Sam Levy's first sales job involved a phone book, a rotary phone, and 200 cold calls for one yes. He was still in college when he started a telemarketing gig with no playbook, no CRM, no email. Eighteen months in, the company went public, and the telemarketing kid was sipping champagne in the boardroom. This episode reveals everything that happened between that room and the one he sits in now: head of go-to-market strategy and execution at Oracle NetSuite, running a business that's grown from $250 million to $4 billion.
Sam walks Devin through how to build a career in software sales, rung by rung: how to pick your first sales job and your first boss; why hustle gets you started but cadence gets you promoted; why the top rep usually makes a rough first-time manager. He tells us when to leave a job, when to let a rep go, and what to do with the lone wolf who crushes quota but poisons the room. Plus, a prediction: 90% of the next generation of software CEOs will come out of sales and marketing, not engineering.
Whether you're an operating partner, an SDR in your first seat or a CRO wondering what's next, this is the insider's guide to success.
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