Anne Raimondi’s actionable culture kit to boost recruitment and performance

Guru’s Chief Customer Officer advocates for an intentional, systematic approach to curating talent and culture.

Spero Ventures
Spero Ventures
Published in
6 min readFeb 17, 2020

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Anne Raimondi, Chief Customer Officer, Guru, presents on the topic of “People & Culture” at the 2019 Spero Ventures Founder Summit

While most everyone acknowledges the importance of “culture” and finding the right “values fit” when hiring, sometimes the need to expeditiously fill a role can lead to a moment of, well, just this time. “It’s kinda not a great values fit,” the reasoning goes, according to Anne Raimondi, “but this person is amazing, skill-wise, and so we’re going to bring him in.”

In her experience, this seldom works out for the better. “Design systems and processes to avoid that,” she advised at the 2019 Spero Ventures Founder Summit, “because the times that we’ve had the greatest failure in any of the companies I’ve been at…is when we slipped on values.”

Raimondi is a veteran tech executive, investor and advisor/educator with experience building teams at eBay, SurveyMonkey, TaskRabbit and Zendesk. She’s currently Chief Customer Officer at Guru, and serves on the boards of Asana and Gusto. At the Founder Summit, she advocated for an intentional, systematic approach to talent and culture, encouraging founders in the audience to apply the same passion for bringing “exceptional solutions” into the world to “building a team and the kind of culture that you’re really proud of.”

Culture by design

Raimondi is less concerned with the attributes that define such a culture than with what goes into building it. Indeed, she observed, everyone recognizes a “good” culture when they see it. Same with a “bad” culture. But can a culture that inspires feelings of pride and brings out the best in people be designed?

Making the affirmative case in her presentation, Raimondi reached into her tool kit and shared insights for curating culture and making hires that boost the effectiveness and cohesion of teams. Some highlights:

1) Prioritize values fit. At Gusto, job candidates meet first with values interviewers. Only if the values fit looks promising does another round of interviews occur with people on the functional team where the candidate is being considered for placement. Regardless of how…

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Spero Ventures
Spero Ventures

Spero Ventures is an early-stage venture capital firm driven to deliver value to shareholders and society.