I joined in 2015 and left after 2 months. I had left a fast growing late-stage startup, AppDynamics, where revenue was doubling every 12 months, from $75M to about $150M when I left. The director of engineering at Optimizely who hired me said their revenue was doubling too, from $40M to $80M. At the next all hands a few weeks later, the CEO said revenue had been declining slightly for 2 straight quarters. At lunch, after the all hands, no one seemed to care. Someone literally complained that their friends at AirBnb got duck for lunch and we didn’t. The director either lied to me or didn’t know. People were nice and smart, but it was clearly going off a cliff. It seems for many B2B startups the march up the value chain to enterprise is challenging, especially with regards to pricing. I remember the president of sales at AppDyanmics would not cut prices to compete against New Relic in the self-serve market. At Optimizely, I recall enterprises were pissed at being charged more just for better SLAs. From other comments it sounds like they finally figured out the enterprise pricing model by jettisoning self-service. Not sure if that was the right call or they could have found better success by avoiding the pricing consultant fiasco. Though I vaguely recall they were losing too much money per customer so that needed fixing. In any event, it’s hard enough to make money in startups as an employee, but declining revenue at a growth stage startup is a death sentence for your equity. I liked the people at Optimizely, the transparent culture was great, and I wished it would have done better, but the writing was on the wall. Sure enough, not long after leaving the first round of layoffs came, private equity invested, and the announcement was revenues doubled over the prior 18 months, minus the detail of the last 6 being flat to down. Sorry to hear about the impact on you. This is a problem with the current state of startups staying private longer and why I likely won’t work for one that doesn’t have an extended exercise window [1].

[1] https://zachholman.com/posts/fuck-your-90-day-exercise-windo...

The pricing consultant they brought in was Simon Kutcher...

I have a sort of general question about this narrative, which seems to apply to lots of startups that begin as self-service, developer-focused projects and end in enterprise hell.

Is it not the case that these startups begin developer-facing, get market traction, are lavishly funded, and then discover that the self-service offering they've built simply can't satisfy the projections they've made to justify their valuation?

Which is to say: would Optimizely be doing much better if they hadn't pivoted into enterprise hell? Or would they be a much smaller company?

I see why customers would have a strong preference! But it's less clear to me what the right decision for the business is. But I'm just asking!

It's possible to do both. At Twilio we started as a self-service, developer-focused company. Today we have many large enterprise customers (and spend a lot of effort to court those kinds of customers), but we still have a huge number of small developers, and one-person hobby shops can and do still easily set themselves up to use our platform. We have added some enterprise-only features, which I sometimes have mixed feelings about, but everything that's traditionally been available to non-enterprises is still available to anyone with a credit card.

I completely agree with you on (at least in terms of Twilio's experience):

> would Optimizely be doing much better if they hadn't pivoted into enterprise hell? Or would they be a much smaller company?

We were definitely going to hit a ceiling if we didn't add enterprise features and work on getting all the various certifications that large companies will require to even start talking to you, and build a sales force that knew how to sell to larger companies. If we hadn't done all that, we'd be a much smaller company today, and likely a competitor would have done it instead and eaten our lunch.

> It's possible to do both.

I think the more interesting question is: can you always do both?

I agree in a general sense, as there are a lot of excellent examples in the wild at this point (of companies consciously maintaining their developer base), such as Cloudflare, Fastly, Stripe, DigitalOcean, Twilio, GitHub and so on.

It may be a case where it's much easier for some types of services than for others.

It's probably true that you can't always do both, but I'm not seeing how it wouldn't be possible with something like Optimizely.

I worked at Optimizely for 4 years and can tell you that pivoting to Enterprise has been one of the best company decisions.

One of the important distinctions between Optimizely and most developer-first platforms is that experimentation is a hard practice to pick up. Most companies have difficulties getting their programs off the ground and keeping them funded, let alone grow or scale them. Small digital businesses struggle more for several reasons: 1) they have few resources, so teams are understaffed and resources are pulled easily, 2) they have little money, so the percentage uplifts are rarely motivating, 3) they have little traffic, so it is harder to get a statistically significant measure in their experiments

Because of these issues, Optimizely always had really poor retention in the SMB space. Nonetheless, the SMB customers helped Optimizely build up a brand name, build up legions of practitioners, and get the skills and experience to go after the Enterprise market. When Optimizely started acquiring enterprise customers, retention improved substantially.

This isn't to say that there aren't lots of problems with Enterprise sales and that Optimizely didn't make tons of cultural mistakes in that pivot. But on the core financials, Enterprise kept Optimizely afloat. The problem wasn't the pivot to enterprise, but the trade-offs that were mismanaged along the way. The path to enterprise was inevitable and correct.

First off, love the username :-).

You argue that pivoting from self-serve to enterprise was one of the company's best decisions. If that were true, Optimizely would be considerably more valuable now than it was four years ago, which is manifestly not the case.

Moreover, if the self serve model was indeed fatally flawed, then it would not be possible for anyone to build a profitable business serving this segment. However, a competitor, VWO, showed that it is possible to build a large, profitable business using this model.

Finally, let's say my prior two arguments are wrong, and the unit economics of the self serve business were fundamentally flawed--an assertion I challenge--the self serve business would still have been useful as a source for attracting future enterprise customers. When Optimizely cut the self serve plans, it also killed its largest source of enterprise deals.

Are you suggesting that revenues fell after bailing on SMB. That is hard to imagine, but I guess possible. Given that the core of the industry is about asking counterfactual questions, I would think the appropriate question would be 'would they be more valuable now if they had not gone to the enterprise - would they even have the deal they did wind up getting?'rather than are they more valuable now then they were 4 years ago. Hard to know, but my guess is that they wouldn't. A simple web editor with a random number generator isn't going to be of interest to anyone looking to buy. The larger problem is that statistical inference is hard - it just is. And, unlike analytics, where you are just placing sensors into an existing system, here you need to also place actuators, so implementation is much more complicated. That means that at any scale, both the marketing team, and the dev/IT teams need to be involved for anyone to get value and not wind up breaking systems all the time. Software like theirs, and ours, isn't magic, and without good editorial and hard work by the client, the entire exercise is more statistical theater than science. And that material fact was always in conflict with the rhetoric that they make AB Testing easy for everyone. It lends itself to a particular type of solutionism that VCs and the larger industry are prone to be seduced by. Self service to SMB clients might be a profitable biz, but perhaps not enough to service such a large amount of venture funding. FWIW VWO also tries compete at the enterprise.

Richard, I appreciate your theoretical arguments. Consider me the applied physicist who has actually seen the data. :)

On the valuation. Optimizely's pre-exit valuation rose in every VC round since changing the focus of the business from SMB (Series B) to Mid-Market (Series C) to Enterprise (Series D). The valuation of the exit took a hit for reasons that were not the enterprise focus. I could say more here, but consciously choose not to.

The self-serve model at Optimizely was certainly flawed. If VWO was able to build it profitably, that's likely because their labor costs, being based in India, are substantially lower than Optimizely's. Keeping a legion of engineers funded in SF has very different unit economics than keeping engineers funded in India.

Now on your last argument, that self-serve customers could acquire enterprise accounts, I certainly agree. If that strategy were better executed, it could have created a valuable pipeline. But the self-serve to enterprise funnel was sorely lacking, and when self-serve was cancelled, the business benefited financially and migrated everyone to the new pricing model for substantial success.

Its easy to look at Optimizely's final fortunes and link that to the enterprise approach, and I won't argue they're completely unrelated, but there were very different factors that caused Optimizely to fold into EPi's acquisition spree.

Thanks for making these points. They seem less hyperbolic and more grounded than your earlier claim ("it was one of optimizely's best decisions") and I appreciate that change in tone.

You characterize my arguments as theoretical, but they are empirical. Optimizely's valuation didn't increase after the decision to kill self serve was made, and VWO was able to build a successful business without killing self serve.

Also, as you now agree, optimizely would have had a better source of enterprise deals with self serve intact. That's important.

Stepping back, every SaaS business has issues converting self serve users to enterprise. Fixing those issues takes hard work, which optimizely was not willing to do. Similarly, every business has higher churn in monthly self serve plans than annual enterprise plans. Fixing this takes hard work too. Things were not unsolvable, optimizely simply had no appetite for solving them.

To address your other points: 1. I donbt that labor costs would have made a difference, but say they would have. Was anything stopping optimizely from reducing costs to have overseas development in india? 3. Your comments about the various foci at different rounds of funding is irrelevant. I'm not arguing that building an enterprise business is bad, I'm arguing that killing self serve was bad.

Ultimately, as Dan predicted in 2013, Optimizely died of indigestion rather than starvation; the market was always there, and still is.

Hope this helps clarify my position, even if we still disagree. If you send me an email, I'd be happy to help squash your skepticism about the $100k too.

PS. I don't think that killing self serve was the only thing that led to optimizely's demise, but I do think it was a factor.

"Optimizely died of indigestion rather than starvation" while it might be true, not sure if Dan ever admitted anything close to that in public.

I think your argument that VWO is a profitable business, is unknown. VWO is also still private. It could be going through the same issues. Additionally, I'd say that valuations are inherently made up. Optimizely was perceived as having more value previously, it doesn't mean it actually was. When it was serving the SMB space, it had a massive churn in that space.

>I think your argument that VWO is a profitable business, is unknown

VWO has been profitable since its first month of inception

(throwaway account + I am a VWO employee)

The big missed opportunity was to build a bounty-based marketplace to serve the SMBs... charge for results vs. the product.

Would the bounties be large enough to cover the work involved? I'm doubtful.

Never dump your prosumer/developer/enthusiast base, no matter what any business expert tells you. Keep them going in parallel.

CROs and VP of Sales types don't like the idea because they can't control the messaging and manage the sales funnel. But if you have people who genuinely love your product and will champion it internally, ignore these fools. Just keep delivering a quality product with value and if there is a market, the revenue will follow.

GitHub, Twilio, and OpenDNS all built their businesses off people taking tools to work.

This. Not least because some of us have invested effort in singing your praises, selling you to teams, and used our reputation to promote your business, indirectly benefiting because clients are happy.

I've been burned twice doing this; once with Fastly [0] and the second time with AppNeta APM, which they then dumped as it didn't fit with their "enterprise" portfolio.

0. https://news.ycombinator.com/item?id=22073520

I think that this is a great question that isn't asked nearly enough. There are all sorts of stories about companies moving up market successfully, but I'd love to see more written about the cases where it's attempted and failed. The DNA of enterprise vs SMB SaaS is really different.

For what it's worth, I would guess that had Optimizely not pivoted to the enterprise they would indeed be smaller, but more importantly would have had a slower growth rate at least at that point in time. In an industry obsessed with high growth rates that's the kiss of death and I imagine the reason behind their pivot. But that's just my guess.

> then discover that the self-service offering they've built simply can't satisfy the projections they've made to justify their valuation?

I suspect a lot of startups sell their investors on enterprise from the get-go. Self-serve can be seen as a foot in the door, a way to prospect potential enterprise opportunities. They watch self-serve sign-ups for a bigcorp.com domain and then hand it over to account sales and swing for the fences.

I think a big problem is differentiating your self-serve from your enterprise offering. You don't want bigcorp.com to feel happy enough with your $20/month foot in the door offering. And at the same time enterprises aren't stupid money fountains and they don't just sign $100k/year contracts unless they see major value. I think this creates a volatile business where a dozen or so enterprises make up the lions share of revenue for a startup and the thousands of self-serve customers are just kind of there like background noise.

SMB and grow into enterprise is the easiest path bc can iterate and grow revenue. In theory, similar effort for more revenue initially and more revenue as seats grow.

Problems are often:

-- Beyond just VC, it becomes an issue ongoing to having full-time dedicated sales: quota, qualified leads, etc, it's a beast. Internal culture and priority shift to start/maintain/grow.

-- if not naturally pulled here and no obvious tier separatation, above can easily destroy the SMB side, instead of using as part of your moat + growth. The marketing+sales org will kill it, unless you split those as well or otherwise solve

-- VC money just means artificially faster deadlines and expectations for all of the above, so even harder to do 2 things, even if long term natural and better to habdle

I agree with the point you're making.

I think the problem is to become "lavishly funded" means that you need to have a pitch that creates a narrative of how you will reach a lavish level of revenue that is believable.

For B2B SaaS, usually that means moving upmarket and raising prices.

I don't think we can say that Optimizely was necessary wrong in doing what they did with knowing what they knew at the time. There are many examples of B2B SaaS companies successfully starting with SMB, then going enterprise. First company that comes to mind is New Relic ($3.6 billion market cap)

To piggyback on this question, I am also curious - would Optimizely choose to go this Enterprise sales route if it weren't for their sky high valuation back in the day. How much of this change was driven by the customers' need vs. a perceived opportunity to grow the company?

You know the answer to this question. Rationalizations may have included lines like “pivoting to enterprise will help us help even more customers” but it’s all about growth and TAM.

Funny - I worked for two SaaS businesses that at one point used Optimizely and loved (and I mean LOVED) it.

But I distinctly remember at the second job, that incredibly rough transition to that vague enterprise pricing structure along with the software getting clunkier and clunkier, which led us to abandon them and never look back.

I think at one point they were trying to get us to go from paying $99 a month (!!!) to like $3,000 a month for virtually the same service??

I'm kinda curious about your >$100k loss on your stock. Your strike price from pre series A options was more than the gains on a near $600 million sale price? Maybe I am misunderstanding, but how is that possible?

Probably the op spent $100k to exercise the options. It's likely this deal will wipe out all common shareholders and only the VCs will get anything. That's a $100k loss. The op will be spending the next decade writing this loss off against capital gains and earned income.

I've been there.

Can you write off just the exercise price or the fair market value at time of exercise?

Confirm this with your tax advisor, but FMV at exercise is your basis in later years (generally because the difference in FMV and strike will have caused you a taxable event).

c.f. https://www.untracht.com/news-insights/vantagepoint-newslett...

Edit: Consider the case where this were not treated as true. You're clearly not going to pay $2 strike, exercise at $5 ($3 of employment income due to the bargain element), sell at $10 in a later year and pay on $8 of capital gains, right?

I'll note for conceptual understanding (by people who aren't patio11, who I'm sure understands this all far better than me) the general point that a gain or loss on the sale of a capital asset is how much money you got from selling it minus how much you "paid". More technically, how much you "paid" is called the basis, and you can do things that adjust the basis as patio11 noted above.

For general information on this topic see https://www.irs.gov/newsroom/capital-gains-and-losses-10-hel...

That's a really good question. I'm not certain of the answer.

When I had this happen to me the FMV was slightly higher than my exercise price, but not enough to trigger AMT. I know I only wrote off the actual cash I lost, and I used a CPA to help me make sure I did it correctly.

I recently asked a tax advisor a similar question: if I do a cashless exercise sale for $5 when the FMV is $6 and my strike price is $2, can I pay income tax only on the $5 sale price? The answer was no: I would owe income at the $6 price and then immediately accrue capital losses on the $1 spread between sale and FMV.

I guess that's a longwinded way of saying "I doubt it". Tax law around employee options is brutal. :/

Yes, capped at $3,000/year.

If the OP is telling the truth, there is no way he lost money on the stock he bought. The early shares are all up.

Not necessarily. There is liquidation preference for the preferred shares.

Yep. They are listed as having taken money from Insight Partners, a growth PE firm. You know they negotiated some preferred terms.

For the record, I think op is probably speculating a bit. That said, I'm not sure how you can be so sure op's not losing money unless you have intimate knowledge of the cap table and the deal.

The acquisition share price is usually told to employees. They probably got the information from current employees. Since they are a shareholder, they'll eventually find out anyway.

I was involved in an acquisition as a shareholder. I was nigh impossible to get anything out of the executives. It was an acquihire so maybe things were different.

That...sounds illegal. You should at least have gotten a document in the mail with the buyout details, after everything was finalized and signed. It may take a few months in some cases but they have to send it out.

You're certain you were a shareholder and not an option holder? That is, you had exercised some of your options?

Another possibility, since you said it was an acquihire, is the company actually shut down operations and sold off its assets to the buyer. Maybe in that case there would be no share price to report since no shares were bought? I'm not an expert.

I was definitely a shareholder. I had early exercised some options, and reached my one year cliff. I believe your conclusion is correct. They shut down the company and sold off assets. The acquihire probably returned some money to the investors.

I spoke with (paid) two attorneys (employment and business) at the time and they said there wasn't much I could do. In the grand scheme of things it was small potatoes. I was pissed at the time though.

I worked there in 2013. I very specifically remember getting a speech about how if we didn't believe that the company would be worth more than google, we should quit. Seems like that may have been a better option for a lot of folks.

Wow, I was interviewing there in 2013. I was interviewing for a fairly senior engineering position.

When they sent me the details for the on-site they sent me a role two levels lower. When I asked about it I was told the Director of Engineering felt that was a suitable role.

I withdrew from the process at that point. I was pretty bummed as I was super high on Optimizely back then. But I knew enough about myself to know that wasn't a good way to start a job (assuming I got an offer).

Was that the one where Dan told people that they were traitors for wanting more cash instead of stock, not super long after some of them cashed out some of their equity?

Surely you're joking, Mr. Feynman. (Sorry, I've kind of always wanted to be able to say that in casual conversation and not have it be a total non sequitor.)

But, seriously, your description does sound exactly like a company on the decline. I couldn't blame you for bailing. What do you think the first signs that things were terminal there?

Speaking as a customer, it feels like this is exactly what is happening to Mode Analytics right now.

As a customer of Mode, why not give Taplytics a shot? :)

That's the phrase I was looking for. Their sales process is impossible.

They appear to have become a great example of why the small businesses I run typically just walk away from any service we were potentially interested in using if we see a pricing page containing the word "call" but no actual pricing. If you're going to aim for high-touch enterprise sales, that's your choice, it's your business. However, the chances that you will then provide either acceptable quality of service or good value to anyone on the smaller end of the scale tends to zero IME, so it saves everyone time if we look elsewhere immediately. The problems start if it turns out that these companies aren't actually generating enough value to justify the enterprise-level costs either.

For example, say you're running a tool that allows people to quickly experiment with multiple versions of their web site, measure some quantifiable success rate for each version, and perform some basic statistical analysis to guide future changes and improve conversion rates. A basic but useful version of this tool can be implemented in a few days by one competent developer and one competent statistician; I suspect quite a few people reading this discussion have done exactly that. Polishing the tool might take longer and improve its utility somewhat, but it's not as though it's using some secret technique that no normal business can implement for themselves in-house.

At the mostly-self-service end of the spectrum, it might still be worth customers spending a bit of money on the pre-existing tool you make to do that job for them, because you're really competing on immediacy and convenience as much as technical capabilities. At the enterprise level, your competition could instead be some in-house team or some freelancer or agency being brought in from outside just to develop a tool directly for your customer. If they're potentially doing that at a cost less than just the first year of annual fees you're demanding up-front, and according to the customer's exact requirements, both of which seem quite plausible in a case like Optimizely's based on information in other comments here, what exactly is your sales pitch?

When I used to work for one of the UK’s largest social networks, I spent a long time researching optimisation platforms. I’d used Optimizely before and liked it, but when I saw the pricing table had been replaced by the dreaded ‘Call’ CTA I knew we were in for a bad time.

When I finally negotiated the rigmarole of callbacks and salespeople, the quote we received was so ludicrously high that there was not a chance that it was ever going to be worthwhile. Especially considering their old self-serve model was pretty good value and the horde of functionally identical and much cheaper competitors.

That's really interesting. I work along side Optimizely in the analytics field and I remember that moment - I used to email into support@ to ask about stuff to help improve data across our platforms, and always had no problem. Almost over night the email support was shut off (in support of optiverse + partners, a route I totally get when you're trying to move upmarket) but it felt really forced, really fast and I think they could have done a better job ramping up enterprise without slamming all the self-serve and free customers.

My company is going through a similar phase of trying to move more up market, and I'm glad we've tried to keep the free/self-serve tiers explicitly because we think they build good mindshare.

If you can share, what was the dishonesty you're writing about? I can't tell if you're saying it was fraudulent dishonesty or self-delusion (where you think you're in a better position than you really are).

And do you know if the self-sever market was drying up for Optimizely in 2015? I assume they wouldn't abandon it if it was growing at a decent rate.

My impression is Optimizely never crossed the chasm. Huge following with VC funded startups and early stage startups but never crossed into "Google Analytics" territory where every company with a website was using it.

Slowing down users meant higher prices to sustain VC promised growth. Higher prices meant enterprise sales. And it went down from there.

I'd say in the early days they were on the way to getting that mindshare. I had SME clients using them, where VWO was cheaper but they didn't like using VWO.

When Optimizely hiked their prices and lost the smallest plan, all these clients went elsewhere. I'm sure their contribution was noise to Optimizely's turnover, but the awareness of what was possible with A/B testing and the way they'd tell their friends about Optimizely and what they'd just done on their website - you couldn't buy that exposure.

Yeah, I agree. I think the use cases weren't substantial enough so people just didn't use it enough to justify subscriptions in most cases. This means high customer churn, especially if they were selling to customers based on strength of their name (which I think they were, to digital marketers who conned themselves into believe it was a product they needed). They received funding from a PE firm (Insight Partners) who were probably eager to get a return.

> The Episerver acquisition is indeed a bad exit, and I think I will lose >$100k in stock I exercised

Based on what information? So far, all that's been publicly confirmed is that the sale price was below $600M, which presumably leaves opportunity for your shares to be worth something.

GP probably got information about the share price offered from current employees and did the math. Once the acquisition is finalized, they'll receive more details since they are a shareholder.

Employees don't know share or exit price yet. Won't be announced for a few more months.

However, if the OP is speaking the truth about the timeframe he got shares from, he is guaranteed to be up. There are definitely people who lost money on this deal, but definitely not Series A people.

Worth noting that Optimizely is the A/B testing tool of choice for donaldjtrump.com.

This is unfair. That contract was sold to the Republican National Committee 3 years ago. They also sold to most of the democrat campaigns. I'd be careful about any business with over 1,000 customers, chances are they have a few shady clients in their portfolio.

To be fair, there was a pretty vigorous internal debate about what to do about that a couple months back. There's a huge segment of the employee base who were advocating for canceling the contract with the RNC (the Trump campaign piggybacked off that).

Wow. I interviewed there in 2015 and got turned down. Wasn't a great interview experience either. Bullet dodged, I supposed.

Me too - super arrogant. While I clearly wasn't what they were looking for, I had a lousy taste in my mouth after that experience. I still remember an awkward moment when I answered a question and the interviewer circled back to remind me I hadn't fully answered his question (he was right, but it just felt unnecessarily didactic).

I wonder how Google Optimize factors into this. Provided its a free service, it seems like Optimizely may have had trouble offering something unique to the self-serve market over something that is completely free. Similar to how it seems Dropbox has less to differentiate itself from Google Drive and other similar services these days.

I think Google is less of a threat than many believe because Google products have to address a Google-sized market which leaves tremendous room for competitors. If you're going to go straight up against Google then, sure, you're going to get clobbered.

I initially misread the title as "optimized to be acquired [..]"

Maybe my serendipitous reading explain your observations of what happened to the company.

Love these insights

Why Stripe will likely win: https://news.ycombinator.com/item?id=24067211

Continuing self-service while expanding "up market" into the enterprise. If AWS can be self-service, pretty much any service can be.

Stripe may expand "up market" at some point, but at the moment they're pretty enterprise unfriendly and don't seem interested in becoming enterprise friendly. You can't pay for phone support, their PCI compliance can cause some enterprise customers to blink and even if you're funneling millions through them they won't negotiate on price like other payment gateways. Also many of their more advanced features, just aren't that well implemented or documented (think connected accounts, etc) and since those cases aren't as heavily used we've had to side-channel to a C-level to get an issue expedited after bouncing around support for a show-stopper bug.

Additionally as a sidenote, that market is quite crowded with a LOT of choices. This is certainly not a winner take all industry, there are literally 20+ choices that will be reliable. Typically most large enterprises will end up with a vendor that will give them a good deal on rates, which isn't Stripe.

Appreciate the feedback. You can pay for phone support (indeed, you get it for free, though you can pay extra for a premium support package if you like). We think that our PCI compliance functionality is best-in-class. And we do negotiate price for larger accounts, as indicated on stripe.com/pricing.

More broadly, Stripe now works with a long list of businesses that are processing more than $1B/year or more, and that list is growing quite quickly. Indeed, there are more enterprises using Stripe than Adyen, which is often cited as an ostensibly enterprise-focused competitor. Larger companies using Stripe include Amazon, Shopify, Instacart, and Peloton. (There's a longer list at https://stripe.com/customers). That's all to say: we're very invested in this enterprise thing.

If any enterprises you work with have had a bad experience, would welcome any details. [email protected]

As someone who recently oversaw the transition from Zuora + Authorize.net to Stripe for a business in the eight figure a year range, can confirm.

Stripe worked with us on pricing discounts (over $150k per year in savings by switching from our previous set up) & the enterprise support is absolutely top notch. I literally could not be happier with the service.

This is different, both Stripe and AWS users are developers.

I don't know how you can be so sure that Stripe will win, Adyen is already on the enterprise space, and they are a bigger company than Stripe.

> Continuing self-service while expanding "up market" into the enterprise.

Things are more complex than a sentence, the whole company needs to operate differently https://blog.luap.info/why-most-saas-companies-cant-be-succe...

Stripe users are also anyone who wants to run a website on Wix or Squarespace or WordPress/WooCommerce and want to sell things. I have personally seen people that can’t spell “HTML” successfully set up basic eCommerce sites and make money off them. There is zero reason to pigeonhole Stripe as being for developers only any more than Square, etc.

This description absolutely nails Foursquare as well.