It's a super interesting space, and it feels like there's new companies every day. Definitely tons of promise. One thing I think is particularly challenging is the inherent variability in the size and structure of sales & marketing teams. Big players in the space try very hard to be one stop shops, which makes it hard for newcomers to find a niche to really dominate or a price point to compete on for a given segment.
For context I'm marketing guy in electronics manufacturing, where the sales cycle is extremely long (~6 months), and involves a huge number of decision makers. One new customer a year is par for the space, one a quarter is performing very well. Our sales team is small, and our marketing team is smaller, but that's fine because the set of companies we're a good fit for is a small target to shoot at in the scheme of things.
Given all that, the two huge priorities are lead qualification, and time management. The former is pretty straightforward, I'll throw money at anyone who can give me good info on decision makers at the companies active on my site at any given time. As you mention, B2B relies on sales, and at least for EMS where I work, anyone who's based in America and survived '08 is probably good at it. In that regard, things like AI generated scripts/nurturing lose appeal because proven strategies exist, knowing who to call (and more importantly, when) is the name of the game. My favorite in that regard is Mattermark. Their sales team is really good, by the way, interested people should sign up for their trial to at a minimum pay attention to what they do.
There's two parts to the time management aspect as I see it. The first is that upkeep of a CMS/CRM becomes a big task in itself, and nobody wants to do it. I want to be working on scripts/nurturing flows for the sales team or making X piece of marketing content, not staring at dashboards all day. Sales wants to be reaching out to their leads. Some new tool that adds a slight twist to functionality that exists in a more all in one system becomes hard to adopt. If something isn't very obviously better at a given function than part of a big CMS/CRM, or provide some new functionality I'd like to have and can't use with my primary tool, it becomes hard to adopt. For me right now that's Mailmunch for newsletter subscription pop forms (sorry world, I'll stop using them when people stop filling them out insanely frequently).
The second aspect to the time problem is the increased adoption time that will happen across generations in the office. For instance, a senior saleswoman where I work (who's awesome/great at her job) gets thrown through a loop by HubSpot UI changes, and basically doesn't touch Slack. From that perspective, new tools that a salesperson interacts with need to be super smooth to adopt, nor not be very 'user facing'. And please, dear god, don't make me schedule a 30 minute demo of the product for trial access.
> But for folks with a predominantly technical background, sales as a function, remains at best a mystery, and at worst something they make fun of
I think spending more time on something like Salesforce, Marketo, HubSpot, etc. would help here. Which may, and probably does happen, I just don't know how common it is. Either way, having a good understanding of what the big tools can do in terms of automation, prospecting, analytics, and all that is valuable.
Of the 4 in this batch I like Riley the most because of their mention of nurturing/drip campaigns, which are critical in industries with big contracts and long sales cycles. Scribe is a close second, but I'm skeptical it's that much better than functionality of bigger CMS/CRMs to justify onboarding/upkeep time. Upcall makes me uncomfortable, but my industry is extremely niche so I'm biased. Clover might be cool, but that landing page to watch the demo vid isn't very nice. Best of luck to all of them though, it's a great space to be in.