Will went up market because "there's a lot more money up market than there is in the SMB type of a space." On sales he had no background — "never done enterprise sales" — so he "jumped in with both feet" and figured it out: conferences, "a specific type of LinkedIn outreach," and inbound.
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Will says SMB can be very successful but "it's very hard to get right" because it requires a lot of distribution and resources. Phonely worked best when they could give customers the support they needed to get up and running, so up market "just made more sense." On the sales transition itself, this was "all net new to me" — he'd never been a salesperson. What worked was "going to conferences, a specific type of LinkedIn outreach and then inbound," plus getting in the press and generating hype while knowing they were solving a real problem.