High Impact #3: How Jeff Diana Helped Turn an Insurance Company into a High-Innovation Business

April 4, 2023

min read


Kerry Wang

Welcome to the third installment of Searchlight High Impact interview series, where I shine the light on People and Talent leaders and the projects they’re most proud of. My intention is to connect a clear line between people work and business work, as well as inspire future change agents with impact projects they can use themselves.

My esteemed guest this time is Jeff Diana, CPO at Calendly. I’m especially excited to share how he accomplished enterprise-wide cultural change in less than two years. This interview could easily have been four separate ones, but ambition is the name of the game. Let’s dive in!

The Guest

Jeff Diana is the Chief People Officer at Calendly, the scheduling platform that helps customers close deals, land candidates, build relationships, and grow their business faster. He was formerly a Chief People Officer at Atlassian, Chief Human Resources Officer at Safeco Insurance, GM of HR at Microsoft, and an HR leader at General Electric. Throughout his career, he’s also been a board member, advisor, investor and growth consultant for a wide range of startups including Tribute, Behavox, Sapling, and yes, Searchlight.

The Situation

In 2006, Jeff was hired as the Chief Human Resources Officer of Safeco Insurance alongside a CEO brought in specifically to turn Safeco into a growth and innovation-oriented business. Since Safeco was a long-running historical company in a field not known for innovation, this was a significant challenge. This post will explain how he supported this shift. 

Inertia was working against him. As an insurance company, Safeco was very efficient. But it wasn’t innovative. Many of its efficient processes had existed for decades and long-running teammates were set in their ways. The current HR team (especially outside of headquarters) were very focused on supporting teammates and building relationships, but didn’t have the right skill set to drive innovation. Many people leaders face similar challenges when tasked with changing a deeply-ingrained company culture.

The Goal

Mold a 200-year-old insurance provider into a growth and innovation-focused company. This involved changing hard structures (organizational design), soft structures (company values) and people.

The Process

To create company-wide culture change, Jeff and his team followed a process that broke down the task into manageable steps across Safeco’s values, organizational structure, incentives and their HR department. 

  1. Define and implement new Leadership Traits. Jeff and his team defined new Leadership Traits they believed would instill innovation-focused values at Safeco. They chose to call these values “Leadership Traits” to encourage every teammate to see themself as a leader, which was not a common mindset in insurance companies. They communicated this with the team and explained what they were, how they worked in action, and the business impact they had. To ingrain them into the culture, performance feedback was shifted to reflect these new traits and a peer-to-peer recognition program allowed teammates to congratulate one another on living out these values.
  1. Create an innovation-focused organizational structure. To meet a new mandate to come up with 2-3 entirely new products, Jeff helped launch an incubator to be run like a startup within the enterprise. This entailed thinking through the physical space, the cultural norms, and the talent who would move into this business.
  1. Change how teammates are rewarded. Jeff’s team changed Safeco’s defined benefit retirement plan to a traditional 401k to free up an additional $25 million. That money was then used to fund Safeco’s first ever stock ownership program so teammates could be real equity owners in the upside created by their innovation. This was the biggest compensation change in 90 years at the company.
  1. Hire a world-class HR team to lead. Jeff quickly realized HR folks at Safeco’s remote sites didn’t have skills to drive an innovation-business, and he made the decision to let all of them go. This change shook up the business in a good way and showed everyone that there was a different way of doing HR (and cemented in people’s minds that things were going to change).

All together, these steps changed the company’s values, structure, incentives and leadership to focus on innovation.  

The Secret Weapon

Jeff and his team’s secret weapon was the startup incubator they created. It was much easier to get a 50 person organization into a high-growth, high-innovation mindset that it was for a 5,000 person company. Then the incubator served as a model for the rest of the company on what a high-innovation company looked like.

Jeff and his team did a private IDEO tour and met with their creative team to help design their new innovation org and incubator. The physical space was set up in an open layout, teammates rang a gong whenever someone came up with a new idea, and people were paid very differently.

Once the incubator was up and running, they had some of the longest-running Safeco teammates rotate through the incubator to give them hands-on experience in that culture. It was instrumental in pulling the rest of the organization along on their innovation journey. 

The Business Impact 

Jeff’s work added real shareholder value leading to its sale to Liberty Mutual for $6.7B dollars. Liberty Mutual specifically cited Safeco’s innovative people and culture as a valuable asset. Jeff was able to negotiate good assurances for Safeco teammates after the acquisition, and many of his teammates chose to stay and keep working on the same problems in this new context. 

All these pieces of Jeff’s process worked together extremely well. Their startup incubator created two new products for the insurance industry: one for people moving into a new home (which research showed was the third-most common traumatic experience for people after death and divorce) and one that tracked movement in a car and driving trends (which has since become common but was new at the time). 

Lessons for the Future

Like many people leaders, Jeff is now focused on optimizing teammate performance in a remote-first environment at Calendly. Despite a more difficult market now, Calendly is still working on familiar issues for any high-growth company, like:

  • Doing more with less incremental spend.
  • Adjusting for culture shifts as the company grows. As they get larger they need more performance management, more process and more leadership.
  • Getting new teammates up to speed in a high-growth environment (they’ve doubled their headcount in each of the past three years).

Final Advice

Always keep your focus on business results. You must have engaged and energized people to drive success, but the role of the Chief People Officer is not to make happy people. It’s about creating a winning business that supports everyone - shareholders, customers, and the people who work there.

Kerry Wang

Co-Founder & CEO

Kerry, our CEO and co-founder, merges Org Psychology and Computer Science expertise. Passionate about people, psychology, and tech, she enjoys weekend reading and reality TV.

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