We feel stuck with Salesforce because alternatives seem geared for smaller organizations (we are 450 people). Would love to hear thoughts.
To answer the first part of your question, I'd have to rely on my opinions and those of others, which probably aren't very helpful. In short, Salesforce doesn't have to be user-friendly. I hear they spend more money on selling it (through commission etc) than they do on R&D.
The second part I can answer with some authority. HubSpot Enterprise is a credible alternative to Salesforce, and we have implemented it for large, complex organisations.
There are only two scenarios in which we wouldn't recommend moving away from Salesforce (or any CRM for that matter):
1 - User-adoption is high. This is the biggest problem in CRM, and if you've got your reps using it consistently and the organisation is getting value from it, don't switch. 2 - You've got highly complex integrations with bespoke back-office systems that took a lot of time and money to build (and nobody wants to go there again).
So if you've got problems getting the reps to use Salesforce properly, and it's possible to replace it without carnage in the back office, I'd recommend evaluating HubSpot before your next licence renewal is due. Talk to a HubSpot Solutions partner - there are a lot of good ones out there (we are one).
There isn't a huge amount of content out there about HubSpot Enterprise (Enterprise Growth Suite is the product you want for the size of the team you are talking about), because it's only really been ready for that for the last year or so. HubSpot spent almost $100m in R&D in 2018, with the majority of that on the Enterprise tools and CRM product.
User-friendliness is what HubSpot is all about. Getting user adoption sorted quickly is the key success factor for your implementation.
If I can wrap up with a top tip, it would be to choose a pilot group and start with the Email Integration and Activity Stream first. Once they get their heads around that, you'll be able to rapidly accelerate the use of all of the other tools.
Every time Salesforce adds functionality to the platform, it increases the complexity users have to deal with.
The Salesforce platform has to be flexible enough to accommodate many different use cases, many different types of organizations, and many different requirements.
In order to do this, Salesforce provides enormous flexibility, and this often means users have to wade through many different options and ways of doing things to find what they need.
Complexity can (and should be) be avoided in a few ways.
Use permissions and roles to lock functionality down. Not all users need access to all screens. Anything you can do to simplify work flow is a good investment.
Next, if your users aren't getting what they need from fewer choices, then customize so they can. That is the beauty of Salesforce.com
Salesforce has a robust ecosystem of consulting partners and apps that help you get exactly what you want from the platform. You can always work with Flow Builder for custom workflows or Flow to bring in external data.
Or, an appexchange tool like Work-Relay provides a simple framework for building work management solutions that shield users from the underlying complexity of the Salesforce platform.