expectation of you you will find yourself a much better worker than when you started. For this reason alone I would say my experience at RedRoute was a formative and valuable one. ---------------------------------------------------------------------------------------------------- Scope of role can go well beyond standard software engineering: For me this was a mixed bag but on the whole was a pro. You’ll get to be a part of the entire life-cycle of the product. My experience at larger companies has been more focused (i.e. only on product and no coding or vice-a-versa). At RedRoute I was able to experience the full life cycle – from communicating with customers to assess their needs, to scoping out the work, to personally building the software. The scope of this work was never quite what it should be, which I’ll discuss in the Cons section, but on the whole this is a pretty cool feature of working at RedRoute. In general, if you are comfortable multi-tasking and yearn for more than a pure software engineering role, RedRoute could be a good fit for you. ---------------------------------------------------------------------------------------------------- Coworkers are awesome: I had great interactions with my peers. Everyone has a “hustler” mentality – people are yearning to work hard and make an impact which is infectious. The CTO has a strong work ethic and it definitely rubs off on the rest of the team. On top of this I thought that the culture vetting was pretty solid. I didn’t experience anyone who was hired during my tenure that was a “bad apple” or contributed negatively to the overall culture. The only critique here was that there were a few people that were great culture fits but probably not good fits for their immediate role. Company events are fun and engaging. The team leans younger, I would guess the average employee was around 27 years old when I left. ---------------------------------------------------------------------------------------------------- Market outlook is generally strong: Products in the space have been able to raise a large amount of capital, so there is market proof that the space is viable. There are loads of customers who want a product in the realm of what RedRoute sells. If RedRoute can figure out how to scale their product effectively the company could be very successful.
Cons
Most of the issues at RedRoute are caused by the founders. I want to preface this by saying that if you want exposure to a number of things then RedRoute could be a good option. However, if you are joining to capitalize on the upside of your equity I would advise against it. I've broken my thoughts into sections below. ---------------------------------------------------------------------------------------------------- The Vision: This is the core issue that drives many of the other problems that will be discussed. The vision for the product is extremely nebulous and changes quarter to quarter. This isn't the end of the world -- it is normal for a startup to be flexible and pivot to find product market fit. The problem is that there aren't any clear steps being done by the founders to test product market fit. The CEO doesn't do any hands-on work communicating with potential customers or folks in the industry, exploring new verticals, or testing hypotheses to help drive a larger vision. He outsources this work (the most critical function a CEO can have), and more or less ignores feedback if it doesn't fit his pre-existing worldview. The result of this is that planning for more than a few days at a time becomes impossible, as there is no vision driving what we should build. You'll often find yourself tasked with trying to make marginal improvements to the nascent product. You'll work long hours doing tons of small tasks and not see any product progress, which leads to burnout. The product was more or less the same when I started as when I left. The product velocity is akin to a large company which is alarming given RedRoute's small size. In general, there is a lack of an appetite for tackling projects that might take more than a few days, which makes meaningful product progress impossible. What's worse is that the founding team will try to create an illusion of collaborative planning. You'll waste time reviewing and working on road maps, but your feedback will be ignored. Without a vision there's nothing guiding "what we should build '' so the default behavior is that the management team decides what everyone works on. This in itself is normal – great companies are often run by benevolent dictators – but the decision for what to work on is often misguided / not well thought out. ---------------------------------------------------------------------------------------------------- Micro Management: There is tremendous focus on project management and process for such a small company. Things like which project management software to use, whether to use Notion or Google Docs, the processes around these tools etc. will come up often, despite having next to no impact on the business. Ironically the engineering team doesn't use any well defined / familiar process like Agile. Rather, there is an ad-hoc process where you loosely have some things you are working on, but without any clear timeline. Everything on slack is public. The expectation is that every conversation -- even a brief question only involving one other party, is expected to happen in a public channel. The purpose of this is not clear, but you'll waste hours a day parsing through slack in an information onslaught. People are publicly reprimanded on slack by the founders for even minor transgressions like missing an email from a customer. Granted, this is not that common, but when it does happen it's embarrassing and unconstructive. The hiring of product folks also didn't make sense and led to more bureaucracy and micro-management. You'd have a near 1:1 ratio between product people / bureaucrats (this includes founders) and engineers which made it hard to get meaningful work done (especially without a vision) ---------------------------------------------------------------------------------------------------- Bringing in good people and telling them what to do: RedRoute will bring in great employees, but they won't properly utilize them. The purpose of getting experienced talent is to let them bring in ideas, lead others, and tackle challenging problems. The founders generally tend to dismiss new or unfamiliar ideas. Given their lack of experience, this applies to almost every idea -- the CEO and COO / head of sales pride themselves on the fact that they've never worked anywhere else (or for anyone, period). Rather than trusting experienced hires, they will direct them to the status quo – mundane, short term tasks that don’t have meaningful outcomes. The competent ones sniff this behavior out and leave quickly. Some of the most hyped up senior hires (Director / VP level) didn't last at the company for more than a few weeks. A few even quit before their first day. There were also a number of really outstanding and experienced engineers that were never formally moved into any leadership / management role, which seemed odd. There were more than enough people to have subteams with targeted focus, but the entire engineering/product org kind of blended together with no clear focus. ---------------------------------------------------------------------------------------------------- Lack of understanding of the product: This is a fundamental issue for the future outlook of the company. In my time at RedRoute it became clear that the founders either didn't understand or were in denial about what they were trying to build. The product fundamentally is a machine learning product. This is obvious to folks in the space, and is supported more concretely by RedRoute’s competitors all being led in some capacity by experienced ML engineers or researchers. Tackling ML related problems is challenging when the founders don't understand the domain or trust the ML engineers at RedRoute. These problems can take months to tackle, but the founders have no appetite for work that takes more than a few days, so nothing gets done on this front. In my time there the founders were much more focused on how to market the product than they were on how to improve the product. They rejected the premise that improving the product itself could actually drive more sales. ---------------------------------------------------------------------------------------------------- Founder In Charge of Sales: The COO (founder running sales / revenue) is particularly problematic. In my time at RedRoute we didn't meet (or even come close) to hitting OKR’s in this area (which this founder set himself). At RedRoute this gross and continued underperformance alone would be grounds for firing for anyone else at the company. Along with poor performance he is generally inconsiderate -- he won’t make any time for his employees during normal working hours. For example, he’ll insist on calling you late at night for you to give him private tutoring on something that is already well documented. Other times he'll give you notice that he needs something done by the next afternoon. The task will oftentimes take hours and take precedence over any of your immediate work. Then you'll find that the product of your work was never even used (again burnout). So beyond already performing as badly as humanly possible at his own job, he manages to be an obstructive force to folks that don’t report to him. For some reason product ideas have to be run by him. He’ll almost uniformly shoot down ideas that are well supported without any convictions about an alternate direction. Lastly, he doesn’t understand how to treat customers. He treats them as a foe and assumes the worst for their intentions. Basic inquiries from a customer will be treated as though they are coup attempts. He lacks a moral compass and his dishonesty will dig holes with customers that you will have to maneuver your way out of. What’s worse is that you’ll be forced to be dishonest to keep up with his BS, which is ethically draining. When I felt like I had to sacrifice my core values I knew it was time to go. A number of employees have quit from working with him directly or indirectly. I can't fathom a world where an experienced direct report would take orders from him, and it is unlikely he would listen to anything they suggest. As a result, it seems impossible that the ship will ever be righted with him at the helm, especially in such a critical function. This is unfortunate because I think RedRoute has a lot of positives going for it.