Centana Advisory Board Q&A Series: Libbie Bock
One of our greatest differentiators at Centana is the strength and diversity of our network. Beyond our own track record and expertise, it’s the operators and advisors we work with, an exceptional group of industry leaders who provide invaluable context, perspective, analysis and support to our portfolio companies. This trusted network is core to how we partner with teams and help drive growth.
To celebrate this, we are excited to launch a new Q&A series featuring conversations with members of Centana’s Advisory Board. These accomplished executives act as thought partners, support our portfolio, and bring decades of operating and industry experience to the table. In each installment, we will share their insights on leadership, innovation, and their views on the ever-evolving landscape of financial services, fintech, and related enterprise technology.
To kick off the series, we sat down with Libbie Bock, a current board member with Centana portfolio company First Connect and who has been part of our Advisory Board since 2017. Libbie brings a wealth of experience from her time as CFO and COO at insurance company Bamboo, and as Group CFO of Kemper’s Property & Casualty division, among other positions.
We’re excited to share Libbie’s story, and we hope you enjoy it as much as we enjoyed the conversation.
Q: You’ve been part of Centana’s Advisory Board since 2017. What made you want to get involved, and what excites you about the firm’s strategy and portfolio today?
I’ve known Ben (Cukier) for a long time. Back when Centana’s founding partners were at a previous firm, I was at The Hartford, which was a limited partner, so I got to know the team. When they asked me to join Centana’s advisory board, I was the only member with a direct insurance background, which I felt brought a unique perspective.
What I have always respected about Centana is their thesis-driven approach: they identify targets early, build relationships with founders, and form partnerships over time rather than rushing into “shotgun weddings.” That philosophy has been there from the start, but the Advisory Board’s role has grown as it’s become larger and more active. While Centana already has strong networks, involving the Board expands that reach even further, tapping into different industries and increasingly helping to source new partnerships.
Q: You’ve spent over two decades in the insurance industry, holding leadership roles across the insurance ecosystem. How did you first get into the industry, and what drew you to stay?
I got into the insurance industry accidentally when I relocated from the West Coast to the East Coast and someone I knew suggested I give it a try. I assumed it would be boring and stodgy, but I was never bored a single day. The industry is full of unique challenges: everything is regulated by state, creating 50 different operating environments across the U.S., plus ongoing issues like climate change, social inflation, and other factors that constantly reshape the landscape. It is never a steady-state environment and something is always changing.
I have also always appreciated how data-driven insurance is. Data does not lie if you use it appropriately; you can manipulate statistics, but the underlying information is sound. It’s fascinating to use data to make predictions and then see how accurate your models are as they play out in the market.
Q: You helped prepare Bamboo for its acquisition. What strategic or operational priorities became clear as you approached an exit? What advice would you give to other executives or founders preparing for a similar outcome?
It’s a great question. In the current market, and really for the past few years, profitability has been key, and I think it will continue to be. When markets are frothy, scaling at any cost doesn’t matter as much. But today, investors want to see profit. For operating teams, that means being laser-focused. Growth is still important, but you also have to pay close attention to expenses so you can show a path to profitability. That focus is absolutely critical right now.
Q: Can you share how you typically engage with Centana’s team or portfolio companies, and where you feel your impact has been most meaningful?
I’ve been involved with Centana at various stages of a deal and beyond. If the team is considering a company, they may call me, or if I come across an opportunity or potential partnership, I’ll reach out. I try to serve in whatever way is most useful, whether that means meeting with management teams of prospective companies or being more involved after an investment is made.
For example, when Centana first invested in One Inc (a former portfolio company), it was marketing to me at the time and gave me the chance to help Centana evaluate their product offering from the perspective of a potential customer. Another example is with ZestyAI. The team there had a strong perspective on certain markets, and at times I had a very different one. For instance, they were very bullish on California, while I raised concerns about the risks there. Of course Centana would have considered those risks on their own, but sometimes I can provide a contrarian point of view that adds value to the long-term positioning of an investment.
Q: You currently sit on the board of First Connect, a Centana portfolio company. What excites you most about the work First Connect is focused on, and what has the collaboration with Centana’s team looked like behind the scenes?
This has been a really fun experience. First Connect is operating in a space that is evolving rapidly. It was also a unique deal because it was a carve-out from Hippo. We essentially acquired not just the company but also the existing team. That creates a different dynamic, and I’m excited about working with the company and supporting its efforts to expand alternative market access quickly and efficiently.
In terms of working with Centana behind the scenes, I talk to Sarah (Kim) and the team outside of board meetings and support however I can, whether that’s making introductions to carriers or contributing to First Connect’s leadership development through coaching and mentorship. And because I am an independent board member, I’m able to bring a perspective that complements Centana’s, giving First Connect another resource to draw on as it grows.
Q: You’ve also held leadership roles at larger public companies like Kemper. How has that big company experience shaped your approach as a board member and advisor today?
It’s helped in a lot of ways, because it really is a different world. Startups often begin with very few processes, little documentation, and only a rough idea of the end game. Larger companies have all of that in place, and having worked at these companies with SOPs, process audits, and Six Sigma-level precision, I have a clear view of where companies ultimately need to go.
As a board member, that allows me to help earlier-stage companies think through a reasonable roadmap, adding process, rigor, and documentation step by step. You don’t need it all on day one, but you do need to build toward it over time.
Q: Many leaders learn the most from what doesn’t go as planned. Can you share a moment from your operating or board career where something didn’t work out, and what it taught you?
We can talk about this all day. At Bamboo, we thought we wouldn’t make all the same mistakes other companies did, but of course we made a bunch of them and we didn’t anticipate other challenges that cropped up. The lesson for me was to always prepare for the worst, even when you think you’ve got things covered.
For example, we relied on one fronting carrier that was later acquired, and the new owner exited California. That forced us to scramble to diversify and secure new partners. Overall, insurance is cyclical, and although you can often anticipate shifts between soft and hard markets, we did not fully account for the impact of climate change on reinsurance.
The lesson here was when you’re modeling, prepare beyond the base case. Models should include reasonable ranges, but you also need to consider near worst-case scenarios. What if inflation reaches 15 percent instead of 5, or a regulatory change suddenly reshapes your business? It may feel extreme, but preparing across the full continuum is essential, not just for scenarios that differ by five or ten percent.
Q: AI is undeniably reshaping innovation across industries, and insurance is no exception. Over the next five years, where do you see AI having the greatest impact in the insurance sector, and where do you think the biggest challenges will lie?
AI is changing so much of what we do, and insurance has actually been an early adopter because the industry is so data driven. Data science and modeling have long been central to underwriting and claims, and AI is only accelerating that.
One of the biggest areas of progress is in customer-facing interactions. Early chatbots were frustrating because they often gave irrelevant answers, but now AI can better understand customer needs and provide logical, helpful responses. That improves the customer experience while also reducing costs for contact centers.
Q: Other than AI, what kind of trends or shifts in the insurance market are you paying close attention to right now, and why?
Regulation is a big unknown. Given how unpredictable political winds are right now, there could be larger regulatory changes than we typically anticipate, and that could significantly impact the industry. Climate change is another area that cannot be ignored. Its effects are being felt globally, and everyone in the industry is watching closely to see how it will continue to reshape insurance.
Q: You recently spent some time in Tanzania building Tabi, a luxury bushcamp in the heart of the Serengeti. What inspired the project, and what have you taken away so far? Is there any way our readers can learn more about the project?
It actually started in insurance. My business partner, a data scientist on my team 20 years ago, also loved wildlife photography and built a bush camp in the Serengeti about six years ago. I visited with my daughters, and we began discussing his idea for an ultra-luxury property. Growing up in rural Colorado gave me a deep love of nature, and the Serengeti feels like one of the last frontiers. Because it is a national park, everything we do must be temporary and low impact, from solar power to trucking in water. The project combined my passions for nature, travel, and international work, and with my years in Japan, we designed a camp that fuses Japanese and African influences.
We also support conservation projects and sponsor local schools and clinics, which has been incredibly fulfilling. The business challenges are very different from insurance, from sourcing parts abroad to navigating logistics in a remote setting, but it has been a tremendous learning experience. Most of all, I have enjoyed meeting the guests, and the work has been both exciting and rewarding.
If you’re interested in learning more about Tabi, please visit: www.tabitanzania.com
Q: What book has changed your life, and why?
A book I read recently that really stuck with me is Be the Giraffe by Chris Jarvis. A friend connected us because of the title, since we often see giraffes at our camp in Africa. It is part business, part life book, and what I liked most is the focus on leveraging what makes you unique instead of trying to blend in. If you are a giraffe with a long neck and spots, embrace it rather than trying to look like a zebra.
What stood out even more was the vulnerability Chris shared. Most business books highlight only successes, but he also wrote about being sued, losing a partner, and facing personal loss. That honesty made the lessons resonate, and it encouraged me to be more open in my own life. I have found that sharing the harder stories creates deeper human connections than presenting only a facade of success.
Important Disclosures
The views expressed in this Q&A are those of the interviewee in her personal capacity. The views expressed in this Q&A are those of the interviewee in her personal capacity. References to portfolio companies are provided for illustrative purposes only and do not constitute investment advice, endorsements, or guarantees of future performance.
