Customer Success Leverage In Bottoms-Up Sales with Jason Mills (Expensify)

Customer success leverage can sometimes be the difference between a winning and losing SaaS business when operating in low ACV environments. The theory is basically that if you are selling software at low prices you must be focused on extracting the highest degree of leverage out of your sales, marketing, and customer success teams to build a highly efficient business that wins. To discuss this topic we brought on our good friend and ultra-marathoner Jason Mills from Expensify to talk through how his business gets leverage through the customer success team. Expensify is a great example of how to build a wonderful engine here with millions of happy customers already served. Jason has learned a ton about this over his almost 4 years with the company. He was one of the early sales hires and really drove home the notion of gaining a lot of leverage out of the customer success team.

We start the discussion on what specifically we mean by customer success leverage and how Jason and his team think about this topic. We really focus the podcast on how Expensify gains leverage without a substantial amount of money to spend. Jason talks about what makes a great customer success person that can give you leverage and lays out how the team works at Expensify (it is quite unique). We then move into how the founding team thought about this from the beginning of the company and how it has evolved over time. Next, we cover some of the thinking around the CAC / LTV specifics of their business and how Jason thinks about spend within his team here. From there we move into the specific tech stack that Expensify uses on this front and some of the tips and tricks that Jason has learned along the way when thinking about how IT can give his team leverage. You will be surprised to find that the company really only uses two pieces of software to handle all of the needs on this front (talk about focus and leverage!). We move on to some thinking about cadence of customer communication as well as how to train customer success team members to think outside the box and give any SaaS founder leverage. Finally, we close on Jason's thinking about how product and customer success are aligned at the hip in his organization and Jason closes with some tips and tricks on gaining customer success leverage in any low priced SaaS business. We hope you enjoy and thank you for listening.