Catch our very own Gary Benitt on the TenOneTen podcast. Gary talks about starting four companies, three of which were in the customer service space. The last one, Assistly, had Howard and Tom as angel investors. They exited to Salesforce about 18 months afterwards, and Gary spent nearly four years running the company Salesforce acquired.
In addition to starting four companies, Gary did a lot of Angel investing while at Salesforce. He loved meeting with founders and hearing their stories, but realized he couldn’t be helpful while running his own company – he didn’t have the time or the mental capacity for it. That said, Gary really wanted to be helpful, which led him to pursue investing full time. Tom and Howard, through their angel vehicle Social Leverage, invested in Assistly, They later raised Fund I while Gary was at Salesforce, and Gary joined them for Fund II at the end of 2014.
One of the key insights from his time with Assistly/Salesforce was the understanding that people really want modern UX and UI. When it comes to customer service and support solutions, companies really want easy administration and configuration when setting up the solution. Specifically, modern, easy to use software that allows for social channels at the core of it. It’s important to be truly omni-channel, meaning you could send an email and say, ‘Oh by the way, I’m leaving my desk, can you text me?’ Customer service reps should have the ability to instantly change the conversation. Everything is in one view, even though you’re using multiple applications. This approach lets reps stop obsessing over cases and interactions, because they’re sub-components; and what you really care about is the customer.
When it comes to sales, Gary tells his founders not to hire a VP of Sales early. Instead, focus on the front lines – selling, understanding objections and understanding what’s working. He also recommends hiring your first four or five AEs before hiring a true leader. The reason is, if you’re hiring someone at the VP level, the right person should be able to scale something that’s already working versus figuring out how to make something work.
Gary also tells his founders to hire multiple AEs at once, especially when they first begin. They’ll say, ‘Oh I’m going to hire an AE’ and Gary tells them to hire two or three. There are multiple reasons for that, churn being the obvious one.
An even better reason for hiring multiple AEs is you’re not really sure in the early stages of a salesperson. Are they doing great? Or maybe the product isn’t in the right place? If you have those salespeople competing against each other, you’ll get a better sense of whether or not it’s a particular person who maybe isn’t doing a good job and someone else could do much better. Your expectations will reset. The competitive aspects of sales come into play. Salespeople want to win. And what are you winning against? Well, if you’re beating the salesperson sitting next to you, then that gives you a more defined target to go after.
Gary also discusses the two primary categories Social Leverage invests in: Fintech and Enterprise SaaS, with the latter being his area of expertise. In addition to investing in horizontal SaaS like customer service, Gary has also recently been investing in vertical SaaS companies that are solving industry specific problems.
The last category Gary invests in is kind of everything else, but tends to focus on what he calls ‘more consumery’. These would be products he can understand, play with, and be helpful with. A good example is Manscaped, a CPG product for below the belt men’s grooming. Gary thought the founder was fantastic and had a really great vision. It turned out to be one of his fastest growing companies.
You can listen to the entire episode here.
