As promised let's dig into the pros/cons of working at well known and/or established companies vs early-stage startups. So really it's a comparison of joining later or getting there early. At the end of the day, our personalities tend to lend to one or the other, I don't believe there's too many of us that fall in between and are happy and/or successful. Full disclaimer, I'm partial to startups and this is evident in the below. Of course, there are plenty of attributes (good/bad) for both but the ones that jump out to me immediately and for most people are:
Well know/established pros: Lots of resources, brand awareness, structure, perks, a status quo
Startups pros: Growth opportunities, autonomy, experimentation, execution velocity, true uncapped commission
Well known/established cons: Bureaucracy, lack of speed, inertia, levels of management tiers, earning ceilings
Startups cons: Volatility, makeshift processes, lack of resources, limited funds, OTE disparities
So what do you want?
Personally, I'm an outcast for the big boys. I have no interest in being a cog in the machine and working as an order taker (no offense to all you yes-men). Which IMO/E is what they're looking for. Now of course, you can get paid fairly well to do just that, but I find it boring after a while. Not to mention the amount of process and the time it takes for things to get done. This doesn't vibe with my run through the wall and get shit done attitude. Again, to each his own.
BTW - There's plenty of articles on the different types of salespeople, and who to hire based on the stage of the company. For you, this is a great way to think about how you're being viewed by hiring managers and a "where I belong" benchmark on knowing where to/not to apply.
Startups on the other hand don't fair well to people who aren't as resourceful, prefer clear direction and aren't interested in doing more than what's asked. It sounds like you just said if you're lazy and dependent on others go work for a bigger company? Maybe that's what I'm saying, but what I'm really saying is that you need to operate as a "franchise owner" at a startup for it to be worth it. Being reactive instead of proactive is not how it works.
I'd also say startups can have too much diplomacy at times, and they can be a "get shit done now and worry about the consequences later." That can cause a lot of headaches, it can create extra work down the road. That's how they operate sometimes, so I don't blame the people who would argue "that's not my job, and I don't get paid to deal with that." I also find them to generally be all of the same but pretend to be different. None the less, I'm more comfortable in these types of orgs. based on the below:
I like to set my own rules (to an extent) and the risk of things not working out is not nearly important to me as catching the wave early and riding it to the bank. Yes, I can make a consistent X with the big co. down the street, but I find there are too many cooks in the kitchen. The opportunity with startups that pay higher commish percentages and provide autonomy is worth the risks.
I'm not as worried about the perks of having a fully stocked kitchen and a tropical offseason president club. I'll pay for my snacks, and my own trip (in season) and reap the benefits of the credit card points too. Good try. I can't be bought for Cliff bars and being paid 8-12% after doing 120% of my goal. Stay woke!
I want the upside that you won't normally get post Series C. Another way I think about it, once a company is up near 200'ish employees it's usually too late for me. Not always, but typically to have better accounts, territory, process ownership, etc. you got to be there before founders start taking too much advice from other founders who are not salespeople. This isn't always the case but at least in my experience generally true.
I also find if you work for a larger company there's less negotiable's. They pretty much have everything buttoned up and are looking to slide you into the flywheel. At a startup, you are the flywheel, and the pressure plate, and the springs, and the clutch disk. So what I'm saying, you will do a lot but the returns can be much higher/better. Plus after you show early performance you can negotiate a higher commish %, base, etc.
For example, I joined a startup as the ninth employee. I did all the same things (sales practices, work ethic, deal sourcing, etc.) as other companies I joined much later and post employee 200 and made 4x the money. Why? It was greenfield, it was a run as fast as you can and work the comp plan how it was designed.
Now, salespeople at bigger orgs. can make the same or more but I would argue only the first-ones-in or the beneficiaries of those people leaving (took over their accounts/territory). Also, I'm referring to the typical sales rep, not the enterprise sales guys/gals who chase down seven-figure accounts for 18 months. I've been in that game too and it just takes one deal to make or break your year. I'd argue that's a similar crapshoot in joining an early startup.
Now, for argument's sake, where would you rather be, a mid-market rep at a Series A startup or a mid-market rep for say, Salesforce?
At Salesforce you have the level of comfort in knowing you'll knock back $X amount off the strength of the name. However, you'll have four bosses, be in a pit with 300 (or more) other "commercial" reps, your territory is South Iowa, and you have no say in anything.
Alternatively, Series A salesperson doesn't have the luxury of Salesforce marketing clout, they will be required to do more outside the sales function to have any substantial financial success, and they are playing roulette with things working out (product-market fit, engineering, etc.).
IF Series A salesperson hit it right, they will have experienced a ton more, had impactful input to the business, and can 2 or 3x what the average Salesforce rep would make. Not just mid-market, all SFDC reps. Don't believe me, just email me and I'll send you my 2016 W2. I'm not saying it's not hard and it's for everyone, but it's the game I choose to play until I can find something better.
So in short do you put it all in on red or do you play the slots? To each his own.