Insights | Podcasts

BC Startup Sales Podcast – Sales Model Evolution From Freemium To Enterprise with Oliver Jay (Asana)

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Michael Brown

April 25, 2020
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This week, the Bowery Capital team hosted Oliver “OJ” Jay, Head of Global Sales at Asana, to discuss “Sales Model Evolution From Freemium To Enterprise.” For those who don’t remember, we had our old friend OJ on the Podcast to talk about selling SaaS overseas when he was at Dropbox. Today, OJ runs the Global Sales organization at Asana. Asana provides an application that makes it easier for teams to track their work with greater clarity, accountability, and efficiency.

Oliver Jay is the Head of Global Sales at Asana. Prior to Asana, he scaled the Dropbox sales team from 20 to 100 people and across multiple geographies. Previously, Oliver worked at Morgan Stanley and New Enterprise Associates (NEA) where he invested and worked alongside entrepreneurs in consumer internet, cleantech and enterprise SaaS companies. Oliver earned his B.A. from the University of Pennsylvania and his MBA from Harvard Business School.

During the Podcast, we had a unique conversation about lessons learned from major SaaS companies growing from freemium up to small and medium sized deals and then to large enterprise deals. First, we ran through the movement from free to freemium and how to think about what matters when making this decision at your own company. Usually these are organizations with a ton of free users and so coming up with an informed decision on when to move into freemium is super important. OJ talked a lot about his experience at Dropbox and now at Asana thinking about how they made the decision as well as product, pricing, competition, and other elements to move from free to freemium. OJ even spoke about how to set up your revenue organization correctly in a freemium business. Second, we walked through how a business should think about moving from freemium up to larger deal sizes which we call SMB for the purposes of this Podcast. OJ runs through an exercise that he did at Dropbox called density mapping and how organizations should use this to make product decisions around moving upmarket. We close on this segment talking about the CAC / LTV ratios of sales organizations and when to move further upmarket into what is commonly known as the enterprise segment. Third, we walk through probably the trickiest stage which is thinking about the option to launch into the enterprise segment (F2000 in our example). This segment is a different muscle altogether and OJ walked us through how to really change and build your organization to get this right. He sees most founders fail here and talked a lot about the main lessons learned over many years. We closed the Podcast with some points of view on who has done well moving from freemium to enterprise: Zendesk, LinkedIn, New Relic, and Box were some that OJ named. On the downside, we talked about Evernote and the danger of giving up too much value up front. All in, it was a great Podcast chock full of information and thinking, so give it a listen!

If you liked “Sales Model Evolution From Freemium To Enterprise” and want to read more content from the Bowery Capital Team, check out other relevant posts from the Bowery Capital Blog. If you haven’t already, subscribe to the podcast to get all our new content each week!