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Jive Software CEO on Hiring Salespeople Dana Oshiro

Former Jive Software CEO and Heavybit Advisor Dave Hersh discussed how tech startups can “bake sales into their DNA.” Says Hersh, “There’s a right and wrong time to hire different types of salespeople…The tough part is that every one of them interviews well.” We sit down with Dave to learn about finding the right people for each stage of building a sales team.

The Initiation Phase

Hersh explains that during the early stage of your business, it’s best to hire people that are flexible, creative, and eventually willing to “work themselves out of a job.” At this early stage in a company’s lifecycle, startups are still finding a repeatable business model. Salespeople who are comfortable with field marketing can interact with customers and test a founder’s assumptions. Hersh often hires this type of employee under the banner of marketing or business development. His reasoning is that when a company is ready to build out its sales infrastructure, it requires a different type of sales leader altogether.

Infrastructure Building and Execution Stage

Hersh learned the hard way that while Senior Sales VPs might close deals, they’re often used to having pipeline tools, a proven process, and a slew of junior staff members building their decks. He explains that until companies have those assets in place, there’s no point in making that kind of hire. Instead, during the transitional infrastructure-building stage, companies should hire someone who has helped design the process of a major organization, but who remains scrappy enough to continue closing deals. This might be a Director-level hire looking to strike out as a leader and strategist in their own right. The foundational work done during this period is what defines a repeatable sales model and paves the way for companies to make more mature enterprise sales hires.

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