S4 EP52: Scaling without compromise and being comfortable with change - Vikki Caruso, Chief People Officer, Clearcover

The Insurance Coffee House

“We learned a lot early on and we continue to learn as we scale the organization remotely. Some of the key things are over communicating. Sometimes you're having a few more meetings to feel that personal connection”, says Vikki.

“We've set up mentor programs, our summit leadership where you're partnered with another leader in the organization.

If you're interested in growing your career, whether that's within your team or learning more about other teams, they have one-on-one mentoring sessions and group mentoring sessions.

We formed, ERG groups and really started making sure that we're celebrating the diversity of our employees. All of those things help people feel really connected.”

On the podcast this week, Vikki shares her 25-year HR career journey.

“I began in the recruiting space, before I expanded my responsibilities to include employee relations, compensation and benefits, succession planning and employee engagement. I eventually made the shift from the staffing industry into the start up space.

Someone recommended I connect with Kyle, our CEO. I did not think I was going to be jumping up and down about insurance. Shortly after I met him, I, I came home and I said, ‘Wow, I'm actually really excited about insurance.’”

Vikki joined Clearcover as VP of People in 2019. At that stage the business had 45 employees. She became Chief People Officer in 2022.

As an insurance company, Clearcover has scaled to over 500 and is using technology to transform customer experience.

“The tech start-ups I've been part of, the technology was the actual product. Insurance, that is ultimately what our product is, but the technology behind it is really what's driving us to be different.”

Vikki explains what’s enabled the business to scale so successfully.

“We launched in California, then in Illinois. Once we got through those first two, we really started launching all over the US, trying to scale the organization as far as, ‘How do we get into more states? How do we offer Clearcover to more customers in as many places as we can?’

In the beginning, we outsourced our claims and our customer service teams and since then, we've brought those in house, which has accounted for a lot of our growth.”

As for future plans, Vikki says,

“The goal hasn’t changed. Our mission is to be a generational insurance company, powered by leading technology and innovation, really leveraging AI to do that as well.

Offering an experience to the customer that is seamless and hopefully less stressful for them if they have a situation where they are in an accident.”

With Clearcover’s headcount having grown tenfold, Vikki discusses building an HR function to handle the business scale.

Vikki highlights how Clearcover have embraced a remote-working model without compromising the cultural values.

She discusses how the remote model has impacted hiring and impacted diversity.

“Truly, it's really opened up a world of opportunity for us by being able to hire remotely. It's helped us diversify our workforce. We continue to strive to improve at all levels of the organization, but we've made tremendous strides because we’re able to recruit people from all over the United States. We aren’t limited to a small talent pool in one geographical area.”

Discussing how team members are encouraged to switch off in a remote world where the boundaries between work and down time are sometimes blurred.

“When employees start, they get a stipend to set up their workspace, to make sure they're set up for success and they have a space available to them.

We understand that people have kids, dogs, spouses that are working in their home too. It's helping people find that right balance. Maybe having a headset is super important to them or being able to work from a coffee shop during a crazy period of the day. Those are things we can be flexible with when we're remote.”

However, Vikki doesn’t discount the value of in-person and explains how Clearcover facilitate employee meet-ups in common locations.

“We do try to get people together. It's not always easy. What's great is we found hubs of people that get together on their own. We provide a map so people can see where others are located.”

Vikki emphasizes her advice to leaders coming for interview at Clearcover.

“You have to be flexible and open to change because even though we're five years in, we still feel like a start-up.

And gives her advice to her insurance industry peers, seeking to hire and develop the very best talent.

“Sometimes, as you get into more senior roles, you think, ‘I'm not doing some of those things, but it becomes just as critical.

Strategy is super important, but can you help a manager who has an employee that's struggling?

Great leaders have to develop great managers who can be future leaders, all the way down.

If you’re a manager, are you developing your supervisors? If you're a supervisor, are you developing your team?”

When working with an external insurance executive search partner, Vikki highlights the importance of being an extension of the Clearcover team.

"The recruiting partners you come back to over and over is when you have that true partnership. It's not just about, ‘I got a candidate for you’. It's, ‘I have a candidate that is perfect because they align with your culture, your vision.’ They know the criteria.”

As for the one lesson her career has taught her, she wants everyone to learn.

“It’s OK to fail. And if you can, fail fast and learn from it.

If you talk to somebody and they can't give you an example of a time they failed, I don't believe it, right. We should use those moments as growth opportunities. Do you learn from those mistakes and how do you do it better next time?”

And in closing, Vikki urges those looking for a linear career path, that a fast-moving, tech-driven business like Clearcover, might not be the best fit.

“If you thrive and get excited about getting exposure to new things and new areas that you would never get exposed to, then you should definitely reach out.

Connect with Vikki Caruso on LinkedIn or find out more about Clearcover

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