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


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 impressed the functional interviewers are with a candidate, the values interviewers always maintain a veto over hiring.

2) Don’t ever not want your culture to change, even when you’re loving it just the way it is. “Your culture is going to change,” said Raimondi. “Your job is to figure out how it changes for the better.”

3) Don’t fall for the myth of the “magical unicorn.” According to Raimondi, this has nothing to do with billion-dollar private valuations but is, rather, a function of wishful thinking along the lines of, “Gosh, if we just hired this one person, all my problems would disappear.” Instead, ask what does success in hiring and culture-building look like in terms of specific business outcomes (customer growth and satisfaction, revenue growth, cost efficiency, market expansion, innovation) and leadership outcomes (team growth and engagement, culture addition, performance, talent expansion, creativity).

4) Hire to drive outcomes and prioritize business impact. Think ahead six months to a year and ask: How will I know a candidate was the right hire? How will business outcomes that they’ve driven be measured, along with outcomes relating to the team as a whole? Is the team healthier and more engaged, and capable of attracting people who couldn’t be attracted before?

Raimondi stressed the importance of mapping where recruiting time is spent against business impact. “If a data scientist is a hard-to-hire role with huge business impact,” she said, “you should just be recruiting all the time — meeting the best data science people out there, having them get to know your company. They might not be ready today but in six months something might change.”

5) Rethink the “must-have” checklist. Raimondi recalled a situation at Zendesk where B2B experience was seen as key to driving a desired outcome around recurring revenue. This assumption was revised, however, when it became clear that there were attractive candidates who had subscription-business experience from B2C. Amending the checklist, she said, not only helped realize a business outcome but “also enabled us to increase diversity and inclusion because the non-obvious candidates most often fit both of those and in fact, were highly motivated to step into new roles.”

6) Assign a test project or working session to get a sense of how a prospective recruit works. Ideally, it should focus on a problem that’s currently being tackled by your team and for which the candidate would share responsibility, if they were to be hired.

7) Avoid time-consuming “onesie-twosie” interviewing, especially when it comes to sales and customer support roles. After receiving funding and the pace of hiring accelerates, have people come in batches for interviews and onboard them in batches.

Making assessment actionable

Applying frameworks and intentionality is just as important in evaluation as it is in hiring. The crucial questions, according to Raimondi: How do you decide on whom to invest and what the right investment is? Her framework for making assessment actionable, is based on determining which of the following buckets team members fall into:

  • Leaders make positive things happen — connecting ideas, people and initiatives both in and outside of the team. They anticipate what’s to come and get in front of it.
  • Keepers improve the team, come up with good, new ideas, have initiative and drive from start to finish.
  • Doers get things done, engage with the team and demonstrate reliability.
  • Watchers wait to be told what to do and don’t add to the team or conversation.
  • Whiners complain more than they contribute, distract the team and are a source of managerial exhaustion.

Watchers and whiners are the “squeaky wheels” who detract from culture and other people’s ability to get things done. Ask yourself: Can you get them to become additive? If not, Raimondi advised, don’t delay making the hard decisions to exit them.

Your culture is going to change. Your job is to figure out how it changes for the better.

Another tool in Raimondi’s kit: using team assessment to create alignment. Focus on:

1) Strategy: deciding and communicating why and where we win

2) Innovation: continually building and developing what sustainably differentiates us

3) People: understanding, attracting and retaining who we need to win

4) Execution: having an operational cadence for how we plan and follow-through

Conducting quick surveys soliciting responses to how individuals and teams are performing based on these components is a great way to spark conversations about gaps in perception, said Raimondi. She recalled having a CEO and his team do the exercise. “His assessment was like, ‘We’re nailing it on strategy and people. I need them to be more innovative, and execution needs to improve. And so, I’ve been pushing on innovation but no one seems to be listening to me.’ ”

“Then I had his team do the same assessment,” Raimondi continued. “They thought they were great on strategy and doing pretty well on innovation. They thought the big focus area was people.”

The upshot was to be able to narrow the focus on where the gaps in alignment existed and make the necessary adjustments to close those gaps.

Raimondi also advocated for utilizing pulse or engagement surveys asking individual team members questions such as: Would you recommend our company? How proud are people to be part of your team? What are you most excited about? What are you most concerned or confused about?

Mining these surveys for gold, said Raimondi, is crucial in startup cultures, where, typically, on a daily basis, there are “a lot of things going wrong” that can cause knee-jerk worries.

So it’s important to “shine a light on what people are excited about and what’s going well.”

Anne Raimondi’s talk was given at the 2019 Spero Ventures Founder Summit. Watch the full talk in the video below.



Spero Ventures
Spero Ventures

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