Leading With Trust and Customer-Centric Messaging to Drive Lifetime Brand Value
Andrea Collins is the Chief Marketing Officer at Hippo Insurance, where she leads the company’s marketing efforts, brand strategy, and customer engagement initiatives. Prior to rejoining Hippo in 2024, Andrea was CMO at Cowbell, a leader in cyber insurance, and previously held the same role at Flyhomes, where she helped evolve the homebuying experience by aligning marketing with product innovation and customer needs.
Andrea is recognized for blending creative storytelling with data-driven decision making, helping companies strengthen brand presence, accelerate customer acquisition, and drive business growth.
Andrea’s work has been featured in major media outlets, including The New York Times, Wall Street Journal, Fast Company, and TechCrunch. Throughout her career, she has built and led high-performing teams and earned recognition for her strategic insight, collaborative leadership, and passion for building brands people trust. She was also a Canvas Ventures Go-to-Market Council member, where she mentored startup founders on growth strategy and brand development. Currently, she serves as a board advisor for growth-stage startups, including Amplify Life Insurance.
The Continuum sat down with Andrea to discuss what she likes about the insurance industry, why she thinks the industry should move past fear-based marketing, and her advice for new CMOs.
We like to start our interviews by asking our guests how they ended up in marketing. Was this a career path you knew you were initially interested in?
No, I started out with a strong passion for journalism. I was always a strong writer and enjoyed it, but I also liked acting. When I went to college, I thought I would major in acting, but my mother—who was an English teacher—said, “No, you’re not, you’re going to major in English.” I started as a creative writing major but later switched to literature. It also enabled me to do my final year of school in Italy. I studied Dante Alighieri and several other Italian writers, but I also got an internship at a magazine there, where I really fell in love with writing.
After graduating, I moved back to California and got another journalist internship. I helped write theater reviews, which was so much fun and tied into my love of acting. It was a phenomenal experience, but I was sleeping in my aunt's spare room because I wasn’t making enough money. So, I started to write press releases for PR firms and eventually got a job in PR.
I enjoyed the work, but I also knew I wanted to move from the Bay Area to New York, expand my skills, and take on bigger clients. I joined a PR agency looking for someone to build creative marketing campaigns.
What were some of the memorable campaigns you worked on?
One of my biggest clients was Travelocity. I worked on that almost full-time for three years. I created grassroots marketing campaigns that blurred the line between PR and marketing. Remember, back then, things like flight alerts were novel. We created one campaign that we called “The Turkey Task Force.” We put people in airports on Thanksgiving to report live on wait times and crowds. The media covered it, but it was really a marketing campaign.
From there, I shifted my focus even more toward how to get content seen—using social media, SEO, and editorial strategies.
When you were in New York, you got involved with startups. What were some of the interesting brands you worked with?
I worked with a group of women who ran a Thursday night meetup for entrepreneurs. We got demos every week, and then some of us would offer some hours of our expertise to help get the new companies off the ground. It was all volunteer hours, but it was an interesting time and place. I wanted to understand how they were fundraising, how they were considering their hiring priorities, and what kind of help they needed to get to the next round.
One company I remember particularly well from the demos and advising days was KeyMe. These are kiosks that they put in grocery stores where you can print new keys. Locksmiths have always been tiny little shops in odd locations with weird hours. Putting them in places you already have to go was a great idea. It was fun to chat with the founder because the company had a product that you could touch and feel, which was kind of rare for startups. It did really well from a fundraising perspective and was fun to watch and learn from.
Many companies I worked with never took off, but there are some recognizable names that came through. That experience gave me my first taste of the startup world, where I discovered the thrill of building something new and meaningful. Despite the challenges and pace, it reinforced the value of working with purpose-driven teams and sparked my entrepreneurial spirit.
Your first role in insurance was for a company called PolicyGenius. Can you explain what they did and how you approached marketing in an industry that was new to you?
PolicyGenius was one of the first insurtechs on the scene. It was a referral-based marketplace, kind of like a Kayak for insurance products with a strong educational bend to it. We helped people understand what insurance products they actually needed and then offered a comparative policy rater to shop.
I was one of the company's first 15 employees and had to build our external communication and content channels. I led a team that built a content marketing program. We put out a magazine, blogs, and education guides, which helped us become a recognized and trusted source. SEO became a primary driver for that company's growth.
As for how I learned to market in an industry that was new to me, I think it’s always a combination of intuition and curiosity. At the core, marketing is about understanding your customer and what they need. From there, it’s testing, learning, and seeking the right information to help you refine your approach. I made a point of befriending people in both insurance and marketing. I sought out people at events and just said, “You’ve got 20 years of experience. Can I come in for a few days and learn how you work?”
It was a really fun stage in my career. I knew I needed some education and was hungry to learn. At one point in my early days, I had three or four mentors I leaned on for advice or structure on problem-solving almost weekly. I’m really trying to give back and mentor others now because I know how much it helped me.
“At the core, marketing is about understanding your customer and what they need. From there, it’s testing, learning, and seeking the right information to help you refine your approach.”
You’ve stayed in the insurance industry. What do you like about it?
I got really hooked on it. It may sound weird, but I like the compliance regulations and the challenges you face. I also find it to be very mission-driven work. One of the things I learned at PolicyGenius was that many families carry some coverage, like health or home insurance, but still face challenges because of underinsurance, coverage exclusions, or high out-of-pocket costs. There is a massive opportunity to help consumers better understand their options and protect themselves against potential financial hardships.
You are now the CMO of Hippo. What is unique about Hippo’s insurance model?
Hippo was built on the idea that if homeowners partner with us to take care of their homes, they will have fewer losses and file fewer claims, which will help them and the company. This comes to life in a few different ways, but we really focus on providing expert education to help homeowners improve and protect their homes and the things in them.
Our app offers checklists of things you could be doing to maintain or improve your home. It pulls in data specific to your home. For example, the app often knows how old your roof is, so we can provide information about re-roofing when it’s time to consider replacing it. Or if it’s time to replace an air filter, the app can tell you when you should service your HVAC system.
We also worked to modernize home insurance plans. Hippo offers home insurance coverage tailored to each property, with the flexibility for homeowners to choose from 70+ carrier partners. Through our mobile app, homeowners can manage their policy, file claims quickly, and receive proactive alerts to stay ahead of potential issues.
You’ve also said you take a different approach to marketing than some of the more traditional insurance companies. Why is that?
I think most insurers have been following the same model for a long time, and it’s mostly a fear-based approach. Just think about Allstate's mayhem commercials. They’ve been on for years, and they’re funny. But every single commercial is about a terrible thing that happens to a customer. The goal seems to be scaring people into buying the products.
I believe that empowering customers and leaning in with education and peace of mind will drive better lifetime value. Insurance is a safety net, and I like messaging the product in such a way that people actually know how to use it and how it can help them have better financial outcomes in the long term.
Over the past couple of months, I interviewed 20 homeowners in their homes. Most people love their homes. I want to tap into that and position us as a support system. Our vision is centered on the joy of homeownership, and I look for opportunities to highlight that rather than resorting to fear-based messaging.
“I believe that empowering customers and leaning in with education and peace of mind will drive better lifetime value.”
What are some of the ways you’ve executed on this more positive vision?
One of my favorites is something we did many years ago for homeowners who had an Alexa. We hired a group of comedy writers, primarily former SNL writers, and gave them some prompts for pretty mundane conversations they’d have in the privacy of their home, and built it into an Alexa skill to make it sound like there were people in the home, even when the home was empty.
They had a broad range of topics to write dialogue around. And then we had actors record the conversations. I remember there was one about a mother trying to explain how to build an Ikea cabinet to a daughter who had just moved into a new home. The idea was that you would tell Alexa to play it when you left the house to deter burglars by making them think people were home.
It gained a lot of traction through PR and social media. I think it was successful because it was funny and unique. It wasn’t saying go out and buy insurance because bad things are going to happen; it was just making you laugh and getting you to think about insurance. It drove a ton of people into our mid-funnel and gave us a fantastic lift in growth for the month.
What do you think is the best way to use performance marketing in an industry like insurance, which is really about building trust?
We focus some of our performance marketing on driving people to our educational content instead of only trying to get them to make a purchase. We want people to visit our blog and learning center to gain a deeper understanding of what’s behind an insurance policy and how an insurance company views your house differently than you do. It can take longer to convert them than if we started showing them products right away, but I think a better customer experience is key to building trust. In the future, we’ll also focus our brand campaigns on homeowner empowerment and partnership to bring our home protection expertise and message to wider audiences, which will help us build trust with a whole new set of potential customers.
Before we let you go, we’ve talked to many CMOs about the pressure to perform quickly and the short tenure people in this position often have. This is your third CMO role. Do you have any advice for someone who is just starting as a CMO?
It is true that you need to prove yourself quickly, so before you start, come up with a couple of potential short-term wins. That could be as simple as asking for performance marketing data and seeing if there are some basic tweaks you can make, or thinking through a couple of campaigns that could be quick and easy to test. Make sure you’ve got those layered into your first two months, so you’ve got something going that feels solid.
But the most important thing is to get the teams on the same page—foundationally—about who you’re targeting, who you are as a company, and what your goals are. Within the first three months, you should have KPIs or OKRs in place (depending on the company), a brand narrative written down and approved, and audience targeting defined—either with first-party data if you have it, or third-party data if you don’t.
I would also advise rethinking spending. Many CMOs come in believing they can only be effective if they have a massive budget. I think it’s the opposite. Use as little as possible until you’ve built some success under you and the company. Once you’ve shown results, you can spend more proving out channels or campaigns where you see initial success and drive forward with bigger changes.
“But the most important thing is to get the teams on the same page—foundationally—about who you’re targeting, who you are as a company, and what your goals are.”
