Seeding and Selling Asana

In December 2019, Oliver Jay, Asana’s Chief Revenue Officer (CRO), was reconsidering his go-to-market (GTM) strategy. Asana was cloud-based work management software that enabled users to break up projects into discrete tasks that could be assigned, scheduled, and tracked on a single, integrated platform. Jay was wondering how to increase annual recurring revenue by year-end 2020. Just three years earlier, when Jay joined Asana as its first CRO, thousands of companies were already using free and paid versions of its software. Since Asana was a software-as-a-service (SaaS) offer, all a new user needed to do was to create an account. This meant individual users and teams could onboard easily and initially for free, using an array of self-service tools, without purchasing approval from their IT departments on conversion to paid subscriptions and without initial sales support from Asana. This mix of free and paid users proved sustainable and profitable for Asana. However, reaching senior directors, vice presidents, and executives of potential client companies to drive larger, enterprise-wide adoptions was a challenge for the Asana sales team. Jay’s desire to improve sales performance led him to a novel concept: to structure the sales team based on where customers were in their adoption cycles with Asana—that is, to organize sales by stages of the customer journey rather than by the time-honored approach of organizing by account size (e.g., SMB, mid-market, and enterprise). Was this radical idea the right structure for Asana to reach its revenue growth goals—or was it fraught with too much risk?